AGECHM1

SCHOOL OF CRIMINAL JUSTICE AND PUBLIC SAFETY
Inorganic and Organic Chemistry

AGECHM1
A Self-regulated Learning Module
A Self-regulated Learning Module 1

AGECHM1
INORGANIC AND ORGANIC CHEMISTRY
MODULE
For the Use of University of Baguio

School of Criminal Justice and Public Safety Students Only
Compiled and Prepared by:
MS. MIROMA R. VILLACRUSIS
MS. RACHELLE B. ROBERTO

INTRODUCTION
Chemistry, the science that deals with the properties, composition, and structure of
substances (defined as elements and compounds), the transformations they undergo, and
the energy that is released or absorbed during these processes. Every substance, whether naturally
occurring or artificially produced, consists of one or more of the hundred-odd species of atoms that have
been identified as elements. Although these atoms, in turn, are composed of more elementary particles,
they are the basic building blocks of chemical substances; there is no quantity of oxygen, mercury,
or gold, for example, smaller than an atom of that substance. Chemistry, therefore, is concerned not
with the subatomic domain but with the properties of atoms and the laws governing their combinations
and how the knowledge of these properties can be used to achieve specific purposes.
A knowledge in chemistry is useful to virtually everyone, we see chemistry occurring around us
every day. An understanding of Chemistry is useful to health care professionals, Crime Laboratory
analyst, forensic pathologist, fire fighters, and environmentalist just to name a few. Even if you’re not
planning to work in any of these fields, chemistry is important and it is used by us every day. Learning
about the benefits and risk associated with chemicals will help you to be an informed citizen, able you
to make intelligent choices concerning the world around you. Studying chemistry teaches you to solve
problems and communicate with others in an organized and logical manner. These skills will be helpful
throughout your career.
Course Description
This course deals with the chemistry of Inorganic and Organic substances. In inorganic chemistry,
the aim is to continue and support the college freshmen’s knowledge of inorganic chemistry as a
foundation of their higher chemistry subjects. The emphasis in the inorganic part is on the mastery of
the properties of the two major classifications of matter namely – pure substances (elements and
compounds) and mixtures (solutions and colloids), where the priority study to be undertaken for pure
substances is in learning their chemical nomenclature and on how to write their correct chemical
formula, but the most important part under this topic is the in-depth understanding of the chemical
reactions of inorganic compounds, which will be highlighted on this part. Included also in the topics to
be studied under inorganic chemistry will be a thorough understanding of the properties and concepts
of solutions and electrolytes (acids, bases, and salts) – which are essential components of biomolecules.
On the other hand, two-thirds of the total hours of this course will focus on the chemistry of the carbons,
hydrocarbons and most especially the chemistry of the hydrocarbon derivatives, taking into
consideration their chemical nomenclatures (IUPAC and common names), structural formula,
preparations or synthesis, and most importantly the study of their physical properties and mechanisms
of their chemical reactions. Highlights will also be given on the importance of the concepts learned from
these topics in the field of forensic analyses and crime investigations. Furthermore, this course will also
hone the laboratory and instrumentation skills of the SCJPS students by performing the different
experimental procedures and laboratory techniques incorporated in each of the prepared experiments
that goes with the lecture part in order to make an efficient and skilled criminologists and forensic
scientists out of the students. Lastly, this course also aims to foster critical thinking among the students
by performing the different experiments and by answering the activities prepared in this course which
will be very helpful later in the conduct of their future professions.

Requirements of the Course:
1. Regular Attendance to classes: You must attend online classes and live quizzes regularly by logging
in to our scheduled online activities. Online lectures will be done through Google meet and/or
facebook live. Assessments shall be given through Quizziz, Pear Deck, Canvas and/or Google
forms. For offline students, your attendance will be monitored through your responses to text
information and through timely correspondence.
2. Submission of required activities : All required activities (assignments, research work, laboratory
illustrations) should be submitted on or before the given deadline. Deadlines will be posted by the
teacher in the google classroom and messenger group chat. It will also be texted to offline students.
For online students, requirements must be submitted to the teacher’s email address which will be
provided during the class orientation. For offline students, requirements must be submitted via mail
or express courier (e.g. LBC, JRS) addressed to: Instructor’s name, School of Natural Sciences,
University of Baguio, Baguio City.
3. Seventy percent (70%) passing score in all required activities: Quizzes, examinations, assignments,
research work, laboratory illustrations.
Computation of grades:
The cumulative system of computing grades shall be followed. Grades computed for midterms and
finals are considered tentative. The final midterm grade is calculated by getting 1/3 of the first grading
grade plus 2/3 of the tentative midterm grade and the final grade is computed by getting 1/3 of the
midterm grade plus 2/3 of the tentative final grade.
The Course Grade is obtained by combining the lecture and laboratory grades (50%:50%) for the
subject.
Study/Learning Guidelines:
A. Manage your time properly. As students of higher education (College), you are expected to be
more responsible in paying attention to course schedules, requirements, and deadlines.
Schedule how you will accomplish all the requirements in all your enrolled courses (reading the
modules, reading on research/ enhancement questions, doing assignments and laboratory
illustrations) and focus your attention when doing your tasks.
B. Observe proper conduct. Despite this online mode of learning, you must still maintain
appropriate behavior at all times. All standards of student conduct outlined in the University of
Baguio Student Handbook remain in full effect during this time of distance learning. Be honest
in answering your quizzes and exams.
For Individual Tasks/Activities -Work independently when accomplishing tasks and assignments
labelled as individual activity.
For Group Tasks/ Activities- Learn to work with your partner/groupmates (even if it is hard and
challenging more so because face to face meeting is not allowed this time). Group activities are
provided for you to be trained to work in harmony with your colleagues in the future.
C. Stay motivated. Your future depends on what you do today. Maintain a positive attitude
towards learning and enjoy a fun-learning environment despite the current circumstances.
D. Maintain a performance of high standard. Give your best in accomplishing all the assigned
tasks. Do not be complacent with just a 70% passing cut-off score. Remember that this is a
board subject, and the best preparation for the board/licensure examination should be during
these formative years. The board review is but supplementary to the knowledge you have
already learned during your four years education.
E. Communicate properly. Promptly respond to notifications by regularly visiting our google
classroom and messenger group chat. If you have confusions or queries in any part of this
module, Your Instructors are here to guide you through. Send your academic concerns using
the same online platforms. For offline students, text messages and mobile calls are welcome
during scheduled hours of the day and week. Be guided by this schedule when communicating:
▪ Respect private hours. Your respected Instructors do not always open their
laptop/email/messenger 24/7. Send your queries and/or concerns during regular
office hours. For concerns that need immediate attention, send through mobile text.
▪ Be patient. Messages received between 8 AM to 8 PM will be responded to within the
same day. Messages received after 8 PM will be answered starting 8 AM the next
day.
▪ Before calling the mobile number of your Instructor, text first for their permission for
they might be giving an online lecture or in a meeting or on private moment at that
very instance.
▪ Saturdays and Sundays are for family and home chores. Your Instructors shall
respond to queries/messages received during these days within the first office hour of
Monday.
F. Show mutual support. Support one another. Let us all be responsible and supportive in making
this new learning process more effective.
G. Live lecture/Video conferencing guidelines:

Be punctual. Live lectures/Video conferences will be scheduled during the official class period/time of
this course. Log in to the platform at least 5-10 minutes before the class period. Prepare your learning
materials such as this module, pens, papers, etc. Attendance will be checked during the lecture/video
conference.
Maintain professionalism.
- Wear appropriate clothing and set your gadget in an appropriate area. You may be
asked to turn on your video/camera at any time during the lecture.
- Log in using your UB gmail account. Unidentified names like nicknames, phone models,
etc. will not be allowed in the video conference.
- Mute your microphone as soon as you log in to the platform to avoid any excess
background noise. Unmute your microphone when instructed to do so.
- Be courteous. Do not interrupt your teacher or a classmate who is speaking. You may
type your question in the Chat area, or use the “raise hand” feature if available, and wait
until you are allowed to speak.
- Respect privacy. Do not take a screenshot, picture, snapshot, etc. of your teacher or
fellow students, nor make any unnecessary audio or video recordings. “Take note of the
data privacy law”.
Remain focused and engaged. Do not be distracted by your gadget. Keep your video conference
platform open and do not navigate other tabs or webpages unless directed by your teacher.
Endorsed by:
Teresa N. Villanueva, RMT, MACT

Dean, School of Natural Sciences
STUDY SCHEDULE
WEEK TOPIC ACTIVITIES

1 Orientation (VMO) Lecture:
Unit 1: Introduction to Inorganic Chemistry Assessment & Quiz
Review of: Laboratory:
1. Elements Laboratory Safety Precautions and
- Periodic Table Symbols
2. Compounds Some Selected Laboratory
- Ionic compounds Apparatus and it’s uses and
- Molecular compounds functions
3. Ions Discuss Measurement in
- cations Chemistry
- anions
2 Unit 2: Nomenclature and Writing Chemical Formulas of Lecture:

Chemical Compounds Assessment & Quiz
- elements
- compounds Laboratory:
- acids, bases and salts including properties, #1 Common Laboratory
preparations, pH numbers, acid-base indicators Operations
3 Unit 3: Chemical Equations and Reactions Lecture:

1. Steps in balancing chemical reactions Assessment & Quiz
2. Types of chemical equations:
a) Synthesis Laboratory:
b) Analysis #2 Chemical Reactions
c) Substitution
d) Metathesis
4 Unit 4: Solutions Lecture:

1) Factors Affecting Solubilities of Solutions Assessment & Quiz
2) Expressing Concentrations of Solutions in:
a. % by Weight Laboratory:
b. % by Volume #3 Properties of Solutions
c. Ppm and Ppb #4 Acid – Base Titrations
5 d. Dilution Post laboratory discussion
3) Electrolytes
a. Acids and Bases
b. pH and pOH
c. Neutraliation & Indicators
c. Salts
- Common salts
- Acidic salts
- Basic salts
- Mixed or complex salts
6 FIRST GRADING EXAMINATION

7 Unit 5: Introduction to Organic Chemistry Lecture:
1. History of organic chemistry Assessment & Quiz
2. Differences between Organic and Inorganic
Compounds Laboratory:
3. Classes of Organic Compounds: Functional Group #5 Comparative Study of the
Classifications of Organic Compounds Properties of Organic and
4. Formula Writing: Inorganic Compounds
a. Structural Formulas; #6 A Separation Technique Used
b. Expanded; Condensed; in Organic Chemistry: Solvent
c. Line and angle Extraction
5. Types of Carbon: primary, secondary, tertiary,
quaternary
8 Unit 6: Hydrocabons: Alkanes and Cycloalkanes, Lecture:

Alkenes, Cycloalkenes, Alkynes Assessment & Quiz
1. Homologous Series Laboratory:

2. Isomerism: structural, position, conformation of #7 – Paper Chromatography: A
hydrocarbons, geometric isomerism in hydrocarbons Separation Technique Used in
3. Nomenclature: IUPAC System, 2. Organic Chemistry
Common/Alternative Names #8 - Purification of Organic Solids:
4. Physical Properties: Boiling and melting points, Sublimation and Recrystallization
Solubility in water and organic compounds
9 5. Chemical Properties: Halogenation - free radical
substitution
- free radical intermediates – their relative stabilities,
Combustion
6. Source and medical importance
10 Unit 7: Aromatic HC Lecture:

1. Structure of benzene: Kekule structure Assessment & Quiz
2. Nomenclature of common aromatic compounds
3. Physical Properties: Boiling and melting points, Laboratory:
Solubility in water and organic compounds #9 – Determination of the Purity of
4. Chemical Properties: Organic Solvents: Boiling Point
4.1. Electrophilic aromatic substitution –mechanism Determination by Capillary Method
5. Medical and important Uses
11 Unit 8: Alkyl Halides Lecture:

1. Nomenclature: IUPAC System and Assessment & Quiz
Common/Alternative Names
2. Uses of some common alkyl halides Laboratory:
3. Physical Properties 10 – ation of the Purity of Organic
3.1. Boiling and melting points Solvents: Boiling Point
3.2. Solubility in water and organic compounds Determination by Capillary Method
4. Chemical Properties
12 MIDTERM GRADING EXAMINATION

13 Unit 9: Alcohols, Ethers and Thiols Lecture:
1. General Structure and Formula Assessment & Quiz
2. Classification of Alcohols
3. Nomenclature: IUPAC and Common/Alternative Laboratory:
4. Preparations of alcohols, ethers & thiols #11 – Comparative Study of the
5. Physical Properties Common Properties of
5.1. Boiling and melting points Hydrocarbon Compounds
5.2. Solubility in water and organic compounds
6. Chemical Properties of alcohols, ethers and thiols
6.1. Acidity of alcohols
6.2. Oxidation of alcohols
7. Importance and uses of common alcohols, ethers and
thiols
14 Unit 10: Phenols Lecture:
1. General structure and formula Assessment & Quiz
2. Importance and uses of common phenols
3. Physical Properties Laboratory:
3.1. Boiling and melting points #12 – Properties and Specific
3.2. Solubility in water and organic compounds Tests for Alcohols and Phenolic
4. Chemical Properties Compounds
4.1. Acidity of phenols
4.2. Electrophilic aromatic substitution
14 Unit 11: Aldehydes and Ketones Lecture:

1. Structure Assessment & Quiz
2. Nomenclature: IUPAC and Common Names
3. Importance and uses of common aldehydes and Laboratory:
ketones #13 - Properties and Specific
4. Preparation of aldehydes and ketones. Tests for Aldehydes and Ketones
5. Physical Properties
5.1. Boiling and melting points
15 6. Chemical Properties
6.1. Nucleophilic addition –mechanism
6.1.1. Addition of HCN to form cyanohydrins
6.1.2. Addition of alcohols to form acetals/ketals
6.3. Oxidation
16 Unit 12: Carboxylic Acids, Esters and Amides

1. General Formula Lecture:
2. Nomenclature: IUPAC and Common/Alternative Assessment & Quiz
Name
3. Sources, uses and importance of common carboxylic Laboratory:
Acids, esters and amides. #14 – Preparations and Properties
4. Physical Properties of Carboxylic Acids and Esters
4.1. Boiling and melting points
5. Preparations of carboxylic acids
17 6. Chemical Properties
6.1. Acidity of carboxylic acids
6.2. Nucleophilic acyl substitution – mechanism

6.2.1. Formation of carboxylic acid derivatives and
their interconversion
7. Preparation of common esters and amides
8. Chemical properties of Esters and amides
18 Unit 13: Amines Lecture:

1. General formula Assessment & Quiz
2. Nomenclature of common amines
3. Sources, uses and importance of common amines Laboratory:
4. Physical Properties #15 – Comparative Study of the
4.1. Boiling and melting points properties of Amines and Amides
FINAL GRADING EXAMINATION

TABLE OF CONTENTS
LECTURES:
Unit 1: Introduction to Inorganic Chemistry…………………………………………………………………………………………….. 11
Unit 2: Nomenclature and
Writing Chemical Formulas of Chemical Compounds………………………………………………….……. 18
Unit 3: Chemical Equations and Reactions……………………………………………………………………………………………. 33
Unit 4: Solutions and Electrolytes ………….…………………………………………………………………………………………………. 43
Unit 5: Introduction to Organic Chemistry…………………………………………………………………………………..………… 49
Unit 6: Hydrocabons: Alkanes and Cycloalkanes, Alkenes, Cycloalkenes, Alkynes…………. 71
Unit 7: Aromatic Hydrocarbons…………………………………………………………………………………………………………………… 112
Unit 8: Alkyl Halides………………………………………………………………………………………………………………………………………… 132
Unit 9: Alcohols, Ethers and Thiols…………………………………………………………………………………………………………… 142
Unit 10: Phenols……………………………………………………………………………………………………………………………………………….. 166
Unit 11: Aldehydes and Ketones………………………………………………………………………………………………………………. 178
Unit 12: Carboxylic Acids, Esters and Amides………………………………………………………………………………….… 192
Unit 13: Amines………………………………………………………………………………………………………………………………………………... 218
LABORATORY ACTIVITIES:
Activity #1 Laboratory Safety Precautions and Symbols……………………………………………………………….. 230
Activity #2 Some Selected Chemistry Laboratory Apparatus: Its Uses and Functions …… 234
Experiment #1 Common Laboratory Operations………………………………………………………………………………… 235
Experiment #2 Chemical Equation……………………………………………………………………………………………………………. 242
Experiment #3 Properties of Solutions…………………………………………………………………………………………………... 249
Experiment #4 Acid Base-Titration…………………………………………………………………………………………………………… 242

Experiment #5 Comparative Study of the Properties of Organic and Inorganic
Compounds …………………………………………………………………………………………………………………………….... 254
Experiment #4 A Separation Technique Used in Organic Chemistry:
Solvent Extraction ……………………….……………………………………………………………………………………… 258
Experiment #5 Paper Chromatography: A Separation Technique Used in
Organic Chemistry ……………………………………………………………………………………………..…………..… 262
Experiment #6 Purification of Organic Solids: Sublimation and Recrystallization ………. 267
Experiment #7 Determination of the Purity of Organic Solvents:
Boiling Point Determination by Capillary Method……………………………………………..... 271
Experiment #10 Purification operations in Organic chemistry: Fractional Distillation…… 275
Activity #11 Comparative Study of the Common Properties of Hydrocarbons………………… 279
Activity #12 Properties and Specific Tests for Alcohols and Phenolic Compounds……… 283
Activity #13 Properties and Specific Tests for Aldehydes and Ketones……..…………………… 290
Activity #14 Preparations and Properties of Carboxylic Acids and Esters ……..…………… 296
Activity #15 Comparative Study of the Properties of Amines and Amides……………………… 303
References…………………………………………………………………………………………………………………………………………………. 308
Module Evaluation Questionnaire……………………………………………………………………………………………………. 310

MODULE 1
Introduction to Inorganic Chemistry
Learning Objectives:
At the end of the learning session, the student must be able to:
1. discuss the application of Inorganic Chemistry
2. explain the difference between elements from compounds and ions,
3. predict properties of elements based on the periodic table
4. identify bonds formed in compounds
5. Familiarize themselves with the common laboratory apparatus and their functions.
LESSON INTRODUCTION
Inorganic chemistry is of fundamental importance not only as a basic science but also as one of the
most useful sources for modern technologies. Elementary substances and solid-state inorganic compounds
are widely used in the core of information, communication, automotive, aviation space industries and in
medical field. Inorganic compounds are also indispensable in the frontier chemistry of organic synthesis using
metal complexes, homogeneous catalysis, bioinorganic functions, etc. One of the reasons for the rapid
progress of inorganic chemistry is the development of the structural determination of compounds by X-ray and
other analytical instruments. It has now become possible to account for the structure-function relationships to
a considerable extent by the accumulation of structural data on inorganic compounds.
Inorganic chemistry is concerned with the properties and reactivity of all chemical elements. Advanced
interests focus on understanding the role of metals in biology and the environment, the design and properties
of materials for energy and information technology, fundamental studies on the reactivity of main group and
transition elements, and nanotechnology. Synthetic efforts are directed at hydrogen storage materials and
thermoelectric, catalysts for solar hydrogen generation, fullerenes and metal porphyrins, metal clusters and
compounds with element-element bonds, as well as nanowires and nanoparticles.
Inorganic Chemistry is not an isolated branch of chemistry. This core science is fully integrated with other
areas of chemistry such as organic, physical analytical chemistry and clinical chemistry. It deals with the
chemistry of all non-organic compounds.
Chem.libretext.org
LESSON 1: Inorganic Chemistry-A SHORT REVIEW
Inorganic Chemistry deals with Matter its composition, properties and its reactions. Matter is anything
that occupies space and has mass. All the objects in the universe, since they occupy space and have mass,
are matter. The mass of an object is the quantity of matter that it contains.
Classification of Matter:
Pure substance/substance have fixed compositions and distinct properties.
1.Elements are substances that cannot be decomposed into simpler substances by chemical means. They are
the basic substances out of which all matter is composed.
2.Compounds are the substances composed of two or more elements united chemically in definite proportions
by mass. They can be decomposed by chemical means into simpler elements.

Mixtures are composed of two or more kinds of matter where each substance retains its own identity and
properties thus it can be separated by physical means. Compositions of mixtures can vary continuously.
1.Homogeneous mixtures have uniform composition throughout. Solutions are classified under this group. i.e.
vinegar, brine, syrup
2.Heterogeneous mixtures are substances whose composition, properties and appearance differ throughout.
i.e. sand in water, chocolate chip ice cream, fruit salad
MATTER
Thoughtco.com
PURE SUBSTANCES/ MIXTURES

SUBSTANCES
Homogenous
Heterogenous
ELEMENTS COMPOUNDS
-Acid
-Metal
-Base
-Nonmetal
-Salt
-Metalloid
Properties of Matter refer to the characteristics that enable one to distinguish one substance from another.
1.Physical properties: color, odor, taste, hardness, physical state, melting point, boiling point, electrical
conductivity, malleability, density, solubility, specific gravity.
2.Chemical properties: rusting metal, burning fuel, milk turning sour
Physical States of Matter

1. Solid 2. Liquid 3. Gas 4. Plasma

Changes of Matter
1.Physical change does not involve a change of one kind of matter into another; no change in the fixed
composition of the substance.
2.Chemical change involves the transformation or change of one kind of matter into another; it results in the
formation of a new substance with different properties.
Physical Change Chemical Change
LESSON 2: Periodic Table of Elements- A Review

The periodic table (also known as the periodic table of elements) is organized so scientists can quickly
discern the properties of individual elements such as their mass, electron number, electron configuration and
their unique chemical properties. Metals reside on the left side of the table, while non-metals reside on the
right. Organizing the elements to help further our understanding was first provided by Dmitri Mendeleev.
1. In the periodic table, there are 8 groups of vertical rows, IA to VIIIA. Each group has 2 families, A and B,
having different elements and properties. There are 7 periods or horizontal rows, the seventh row is
incomplete. The 6 periods end with the inert gases. The elements are generally classified as: Metals –
most elements are metals. They occupy the lower left – hand region of the periodic table to the left of a
diagonal line drawn approximately from B to At.

2. Non-metals – are found among the representative elements in the upper right hand region of the
periodic table; halogen family, oxygen family, nitrogen family, etc.
3. Metalloids – occupy a narrow band between the metal and non-metals like silicon and germanium.
Usefulness of the Periodic Table
1. The periodic table is a great help in understanding of the physical and chemical properties of many
elements.
2. The periodic table helps us remember and understand chemical data.
3. The table is the guide to chemical prediction and theory. Similar elements act alike, so do their
compounds.
4. The periodic table can be used to determine the formula of compounds.
https://www.sigmaaldrich.com/technical
LESSON 3: Ionic and Covalent Compounds- A Review
The physical state and properties of a particular compound depend in large part on the type of chemical
bonding it displays. Molecular compounds something called covalent compounds, display a wide range of
physical properties due to the different types of intermolecular attractions such as different kinds of polar
interactions. The melting and boiling points of molecular compounds are generally quite low compared to those
of ionic compounds. This is because the energy required to disrupt the intermolecular forces between molecules
is far less than the energy required to break the ionic bonds in a crystalline ionic compound. Ionic solids typically
melt at high temperatures and boil at even higher temperatures. For example, sodium chloride melts at 801 °C
and boils at 1413 °C. (As a comparison, the molecular compound water melts at 0 °C and boils at 100 °C.). The
water solubility of molecular compounds is variable and depends primarily on the type of intermolecular forces
involved.

Libretxt.com
Comparison of Ionic and Molecular Compounds

Property Ionic Compounds Molecular Compounds
Type of elements Metal and nonmetal Nonmetals only
Bonding Ionic Covalent
Representative unit Formula unit Molecule
Water Solubility Usually high Variable
Physical state at room temperature Solid Gas, liquid or solid
Melting and boiling temperatures Generally high Generally low
Electrical conductivity Good when molten or in solution Poor
Introduction to General Organic Chemistry & Biochemistry 9th ed-Morris Hein et.al
LESSON 4: IONS
Elements and compounds that are electrically neutral. They have the same number of electrons as
protons, so the negative charges of the electrons is balanced by the positive charges of the protons. However,
this is not always the case. Electrons can move from one atom to another; when they do, species with overall
electric charges are formed. Such species are called ions. Species with overall positive charges are
termed cations, while species with overall negative charges are called anions. Remember that ions are formed
only when electrons move from one atom to another; a proton never moves from one atom to another.
Compounds formed from positive and negative ions are ionic compounds.
Individual atoms can gain or lose electrons. When they do, they become monatomic ions. When atoms gain or
lose electrons, they usually gain or lose a characteristic number of electrons and so take on a characteristic
overall charge. Some common ions in terms of how many electrons they lose (making cations) or gain (making
anions), as well as their positions on the periodic table.
There are several things to notice about the ions ;

First, each element that forms cations is a metal, except for one (hydrogen), while each element that
forms anions is a nonmetal. This is actually one of the chemical properties of metals and nonmetals: metals
tend to form cations, while nonmetals tend to form anions.
Second, elements that live in the first two columns and the last three columns of the period table show a
definite trend in charges. Every element in the first column forms a cation with charge 1+. Every element in the
second column forms a cation with charge 2+. Elements in the third to last column almost all form an anion with
a 2- charge and elements living in the second to last column almost all form anions with a 1- charge.
The elements at the end of the periodic table do not form ions. We'll learn more about why this is the case in
future chapters but for the time being if you can learn this trend it's fairly easy to determine the charge on most
of the elements we see. Finally, most atoms form ions of a single characteristic charge. When sodium atoms
form ions, they always form a 1+ charge, never a 2+ or 3+ or even 1− charge.
chemlibre.txt.org
Further Reading / Supplemental Links
https://pubchem.ncbi.nlm.nih.gov/periodic-table/
https://chem.libretexts.org/Courses/Sacramento_City_College/SCC%3A_Chem_330_-_Adventures_in_Chemistry_(Alviar-
Agnew)/06%3A_Gases%2C_Liquids%2C_Solids%2C_..._and_Intermolecular_Forces/6.2%3A_Comparing_Ionic_and_Molecular_Substances
Review Questions and Individual Exercises
A. Review Questions
Classify the following according to the choices below (1point each)
A.Pure substance- Element A. Molecular Compound

B.Pure substance-Compound B. Ionic Compound
C.Mixture- Homogenous
D.Mixture- Heterogenous
1. Gold 11. Sodium Chloride
2. Sodium Chloride 12. Carbon Dioxide
3. Salt water 13. dinitrogen trioxide
4. Blood Plasma 14. Aluminum Oxide
5. Silverware 15. Zinc Chloride
6. Epithelial cells in urine
7. Mercury
8. Carbon Dioxide
9. Air
10. Zinc

B. Individual/Group Exercises
Using a Venn Diagram, come-up with a complete list of elements grouped according to their Types. (use the
symbols and the name of the elements ex. Na-sodium)10 points
Rubrics in Rating
Assessment of
5 4 3 2 1
Outcomes
1-2 information / 3-4 information / 4-5 information / 6 and above
Presence of All information
answer required is answer required is answer required is information /
required and/or answer
missing or missing or missing or answer required is
information or are present and
incorrect incorrect incorrect missing or incorrect
answers correct groupings
groupings groupings groupings groupings
Clean and free 6 and above
1-2 erasures/ 3-4 erasures/ 4-5 erasures/
Quality of work from erasures/ erasures/
alterations alterations alterations
alterations alterations
Laboratory Activity #1: Laboratory Safety

Please see Laboratory Manual at the back part of the module
https://www.youtube.com/watch?v=KIqH3oqJk0M
https://www.mynewlab.com/blog/a-visual-guide-to-science-safety-symbols-in-a-laboratory/
Click the link above before you perform Laboratory Activity #1
Note: Watch video of Experiment#1 as performed by your Instructor/s in the real laboratory to be posted on
Google class as scheduled.
MODULE 2
Nomenclature and Writing Chemical Formulas of Chemical Compounds
1. Name inorganic compounds systematically.
2. Cite inorganic compounds that are commonly encountered at home or outside the classroom by
giving the common and IUPAC names.
3. Write chemical formulas of compounds based on IUPAC rules
4. Discuss the properties and preparations of acids, bases and salts.
5. Classify compounds based on the calculated pH value.
LESSON INTRODUCTION
Chemical compounds are substances which are made of more than one atom or element. What holds
these atoms together are strong forces of attraction known as chemical bonds. Chemical compounds can be
classified according to the type of bond which forms them.
VALENCE ELECTRONS
Electrons involved in bonding are the outermost electrons in an atom and are called as valence
electrons.
Lewis Electron-dot Structure
These structures are named after G.N. Lewis, an American chemist who pioneered the relationship
between electronic structure and chemical bonds. Dots are often used to represent the valence electrons in
atoms and molecules. The electron dot structure consists of the symbol for the element and a dot(s) to
represent the outermost electron(s) in the atom.
Octet rule – the completion of the maximum 8 number of electrons.
CHEMICAL BONDS
1. Ionic Bond results from the electrostatic attraction between two oppositely charged ions, the action and
the anion. An atom that loses one or more valence electrons gains a positive charge and becomes a
positive ion called cation. Atoms that pick up the electrons lost by metals become negative ions or
anions.
2. Covalent Bond arises from the sharing of one or more pairs of electrons between two atoms which
have the same tendency to give or pick up electrons. In general, when a non-metallic element combines
with another non-metallic element, electrons are neither gained nor lost by the atoms but are shared.
Compounds containing these bonds are called covalent compounds.
LESSON 1: Writing Chemical Formulas of Chemical Compounds

Chemical formula is a combination of symbols for atoms or ions that are held together chemically.
WRITING CHEMICAL FORMULAS
In writing the chemical formula of a compound, we need the term that will describe the combining
capacity of an element and also indicate the positive (+) or negative (-) nature of the atoms in the compound.
Oxidation Number or Oxidation State - is a positive or negative integer that is related to the electronic structure
of the atom.

o The atom that loses electrons has the positive oxidation number and the atom that gains electrons has
the negative oxidation number.
o The atom that is more electropositive has the positive oxidation number and the atom that is more
electronegative has the negative oxidation number.
IONIC COMPOUNDS
Compounds formed between metals and non-metals are called ionic compounds. Many ionic
compounds are binary compounds, that is, compounds formed from the combination of two elements.
A number of ionic compounds contain a metal cation and two different elements in the anion group.
These compounds containing three elements are called ternary compounds.
WRITING FORMULAS OF IONIC COMPOUNDS
To write formula for ionic compounds, we must first find their symbols as well as the charges (oxidation
numbers) of the ions involved. For the representative elements, we make use of the group number from the
periodic table and the corresponding electronic configuration to recall ion charges.
Analyze the samples below:
Na +1 + Cl -1 = Na1Cl1 = NaCl
+2 -1
Mg + Cl = Mg1Cl2 = MgCl2
Zn +2 + O-2 = Zn2/2O2/2 = Zn1O1 = ZnO
+3 -2
Al + O = Al2O3
+3 -2
Fe + (SO4) = Fe2(SO4)3
Al+3 + (PO3)-3 = Al3/3 (PO3)3/3 = AlPO3
Ba+ 2 + (OH)-1 = Ba1 (OH)2 = Ba(OH)2
Practice Activity 1: Write the correct Chemical Formula

1. Iron III + Phosphate____________________________
2. Ammonium + Hydroxide ___________________________
3. Potassium + Chlorine ___________________________

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4. Copper II + Oxygen ___________________________
5. Lead II + Acetate ___________________________
LESSON 2: Nomenclature
NAMING IONIC COMPOUNDS
An ionic compound is named in the order in which the ions appear in the formula. The name of the
metal (+ ion), is given first followed by that of the non-metal (- ion). The cation carries the name of the metal
while the name of the anion is derived by changing ending to –ide.
Example
NaCl Al2O3
Sodium Chloride Aluminum Oxide

Some metals have variable oxidation states. Bivalent element (element with 2 valence number) and
Polyvalent element (elements with more than 2 valence number)
The cations of these metals may be named in two ways.
1. In the “Classical System” the Latin name of the cation with the lower oxidation state is modified to end
in -ous, while the cation with the higher oxidation state will end in –ic.
Some Bivalent Element Classical Name Name

Fe +2,+3 Ferrum Fe +2
- Ferrous
Fe+3 - Ferric
Cu +1, +2 Cuprum Cu+1 – Cuprous
Cu+2 - Cupric
Au +1,+3 Aurum Au+1 - Aurous
Au+3 - Auric
Pb +2,+4 Plumbum Pb+2 - Plumbous
Pb+4 - Plumbic
Example
FeO Fe2O3 Pb(C2H3O2)2 Pb(C2H3O2)4

Ferrous Oxide Ferric Oxide. Plumbous Acetate Plumbic Acetate
2. In the “Stock System”, the English name of the metal is used but the oxidation state is indicated by a
Roman numeral enclosed in parentheses.
Some Bivalent Element Name
Fe +2,+3 Fe+2 - Iron (II)

Fe+3 - Iron (III)
Cu +1, +2 Cu+1 – Copper (I)
Cu+2 - Copper (II)
Au +1,+3 Au+1 - Gold (I)
Au+3 - Gold (II)
Pb +2,+4 Pb+2 - Lead (II)
Pb+4 - Lead (IV)
Example
FeO Fe2O3 Pb(C2H3O2)2 Pb(C2H3O2)4
Iron(II) Oxide Iron(III) Oxide. Lead (II) Acetate Lead (IV) Acetate
Practice Activity 2: Name the following Compounds
1. Zn(OH)2 ____________________________________________
2. Mn(O)2 ____________________________________________
3. CaS ______________________________
musictheory.com 4. K2O ______________________________

5. PbSO4 _____________________________________________
COVALENT COMPOUNDS
When a pair of non-metals forms only one compound, it is named quite simply. The name of the
element whose symbol appears first in the formula is written first. The second part of the name is formed by
adding the suffix –ide to the stem of the name of the second non-metal.
If more than one compound is formed by a pair of non-metals, Greek prefixes are used to indicate the
number of atoms of each element present.
Note: when the prefixes “tetra” and “penta” precede a vowel, the final “a” is dropped to make the word easier
to say. Hence, tetroxide is used instead of tetraoxide and pentoxide instead of “pentaoxide”.
Introduction to General Organic Chemistry & Biochemistry 9 th ed-Morris Hein et.al

Example :
CO Carbon Monoxide
CO2 Carbon Dioxide
N2O Dinitrogen Monoxide

Check the
FIRST ELEMENT
of the compound
Is the First element is metal?
Check the YES NO

It is a Covalent Compound
valence number
Use the GREEK PREFIXES
of the first element
Is the element monovalent?
YES NO
Name the First element

followed by the Next Use the Classical System
element Changing the last or
letters into “ide” the Roman Numerals System in
naming
FLOW CHART OF NAMING INORGANIC COMPOUNDS
NAMING ACIDS
Binary Acids
Binary acids are certain molecular compounds in which hydrogen is combined with a second nonmetallic
element; these acids include HF, HCl, HBr, and HI. HCl, HBr, and HI are all strong acids, whereas HF is a
weak acid.
Example:
HF – Hydro + fluor + ic acid Hydrofluoric acid

HCl - Hydro + chlor + ic acid Hydrochloric acid
HBr - Hydro + brom + ic acid Hydrobromic acid
HI - Hydro + Iod + ic acid Hydroiodic acid
Oxy-acids
Oxyacids are derived from the oxyanions. These include the following:
Chlorine Bromine
ClO4- perchlorate BrO4- perbromate

ClO3- chlorate BrO3- bromate
-
ClO2 chlorite BrO2- bromite
-
ClO hypochlorite BrO- hypobromite
The name of the oxyacid is derived from the name of the oxyanion with some modification in the suffix.
1. If the name of the oxyanion ends in –ate, the name of the oxyacid will be ______________-ic acid.
2. If the name of the oxyanion ends in –ite, the name of the oxyacid will be ______________-ous acid.
NAMING BASE
Name the metal + Hydroxide
Example
KOH - Potassium Hydroxide
Mg(OH)2. - Magnesium Hydroxide
Al(OH)3 - Aluminum Hydroxide
Name the following Chemical formula

1. PI3 __________________________________________
2. HC2H3O2 ___________________________________________
3. H2S ___________________________________________
4. H3PO4 ___________________________________________
5. H3P ___________________________________________
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LESSON 3: Acids, Bases and Salts (including properties, preparations, pH numbers, acid-base indicators)
The acid-base properties of substances are found in all areas of our lives.
Definition of Terms
1. Ionization – refers to the formation of ions from atoms or molecules

2. Electrolyte – a substance that breaks up into ions in solution
3. Strong electrolyte – if a substance completely ionized
4. Weak electrolyte – if a substance is only partially ionized
5. Weak acid or base – one that is only partially ionized
6. Strong acid or base – one that is completely ionized
7. Amphiprotic or amphoteric – type of compound which can act either as acid or base (“amphi” means
both kinds)
8. Buffers – a solution which contains a weak acid and its conjugate base or a weak base or conjugate
acid. It has a remarkable property of maintaining an almost constant pH even though a strong acid or
base is added to the solution
9. Alkalosis – high pH of blood

10. Acidosis – low pH of blood
11. Ionic equations – weak acids and bases are written in molecular form, and strong acids and bases are
written in the form of ions
12. Net ionic equation – shows only those ions that actually undergone a chemical change
13. Spectator ion – ions which do not undergo any change
Properties
Acids
1. Turns litmus paper to red
2. Has a sour taste
3. Neutralizes base
4. Reacts with active metals to produce hydrogen gas
Base
1. Turns litmus paper to blue
2. Has a bitter, biting taste
3. Has a slippery, soapy feeling (due to dissolving a thin layer of the skin)
4. Neutralizes acids
Summary of the Three Theories
Theories Acid Base

Arrhenius Increase H3O+ in aqueous solution Increase OH- in aqueous solution
Bronsted-Lowry Donates proton Accepts protons
Lewis Accepts electron pair Donates electron pair
Common Acids and Bases
A. Common Acids Formula Use

Sulfuric acid H2SO4 It is the “battery acid” found in automobile batteries. It is also used as a
dehydrating agent (one that has the ability to remove water)
Hydrochloric acid HCl The gastric juice in the stomach is 0.1M HCl. It is called Muriatic acid
in industry and is used to clean rust and paint from metals and
concrete
Nitric acid HNO3 It is used to make fertilizers and explosives
Phosphoric acid H3PO4 It is used in dilute form in softdrinks and in detergents and in fertilizers
Acetic acid CH3COOH The acid in vinegar is dilute acetic acid
Citric acid C6H8O7.H2O The acid in citrus fruits is citric acid
Carbonic acid H2CO3 It is found in carbonated drinks
B. Common bases Formula Use
Sodium hydroxide NaOH It is known as lye. It is used in soap manufacture and paper
production. It is also used as drain cleaner
Potassium hydroxide KOH Like NaOH, it is a strong base and is used to dissolve grease and hair
in clogged drains
Magnesium Mg(OH)2 As a suspension, it is known as milk of magnesia. In small dosage, it is
Hydroxide used as an antacid, but in large amount, it is used as a laxative
Aluminum hydroxide Al(OH)3 It is used as an antacid with no dosage restrictions
Ammonium hydroxide NH4OH It is ammonia dissolved in water. A 2% solution of ammonia is used to
revive patients who have fainted, it is used in the production of
fertilizers
Acid Anhydride
➢ Non-metal oxide
➢ Acid oxides
➢ Recall: non-metal + water = oxyacid
➢ SO3, SO2, NO3, NO2, P2O5, CO2 etc
Basic Anyhydride
➢ Metal oxide
➢ Basic oxide
➢ Recall: metal oxide + water = metal hydroxide (base)
➢ CaO, MgO, Na2O, K2O, Al2O3
pH and POH concepts
➢ Developed as a more convenient way of expressing hydrogen ion concentration
pH
➢ Under the Brønsted-Lowry definition, both acids and bases are related to the concentration of hydrogen
ions present. Acids increase the concentration of hydrogen ions, while bases decrease the concentration
of hydrogen ions (by accepting them). The acidity or basicity of something, therefore, can be measured by
its hydrogen ion concentration.
➢ In 1909, the Danish biochemist Sören Sörensen invented the pH scale for measuring acidity. The pH
scale is described by the formula:
pH = -log [H+] Note: concentration is commonly abbreviated by using square

brackets, thus [H+] = hydrogen ion concentration. When measuring
pH, [H+] is in units of moles of H+ per liter of solution.
For example, a solution with [H+] = 1 x 10-7 moles/liter has a pH equal to 7 (a simpler way to
think about pH is that it equals the exponent on the H + concentration, ignoring the minus sign). The pH
scale ranges from 0 to 14. Substances with a pH between 0 and less than 7 are acids (pH and [H+] are
inversely related - lower pH means higher [H+]). Substances with a pH greater than 7 and up to 14 are
bases (higher pH means lower [H+]). Right in the middle, at pH = 7, are neutral substances, for example,
pure water. The relationship between [H+] and pH is shown in the table below alongside some common
examples of acids and bases in everyday life.
pH
➢ Power of hydrogen

➢ Measure of the relative acidity of a solution
➢ pH = -log (H+)
➢ (H+) = antilog (-pH)
pOH
➢ Power of hydroxide
➢ Measure of basicity
➢ pOH = -log (OH-)
➢ (OH-) = antilog (-pOH)
14 = pH + pOH
pH range is 0-14, a pH close to 14 is strongly basic and a pH close to ) or 1 is strongly
if pH = 7
➢ neutral solution
if pH = more than 7
➢ solution is basic
if pH = less than 7
➢ solution is acidic
Sample computation
What are the pOH and the pH of a 0.0125-M solution of potassium hydroxide, KOH?
Solution
Potassium hydroxide is a highly soluble ionic compound and completely dissociates when dissolved
in dilute solution, yielding [OH−] = 0.0125 M:
The pH can be found from the pOH:
Calculate the pOH of NaOH given the [OH-] is 3.0 x 10-2 M
pOH=-log[OH-]
=-log [3.0 x 10-2 M]
= 1.52

Practice Activity 3: pH and pOH calculation
Calculate the [H3O+] of HCl with the pH of 1.20
Ans.
musictheory.com
6.3 x 10-2 M
Indicators
➢ it is an acid base system in which weak acid (conjugate acid) has one color and its conjugate base has
another color
➢ it is used to determine the pH of a solution experimentally
➢ used only in small quantities
➢ it is used for rough estimation of pH or for detecting large changes in pH
Common Indicators
Indicator pH at which color Color at lower pH Color at higher pH
changes
Methyl orange 4 red Yellow
Methyl red 5 red Yellow
Litmus 7 red Blue
Phenolphthalein 9 colorless Pink
Thymolphthalein 10 colorless Blue
Alizarin yellow 11 yellow Red
pH values of some common substances and foods
Substance/Food pH
Gastric juice 1.6
Kalamansi 2.2
Vinegar 2.8
Apple 3.1
Carbonated drink 3.0
Tomato 4.2
Coffee 5.1
Urine 6.1
Blood 7.4
Detergent 8.5
Ammonia 11
Bleaching powder 12
1M NaOH 14
th
Introduction to General Organic Chemistry & Biochemistry 9 ed-Morris Hein et.al

pH meter
➢ used for accurate measurement of pH
➢ it is a galvanized cell whose electromotive force (emf) depends on the pH of the solution
Buffers
➢ solution which contains a weak acid and its conjugate base or a weak base and its conjugate acid
➢ it has a remarkable property of maintaining an almost constant pH even though a strong acid or base is
added to the solution
➢ e.g. blood
Normal pH range of blood = 7.35 – 7.45

➢ less than 7 or more than 7.8
➢ crucial
➢ the hemoglobin of rbc loses its ability to transport oxygen to the tissues and death usually
follows
pH less than 7.35 = acidosis

Causes and symptoms
➢ has untreated diabetes mellitus
➢ undergoes fasting, starvation, or has low carbohydrate diet
➢ under breaths, dyspnea
pH more than 7.45 = alkalosis

Causes and symptoms
➢ prolonged vomiting because a person has lost an unusual amount of gastric juice
➢ excessive use of antacid preparations
➢ over breathing – hyperventilation, can be due to a disorder in the CNS, neurotic disorder or high altitudes
• blood is buffered by bicarbonate-carbonic acid buffer (HCO3-/H2CO3)

• if the blood becomes basic, the carbonic acid will neutralize the hydroxyl ion as shown in the
reaction below
o H2CO3 + OH- H2O + HCO3-
• If the kidneys fails to remove excess hydrogen ions due to certain metabolic diseases. HCO 3- acts
as a base
o HCO3- + H3O+ H2O + H2CO3
o H2CO3 H2O + CO2
• The kidneys are also buffered by monohydrogen-dihydrogen phosphate buffer (H2PO4-/HPO4-2)
• The proper pH in cellular fluid is maintained by the following reactions
o HPO4-2 + H3O+ H2PO4-/ + H2O
o H2PO4- + OH- HPO4-2 + H2O
Neutralization
➢ The reaction between an acid and a base to form a neutral solution
➢ It occurs when an equivalent amount of an acid reacts with an equivalent amount of base
➢ HCl + NaOH NaCl + H2O
➢ Equivalence point – the point where an acid or base has been added in amounts equivalent to each other

Titration
➢ Used to accomplish equivalence point
➢ The progressive addition of a solution (acid or base) of known concentration to a known amount of an acid
or base of unknown concentration
➢ Standard solution – the known solution
➢ End point – the point in titration where the indicator used undergoes a color change
https://aperainst.com/blog/what-is-ph/

https://chem.libretexts.org/Bookshelves/Inorganic_Chemistry/Modules_and_Websites_(Inorganic_Chemistry)/
Chemical_Compounds
https://aperainst.com/blog/what-is-ph/

A. Review Questions
Show your computations
1. What is the pH of a solution if the [H1+] is 1.4x10-5 M?
a. 4.85 c. 5.00
b. -4.85 d. -5.00
2. Given the [OH-] 3.0x10-2, what is the pOH of NaOH?
a. 0.15 c. 2.5
b. 1.52 d. 3.0

B. Group/ Individual Exercises
ACTIVITY – A
Chemical Formula Writing
Cations Anions Chemical Formula
1.) Pb+4 N-3

2.) Zn+2 O-2
3.) Fe+3 (C2O4)-2
4.) (NH4)+1 (PO4)-3
5.) Ba+2 I-1
6.) K+1 (CrO4)-2
7.) Sn+4 O-2
8.) Cu+2 (SO3)-2
9.) Al+3 (OH)-1
10.) Mg+2 (SiO4)-4
11.) Na+1 P-3
12.) S+6 O-2
13.) Fe+3 (PO4)-3
14.) (NH4)+1 (NO3)-1
15.) Ca+2 F-1
16.) K+1 (ClO4)-1
17.) Mn+4 O-2
18.) Pb+4 (SO4)-2
19.) Zn+2 Br-1
20.) Hg+2 O-2

ACTIVITY -B
NOMENCLATURE
Chemical Formula Systematic Name ofCompounds
1. CoBr2
2. PCl5
3. SF6
4. CrCl3
5. Au2O3
6. SnF2
7. XeF4
8. Ni2O3
9. P2O7
10. Ag3N
11. Sn3(PO4)4
12. Fe(BrO4)3
13. Zn(NO2)2
14. Mn2(SO4)7
15. KH2PO4
16. Na2SeO4
17. (NH4)2CO3
18. AgNO3
19. Sb2(CrO4)3
20. BAsO3
21. H3PO4
22. HBrO
23. HNO2
24. H2S
25. H2CO3
26. H3BO3
27. HC2H3O2
28. HIO4
29. H3AsO4
30. HI

ACTIVITY- C
WRITING CHEMICAL FORMULA
Name of Chemical Compounds Correct Chemical Formula
1. Aluminum Iodide
2. Lithium Sulfate
3. Magnesium Dichromate
4. Hydrosulfuric Acid
5. Hydroiodic Acid
6. Potassium Oxide
7. Chromous Nitrate
8. Chromic Acid
9. Calcium Sulfate Decahydrate
10. Sodium Aluminate
11. Stannic Bromate
12. Cupric Oxide
13. Dinitrogen Pentoxide
14. Perchloric Acid
15. Nitrogen Monoxide
16. Carbon Tetrachloride
17. Cobaltous Sulfite
18. Sodium Metaphosphate
19. Oxalic Acid
20. Calcium Carbide
Experiment #2
Note: Watch video of Experiment #2 as performed by your Instructor/s in the real laboratory to be
posted on Google class as scheduled.

MODULE 3
Solutions
1. Differentiate the types of solutions
2. Discuss the factors affecting the solubility of solute in the different kinds of solvents.
3. Analyze problems involving concentration of solutions.
4. Manifest honesty in performing activities in the lecture and laboratory.
LESSON INTRODUCTION
Solutions are homogeneous mixtures. The major component is called solvent, and the minor components
are called solute. If both components in a solution are 50%, the term solute can be assigned to either
component. When gas or solid material dissolves in a liquid, the gas or solid material is called the solute. When
two liquids dissolve in each other, the major component is called the solvent and the minor component is called
the solute.
Many chemical reactions are carried out in solutions, and solutions are also closely related to our
everyday lives. The air we breathe, the liquids we drink, and the fluids in our body are all solutions.
Furthermore, we are surrounded by solutions such as the air and waters (in rivers, lakes and oceans).
Types of Solutions
At the molecular level, molecules and ions of a solute are completely mixed with and interact with those
of the solvent when a solute dissolves in a solvent. This type of mixing is homogeneous because no boundary
is visible in the entire solution. In a mixture, differences may exist between regions or parts of the whole system.
Material exists in three states: solid, liquid, and gas. Solutions exist in all these states:
1. Gaseous mixtures are usually homogeneous and all gas mixtures are gas-gas solutions. For
quantitative treatment of this type of solutions, we will devote a unit to gases. The atmosphere is a
gaseous solution that consists of nitrogen, oxygen, argon, carbon dioxide, water, methane, and some
other minor components, but its water and carbon dioxide contents may vary depending on the
temperature and place.
2. When molecules of gas, solid or liquid are dispersed and mixed with those of liquid, the homogeneous
(uniform) states are called liquid solutions. Solid, liquid and gas dissolve in liquid to form liquid
solutions. In general, the terms solution and liquid solution are synonymous. Gases and liquid solutions
have attracted the attention of most chemists, while material scientists and engineers are more
interested in the manufacture and properties of solid solutions.
3. Many alloys, ceramics, and polymer blends are solid solutions. Within a certain range, copper and zinc
dissolve in each other and harden to give solid solutions called brass. Silver, gold, and copper form
many different alloys with unique colors and appearances. Alloys and solid solutions are important in
the world of materials.
LESSON 1: Factors Affecting Solubilities in Solutions
The maximum amount of a substance dissolved in a given volume of solvent is called solubility. Often,
the solubility in water is expressed in gram/100 mL. For example, the solubilities of some common substances
are given in the Table of Solubility.
A solution that has reached the maximum solubility is called a saturated solution. Often, another phase
such as gas, liquid, or solid of the solute is present and in contact within the solution. In general, there is no net
change in the amount of solute dissolved, but the system is by no means static. In fact, the solute is constantly
being dissolved and deposited at an equal rate. Such a phenomenon is called equilibrium.
In case another phase is not present, a solution may be unsaturated or supersaturated. Yes, due to what
can be attributed to a kinetic factor, a solution may stay supersaturated for a long time. When promoted by a
seed, a solution may start to precipitate quickly. Sodium acetate has a very high solubility at say 270 K. In fact,
it can dissolve in the water of crystallization similar to melting. When cooled, such a solution stays in a meta-
stable state. When a seeding crystal is present or started due to the surface of another medium, the entire
solution will solidify. During the crystallization process, heat is evolved, and the solution becomes warm. Thus,
such a solution, when properly packaged, has been used as hand warmer packs for skiers.
One useful classification of materials is polarity. Substances such as H2, O2, N2, CH4, CCl4 etc. are
called non-polar compounds, whereas H2O, NH3, CH3OH, NO, CO, HCl, H2S, H3P etc. are called polar
compounds.
Solubility describes the amount of solute that will dissolve in a specified amount of solvent.
Terms that describe the extent of solubility of a solute in a solvent:
– very soluble
– soluble
– moderately soluble
– slightly soluble
– insoluble
Terms that describe the solubility of liquids:
miscible: liquids that are capable of mixing and forming solutions. (methyl alcohol and water)
immiscible: liquids that are insoluble in each other. (oil and water)
Solubility of Various Common Ions in Cold Water

The Nature of the Solute and Solvent
The general rule for predicting solubility is “like dissolves like”.
Polar compounds tend to be more soluble in polar solvents than nonpolar solvents.
Example. NaCl (sodium chloride) is
soluble in water
slightly soluble in ethyl alcohol
Insoluble in ether and benzene
Dissolution of sodium chloride in water
The hydrated ions slowly diffuse away from the crystal to

become dissolved in solution. move apart and become
surrounded by water dipoles.
Polar water molecules are attracted to Na + and Cl- ions in the

salt or crystal, weakening the attraction between the ions.
Nonpolar compounds tend to be more soluble in nonpolar solvents than in polar solvents.
Example
benzene is:
insoluble in water
soluble in ether
The Effect of Temperature on Solubility

Most solutes have a limited solubility in a specific solvent at a fixed temperature. For most solids dissolved in
a liquid, an increase in temperature results in increased solubility.
– Some solids increase in solubility only slightly with increasing temperature.
– Some solids decrease in solubility with increasing in temperature.
The solubility of a gas in water usually decreases with temperature.
– Kinetic molecular theory accounts for this decreased solubility.
– For the gas to dissolve it must form bonds of some sort with the molecules of the liquid.
– At higher temperatures the kinetic energy of the gas molecules is sufficient to break the gas
water bond.
The Effect of Pressure on Solubility
Small pressure changes have little effect on the solubility of solids in liquids and liquids in liquids.
While small pressure changes have a great effect on the solubility of gases in liquids. The solubility of a gas in
a liquid is directly proportional to the pressure of that gas above the liquid.

Rate of Dissolving Solids
In most cases, the rate of dissolving of a solid increase with temperature. This occurs because
solvent molecules strike the surface of the solid more frequently and harder, causing the solid to dissolve more
rapidly. A solid can dissolve only at the surface that is in contact with the solvent. Smaller crystals have a larger
surface to volume ratio than large crystals. Smaller crystals dissolve faster than larger crystals. When a solid is
first put into water, it comes in contact only with water. The rate of dissolving is then at maximum. Stirring or
Agitating distributes the dissolved solute throughout the water, more water is in contact with the solid, causing it
to dissolve more rapidly.
LESSON 2: Expressing Concentrations of Solutions

The concentration of a solution expresses the amount of solute dissolved in a given quantity of solvent or
solution.
The terms dilute and concentrated are qualitative expressions of the amount of solute present in a solute. A
dilute solution contains a relatively small amount of dissolved solute, concentrated solution contains a relatively
large amount of solute.
Mass Percent Solution
Mass percent expresses the concentration of solution as the percent of solute in a given mass of solution.
g solute g solute
mass percent = x 100 = x 100
g solute + g solvent g solution
Sample computation
1.What is the mass percent of sodium hydroxide in a solution that is made by dissolving 8.00 g
NaOH in 50.0 g H2O?
Given:
grams of solute (NaOH) = 8.0 g
grams of solvent (H2O) = 50.0 g
æ g solute ö
mass percent = ç ÷ x 100
è g solute + g solvent ø
æ 8.00 g NaOH ö
ç 8.00 g NaOH + 50.0 g H O ÷ x 100 = 13.8% NaOH solution
è 2 ø
2 What masses of potassium chloride and water are needed to 250 g of 5.00% solution?
Given:
250 g = total mass of solution
The percent expresses the mass of the solute.
Dissolving 12.5 g KCl in 238 g H2O gives a 5.00% KCl solution.
æ mass percent x g solution ö = g solute
ç ÷
è 100 ø
æ 5.00 x 250. g ö = 12.5 KCl solute
ç ÷
è 100 ø
250g – 12.5 g = 238 g H2O

Practice Activity 4
A 34.0% sulfuric-acid solution has a density of 1.25 g/mL. How many grams
of H2SO4 are contained in 1.00 L of this solution?
Guide steps
Step 1. Determine grams of solution. (Grams of solution are determined
musictheory.com from the solution density.)
Step 2. Solve the mass percent equation for grams of solute
Ans:
425 g H 2SO4
Mass/Volume Percent (m/v)

Mass volume percent expresses the concentration as grams of solute per 100 ml solution.
g solute
mass/volume percent = x 100
mL solution
Sample Computation
A 3.0% H2O2 solution is commonly used as a topical antiseptic to prevent infection. What volume
of this solution will contain 10 g of H2O2?
Solve the mass/volume equation for grams of solute.
g solute
mass/volume percent = x 100
mL solution
mL solution = æç
g solute ö
÷ x 100
è m/v solution ø
mass of solution = 1250 g
(10 g H 2O2 ) x 100 =
mL of Solution = ( 3.0 m/v percent ) 330mL
Volume Percent
Solutions that are formulated from liquids are often expressed as volume percent with respect to the
solute. The volume percent is the volume of a liquid in 100 ml of solution.
volume of liquid in question
volume percent = x 100
total volume of solution
Molarity
Molarity of a solution is the number of moles of solute per liter of solution.
number of moles of solute moles
molarity = M = =
liter of solution liter
Molarity can be expressed in grams of solute rather than moles of solute.
number of moles of solute moles
molarity = =
liter of solution liter

g solute
moles solute =
molar mass
æ g solute ö
ç ÷ g solute moles
molarity = è
molar mass ø moles molarity = =
=
liter of solution liter molar mass x liter of solution liter
Sample Computation
What is the molarity of a solution containing 1.4 mol of acetic acid (HC2H3O2) in 250. ml of
solution?
It is necessary to convert 250. mL to L since molarity = mol/L.
mol mol
The conversion is: ® =M
mL L
æ 1.4 mol ö æ 1000 mL ö 5.6 mol
ç ÷ç ÷= = 5.6 M
è 250 mL ø è L ø L
How many grams of potassium hydroxide are required to prepare 600mL of 0.450 M KOH
solution?
Convert: mL ® L ® mol ® g
The data are:
volume = 600 mL
0.450 mol 56.11 g
M= molar mass KOH =
L mol
The calculation is:
æ 1L ö æ 0.450 mol ö æ 56.11 g KOH ö =
( 600 mL ) çè 1000 mL ÷ø çè L
÷ç
øè mol
÷
ø 15.1 g KOH
Practice Activity 5
Calculate the number of moles of nitric acid in 325 mL of 16 M HNO3?
Use the equation: moles = liters x M
Convert: mL ® L
Ans.
musictheory.com 5.2 mol HNO3

For many purposes, the use of molarity is very convenient. However, when we want to know the
concentration of solute present in situations where there are temperature changes, molarity won't work. The
volume of the solution will change somewhat with temperature, enough to make accurate data observations
and calculations in error. Another parameter is needed, one not affected by the temperature of the material
we are studying.
Molality
A final way to express the concentration of a solution is by its molality. The molality (m)(m) of a solution is
the moles of solute divided by the kilograms of solvent. A solution that contains 1.0mol1.0mol of NaCl
dissolved into 1.0kg1.0kg of water is a "one-molal" solution of sodium chloride. The symbol for molality is a
lower-case mm written in italics.
Sample computation
Determine the molality of a solution prepared by dissolving 28.60g of glucose (C6H12O6) into 250gof
water.
Solution:
Step 1: List the known quantities and plan the problem.
Known
• Mass solute =28.60gC6H12O6

• Mass solvent =250.g=0.250kg
• Molar mass C6H12O6=180.18g/mol
Unknown
• Molality =?m
Convert grams of glucose to moles and divide by the mass of the water in kilograms.
Step 2: Solve.

Molality and molarity are closely related in value for dilute aqueous solutions because the density of those
solutions is relatively close to 1.0g/mL1.0g/mL. This means that 1.0L1.0L of solution has nearly a mass
of 1.0kg1.0kg. As the solution becomes more concentrated, its density will not be as close
to 1.0g/mL1.0g/mL and the molality value will be different than the molarity. For solutions with solvents
other than water, the molality will be very different than the molarity. Make sure that you are paying
attention to which quantity is being used in a given problem.
What is the molality (m) of a solution prepared by dissolving 2.70g of CH3OH in

25.0g H2O?
musictheory.com Ans. 3.37m
Normality
is a measure of concentration equal to the gram equivalent weight per liter of solution. Gram
equivalent weight is the measure of the reactive capacity of a molecule. The solute's role in the reaction
determines the solution's normality. Normality is also known as the equivalent concentration of a solution.
One of the main differences between the normality and molarity of a solution is
that normality describes the amount of gram equivalent of compound present in the solution
while molarity describes the number of moles present in the solution.
N = M (molarity) x n (# of Hydronium ion in acids and Hydroxide in base)
Sample computation
Given the Molarity of the following compound, compute for the Normality
1. 0.15M HCl = 0.15M x 1 = 0.15N
2. 1.4 M H2SO4 = 1.4 M x 2 = 2.8N
3. 2M NaOH = 2M x 1 = 2N
4. 0.4 M Ba (OH)2 = 0.4 x 2 =0.8N
What is the Normality of a solution that contains 50g of H2SO4 dissolved in 15L? 0.068N
N=M x n
Find first the molarity
M= moles of solute N= 0.034M x 2 = 0.068N
Liter of solution
Molar weight of H2SO4

H=1x2 2 50g H2SO4 x 1mole H2SO4 = 0.51moles H2SO4 = 0.034M
S= 32x1 32 98g H 2SO4 15L
O=16x4 64
98g/mole

What is the Normality of a solution that contains 1.5g of Ca(OH) 2
dissolve in 850 mL?
Ans.
musictheory.com
0.0476N

https://www.youtube.com/watch?v=96oNrVnTk50
https://chem.libretexts.org/Bookshelves/General_Chemistry/Book%3A_Chemistry_(OpenSTAX)/03%3A_Com
position_of_Substances_and_Solutions/3.3%3A_Molarity

Group/Individual Exercises
Show your computations, (no computations answers will not be considered) – 5 points each
1. What is the mass percent of sodium hydroxide in a solution that is made by dissolving 8.00g NaOH in 50.0 g
Water?
a. 13.80% of NaOH c. 32.80% of NaOH
b. 16.80% of NaOH d. 50.80% of NaOH
2. What is the molality of a solution in 32.5g of NaF dissolved in 425g of water?
a. 0.182 m c. 18.200m
b. 1.820 m d. 182.000m
3. What is the molarity of a solution in 32g of sodium hydroxide dissolved in enough water to make 325mL
solution?
a. 0.246M c. 24.600M
b. 2.460M d. 246.000M
4. What is the normality of a solution that contains 25g H3PO4 dissolved in 300 mL?
a. 0.87N c. 5.00N
b. 8.67N d. 2.61N
For Application of the concepts above please answer

Experiment #3 - Solutions
Note: Watch video of Experiment #3 as performed by your Instructor/s in the real laboratory to be posted
on Google class as scheduled.

MODULE 4
Chemical Equations and Reactions
1. Balance chemical reactions.
2. Predict products of chemical equations.
3. Demonstrate examples of chemical changes in the laboratory.
4. Manifest honesty in performing activities in the lecture and laboratory.
5. Observe safety in performing activities in the laboratory.
LESSON INTRODUCTION
Chemical Equation reactions always involve change. Atoms, molecules, or Ions rearrange to form
different substances, sometimes in a spectacular manner. For example the thermite reaction, a reaction
between aluminum metal and Iron III Oxide, which produces molten iron and aluminum oxide. The
substances entering the reaction are called the reactants and the substances formed are called the products.
(Reactant) (Product)
Aluminum Metal + Iron III Oxide Iron III + Aluminum Oxide
Al Fe2O3 Fe Al2O3
During reactions chemical bonds are broken and new bonds are formed. The reactants and products
may be present as solid, liquids, gases, or in solution.
In a chemical reaction atom are neither created nor destroyed. All
atoms present in the reactants must also be present in the products.
A chemical equation is a shorthand expression for a chemical change or reaction. A chemical
equation uses the chemical symbols and formulas of the reactants and products and other symbolic terms to
present a chemical reaction. The Equations are written according to this general format.
1. The reactants are separated from products by an arrow ( )that indicates the direction of the
reaction. The reactants are placed to the left and the products to the right of the arrow. A plus sign (+)
is placed between reactants and between products when needed.
2. Coefficients (Whole numbers) are placed in front of the substances to balance the equation and to
indicate the number of units (atoms, molecules, moles, ions) of each substance reacting or being
produced. When no number is shown, it is understood that one unit of the substance is indicated
2Al + Fe2O3 2Fe + Al2O3
Al2O3 2Al2O3
2 Aluminum and 3 Oxygen 4 Aluminum and 6 Oxygen
3. Conditions required to carry out the reaction may, if desired, be placed above or below the arrow or
equality sign. For Example, a delta sign place above the arrow (∆)indicates that heat is supplied to
the reaction
2Al + Fe2O3 ∆ 2Fe + Al2O3

4. The physical state of a substance is indicated by the following symbols;
(s) - solid state
(l) - liquid state
(g) - gaseous state
(aq)- aqueous solution (substance dissolved in water)
2Al (s) + Fe2O3 (s) ∆ 2Fe (l) + Al2O3 (s)
LESSON 1: Steps in balancing Chemical Reactions

Writing and Balancing Chemical Equations
To represent the quantitative relationships of a reaction, the chemical equation must be balanced. A
balanced equation contains the same number of each kind of atom on each side of equation. The balanced
equation therefore obeys the law of conservation of mass.
The general procedure for balancing equations is as follows;
STEP 1- Identify the reaction. Write a description or word equation for the reaction. For example consider
Mercury (II) Oxide decomposing into Mercury and Oxygen.
Mercury (II) Oxide ∆ Mercury + Oxygen
STEP 2- Write the unbalanced (skeleton) equation. Make sure that the formula for each substance is correct
and that reactants are written to the left and products to the right of the arrow.
HgO ∆ Hg + O2
1Hg and 1O 1Hg and 2O (unbalanced)
STEP 3- Balance the equation. Compare the number of atoms of each element of the reactant to the product,
to determine those that must be balance.
(a) HgO ∆ Hg + O2
1Hg and 1O 1Hg and 2O (unbalanced)
(b) 2HgO ∆ 2Hg + O2 (using the lowest coefficient)
2Hg and 2O 2Hg and 2O (balanced)
Write the chemical equation based on the word equation below, then balance.
Phosphoric Acid + Magnesium Hydroxide Magnesium Phosphate + Water
Zinc + Hydrochloric acid Zinc Chloride + Hydrogen

musictheory.com

LESSON 2: Types of chemical equations:
During a chemical reaction both the form and composition of matter are changed. Old substances are
converted to new substances, which have unique physical and chemical properties of their own. Some of the
observable signs that a chemical reaction has occurred include the following:
• A metallic deposit appears
• Bubbles appear
• A temperature change occurs
• A color change occurs
• A precipitate (cloudy, tiny particles) appears
Note that there are many other observable signs for chemical reactions, but these are the ones most likely to
be encountered.
Types of Chemical Reaction
Chemical equations represent chemical changes or reactions. Reactions are classified into types to assist in
writing equations and in predicting other reactions. Many Chemical reactions fit one another of the four
principal reaction types that we discuss in the following paragraphs. Reactions are also classified as oxidation-
reduction equations.
Combination Reaction
A reaction in which two or more substances combine to form a single new substance. Combination
reactions can also be called synthesis reactions. The general form of a combination reaction is:
A+B AB
One combination reaction is two elements combining to form a compound. Solid sodium metal reacts with
chlorine gas to produce solid sodium chloride.
Na(s)+Cl2(g)→NaCl(s) (unbalanced)
2Na(s)+Cl2(g)→2NaCl(s) ( balanced )
Notice that in order to write and balance the equation correctly, it is important to remember the seven elements
that exist in nature as diatomic molecules (H2, N2, O2, F2, Cl2, Br2, and I2).
One sort of combination reaction that occurs frequently is the reaction of an element with oxygen to form an
oxide. Metals and nonmetals both react readily with oxygen under most conditions.
Magnesium reacts rapidly and dramatically when ignited, combining with oxygen from the air to produce a fine
powder of magnesium oxide.
Mg(s)+O2(g)→ MgO(s)
2Mg(s)+O2(g)→2MgO(s)
Sulfur reacts with oxygen to form sulfur dioxide.
S(s)+O2(g)→SO2(g)
When nonmetals react with one another, the product is a molecular compound. Often, the nonmetal reactants
can combine in different ratios and produce different products. Sulfur can also combine with oxygen to form
sulfur trioxide.
S(s)+O2(g)→SO3(g)
2S(s)+3O2(g)→2SO3(g)
Transition metals are capable of adopting multiple positive charges within their ionic compounds. Therefore,
most transition metals are capable of forming different products in a combination reaction. Iron reacts with
oxygen to form both iron (II) oxide and iron (III) oxide.
Iron II- Fe(s)+O2(g)→ FeO(s)

2Fe(s)+O2(g)→2FeO(s)

Iron III- Fe(s)+ O2(g)→2Fe2O3(s)
4Fe(s)+3O2(g)→2Fe2O3(s)
Some of the reactions that fall into this category are given here:
1. Metal + Oxygen Metal Oxide
2. Nonmetal + Oxygen Nonmetal Oxide
3. Metal + Nonmetal Salt
4. Metal Oxide + Water Metal Hydroxide
5. Nonmetal Oxide + Water Oxy-acid
Decomposition Reaction
Starts from a single substance and produces more than one substance; that is, it decomposes. One
substance as a reactant and more than one substance as the products is the key characteristic of a
decomposition reaction. For example, in the decomposition of sodium hydrogen carbonate (also known as
sodium bicarbonate),
2NaHCO3(s)→Na2CO3(s)+CO2(g)+H2O(ℓ)
sodium carbonate, carbon dioxide, and water are produced from the single substance sodium hydrogen
carbonate.
Composition and decomposition reactions are difficult to predict;

however, they should be easy to recognize.
Some of the reactions that fall into this category are given here:
1. Metal Oxides. Some metal oxides decompose to yield the free metal plus oxygen; others give another
oxides and some are very stable, resisting decomposition by heating.
2. Carbonates and Hydrogen Carbonates decompose to yield CO 2 when heated:
3. Miscellaneous reactions in this category:
Single Displacement Reactions

All single displacement reactions have the general form:
A(+) + BC → B + AC
A(-) + BC → C + BA
Here, A is an element and BC is usually an aqueous ionic compound or an acid (consisting
of B+ and C− aqueous ions). A displaces B in BC, resulting in the formation of a new element B and a new
ionic compound or acid, AC. If the new element Bis a metal, it will appear as a metallic deposit. If it is a gas, it
will appear as bubbles.
An Activity Series of elements is often used to determine if A will displace BB in a single displacement
reaction.
Increasing Activity
Metal Au Hg Ag Cu H2 Pb Sn Ni Fe Zn Al Mg Na Ca K Li
Non-Metal F2 Cl2 Br2 I2
A common chemical reaction is the displacement of hydrogen from water or acids. This reaction is good
illustration of the relative reactivity of metals and the use of the activity series. For example,
➢ K, Ca, and Na displace hydrogen from cold water, steam (H2O) and acids.
➢ Mg, Al, Zn, and Fe displace hydrogen from steam and acids.
➢ Ni, Sn and Pb displace hydrogen only from acids.
➢ Cu, Ag, Hg, and Au do not displace hydrogen.

Double Displacement Reactions
Two compounds exchange partners with each other to produce two different compounds. All double
displacement reactions have the general form:
AB + CD → AD + CB
Reactions that can be classified as double displacements include precipitation reactions, neutralization
reactions and gas forming reactions.
Neutralization reaction of an Acid an Base
HCl + NaOH NaCl + HOH

H3PO4 + Mg(OH)2 Mg3(PO4)2 + HOH

https://chem.libretexts.org/Bookshelves/Introductory_Chemistry/Book%3A_Introductory_Chemistry_(CK-
12)/11%3A_Chemical_Reactions/11.4%3A_Combination_Reactions

Individual/Group Exercises
Given the Chemical Reaction below;

1. Balance the reaction
2. Identify the type of Chemical Reaction
TYPE OF CHEMICAL REACTION

1. Fe + O2 → Fe2O3 =________________________
2. Al(OH)3 + Na2SO4 → Al2(SO4)3 + NaOH = ______________________
3. Na + CaCr2O7 → Na2Cr2O7 + Ca =_______________________
4. KClO3 → KCl + O2 =________________________
5. H2SO4 + Zn → ZnSO4 + H2 =________________________
6. (NH4)2CO3 + NaOH → Na2CO3 + NH4OH =______________________
7. LiHCO3 → Li2CO3 + H2O + CO2 =_____________________
8. N2O5 + H2O → HNO3 =_______________________

9. Al + NaOH → Na3AlO3 + H2 =________________________
10. CaCO3. 5H2O → CaCO3 + H2O =________________________
11. Ca(HCO3)2 → CaO + CO2 + H2O =_______________________
12. Al2(SO4)3 + Ba(OH)2 → BaSO4 + Al(OH)3 =______________________
13. CaSO4 + LiOH → Ca(OH)2 + Li2SO4 = _____________________
14. Pb(NO3)2 + KI → PbI2 + KNO3 =_____________________
15. Cu(NO3)2 → CuO + NO2 + O2 =_____________________
For Application of the concepts above please answer
Experiment #2 : Chemical Reactions

MODULE 5
Introduction to Organic Chemistry
Learning Objectives
At the end of these lessons, the students must have:
1. listed the differences between inorganic and organic compound;
2. identified and named the different organic compound functional groups;
3. differentiated the general formula of each organic compound functional groups;
4. illustrated with competence the different structural formulas of organic compounds;
5. distinguished and discussed the structure and bonding of the carbon atom.
LESSON INTRODUCTION
Organic chemistry plays a role in all aspects of our lives, from the clothing we wear, to the pixels of
our television and computer screens, to preservatives in food, to the inks that color the pages of this
material. If you take the time to understand organic chemistry, to learn its overall logic, then you will truly
have the power to change society. Indeed, organic chemistry provides the power to synthesize new drugs,
to engineer molecules that can make computer processors run more quickly, to understand why grilled
meat can cause cancer and how its effects can be combated, and to design ways to knock the calories out
of sugar while still making food taste deliciously sweet. It can explain biochemical processes like aging,
neural functioning, and cardiac arrest, and show how we can prolong and improve life. It can do almost
anything.
Organic chemistry is the study of carbon containing compounds and their properties . This includes
the great majority of chemical compounds on the planet, but some substances such as carbonates and
oxides of carbon are considered to be inorganic substances even though they contain carbon.
The term organic literally means “derived from living organisms.” Originally, the science of organic
chemistry was the study of compounds extracted from living organisms and their natural products.
Compounds such as sugar, urea, starch, waxes, and plant oils were considered “organic,” and people

accepted vitalism, the belief that natural products needed a “vital force” to create them. Organic chemistry,
then, was the study of compounds having the vital force . Inorganic chemistry was the study of gases, rocks,
and minerals, and the compounds that could be made from them.
In the 19th century, experiments showed that organic compounds could be synthesized from
inorganic compounds. In 1828, the German chemist Friedrich Wöhler, who later became the “Father of
Organic Chemistry”, converted ammonium cyanate, made from ammonia and cyanic acid, to urea simply by
heating it in the absence of oxygen.
NH4NCO NH2CONH2
Ammonium Cyanate (inorganic) (Heat) Urea (organic)
Urea (a component of urine) had always come from living organisms and was presumed to contain
the vital force, yet ammonium cyanate is inorganic and thus lacks the vital force. Some chemists claimed that
a trace of vital force from Wöhler’s hands must have contaminated the reaction, but most recognized the
possibility of synthesizing organic compounds from inorganics. Many other syntheses were carried out, and
the vital force theory was eventually discarded.
LESSON 1: Differences between Organic and Inorganic Compounds
The question that comes to mind is this: why should an entire field of chemistry be based on the
chemistry of compounds that contain this one element, carbon? There are several reasons, the primary one
being this: carbon compounds are central to the structure of living organisms and therefore to the existence of
life on Earth. We exist because of carbon compounds.
What is it about carbon that makes it the element that nature has chosen for living organisms? There
are two important reasons: (1) carbon atoms can form strong bonds to other carbon atoms to form rings and
chains of carbon atoms, and (2) carbon atoms can also form strong bonds to elements such as hydrogen,
nitrogen, oxygen, and sulfur. Because of these bond-forming properties, carbon can be the basis for the huge
diversity of compounds necessary for the emergence of living organisms.
Even though organic compounds do not need a vital force, they are still distinguished from inorganic
compounds. The distinctive feature of organic compounds is that they all contain one or more carbon atoms.
Table 6.1 – Comparison of the Properties of Organic and Inorganic Compounds
Properties Organic Compounds Inorganic Compounds

1. Elements Involved Relatively Few, mainly: C, H, O, N, All 118 elements discovered
S, P, F, Cl, Br, I
2. Type of Bonding Covalent Ionic
3. Boiling Point (B.P.) Low Boiling Point High B.P.
4. Melting Point (M.P.) Low Melting Point High M.P.
5. Stability Towards Heat Less Stable More Stable
6. Combustibility More Combustible Less Combustible
7. Flammability More Flammable Non-flammable
8. States at Room Temperature Usually Gases, Liquids and Solids Predominantly Solids
9. Solubility in Water Mostly Insoluble Mostly Soluble

10. Solubility in Organic Solvents Mostly Soluble Mostly Insoluble
11. Volatility Very Volatile Mostly Non-volatile
12. Conductivity of Salts Non-electrolytes Electrolytes
13. Acidity and Alkalinity Weaker acids and bases Stronger acids and bases
14. Reactions occur between. Molecules Ions
15. Reaction Rates @ Room Slow Fast
Temperature
16. Reaction Rates @ High Moderately Fast to Explosive Very Fast
Temperature
17. Chemical Structure Complex Simple
18. Isomerism Illustrates most of the isomers Have limited isomers
LESSON 2: Classes of Organic Compounds and the Functional Group Classifications
Organic compounds are any of a large class of chemical compounds in which one or more atoms of
carbon are covalently linked to atoms of other elements, most commonly hydrogen, oxygen, nitrogen, or sulfur.
The few carbon-containing compounds not classified as organic include carbides, carbonates, and cyanides.
Organic compounds are divided into two major classifications, the hydrocarbons and the hydrocarbon
derivatives or simply referred to as the organic functional groups.
Figure 6.1: Hierarchy of Organic Compounds
Organic Compounds
Hydrocarbon
Hydrocarbons
Derivatives
Aliphatic Cyclic 1. Alcohols

2. Phenols & Thiols
3. Ethers
4. Aldehydes
Saturated Unsaturated 1. Alicyclic 5. Ketones
2. Heterocyclic 6. Carboxylic Acids
3. Aromatic 7. Esters
8. Amines
1. Alkenes
Alkanes 9. Amides
2. Alkynes
10. Halides
11. Nitriles
A. Hydrocarbons – are the simplest organic compounds, composed only of carbon and hydrogen.
➢ They are grouped into several families with altogether different characteristics – namely alkanes,
alkenes, alkynes, and aromatic hydrocarbons. These families are based mainly on the type of bonding
between carbon atoms.
B. Aliphatic Hydrocarbons (or Acyclic) – are the hydrocarbons derived from the word “aleiphatos” meaning
“fat”. It is used to denote non-cyclic, or open-chain carbon compounds such as fats.
Classifications of Aliphatic Hydrocarbons
(1.) Saturated Hydrocarbons – are those in which each atom in the molecule forms four single covalent
bonds with each other. The Alkanes are saturated hydrocarbons because they contain only carbon
and hydrogen and have only carbon-to-hydrogen and carbon-to-carbon single bonds.
(a.) Alkanes – also known as paraffins (which means “little affinity”) or saturated hydrocarbons, are
straight- or branched-chain hydrocarbons with only single covalent bonds between the carbon
atoms. It is an aliphatic compound.
H H H
l l l
Examples: Methane, CH4 or H – C – H and, Ethane, CH3CH3 or H – C – C – H
l l l
H H H
(2.) Unsaturated Hydrocarbons – the Alkenes and Alkynes are unsaturated hydrocarbons because they
contain at least one carbon-to-carbon double or triple bond respectively. While the aromatic
compounds are depicted as having alternating single and double carbon-to-carbon bonds.
(a.) Alkenes – are unsaturated hydrocarbons whose characteristic functional group is the carbon-to-
carbon double bond. The alkenes are sometimes called the olefin series.
H H H H H
l l l l l
Examples: Ethene, H2C = CH2 or C = C and Propene, H2C = CHCH3 or C = C – C – H
l l l l
H H H H
(b.) Alkynes – are unsaturated hydrocarbons whose characteristic functional group is the carbon-to-
carbon triple bond. This series is sometimes called the acetylene series because the simplest
alkyne has the common name acetylene (ethyne), C 2H2.
H
l
Examples: Ethyne, C2H2 or H – C Ξ C – H and Propyne, HC Ξ C – C – H
l
H
(c.) Alkenynes – are the unsaturated hydrocarbons with both double and triple bonds.
H H
l l
Examples: H – C = C – C Ξ C – H or H2C=CHCΞCH; 1–Buten–3–yne
C. Cyclic Hydrocarbons (or Alicyclic) – are the closed chain or cyclic organic compounds, which in many
respects possess properties differing from those of the aliphatic series.

Classifications of Cyclic Hydrocarbons:
(1.) Alicyclic – are the compounds containing a carbon ring whose properties are aliphatic in nature rather
than aromatic.
Figure 6.2: Examples of Cycloalkanes and cycloalkenes
(2.) Heterocyclic – are the compounds containing a ring which, in addition to carbon atoms, may contain one
or more atoms of other elements.
Figure 6.3: Examples of heterocyclic hydrocarbons
(3.) Aromatics – are cyclic compounds containing the “benzene ring” or a derivative of the benzene ring.
Aromatic HC’s are the organic compounds whose functional groups are characterized by a stable
cyclic (aromatic ring), six carbon compounds and sometimes depicted as having alternating single and

double carbon-to-carbon bonds. This arrangement of alternating single and double bonds is called a
conjugated system of double bonds. They were originally named for their pleasant aromas, but not all
aromatic compounds have pleasant fragrances. Structurally, each member of this family contains an
aromatic ring. The most common is Benzene (C6H6), which has a variety of molecular structure.
Two ways of representing benzene
D. Substituted Hydrocarbons – are those hydrocarbons that are classified according to the functional groups
they contain. A “functional group” is an atom or group of atoms bonded to a hydrocarbon in a particular
way that is primarily responsible for the specific properties of the resulting organic compound. The
functional groups are substituted for “H” atoms in some cases and in other cases for the “C” atoms, thus
the name “substituted hydrocarbons”.
Functional groups are common and specific arrangements of atoms that impart predictable
reactivity and properties to a molecule. Even though there are millions of organic compounds, you may
be relieved to know that there are only a few functional groups, and we can readily understand much
about whole families of compounds simply by learning about their properties. Members of each
functional group family share common chemical properties and reactivity, and this fact helps greatly in
organizing our knowledge of organic chemistry.
Table 6.2: The Most Important Functional Groups:
Type of
Functional Group Compound Typical Examples
IUPAC Name
Gen. Formula Family Name Structural Formula (Common Name)
R–X Alkyl Halide H3C – Cl Chloromethane

( X = F, Cl, Br, I) (Methyl chloride)
Methanol
R – OH Alcohol H3C – OH (Methyl Alcohol)
Ar – OH Phenol Hydroxybenzene
–OH (Phenol)
(Ar = Aromatic)
R – SH Thiol H3C – SH Methanethiol

(Mercaptan) (Mercaptomethyl)
Methoxymethane
R – O – R’ Ether H3C – O – CH3 (Dimethyl ether)

O O
ll Aldehyde ll Ethanal
R–C–H H3C – C – H (Acetaldehyde)
O O
ll Ketone ll Propanone
R – C – R’ H3C – C- CH3 (Acetone)
O O
ll Carboxylic ll Ethanoic Acid
R – C – OH Acid H3C – C – OH (Acetic Acid)
O O
ll Ester ll Methyl ethanoate
R – C – OR’ H3C – C – O – CH3 (Methyl Acetate)
R– NH2 Primary Amine H3C – NH2 Methylamine

(Aminomethane)
R – NH – R’ Secondary H3C – NH – CH3 Dimethylamine

Amine
CH3
R’
l Trimetylamine
l
Tertiary Amine CH3 – N – CH3
R – N – R”
O O
ll ll Ethanamide
R – C – NH2 Primary Amide H3C – C – NH2 (Acetamide)
O H O
ll l Secondary ll N–Methyl ethanamide
R – C – N – R’ Amide H3C – C – NH – CH3
O R’ O CH3
ll l Tertiary Amide ll l N,N – Dimethyl ethanamide
R – C – N – R” H3C – C – N – CH3
O O Carboxylic O O Ethanoic Anhydride

ll ll Acid ll ll (Acetic Anhydride)
R – C – O – C – R’ Anhydride H3C – C – O – C – CH3 or
(Acetyl Anhydride)
Ethanenitrile
Nitriles (Acetonitrile)
R – C=N or H3C – CΞN or
Alkyl Cyanides Cyanomethane
(Methyl cyanide)

(A) ALKYL HALIDES, (R–X) and ARYL HALIDES (Ar – X) – are organic halogen compounds in which one or
more hydrogens of a hydrocarbon have been replaced with a halogen (F, Cl, Br, I). Also known as
“organohalides” – are widespread throughout nature and have a vast array of uses in modern industrial
processes.
(B) ALCOHOLS, (R – OH) – are organic compounds of the substituted hydrocarbons that contain one or more
hydroxyl units (R—OH) bonded to an alkyl group. They are derived from saturated and unsaturated
hydrocarbons by replacing a hydrogen atom with a hydroxyl group.
(C) PHENOLS (Ar – OH) – are organic compounds in which the hydroxyl group is attached to a benzene ring.
Like alcohols, they are polar compounds because of the polar hydroxyl group.
(D) THIOLS (R – SH) – are the organic compounds which are the sulfur analogs of alcohol. The oxygen atom
of the hydroxyl group of the alcohol compound is replaced by a sulfur atom. The – SH group itself is referred
to as a “mercapto group”.
(E) ETHERS, (R–O–R’) – are a group of organic compounds in which two hydrocarbon groups are bonded to
the same atom of oxygen. They may be represented by the general formula R-O-R’, in which R and R’
indicate two alkyl groups. These alkyl groups may or may not be the same.
O
ll
(F) ALDEHYDES, (R – C – H) – is another family of organic compounds that contain the carbonyl group (C=O),
it has a hydrogen atom attached to the carbonyl carbon.
O
ll
(G) KETONES, ( R – C – R’) – are organic compounds that has the carbonyl carbon (C=O) attached to two
other carbon atoms. Ketones have only alkyl or aryl (aromatic) groups bonded to the carbonyl group.
General Formulas:
O O O
ll ll ll
R – C – R’ R – C – Ar Ar – C – Ar
O
ll
(H) CARBOXYLIC ACIDS, (R – C – OH) – are the family of organic compounds which is the functional group of
organic acids. The functional group of carboxylic acids is called the carboxyl group (– COOH). Like
aldehydes and ketones, these structures are often written in one line with the C=O understood:
– COOH (a carboxyl group) ; R – COOH (a carboxylic acid)

O
ll
(I) ESTERS, (R – C – OR’) – are the organic compounds whose functional groups are derived from carboxylic
acids and alcohols or phenols. The name of an ester ends in – ate and is formed by naming the part from
the alcohol first and the part from the carboxylic acid last.
(J) AMINES, (R–NH2) – are the organic substances that contain the elements carbon, hydrogen, and nitrogen.
Amines are derivatives of ammonia in which one or more of the hydrogen atoms has been replaced by an
alkyl or aryl group.
Classification of Amines: Amines are classified according to the number of carbons directly bonded to
the nitrogen.
1. Primary (1º), Secondary (2º) & Tertiary (3º) amines have one, two or three carbons directly bonded to
the nitrogen.
2. Aromatic (Aryl) Amine – is an amine in which at least one benzene or other aromatic group is directly
bonded to nitrogen.
3. Aliphatic Amine – is an amine in which no benzene or other aromatic groups are directly bonded to
nitrogen.
O
ll
(K) AMIDES (R–C–NH2)– is another important nitrogen derivatives of carboxylic acids. It contains an oxygen
bonded to the same carbon as nitrogen . Thus, an amine has the nitrogen atom attached directly to a
carbonyl group:
O O O O
ll ll ll ll
–C–N– R – C – NH2 R – C – NHR’ R – C – NHR’R’’
Amide functional group The Three Formulas of Amides
Amides – are neutral (non-basic) molecular substances and exist as molecules (not ions) both in the
crystalline form and when dissolved in water.
(L) NITRILES or ALKYL CYANIDES (R–C≡N) – are organic compounds containing the “cyano” (–C≡N)
functional group attached to an alkyl group. Simple acyclic nitriles are named by adding –nitrile as suffix to
the alkane name, with the nitrile carbon numbered C1 (Carbon no. 1).
(M) CARBOXYLIC ACID ANHYDRIDES (RCO 2COR) – are the organic compounds formally derived from two
molecules of carboxylic acid by removing one molecule of water.

LESSON 3: Formula of Organic Compounds: Expanded Condensed Line and Geometric Structures
A. Bond Formation: The Octet Rule
In 1915, G. N. Lewis proposed several new theories describing how atoms bond together to form
molecules. One of these theories states that a filled shell of electrons is especially stable, and atoms transfer
or share electrons in such a way as to attain a filled shell of electrons. A filled shell of electrons is simply the
electron configuration of a noble gas, such as He, Ne, or Ar. This principle has come to be called the octet
rule because a filled shell implies eight valence electrons for the elements in the second row of the periodic
table. Elements in the third and higher rows (such as Al, Si, P, S, Cl, and above) can have an “expanded
octet” of more than eight electrons because they have low-lying d orbitals available.
Table 6.3: Electronic Configuration and Valence Electron of the First and Second Row of the Periodic Table
B. Lewis Dot Structure
Chemists often focus on the electrons in the outermost shell of the atom because these electrons are
involved in the formation of chemical bonds and in chemical reactions. Carbon, for example, with the ground-
state electron configuration 1s2 2s2 2p2, has four outer-shell electrons. Outer-shell electrons are called valence
electrons, and the energy level in which they are found is called the valence shell. To illustrate the outermost
electrons of an atom, chemists commonly use a representation called a Lewis dot structure, named after the
American chemist Gilbert N. Lewis (1875–1946), who devised it. A Lewis dot structure shows the symbol of the
element surrounded by the number of dots equal to the number of electrons in the outer shell of an atom of that
element. In Lewis dot structures, the atomic symbol represents the core (i.e., the nucleus and all inner shell
electrons).

Table 6.4: Lewis Dot Symbols for the Elements in Period 2
C. Formation of Chemical Bonds

According to Lewis’s model, atoms interact in such a way that each participating atom acquires a
completed outer-shell electron configuration resembling that of the noble gas nearest to it in atomic number.
Atoms acquire completed valence shells in two ways.
1. An atom may become ionic (i.e., lose or gain enough electrons to acquire a completely filled valence
shell). An atom that gains electrons becomes an anion (a negatively charged ion), and an atom that
loses electrons becomes a cation (a positively charged ion). A positively charged ion and a negatively
charged ion attract each other. This attraction can lead to the formation of ionic crystals such as sodium
chloride, in which each positive ion is surrounded by negative ions and vice versa, in a definite
geometric arrangement that depends on the crystal. When atoms are held together primarily by
attraction of oppositely charged ions, we say that an ionic interaction exists between them. (This ionic
interaction is often referred to as an ionic bond.)
2. An atom may share electrons with one or more other atoms to complete its valence shell. A chemical
bond formed by sharing electrons is called a covalent bond.
3. Bonds may be partially ionic and partially covalent; these bonds are called polar covalent bonds. Polar
covalent bonds are defined more precisely in the next section.
Organic Compounds – compounds of carbon – are held together by covalent bonds. A covalent bond is
formed between atoms that share one or more pairs of electrons to give a noble gas configuration to each
atom. The simplest example occurs in the hydrogen molecule (figure 6.4a). When two hydrogen atoms
bond, the single electrons from each combine to form an electron pair. This shared pair completes the

valence shell of each hydrogen. According to the Lewis model, a pair of electrons in a covalent bond
functions in two ways simultaneously: it is shared by two atoms and at the same time fills the outer
(valence) shell of each. We use a line between the two hydrogens to symbolize the covalent bond formed
by the sharing of a pair of electrons.
Although all covalent bonds involve the sharing of electrons, they differ widely in the degree of sharing.
Homonuclear diatomics such as H2, N2, O2, and F2 share the electrons equally between the two atoms and
are said to have nonpolar covalent bonds. Many compounds such as HCl and H2O share the electrons in
the bond unequally and are said to contain polar covalent bonds (figure 6.4b). The polarity in the bond
increases with increasing difference in electronegativity between the bonded atoms.
Figure 6.4a Figure 6.4b
❖ Other Forms of Covalent Bonds

a. Sigma bond (ơ) – single bonding brought about by hybridization that holds two electrons tightly between
two atoms.
b. Pi bond (∏) – causes double or triple bonding of atoms in organic molecules. It holds electron pairs
less tighter than a sigma bond.
❖ 3 Types of Covalent Bonds

a. Single Bond – sharing of one electron pair between two atoms consisting of one sigma bond.
b. Double bond – sharing of two electron pairs between two atoms consisting of one sigma bond and
one pi bond.
c. Triple bond - sharing of three electron pairs between two atoms consisting of one sigma bond and
two pi bonds.
D. Bonding in the Organic Elements
➢ Each Carbon atom forms four covalent bonds.

➢ Likewise, since the Oxygen atom has 6 valences and an oxidation number of -2, it forms two covalent
bonds (double bond).
➢ Nitrogen, with 5 valences and an oxidation number of -3, forms three covalent bonds.
➢ Hydrogen, with an oxidation number of +1, forms only one covalent bond.
➢ The halogens, Fluorine, Chlorine, Bromine and Iodine, all with an oxidation number of -1, also form only
one covalent bond each.

Table 6.5: Summary: The Number of Covalent Bonds formed by the Organic Elements
Carbon, C = 4 Nitrogen, N = 3
Hydrogen, H = 1 Chlorine, Cl = 1
Oxygen, O = 2 Fluorine, F = 1
Sulfur, S = 2 Bromine, Br = 1
Phosphorus = 3 Iodine, I = 1
Table 6.6: The Formal Charges of the Most Common Organic Elements
E. Drawing Lewis Structures from Condensed Structural Formulas
Lewis structures are the way we write organic chemistry. Learning now to draw them quickly and
correctly will help you throughout this course. You should follow three steps to draw a correct structure.
1. From a structural formula, obtain information about which atoms are bonded to each other in a molecule.
Connect all of the appropriate atoms with single bonds (single lines) first.
Example: CH3CH2CH2COOCH3
H H H O H
l l l l l
H–C–C–C–C–O–C–H
l l l l
H H H H
2. Determine how many electrons have been used for the bonds and how many remain. Add all of the
additional valence electrons for each atom that does not already have a filled valence shell due to the
single bonds. Remember to assign one electron to each atom taking part in a single bond for the

purpose of counting valence electrons around atoms. Keep track of any formal charges that may be
present in the condensed structural formula (the present example has none).
Example: ..
H H H O: H
l l l l .. l
l l l ‘’ l
H H H H
3. Add multiple bonds to eliminate unpaired electrons. Draw the remaining nonbonding electrons as lone
pairs. The Lewis structure is now complete. The good news is that drawing Lewis structures gets easier
with practice.
Example: ..
H H H O: H
l l l ll .. l
l l l ‘’ l
H H H H
F. Structural Formula of Organic Compounds
Organic chemists use several kinds of formulas to represent organic compounds. Some of these
formulas involve a shorthand notation that requires some explanation. Structural formulas actually show
which atoms are bonded to which. Structural formulas are of two major types: complete Lewis structures and
condensed structural formulas. In addition, there are several ways of drawing condensed structural formulas.
As we have seen, a Lewis structure symbolizes a bonding pair of electrons as a pair of dots or as a dash (--).
Lone pairs of electrons are shown as pairs of dots.
Figure 6.5: Examples of Lewis Structures with Lone pairs:
1. The Condensed Structural Formula
Condensed structural formulas are written without showing all the individual bonds. In a
condensed structural formula, each central atom is shown together with the atoms that are bonded to it.
The atoms bonded to a central atom are often listed after the central atom (as in CH3CH3 rather than
H3C-CH3) even if that is not their actual bonding order. In many cases, if there are two or more identical
groups, parentheses and a subscript may be used to represent all the identical groups. Nonbonding
electrons are rarely shown in condensed structural formulas. When we write a condensed structural
formula for a compound containing double or triple bonds, the multiple bonds are often drawn as they
would be in a Lewis structure. Figure 6.8 below shows examples of condensed structural formulas
containing multiple bonds. Notice that the ¬CHO group of an aldehyde is actually bonded differently
from what the condensed notation suggests. Condensed structures are assumed to follow the octet rule
even if the condensed notation does not show the bonding.
Figure 6.6: The Lewis and Condensed Structural Formula of Butane and Methylpropane
H H
H H H
H H H C C C H
C C H H
H C C H
H H C
H H H H
H
Butane, C4H10 Methylpropane, C4H10
CH3CH2CH2CH3 CH3CH(CH 3)CH3
Figure 6.7: The Lewis structure and Condensed formula of Octane
C8H18 is molecular formula but there are 18 possible structural isomers
H
H H H H H H CH3CH2CH2CH2CH2CH2CH2CH3
H
H C C C C C C C C
H CH3(CH2)6CH3
H H H HH H HH
Lewis structure condensed structural formula
Figure 6.8: Multiple bonding

2. The Line-angle or Zig-zag Structure
Another kind of shorthand used for organic structures is the line–angle formula, sometimes called
a skeletal structure, a stick figure, or zig-zag structure. Line–angle formulas are often used for cyclic
compounds and occasionally for noncyclic ones. In a stick figure, bonds are represented by lines, and
carbon atoms are assumed to be present wherever two lines meet or a line begins or ends. Nitrogen,
oxygen, and halogen atoms are shown, but hydrogen atoms are not usually drawn unless they are
bonded to an atom that is drawn. Each carbon atom is assumed to have enough hydrogen atoms to
give it a total of four bonds. Nonbonding electrons are rarely shown. Figure 6.9 shows some examples
of line–angle drawings.
Figure 6.9: Lewis structure and Line – angle or Zig-zag structures of Octane, C8H18
H
H H H H H H
H
H C C C C C C C C
H
H H H H H H HH
Lewis structure
Line-angle or "zig-zag" structures
Figure 6.10: Lewis Structure and Line-angle Formula of Dodecane
H C12H26 H
H H H H
C
H H H
C H
H C H
H H H
H H H
H H H H H H H
H
C C C C H H
C H
C C H
H H H H
H H H H H H
H C H H H
H
H
C
H H H H
H H

At the end of every line and at the intersection of any lines
there is a carbon atom with 4 bonds. Hydrogen atoms
are mentally supplied to fill the valency to 4.
H
H H
H H
H H H H
H H H
H
H
H H H
H H H H
H H
H H
H
Figure 6.11: Line-Angle Structure Superimposed on Lewis Structure
H
H H
C
H H
C
H
H
C H
H H H
H H
C C C C H
C H
C C H
H
H H H H
H C H
C
H H
H
Figure 6.12: Lewis Structure and Line-angle Structure of Hexanal, an Aldehyde
H H H H H O O
H C C C C C C
H H H H H H H
Lewis structure Line-angle structure
Figure 6.13: Polygon Structure for Cyclic Compounds

Cyclohexane
H H
H H
C
H C C H
H C C H
H C
H
H H
Figure 6.13: Polygon and Line-angle Structures for some Steroids
OH
HO O
Cholesterol Testosterone
C27H44O C19H26O2
LESSON 4: The Carbon Atom Degree of Substitution
The carbon atoms can be classified as primary, secondary, tertiary, or quaternary. These terms refer to
the substitution level that a given carbon has in a molecule. In other words, these terms are used to describe
how many other carbons a given carbon is attached to. This classification applies only to saturated carbons.
• Primary (1°) carbon atom – bonded to one other carbon atom,
• Secondary (2°) carbon atom – bonded to two other carbon atoms,
• Tertiary (3°) carbon atom – bonded to three other carbon atoms,
• Quaternary (4°) carbon atom – bonded to four other carbon atoms.

This can be explained by one of the important properties of carbon and is its tetravalency. Carbon is a
strict octet follower, which means it needs a maximum of 8 electrons to form stable compounds. Since a carbon
atom has 4 valence electrons, it can form up to 4 bonds with different elements. Part of the reason why there
are millions of compounds of carbon is its ability to form a very stable bond with another carbon atom.
The same terminology is used for carbocations. A primary carbocation is attached to one other carbon,
a secondary to two, and a tertiary to three. A quaternary carbocation does not exist without violating the octet
rule.
For example, you get the following compound to determine which primary, secondary, tertiary, or
quaternary carbons are. As mentioned above, a primary is attached to one carbon atom, a secondary to two,
a tertiary to three, and a quaternary to four other carbon atoms. For each carbon atom, you need to count how
many carbon atoms next to it that particular carbon atom is connected to.
There is another rule:

1. Primary carbon atoms are always at the end;
2. Secondary carbon atoms are in the middle (between two other carbon atoms);
3. Tertiary carbon atoms are branched out in three different ways;
4. Quaternary carbon atoms have the most carbon atoms around (max 4).
https://www.academia.edu/34592551/Solomons_Fryhle_Organic_Chemistry_10_Edition
➢ Chapter 1 & 2

https://www.academia.edu/39753150/McMurry_Organic_Chemistry_PDF
➢ Chapter 1& 2
Note: Other readings will be posted on Google classrooms by your respective instructors!
I. Indicate whether the following properties are more typical of organic or inorganic compounds:
1. is not soluble in water
2. has a high melting point
3. burns in air
4. has low boiling point
5. it conducts electricity
6. has low reactivity at room temperature
7. more stable towards heat
8. mostly very volatile
9. they are stronger acids and bases
10. has complex structures
II. Examine the given Structural Formula of organic compounds in the first column and match it with their
correct family or functional group in the second column.
STRUCTURAL FORMULA FAMILY NAMES
1. CH3CH2OH A. Alkene
O
II B. Alkyne
2. CH3 – C – H
C. Alkyl Halide
3.
4. CH3 –N–H
l D. Alcohol
CH3
5. H2C = CH2 E. Aldehyde
O
ll F. Amide
6. CH3 – C – NH2

O
ll G. Amine
7. CH3 CH2 – C – OH
O
ll H. Aromatic H.C.
8. CH3 – C – CH3
9. CH3CH2–SH I. Carboxylic Acid
10. CH3CH2–O–CH2CH3 J. Carboxylic Acid Anhydride
11. OH K. Ether
12. CH3 – C Ξ N L. Ester
O
ll M. Heterocyclic HC
13. CH3 – C – O – CH3
Cl
l N. Ketone
14. F – CH – F
15. O O O. Nitrile
ll ll
CH3 – C – O – C – CH3
P. Thiol
Q. Phenol
III. Draw complete Lewis structures for the following condensed structural formulas.
1. N2H4
2. CH3(CH2)3CH(CH3)2
3. (CH3)2CHCH2Cl
4. CH3CH2COCN
5. CH2CHCHO
6. (CH3)3CCOCHCH2
7. CH3COCOOH

8. (CH3CH2)2CO
9. (CH3)3COH
10. CH3C(NH)CH3
I. Illustrate the following condensed structural formulas to its line – angle or zig-zag structure.
1. (HO)3C(CH2)2N(CH2CHO)CH(CH2CH3)2
2. CH3(CH2)3CH(CH3)(CH2)2OCH2CH3
3. HOOCCH2O(CH2)2N(CH2CH3)2
4. HOCCH2CH(CH3)CH2CH(CH2)(CH2)2COOCH3
5. H2NCH2[CH(CH3)]2(CH)4CO(CH2)2CH3
6. ClCH2CH(CH3)COCH2CH2CO(CH2)2CH3
II. Illustrate the maximum possible isomers of each of the following organic compounds.
1. CH3CH2CH2CH2CH3
2. CH3CH2CH2CH2CH2CH3
3. CH2 = CHCH2CH2CH3
4. CHΞC–CH2CH2CH2CH3
5. CH3CH2CH2CH2OH
Experiments #5 and #6

MODULE 6
The Hydrocarbons: Alkanes, Cycloalkanes, Alkenes, Cycloalkenes and Alkynes
1. Drawn and created structures of hydrocarbons;
2. Formulated the isomers of cyclic hydrocarbons;
3. Named hydrocarbons using IUPAC rules and their corresponding common or alternative names;
4. Identified the sources and the practical and medical applications of hydrocarbons;
5. Simulated the preparation and reactions of hydrocarbons in the laboratory;
6. Differentiated and explained the physical and chemical properties of hydrocarbons;
LESSON INTRODUCTION
Organic compounds all contain carbon, but they can also contain a wide variety of other elements.
Before we can appreciate such chemical diversity, however, we have to begin at the beginning. In this
module, we begin our study of organic compounds – the hydrocarbons, starting with their physical and
chemical properties including their nomenclature and structural formulas as well as some of their important
uses and functions.
The hydrocarbons are compounds composed entirely of carbon and hydrogen. Hydrocarbons are
divided into two broad classes: aliphatic hydrocarbons and aromatic hydrocarbons. (The term aliphatic
comes from the Greek aleiphatos, which means “fat.” Fats contain long carbon chains that, as you will learn,
are aliphatic groups.) The aliphatic hydrocarbons consist of three hydrocarbon families: alkanes, alkenes,
and alkynes. We’ll begin our study of aliphatic hydrocarbons with the alkanes, which are sometimes known
as paraffins. Alkanes are hydrocarbons that contain only single bonds. Methane and ethane are the simplest
alkanes. Later in the module, we’ll consider the alkenes, or olefins, hydrocarbons that contain carbon–carbon
double bonds; and the alkynes, or acetylenes, hydrocarbons that contain carbon–carbon triple bonds.
methane gas A catalytic petroleum plant that produces ethane gas

LESSON 7.1. THE SATURATED HC’s: ALKANES AND CYCLOALKANES
Lesson 7.1.1. The Alkanes

Alkanes are saturated hydrocarbons; that is, they contain only carbon-carbon single bonds. In this
context, saturated means that each carbon has the maximum number of hydrogens bonded to it. We often
refer to alkanes as aliphatic hydrocarbons because the physical properties of the higher members of this
class resemble those of the long carbon-chain molecules we find in animal fats and plant oils (Greek:
aleiphar, fat or oil).
Carbon chains take many forms in the alkanes; they may be branched or unbranched, and they can
even exist as rings (cyclic alkanes). Alkanes with unbranched carbon chains are sometimes called normal
alkanes, or n-alkanes. A few of the unbranched alkanes are shown in Table 7.1. You should learn the names
of the first 12 unbranched alkanes because they are the basis for naming many other organic compounds. The
names methane, ethane, propane, and butane have their origins in the early history of organic chemistry, but
the names of the higher alkanes are derived from the corresponding Greek numerical names: pentane (pent
5 five); hexane (hex 5 six); and so on.
Table 7.1: The First 12 – Homologous Series of Alkanes.
Alkane Name Molecular Structural Formulas

Formulas (Condensed)
1. Meth-ane CH4 CH4
2. Eth-ane C2H6 CH3CH3
3. Prop-ane C3H8 CH3CH2CH3
4. But-ane C4H10 CH3CH2CH2CH3
5. Pent-ane C5H12 CH3CH2CH2CH2CH3
6. Hex-ane C6H14 CH3(CH2)4CH3
7. Hept-ane C7H16 CH3(CH2)5CH3
8. Oct-ane C8H18 CH3(CH2)6CH3
9. Non-ane C9H20 CH3(CH2)7CH3
10. Dec-ane C10H22 CH3(CH2)8CH3
11. Undec-ane C11H24 CH3(CH2)9CH3
12. Dodec-ane C12H26 CH3(CH2)10CH3
Organic molecules are represented in different ways, which we’ll illustrate using the alkane hexane.
The molecular formula of a compound (for example, C6H14 for hexane) gives its atomic composition. All
noncyclic alkanes (alkanes without rings) have the general formula CnH2n+2, in which n is the number of
carbon atoms. The structural formula of a molecule is its Lewis structure, which shows the connectivity of its
atoms—that is, the order in which its atoms are connected. For example, a structural formula for hexane is the

following:
H H H H H H
l l l l l l
H–C–C–C–C–C–C–H
l l l l l l
H H H H H H
hexane
General Formula is: CnH2n+2; where “n” represents the number of carbon atoms in the molecule.
(Notice that the above type of formula does not portray the molecular geometry.) Writing each
hydrogen atom in this way is very time-consuming, and a simpler representation of this molecule, called a
condensed structural formula, conveys the same information.
CH3 – CH2 – CH2 – CH2 – CH2 – CH3 - hexane
In such a structure, the hydrogen atoms are understood to be connected to carbon atoms with single
bonds, and the bonds shown explicitly are bonds between carbon atoms. Sometimes even these bonds are
omitted, so that hexane can also be written CH3CH2CH2CH2CH2CH3. The structural formula may be further
abbreviated as shown in the third column of Table 7.1. In this type of formula, for example, (CH2)4 means
¬CH2CH2CH2CH2¬, and hexane can thus be written CH3(CH2)4CH3.
CH3(CH2)4CH3 or CH3 – CH2 – CH2 – CH2 – CH2 – CH3, two other representations of hexane
The family of unbranched alkanes forms a series in which successive members differ from one another
by one ¬CH2¬ group (methylene group) in the carbon chain. A series of compounds that differ by the addition
of methylene groups is called a homologous series. Thus, the unbranched alkanes constitute one homologous
series. Generally, physical properties within a homologous series vary in a regular way.
The French chemist Charles Gerhardt (1816–1856) made an important chemical observation in 1845
about members of homologous series. His observation still has significant implications for learning organic
chemistry. He wrote, “These (related) substances undergo reactions according to the same equations, and it
is only necessary to know the reactions of one in order to predict the reactions of the others.” What Gerhardt
was saying, for example, is that we can study the chemical reactions of propane with the confidence that
ethane, butane, or dodecane will undergo analogous reactions.

Methane, CH4, is the first member of the alkane series. It is the simplest organic compound . It is one of
the gases arising from marshes hence its name, “marsh gas” or “bio-gas”. It is also one of the gases produced
from intestinal putrefaction. When each member of a series differs from the next member by a CH2 group, the
series is called a “homologous series”. All classes of organic compounds exist in homologous series. For all
open-chain alkanes.
The Different Representation or Models of Methane
Note: In an Alkane, each carbon atom is joined to four other atoms by four single covalent bonds. Alkane
molecules contain only carbon-to-carbon and carbon-to-hydrogen bonds and are essentially nonpolar.
Lesson 7.1.2. Nomenclature of Alkanes

In the early nineteenth century, organic compounds were often named at the whim of their discoverers.
Here are just a few examples:
(a) Formic acid - isolated from ants and named after the Latin word for ant, formica;
(b) Urea - Isolated from urine;
(c) Morphine - A painkiller named after the Greek god of dreams, Morpheus; and
(d) Barbituric acid - Adolf von Baeyer named this compound in honor of a woman named Barbara
A large number of compounds were given names that became part of the common language shared by
chemists. Many of these common names are still in use today.
As the number of known compounds grew, a pressing need arose for a systematic method for naming
compounds. In 1892, a group of 34 European chemists met in Switzerland and developed a system of organic
nomenclature called the Geneva rules. The group ultimately became known as the International Union of Pure

and Applied Chemistry, or IUPAC (pronounced “I–YOU–PACK”). The original Geneva rules have been regularly
revised and updated and are now called IUPAC nomenclature.
Names produced by IUPAC rules are called systematic names. There are many rules, and we cannot
possibly study all of them. The upcoming sections are meant to serve as an introduction to IUPAC
nomenclature system.
Systematic Names of Organic Compounds consists of Three Main Parts:
PREFIX – STEM or PARENT – SUFFIX
a. STEM – indicates the number of carbon atoms in the “backbone” or the “parent chain” of the molecule. It
answers the question: “how many carbons are present”?
Parent Chain – is the longest continuous chain of carbon atoms. Refer to Table 7.2
b. PREFIX – the attachments to the longest continuous carbon chain or “backbone”. They are the side chains
or substituents. The substituents present in organic compounds are indicated by the prefix. In alkanes, the
substituents or side-chains are called “alkyl group” (Table 7-3).
c. SUFFIX – indicates the family of the carbon compound or the name ending of the compound. For alkane,
the suffix is – ane.
TABLE 7.2: List of Prefixes Used to Name Aliphatic Hydrocarbons and their different Backbones.
BACKBONE NAME of Name of Alkane BACKBONE NAME of STEM Name of Alkane

(No. of STEM or (No. of or PARENT
Carbon) PARENT Carbon)
1 Meth- Methane 30 Triacont or Triacontane or

Triacos- Triacosane
2 Eth- Ethane 31 Hentriacos- Hentriacosane
3 Prop- Propane 32 Dotriacos- Dotriacosane
4 But- Butane 33 Triacos- Tritriacosane
5 Pent- Pentane 34 Tetratriacos- Tetratriacosane
6 Hex- Hexane 35 Pentatriacos- Pentatriacosane
7 Hept- Heptane 40 Tetracont- Tetracontane
8 Oct- Octane 41 Hentetracont- Hentetracontane
9 Non- Nonane 42 Dotetracont- Dotetracontane
10 Dec- Decane 50 Pentacont- Pentacontane
11 Undec- Undecane 53 Tripentacont- Tripentacontane
12 Dodec- Dodecane 54 Tetrapentacont- Tetrapentacontane
13 Tridec- Tridecane 60 Hexacont- Hexacontane
14 Tetradec- Tetradecane 65 Pentahexacont- Pentahexacontane
15 Pentadec- Pentadecane 66 Hexahexacont- Hexahexacontane
16 Hexadec - Hexadecane 67 Heptahexacont- Heptahexacontane
17 Heptadec- Heptadecane 70 Heptacont- Heptacontane
18 Octadec- Octadecane 72 Doheptacont- Doheptacontane
19 Nonadec- Nonadecane 77 Heptaheptacont- Heptaheptacontane
20 Eicos or Eicosane or 80 Octacont- Octacontane
Icos- Icosane
21 Henicos- Henicosane 81 Henoctacont- Henoctacontane
22 Docos- Docosane 88 Octaoctacont- Octaoctacontane
23 Tricos- Tricosane 90 Nonacont- Nonacontane
24 Tetracos- Tetracosane 99 Nonanonacont- Nonanonacontane
25 Pentacos- Pentacosane 100 Hect- Hectane
Note: The prefixes used to name the alkanes denote a specific number of carbon atoms. The prefixes for the
first four alkanes are meth, eth, prop, and but.
The prefixes for the next six alkanes follow a definite pattern; the prefixes correspond to the roots of the Greek
words for numbers five to ten (5-10).
For Alkanes, the suffix –ane is added to denote that the compound has a single bond. This systematic way of
naming is in accordance with the rules of the IUPAC.
Lesson 7.1.3. The Alkyl Group

An alkyl group is simply the neutral species formed when one hydrogen atom is removed from the “parent
alkane” molecule.
The simplest alkyl molecule is methyl – a methane with one of the hydrogen atoms removed (–CH3). The
methyl and other alkyl groups are neutral – they have the same number of protons and electrons. Table
7.3 below is a list of the first ten alkyl groups with their names, molecular and structural formulas.
Table 7.3. The Homologous Series of Alkyls

Alkyl Groups Molecular Structural Formula
Formulas
1. Methyl CH3 –CH3
2. Ethyl C2H5 –CH2–CH3
3. Propyl C3H7 –CH2–CH2–CH3
4. Butyl C4H9 –CH2–CH2–CH2–CH3
5. Pentyl (Amyl) C5H11 –CH2–CH2–CH2–CH2–CH3
6. Hexyl C6H13 –CH2–CH2–CH2–CH2–CH2–CH3
7. Heptyl C7H15 –CH2–CH2–CH2–CH2–CH2–CH2–CH3
8. Octyl C8H17 –CH2–CH2–CH2–CH2–CH2–CH2–CH2–CH3
9. Nonyl C9H19 –CH2–CH2–CH2–CH2–CH2–CH2–CH2–CH2–CH3
10. Decyl C10H21 –CH2–CH2–CH2–CH2–CH2–CH2–CH2–CH2–CH2–CH3

The General Formula for Alkyl Groups is: R = CnH2n+1 (one less hydrogen atom than the corresponding
alkane).
The name of the group is formed from the name of the corresponding alkane by simply dropping – ane
and substituting an –yl ending.
The letter “R” is often used in formulas to mean any of the many possible alkyl groups (e.g. R – OH or R
– OR’).
Just as n-alkyl groups are generated by removing hydrogen from an end carbon, branched alkyl groups
are generated by removing a hydrogen atom from an internal carbon.
There are two 3-carbon alkyl groups and four 4-carbon alkyl groups that are possible.
The prefixes used for the C4 alkyl groups such as: sec – (for secondary) and tert –- (for tertiary) refer to the
degree of alkyl substitution at the branching carbon atom.
We recall from module six that there are four (4) possible degrees of alkyl substitution for carbon, denoted
as 1, 2, 3, and 4.
Table 7.4. Names and Formula of Selected Alkyl Groups
Condensed Structural Condensed

Formula NAME Structural Formula NAME
CH3 CH3 tert-Butyl or

l Isopropyl l t-Butyl
CH3 – CH – CH3 – C – (tertiary butyl)
l
CH3
CH3
l Isobutyl Quaternary-Carbon
CH3 – CH – CH2 – CH3 (4) is bonded to four
l other carbon
CH3 sec-Butyl CH3 – C – CH3
l (secondary butyl) l
CH3CH2 – CH – CH3

Lesson 7.1.4. Rules for Naming Alkanes: IUPAC System
The Name of Alkanes end in “–ane”
1. Locate the “Parent Chain”.

(a) Find the longest continuous carbon-chain present in the molecule and use the name of that chain as
the parent name of the compound.
(b) If there are two different chains of equal length, choose the one with the larger number of branched
points or side-chains as the parent chain.
(c) Consider all alkyl groups attached to the parent chain as side-chains that have replaced hydrogen
atoms of the parent hydrocarbon.
Examples:
3 – Isopropyl – 4,5 – dimethylheptane 3 – Ethyl, 2,4,5 - trimethylheptane
2. Number the carbon atoms in the parent chain starting from the “end closest to the first carbon atom” that
has an alkyl or side-chains so that the side-chains are given the “lowest position numbers”.
Examples:
Correct Wrong
4 – Ethyl – 3 – methylheptane 4 – Ethyl – 5 – methylheptane
Correct Wrong
3 – Ethyl – 2 – methylhexane 3 – Isopropylhexane
3. Identify the side-chains and the position of the carbon atoms to which they are attached.
(a) If there are two substituents on the same carbon, assign them both the same number.
(b) There must always be as many numbers in the name as there are side-chains.
Examples:
(a) 2 – methylpentane (b) 3 – Ethyl – 2 – methylpentane (c) 2,2,4 – Trimethylpentane
4. Write the name as a simple word, using hyphens to separate the different prefixes and using commas to
separate numbers (e.g., 2,3–dimethyl).
(a) If there are different kinds of alkyl groups present, arrange them in an alphabetical order (e.g., ethyl
before methyl in 3-ethyl-2-methylpentane, in example “b” above).
(b) If the same alkyl group occurs more than once as side-chain, indicate this by numerical prefixes (di-,
tri-, tetra-, penta-, etc) written in front of the alkyl-group name (e.g. dimethyl indicates two methyl
groups). In example (c) above, 2,2,4 – Trimethylpentane, it means that on carbon number 2 – there
are 2 – methyl groups attached, and that on carbon no. 4, another methyl group is also attached.
(c) Do not use the numerical prefixes for alphabetizing purposes.
Examples:
1. Isopropyl – consider the “propyl” group as the basis for alphabetizing
2. Isobutyl, Sec.butyl, and Tert.butyl - consider the “butyl” group as the basis for alphabetizing. So,
a butyl comes first before an ethyl or a methyl.

Other Examples:
6 – Isobutyl, 2,3 – dimethyldecane 2- methylpropyl = Isobutyl
Correct – No other possible name
LESSON 7.1.5: Cycloalkanes
Chemists have known for over 100 years that compounds with rings of carbon atoms also exist. Such
compounds are called alicyclic (aliphatic-cyclic) compounds. Therefore a hydrocarbon that contains carbon
atoms joined to form a ring is called a cyclic hydrocarbon or closed-chain alkanes. When all carbons of the
ring are saturated, the hydrocarbon is called a cycloalkane. Cycloalkanes are also called cycloalkanes, or
cycloparaffins, or naphthenes.
Since cycloalkanes consists of rings of –CH2– units, they have the General Formula: (CH2)n, or CnH2n,
and are represented by polygons in skeletal drawings. Four examples are shown below.

Lesson 7.1.6. Nomenclature of Cycloalkanes
Substituted cycloalkanes are named by rules similar to those for open-chain alkanes. For most
compounds, there are only four steps:
STEP (1): Count the number of carbon atoms in the ring , and add the prefix “cyclo” to the name
of the corresponding alkane.
STEP (2): If a substituent is present on the ring, the compound is named as an alkyl-substituted
cycloalkane rather than as a cycloalkyl-substituted alkane.
STEP (3): For substituted cycloalkanes, start at a point of attachment and number the
substituents on the ring so as to arrive at the lowest sum.
STEP (4): If two or more different substituents are present, number them by alphabetical priority.
Examples:

LESSON 7.1.7: Isomerism in Alkanes
Compounds with the same molecular formulas, but different structures are called isomers. Isomers
have different chemical and physical properties . Compounds which differ in their carbon connectivity are called
structural isomers or constitutional isomers.
Constitutional isomers are compounds that have the same molecular formula but different structural
formulas. By “different structural formulas,” we mean that constitutional isomers differ in the kinds of bonds they
have (single, double, or triple) and or in the connectivity of their atoms.
For the molecular formulas CH4, C2H6, and C3H8, only one connectivity is possible. For the molecular
formula C4H10 (butane), two connectivities are possible. In one of these, the four carbons are bonded in a
chain; in the other, named 2-methylpropane (C4H10), three carbons are bonded in a chain with the fourth
carbon as a branch on the chain.

CH3
l
Structural Formula: CH3CH2CH2CH3 CH3 – CH – CH3
Molecular Formula: C4H10 C4H10
IUPAC Name: Butane 2 – Methylpropane
Therefore, butane and 2-methylpropane are constitutional isomers; they are different compounds and
have different physical and chemical properties . Their boiling points, for example, differ by approximately 118C.
Other examples of constitutional isomers are the two alcohols with the molecular formula C3H8O, two
aldehydes with the molecular formula C4H8O, and two carboxylic acids with the molecular formula C4H8O2.
The number of possible constitutional isomers increases dramatically as the number of carbon atoms
increases. See table 7.5 for the possible number of isomers for n-alkanes.
Table 7.5. The Number of Possible Isomers of N-Alkanes
Formula of Alkane Number of Isomers

CH4 1
C2H6 1
C3H8 1
C4H10 2
C5H12 3
C6H14 5
C7H16 9
C8H18 18
C9H20 35
C10H22 75
C15H32 4347
C40H82 62,491,178,805,831
Stereoisomers are compounds that have (1) the same molecular formula, (2) the same connectivity of
their atoms, (3) but a different orientation of their atoms in space. Recall that constitutional isomers, the only
other type of isomers we have studied so far, also have the same molecular formula but a different connectivity.
We begin our study of stereoisomers with the study of cis,trans isomerism in cycloalkanes. Cycloalkanes
with substituents on two or more carbons of the ring show a type of stereoisomerism called cis,trans
isomerism, which we can illustrate by considering 1,2-dimethylcyclopropane. In the following structural

formulas, the cyclopropane ring is drawn as a regular triangle viewed through the plane of the ring. Carbon-
carbon bonds of the ring projecting toward you are shown as heavy lines.
In one isomer of 1,2-dimethylcyclopropane, the methyl groups are on the same side of the ring; in the
other, they are on opposite sides of the ring. The prefix cis (Latin: on the same side) indicates that the
substituents are on the same side of the ring ; the prefix trans (Latin: across) indicates that they are on opposite
sides of the ring. The cis isomer cannot be converted to the trans isomer and vice versa without breaking and
reforming one or more bonds, a process that does not occur at or near room temperature. The cis isomer is
approximately 7.1 kJ (1.7 kcal)/mol higher in energy (less stable) than the trans isomer because of the steric
strain of the methyl groups on adjacent carbons in the cis isomer.
Comparison between Constitutional isomers from a Stereoisomers
Other Examples:

Lesson 7.1.8. Physical Properties of Alkanes
The most important physical properties of organic compounds are physical state (including boiling and
melting points), solubility, and density.
A. Physical State
Both melting and boiling points of hydrocarbons increase with increasing molecular weight .
Low molecular weight alkanes, including cycloalkanes, up to about 5 carbons, are gases at room
temperature.
Alkanes from 5 to 17 carbons, are liquids.
Larger alkanes are white, waxy solids like Solid paraffin.
Table 7.6. The Melting and Boiling Points of Some Selected Alkanes
Compound Formula Boiling Point Melting Point
pentane CH3(CH2)3CH3 36ºC –130ºC
hexane CH3(CH2)4CH3 69ºC –95ºC
heptane CH3(CH2)5CH3 98ºC –91ºC
octane CH3(CH2)6CH3 126ºC –57ºC
nonane CH3(CH2)7CH3 151ºC –54ºC
decane CH3(CH2)8CH3 174ºC –30ºC
tetramethylbutane (CH3)3C-C(CH3)3 106ºC +100ºC
In any state, alkanes are colorless, odorless, and tasteless organic compounds.
B. Solubility. Alkanes are nonpolar compounds. Therefore they are not soluble in water; which dissolves only
ions and polar compounds. Alkanes are soluble in each other (like dissolves like) as well as in other
nonpolar organic compounds, such as benzene, diethyl ether, and carbon tetrachloride.
C. Density. Each liquid alkane has a slightly different density, but all are less dense than water. Since none of
them are soluble in water, this means that alkanes always float on water.

Lesson 7.1.9. Chemical Properties of Alkanes
The most important chemical property of alkanes is that they “burn”, a property called “combustion”.
The “complete combustion” of alkane gives only two products: Carbon Dioxide and Water. Its
“incomplete combustion” will also yield Carbon Monoxide – a colorless, odorless, but highly poisonous
gas because it strongly combines with hemoglobin and prevents the transport of oxygen to the tissues.
But, the chief chemical property of alkanes (including cycloalkanes) is that they are “chemically inert”,
meaning that they are very volatile.
A. Introduction to the Reactions of Hydrocarbons
Carbon like most elements can undergo oxidation-reduction reactions. When carbon atoms are oxidized,
they often form additional bonds to “oxygen” to form “carbon dioxide” and “water”:
CH4 + 2O2 + (Heat) ----------› O=C=O + 2H2O

Methane oxygen a carbon dioxide water
When carbon atoms are reduced, they often form additional bonds to ‘hydrogen”. During this reaction,
the carbon may decrease the no. of bonds to oxygen and increase the number of bonds to hydrogen.
O=C=O + 3H2 ----------› CH3OH + H2O

Carbon dioxide Methanol
Note: Each class of organic compounds can undergo important oxidation-reduction reactions. The
reactions can be usefully categorized by “counting the number of atoms bonded to a reactive carbon” –
that carbon can be bonded to a maximum of four atoms.
B. Types of Hydrocarbon Reactions
1. Substitution Reaction – is a reaction wherein one atom in a molecule is exchanged by

another atom or group of atoms.
H H
l l
H–C–H + I2 ----------› H–C–I + H-I
l l
H H
Methane Iodine Iodomethane Hydrogen Iodide

(colorless gas) (halogen) (colorless liquid) (acid halide)
2. Elimination Reaction – is a reaction in which a single reactant is split into two products, and
one of the products is eliminated.
H H H H
l l l l
H – C – C – Br ----------› C=C + H-Br
l l l l
H H H H
Bromoethane Ethene Hydrogen Bromide

(colorless liquid) (colorless gas) (acid halide)
3. Addition Reaction – a reaction wherein two reactants are added together to form a single
product. Addition reaction can be thought of as the “reverse” of elimination reaction.
H H H H
l l l l
C=C + HCl ----------› H–C– C – Cl
l l l l
H H H H
Ethene Hydrogen Chloride Chloroethane
C. Reactions of Alkanes
I. Combustion Reactions
Alkanes as well as other hydrocarbons undergo combustion with oxygen with the evolution of large
amounts of heat energy. For example, Methane reacts with oxygen as follows:
CH4 (g) + 2O2 (g) ----------› CO2 (g) + 2H2O (g) + 802.5 KJ
Methane oxygen carbon dioxide water (heat energy)
Aside from their combustibility, alkanes are “relatively sluggish” and limited in reactivity. But with proper
activation, such as with high temperature or catalysts, alkanes can be made to react in a variety of ways.
II. Non-Combustion Reactions of Alkanes
1. Halogenation Reaction - a substitution reaction. In this type of reaction, a “halogen” is substituted for a
hydrogen atom. If the specific halogen used in the reaction is “chlorine”, the reaction is called
“chlorination” and if the halogen used in the reaction is “bromine”, then the reaction is called
“bromination”. The “RH” is an alkane that reacts with halogens (X) in this manner:

G.F.: RH + X2 ----------› RX + HX ; (X = Cl, Br, F, or I)
CH3CH3 + Cl2 ----------› CH3CH2Cl + HCl

ethane chlorine chloroethane hydrogen chloride
The letter “X” is commonly used to indicate a “halogen” atom. The formula “RX” indicates a halogen
atom attached to an alkyl group and represents the class of compounds known as the “Alkyl Halides”.
Monosubstitution – refers to a type of substitution reaction where one hydrogen atom in an organic
molecule is substituted by another atom or by a group of atoms. In the above example, the new
compound (chloroethane) is a mono-substitution (monochlorosubstitution) product. In a like manner,
we can have a di-, tri-, tetra-, and so on, substitution products.
Cl2 Cl2 Cl2 Cl2

Ex: CH4 CH3Cl CH2Cl2 CHCl3 CCl3 + 4 HCl
Methane chloromethane Dichloromethane Trichloromethane Tetrachloromethane

(methyl chloride) (methylene chloride) (chloroform) (carbon tetrachloride)
Halogenation is used extensively in the manufacture of petrochemicals (chemicals derived from

petroleum and used for purposes other than fuels).
2. Dehydrogenation - an elimination reaction. In this type of alkane reactions, a hydrogen is lost from an
organic compound during dehydrogenation.
CnH2n + 2 ----------› CnH2n + H2
CH3CH2CH3 ----------› CH3CH = CH2 + H2

propane propene hydrogen gas
3. Cracking – is the breaking up large molecules to form smaller ones .
C16H34 C8H18 + C8H16 (one of several possibilities)

Heptadecane Octane Octene
alkane alkane alkene

C16H34 C9H10 + C7H14 (another of several possibilities)
Heptadecane Nonane Heptene
alkane alkane alkene
4. Isomerization Reaction – a rearrangement of molecular structures.
CH3 – CH2 – CH2 – CH2 – CH3 CH3 – CH2 – CH – CH3

l
CH3
Pentane 2 – methylbutane
The other three types of reactions – dehydrogenation, cracking, and isomerization – singly or in
combination, are of great importance in the production of motor fuels and petrochemicals.
Lesson 7.1.10. Sources and Importance of Alkanes
Alkanes gained great technical importance through the various uses of crude oil. The diverse crude
oil products, particularly in the area of polymeric materials, are an indispensable part of daily life. These
three areas - crude oil, alkanes as natural products and polymers are discussed here.
Alkanes are found in nature mainly in natural gas and crude oil from which they are produced on a
technical scale in large amounts by distillation and extraction.
Alkanes do not only occur naturally in crude oil and natural gas but can also be found in living matter.
Thus, methane, also called biogas, is generated from organic matter by fermentation or putrefaction.
A. Natural Gas – is formed by the anaerobic decay of plants and animals (putrefaction) . Its main component
is Methane (80 – 95%), the balance being varying amounts of other hydrocarbons.

➢ Natural gas mainly consists of methane, ethane and small amounts of propane. Propane is the main
component of liquified gas which, compressed in steel bottles, is being used as heating fuel.
B. Petroleum (crude oil) – is a thick (viscous) black liquid found underground consisting of a mixture of
hundreds to thousands of different alkanes with varying amounts of sulfur-, oxygen-, and nitrogen-
containing organic compounds.
➢ Crude oil is mainly composed of alkanes and cycloalkanes which have been generated by
decomposition of animal and plant matter.
➢ The following analysis of crude oil as shown below points to an organic origin:
• Carbon: 85 - 90%
• Hydrogen: 10 - 14%
• Oxygen: 0 – 1.5%
• Sulfur: 0.1 - 3% (very seldom to 7%)
• As well as traces of nitrogen, chlorine, iodine, sodium, and potassium 0.001–0.05%
➢ Crude oil or petroleum is not a pure compound but a mixture of hundreds of compounds of which
hydrocarbons represent the majority.
➢ Crude oil is mostly found in sedimentary rocks, such as limestone, sandstone and clay, which are
part of ocean sediments. Oil reservoirs such formed represent 80% of total crude oil deposits. The
areas of these deposits are called secondary deposits. The oldest reservoir discovered up to now
was formed about 2 billion years ago concurring with the existence of primitive life forms. However,
the most important reservoirs were only formed 500 to 100 million years ago. Additional findings can
also be dated to the Triassic, Jurassic and Cretaceous periods.
LESSON 7.2. THE UNSATURATED HC: ALKENES, ALKYNES AND CYCLOALKENES
Lesson 7.2.1. Introduction to Alkenes and Alkynes
Unsaturated hydrocarbons (Aliphatics) are comprised of the Alkenes and Alkynes and even
Aromatic Compounds. They are unsaturated hydrocarbons because they contain at least one carbon-to-
carbon double or triple bond respectively while the aromatic compounds are depicted as having
alternating single and double carbon-to-carbon bonds.
Alkenes are hydrocarbons with carbon–carbon double bonds. Alkenes are central to organic
chemistry because they are manufactured in large quantities from crude petroleum, and they are readily
converted to many of the other functional groups. Hydrocarbons whose molecules contain the carbon–

carbon triple bond are called alkynes. The common name for this family is acetylenes, after the simplest
member, HCΞCH.
In this lesson, we will study the nomenclature and structures of both alkenes and alkynes. We will
also consider the characteristics of both alkenes and alkynes and some of the ways they are
synthesized. We will also study the wide variety of addition reactions that both alkenes and alkynes can
undergo.
Lesson 7.2.2. Alkenes and Cycloalkenes
Alkenes are hydrocarbons whose molecules contain a carbon–carbon double bond. An old name
for this family of compounds that is still often used is the name olefins. Ethene (ethylene), the simplest
olefin (alkene), was called olefiant gas (Latin: oleum, oil + facere, to make) because gaseous ethene
(C2H4) reacts with chlorine to form C2H4Cl2, a liquid (oil).
Alkenes or “Olefins” occur abundantly in nature, and many have important biological roles. The
simplest alkenes, with only one double bond, form a homologous series with a General formula: CnH2n.
Table 7.7. The First Ten Homologous Series of Alkenes
Alkene Name Molecular Formulas Structural Formulas

(1st Ten Series) (CnH2n) (Condensed)
1. Ethene (ethylene) C2H4 CH2=CH2
2. Propene C3H6 CH2 =CHCH3
3. Butene C4H8 CH2=CHCH2CH3
4. Pentene C5H10 CH2=CH(CH2)2CH3
5. Hexene C6H12 CH2=CH(CH2)3CH3
6. Heptene C7H14 CH2=CH(CH2)4CH3
7. Octene C8H16 CH2=CH(CH2)5CH3
8. Nonene C9H18 CH2=CH(CH2)6CH3
9. Decene C10H20 CH2=CH(CH2)7CH3
10. Undecene C11H22 CH2=CH(CH2)8CH3
Lesson 7.2.3. Nomenclature of Alkenes: IUPAC Rules
STEP 1: Name the parent hydrocarbon. Find the longest carbon chain that contains the double bond,
and the name the compound using the suffix – ene.
PREFIX – STEM – “ENE”
Examples:

STEP 2: Number the carbon atoms in the chain, beginning at the end nearer the double bond. If the
double bond is equidistant (the same distance) from the two terminal ends of the chain, begin numbering
at the end nearer the first branch point (side chain). This rule ensures that the double-bond carbons
receive the lowest possible numbers.
Examples:
STEP 3: Write the full name, numbering the substituents according to their position in the chain and
listing them alphabetically. Indicate the position of the double bond by giving the number of the first
alkene carbon. If more than one double bond is present, give the position of each and use one of the
suffixes –diene, -triene, and so on.
Examples:

Other Examples:
Trivial Names – are names used for simple alkenes. “Vinyl” and “allyl” are two groups that often appear in
the structures of so many compounds.
CH2 = CH – (Vinyl) CH2 = CHCH2 – (Allyl)

Example: CH2 = CHCl CH2 = CHCH2Cl
Common: Vinyl Chloride Allyl Chloride
IUPAC: Chloroethene Chloropropene
Vinyl Chloride – is used in the manufacture of floor tiles, raincoats, fabrics, furniture covers and
polyvinyl chloride (PVC) a plastic. However, evidence has shown that several workers exposed
to vinyl chloride at the workplace have died from a very rare form of liver cancer. In addition, it
is also suspected to be the cause of certain types of birth defects.
Alkadienes are the straight – or branched-chain hydrocarbons that have two double covalent bonds
between carbon atoms in each molecule.
Table 7.8. Common Names of Some Alkenes
Compound Systematic Name Common Name
H2C = CH2 Ethene Ethylene
CH3CH = CH2 Propene Propylene

CH3
l 2-Methylpropene Isobutylene
CH3C = CH2
CH3
l 2-Methyl-1-3-butadiene Isoprene
H2C = C – CH = CH2
* Both Common and Systematic Names are recognized by IUPAC.
Alkyl halides - The halogen is treated as a substituent on an alkane chain. The halo- substituent is
considered of equal rank with an alkyl substituent in the numbering of the parent chain. The halogens are
represented as follows:
F fluoro-
Cl chloro-
Br bromo-
I iodo-
Lesson 7.2.4. ALKYNES
Alkynes - are unsaturated hydrocarbons whose characteristic functional group is the carbon-to-
carbon triple bond. This series is sometimes called the acetylene series because the simplest alkyne has
the common name acetylene (ethyne), C2H2.
Table 7.9. The Nine Homologous Series of the Alkynes Compounds

Alkyne Name Molecular Formulas Structural Formulas
(Condensed)
1. Ethyne (acetylene) C2H2 CHΞCH
2. Propyne C3H4 CHΞC – CH3
3. Butyne C4H6 CHΞC – CH2CH3
4. Pentyne C5H8 CHΞC – CH2CH2CH3
5. Hexyne C6H10 CHΞC – (CH2)3CH3
6. Heptyne C7H12 CHΞC – (CH2)4CH3
7. Octyne C8H14 CHΞC – (CH2)5CH3
8. Nonyne C9H16 CHΞC – (CH2)6CH3
9. Decyne C10H18 CHΞC – (CH2)7CH3
General Formula is: CnH2n - 2
Ethyne, (acetylene), C2H2, - a colorless gas, is a minor component of the atmospheres of Jupiter
and Saturn. Ethyne molecules have also been detected in interstellar space. Ethyne can be prepared
commercially and in the laboratory by the action of water on calcium carbide (CaC 2). An alternate
commercial preparation is by the partial oxidation of methane. Ethyne burns in air with a very smoky
flame. Carbon, carbon dioxide and water vapor are the products of combustion of ethyne. The
oxyacetylene welding torch burns ethyne in the presence of oxygen and reaches a temperature of over
3200ºC.
Lesson 7.2.5. Nomenclature of Alkyne: IUPAC SYSTEM
Alkynes are named by general rules similar to those for alkanes and alkenes. The suffix – yne is
used in the parent hydrocarbon name to denote an alkyne, and the position of the triple bond is indicated
by its number in the chain. Numbering begins at the chain end nearer the triple bond so that the triple
bond receives as low a number as possible.
9 8 7 6 5 4 32 1
CH3CH2CH2CHCH2C Ξ CCH2CH3 ; 6-Methyl-3-nonyne
l
CH3

Other Examples
Compounds containing both double and triple bonds are called “enynes”. Numbering of the
hydrocarbon chain starts from the end nearer to the first multiple bonds, whether double or triple bond. If
there is a choice in numbering, double bonds receive lower numbers than triple bonds.
7 65 4 3 2 1 1 23 4 5 6 7 8 9
HC Ξ CCH2CH2CH2CH = CH2 HC Ξ CCH2CHCH2CH2CH = CHCH3
l
CH3
1-Hepten-6-yne 4-Methyl-7-nonen-1-yne

Lesson 7.2.6. CYCLOALKENES
Cycloalkanes are cyclic compounds that contain a carbon-to-carbon double bond in the ring. The most
common cycloalkenes are the cyclopentene and cyclohexene. The double bond may be placed between any
two carbon atoms.
STEP 1: Cyclic compounds containing double bonds are called “cycloalkenes”. When there is only
one double bond in a ring, it always goes from the no. one (1) to the no. two (2) position, so it is not
necessary to show the number in the name. The carbon of the double bond are assigned numbers
1 and 2. Thus the positions of the double bond need not be indicated in the name of the compound.
Other substituents on the rings are named in the usual manner, and their positions on the ring are
indicated with the smallest possible numbers.
No cis-trans designation is necessary for cycloalkenes that contain up to seven carbon atoms in the
ring. Cyclooctene has been shown to exist in both cis and trans-forms.
Lesson 7.2.7. PREPARATIONS OF ALKENES AND ALKYNES
1. Cracking Alkanes. The commercial method of producing alkenes is by cracking petroleum. Cracking
is a process in which complex organic molecules are broken up into simpler molecules. This process
involves the action of heat and sometimes involves a catalyst. Cracking that involves heat alone is
known as thermal cracking, while the cracking process that involves heat and requires a catalyst is
called catalytic cracking.
C3H8 (460ºC) ----------› C3H6 + H2

Propane Δ Propene Hydrogen gas

C3H8 (460ºC) ----------› C2H4 + CH4
Propane Δ Ethene Methane
2. Dehydration of Alcohols. Ethene can be prepared in the laboratory by dehydrating (removing water)
ethyl alcohol by using hot concentrated sulfuric acid as the dehydrating agent.
170ºC
C2H5OH -------------› C2H4 + H2O
H2SO4
3. Alkynes like Acetylene can be prepared inexpensively from the reaction of Calcium Carbide and Water.
CaC2 + H2O ----------› HC Ξ CH + Ca(OH)2
4. Acetylene is also prepared by the cracking of Methane in an electric arc.
1500ºC
2 CH4 -------------› HC Ξ CH + 3 H2
Lesson 7.2.8. Chemical Properties of Alkenes and Alkynes
A. Alkenes
The boiling points of alkenes are slightly lower than the alkanes since they have a slightly smaller molar
mass.
The smaller alkenes (1-5 carbons) are gases at room temperature. As the chain lengthens (5 -17
carbons), the alkenes are liquid, and above 17-carbons, they are solid.
Alkenes are non-polar, like the other hydrocarbons, and so are insoluble in water but soluble in organic
solvents.
The densities of most alkenes are much less than water.
Some isomers (C4H8) have similar boiling points but different melting points because the isomers have
different shapes and therefore fit into their crystalline structures in significantly different ways.
B. Alkynes
Acetylene is a colorless gas, with little odor when pure. The disagreeable odor associated with it is the
result of impurities (usually PH3).
Acetylene is insoluble in water and is a gas at normal temperature and pressure (bp = - 84C).
As a liquid, acetylene is very sensitive and may decompose violently (explode), spontaneously, or from
a slight shock. To eliminate the danger of explosions, acetylene is dissolved in acetone and is packed
in cylinders that contain a porous inert material.

CH Ξ CH ---------› H2 + 2C + 227 kJ
Acetylene is used mainly as a fuel for oxyacetylene cutting and welding torches which can produce
flame temperatures of about 2800C.
Acetylene is also used as an intermediate in the manufacture of other substances.
Lesson 7.2.9. Physical Properties of Alkenes and Alkynes
Alkenes and alkynes are more reactive than alkanes and readily undergo addition reactions. This
involves the addition of two atoms or groups of atoms to a double bond.
1. ADDITION REACTIONS Addition at the carbon-carbon double bond is the most common reaction of
alkenes. Hydrogen, halogens, hydrogen halides, sulfuric acid, and water are some of the reagents that
can be added to unsaturated hydrocarbons.
a. HYDROGENATION: Addition of Hydrogen, H2
Alkene Pt, Pd, or Ni Alkane

H2C = CH2 + H2 --------------------› H3C – CH3
Ethene Hydrogen Heat &/or Pressure Ethane
Alkyne Pt, Pd, or Ni Alkene Pt, Pd or Ni Alkane

HC Ξ CH + H2 -------------------› H2C = CH2 + H2 ----------------› H3C – CH3
Ethyne Hydrogen (Heat or Pressure) Ethene Δ Ethane
b. HALOGENATION: Addition of a Halogen, X2 (Cl2 or Br2)
Alkene Halogen No Catalysts Alkyldihalide

H2C = CH2 + Cl2 ---------------› ClCH2 – CH2Cl
Ethene Chlorine 1,2 - Dichloroethane
Alkyne Alkene dihalide Alkyl halide

HC Ξ CH + Cl2 ------------› ClCH2 = CH2Cl + Cl2 -------› ClCH2Cl – ClCH2Cl
Ethyne Chlorine 1,2 - Dichloroethene 1,1,2,2 – Tetrachloroethane
c. HYDRATION: Addition of Water, H2O – this reaction requires a trace of strong acid (H +) as a catalyst. The
product is an Alcohol.

Alkene H+ Alcohol
H2C = CH2 + H - OH ----------› CH3CH2OH
Ethene Water Ethanol
H+ Major product Minor product

CH3CH = CH2 + H - OH --------› CH3CH – CH3 + CH3CH2CH2 – OH
l
OH
Propene Water 2 - Propanol 1 – Propanol
(Propylene) (Isopropyl alcohol) (Propyl alcohol)
Markovnikov’s Rule (1869) – (Vladimir Markovnikov, a Russian chemists formulated a rule that predicts
which product will be predominantly formed by these type of reactions) states that “when an unsymmetrical
molecule such as HX (HCl) adds to a carbon-carbon double bond, the hydrogen (H) of HX goes to the
carbon atom that has the greater number of hydrogen atoms”.
Hydration of an Alkyne is a more complex process because the initial product is not stable and is rapidly
isomerized. The product is an alcohol but, in this case, one in which the hydroxyl group (– OH) is bonded
to one of the carbons of a carbon-carbon double bond. This type of molecule is called an “enol” because it
is both an alkene (ene) and an alcohol (ol). The enol cannot be isolated from the reaction mixture because
it is so quickly isomerized into either an Aldehyde or a Ketone.
H H
l l
R – C Ξ C – R’ + H – OH -----› R – C = C – R’ ------› R – C – C – R’
l l l
OH H O
Alkyne Water Enol Aldehyde if R’ = H and Ketone if R’ = alkyl group
OH H O
l l l
CH3 – C Ξ CH + H – OH -----› CH3 – C = CH -----› CH3 – C – C – H
l l
1 – Propyne H H
Propen – 2 - ol Propanal or Priopionaldehyde
OH H O
l l ll
CH3C Ξ CCH3 + H – OH -----› CH3 – C = C – CH3 -----› CH3 – C – C – CH3
l l
2 – Butyne H H
2 – Buten – 3 – ol Butanone or Ethyl methyl ketone

d. HYDROHALOGENATION: Addition of Hydrogen Halide, HX (HCl, HBr, or HI)
Alkene Hydrogen Halide Alkyl Halide

H2C = CH2 + H - Br ----------› CH3CH2 – Br
Ethene Hydrogen Bromide Bromoethane
Major product Minor product

CH3CH = CH2 + H – Br --------› CH3CH – CH3 + CH3CH2CH2 – Br
l
Br
Propene Hydrogen Bromide 2 - Bromopropane 1 – Bromopropane
Alkyne Hydrogen Halide Halogenated Alkene Alkyl halide

HC Ξ CH + H - Cl ----------› CH2=CH – Cl + H – Cl ----------› CH3 – CH – Cl2
Ethyne Hydrogen Chloride 1 - Chloroethene 1,1 - Dichloroethane
(Vinyl Chloride)
e. SULFONATION: Addition of Sulfuric Acid, H2SO4
Alkene Sulfuric Acid (conc.) Alkyl Halide

H2C = CH2 + HO – SO3H ----------› CH3CH2 – OSO3H
Ethene Dihydrogen Sulfate Ethyl hydrogen sulfate
2. OXIDATION. This is another reaction of alkenes at the double bond. For example, when shaken with a
cold, dilute solution of Potassium Permanganate, KMnO4, an alkene is converted to a glycol (glycols are
dihydroxy alcohols).
Alkene Dihydroxy Alcohol

H2C = CH2 + KMnO4 + H2O -------› CH2 – CH2 + MnO2 + KOH
Ethene (purple) 1,2 - Ethanediol (Brown)
(Ethylene glycol)
The Baeyer Test makes use of this reaction to detect or confirm the presence of double (or triple) bonds
in hydrocarbons. Evidence of reaction (positive Baeyer test) is the disappearance of the purple color
of permanganate ions.
The Baeyer test is not specific for detecting unsaturation in HC’s because other classes of compounds
may also give a positive Baeyer test like other oxidizing agents such as O 2 in air and especially with
ozone, O3.

Lesson 7.2.10. ALKENES and ALKYNES in NATURE
1. Ethene – the simplest alkene is produced by ripening fruits, it is a plant growth substance. It is produced
during fruit ripening, during leaf fall and flower senescence, as well as under conditions of stress,
including wounding, heat, cold, or water stress, and disease.
2. Isoprene – is the building block molecule of the polyenes, alkenes with several double bonds found in
nature. The molecules that are produced are called Isoprenoids, or Terpenes.
Terpenes – include the steroids; chlorophyll and carotenoid pigments (-carotene) that function in
photosynthesis; and the lipid-soluble vitamins A, D, E, and K.
a. Geraniol – the familiar scent of geraniums is a terpene. It is a molecule made up of two isoprene
units. Purified, it is the active ingredient in several natural insect repellants applied to the skin to
provide 4 hrs. of protection against insect bites.
b. D – Limonene – (oil of lemon or orange) is a terpene used as a flavor and fragrance additive in foods
because of its pleasant citrus aroma. Its most expanding use is as a solvent because it can be
used in place of more toxic solvents such as mineral spirits, methyl ethyl ketone, acetone, toluene,
and fluorinated and chlorinated organic solvents. It can also be formulated as a water-based
cleaning product in place of more caustic cleaning solutions. Its molecular mirror image L-
Limonene has a pine or turpentine aroma.
c. Myrcene (Oil of Bayberry) – is a terpene extracted from bayberry and it is used in perfumes and
scented candles because it adds a refreshing, spicy aroma to them. Trace amounts of myrcene
may be used as a flavor component in root beer.
d. Farnesol – is a terpene found in roses, orange blossom, wild cyclamen, and lily of the valley. It is
used by cosmetic companies in skin care products in the early 1990s. it is claimed to smooth
wrinkles and increases skin elasticity. It is also thought to reduce skin aging by promoting
regeneration of cells and activation of the synthesis of molecules, such as collagen, that are
required for healthy skin.
e. Retinol – is another terpene which is a form of vitamin A. it is able to penetrate the outer layers of
skin and stimulate the formation of collagen and elastin. This reduces wrinkles by creating skin that
is firmer and smoother.
3. Capillin – an alkyne produced by the oriental wormwood plant in a dilute solution, can inhibit the growth
of fungi. It may one day be developed to combat fungi infections in humans.

4. Cicutoxin – a toxic alkyne, has been described as the most lethal toxin native to North America. It is a
neurotoxin that is produced by the water hemlock (Cicuta maculata). Eating 2-3 cm2 of its roots can be
fatal to adults because it acts directly to the CNS. Signs and symptoms of cicutoxin poisoning include
dilation of pupils, muscle twitching, rapid pulse and breathing, violent convulsions, coma, and death.
Onset of symptoms is rapid and death may occur within 2 – 3 hrs. No antidote exists for cicutoxin
poisoning. The only treatment is to preserve normal heart and lung function.
5. Squallene - is a 30-carbon alkene with six carbon–carbon double bonds. Squalene occurs in all plants
and animals to make the steroid compounds used as hormones, vitamins, emulsifiers, and cell
membrane components. Squalene is used in cosmetics and as an adjuvant (makes the immune
system respond more strongly) in vaccines. Squalene was originally obtained from shark livers,
where sharks use it as an incompressible low-density liquid to make them neutrally buoyant in salt
water. Plant sources, such as olive oil, are now used as cheaper and more sustainable sources of
squalene.
➢ Chapters 4, 7 & 8
➢ Chapters 3,4,7 & 8
A. Review Questions
I. Properties of Alkanes

1. Heptane, used as a solvent for rubber cement, has a density of 0.68 g/mL and boils at 98 °C.
a. Draw the condensed structural formula and skeletal formula for heptane.
b. Is heptane a solid, liquid, or gas at room temperature?
c. Is heptane soluble in water?
d. Will heptane float on water or sink?
e. Write the balanced chemical equation for the complete combustion
of heptane.
2. Nonane has a density of 0.79 g>mL and boils at 151 °C.
a. Draw the condensed structural formula and skeletal formula for nonane.
b. Is nonane a solid, liquid, or gas at room temperature?
c. Is nonane soluble in water?
d. Will nonane float on water or sink?
e. Write the balanced chemical equation for the complete combustion of nonane.
II. Properties of Alkanes, Alkenes and Alkynes

TRUE or FALSE: Write True if the given statement is correct, and write False if the given statement is not
correct.
1. Gaseous alkanes are colorless, odorless, and tasteless compounds.
2. The melting and boiling points of hydrocarbons increase with increasing molecular weights.
3. Alkanes are not soluble in water because they are polar compounds.
4. Liquid alkanes are less dense than water and this means that they float on water.
5. Alkanes containing about 1-5 carbon atoms are solid at room temperature.
6. Larger alkanes containing about 20 or more carbon atoms are liquid at room temperature.
7. Alkanes are chemically inert which means that they are very volatile.
8. The most important chemical property of alkanes is that they burn.
9. One of the main products of the complete combustion of alkanes is Carbon Monoxide.
10. The other name of alkane is Olefin.
11. The boiling points of Alkenes are slightly higher than the alkanes.
12. Alkenes with about 1 – 5 carbon atoms are gases at room temperature.
13. Alkenes with 5 – 17 carbon atoms are liquids at room temperature.
14. Liquid alkenes are polar solvents and are soluble in water.
15. Alkenes are also referred to as paraffins.
16. One method of preparing Alkenes is by the dehydration of alcohols.
17. Acetylene, the simplest alkyne is a colorless gas with little odor when pure.
18. Acetylene is insoluble in water because it is a polar compound.
19. As a liquid, acetylene is very sensitive and may decompose violently.
20. Alkenes and alkynes are more reactive than alkanes and readily undergo addition reactions.
B. Individual Exercises

I. Name the following Alkanes by the IUPAC Rules.
CH3
l
1. CH3 – CH – CH2 – CH3
l
CH2CH3
2. CH3 – CH2 – CH – CH3

l
CH3
3. CH3 – CH – CH2 – CH – CH3

l
CH3
CH3 CH2CH3
l l
4. CH3 – CH – CH2 – CH – CH3
CH3 CH2CH3
l l
5. CH3 – C – CH2 – CH2 – CH – CH3
l
CH2CH3
CH3 CH2CH3
l l
6. CH3 – C – CH2 – CH – CH – CH3
l l
CH3 CH2CH3
CH3CHCH3 CH3
l l
7. CH3 – C – CH2 – CH – CH – CH3
l l
CH3 CH3
8. CH3 – CH – CH2 – CH2 – CH – CH3

l l
CH2 CH – CH3
l l
CH3 CH3 – CH – CH3
CH3 – CH – CH3 CH2CH3

l l
9. CH – CH2 – CH – CH – CH – CH2CH3
l l l
CH2CH3 CH3 CH2CH3
CH3 CH3 CH3
l l l
10. CH – CH – CH – CH – CH – CH2 – CH3
l l l
CH3 CH3 CH – CH2 – CH3
l
CH2 – CH2 – CH3
II. Name the following Cycloalkanes by the IUPAC Rules
CH3
CH3
3. CH3
CH3
H3C
2. CH2CH3
Cl
3.
Cl
CH2CH3
CH2CH3
Br
4.
Br
CH3
Cl
5. CH2CH3
Cl CH2CH3
III. STRUCTURAL FORMULA WRITING. Illustrate the correct (a) Expanded; (b) Condensed; and (c) Line
& Angle Structural Formula of the following compounds of Alkanes and Cycloalkanes given their IUPAC
name.
1.) 4 – Ethyl – 2,2 – dimethylhexane (a.)
(b.)
(c.)

2.) 1,1,3 – Trimethylpentane: (a.)
(b.)
(c.)
3.) 2 – Ethyl – 1,3,5 – trimethylheptane: (a.)
(b.)
(c.)
4.) 2 – Chloro – 1 – Ethyl – 1,3 – dimethylcyclohexane: (a.)
(b.)
(c.)
IV. CHEMICAL REACTIONS OF ALKANES: (a.) Write the main PRODUCT formed by the given reaction;
(b.) Give the IUPAC Name of the alkane reactant; (c.) Give the IUPAC name of the Product formed. (d.)
Determine the Specific Type of Reaction.
1. CH3 – CH2 – CH2 – CH3 + Br2 -------› (a.) + HBr
(b.) ________________________________
(c.) ____________________________
2. CH3 – CH2 – CH2 – CH2 – CH3 --------› (a.) + H2
(b.) ___________________________________
(c.) ______________________________
Heat
3. CH3 – CH2 – CH3 + O2 --------› (a.) + Energy
(b.) ___________________________________
(c.) _______________________________

4. + Cl2 --------› (a.) + HCl
(b.) ___________________________________
(c.) _______________________________
5. -------› (a.) + H2
(b.) ___________________________________
(c.) ______________________________
V. Study the following Unsaturated Organic Compounds and Write their correct IUPAC names.
CH3
l
1. CH3 CH CH2–C–CH2CH3
l l
CH3 CH = CH2
CH3
l
2. CH3 CH–CΞC–CHCH3
l
CH3
CH3
l
3. CH3 CH=CH–C–CH2CH=CH2
l
CH3
CH3
l
4. CH2 C=CHCH2CH3
l l
CH3 CH2CH2CH2CH2CH3

CH3
l
5. CH3 CH3
l
CH3
CH3
l
6. CHΞC–CH – CH–CH–CH2CΞCH
l l
CH3 CH3
CH3 CH2CH3
7.
CH3
CH3
8. CH3CH–CΞC–CH=CH–CH–CH3
l l
CH2CH3 CH3
CH2CH2CH3
l
9. CH3CH–CΞC–CHCH2CH2C=CH2
l l
CH2CH3 CH3
CH3
10. CH=CH2
VI. CHEMICAL REACTIONS OF UNSTURATED HYDROCARBONS: (a.) Determine and illustrate the
product/s formed by the given reaction; (b.) give the IUPAC name of the unsaturated hydrocarbon
reactant; (c.) give the IUPAC name of the main product formed. (d.) determine the type of reaction
(e.g. Halogenation, Hydrogenation, Dehydrogenation, Hydration, Hydrohalogenation, Sulfonation,
Oxidation, or Cracking).

1. CH3 – CH = CH – CH3 + HBr (a.)
(b.) ______________________________ (c.) __________________________________
(d.) ___________________________
2. CH3 CH = CH2 + H2SO4 (a.)
(b.) ____________________________ (c.) ____________________________________
(d.) ____________________________
3. CH3–CΞC–CH3 + H2 (a.)
(b.) _____________________________ (c.) ____________________________________
(d.) ___________________________
4. CH3CH2CH=CH2 + HOH (a.)
(b.) ____________________________ (c.) ____________________________________
(d.) ____________________________
5. CH3CH2CΞCH + HCl (a.)
(b.) ____________________________ (c.) _____________________________________
(d.) ___________________________
6. CH3–CΞC–CH3 + Br2 (a.)
(b.) ____________________________ (c.) _____________________________________
(d.) __________________________

7. + H2 (a.)
(b.) ___________________________ (c.) _______________________________
(d.) ___________________________
8. CH3 CH2 – C Ξ CH + HOH (a.)
(b.) ______________________________ (c.) ____________________________________
(d.) _____________________________
9. CH3 CH2 CH = CH2 + Cl2 (a.)
(b.) ______________________________ (c.) ____________________________________
(d.) ______________________________
10. + H2 (a)
(b.) ____________________________ (c.) ____________________________________
(d.) ____________________________
Experiments #7, and #8
Note: Watch video of Experiment #7 and #8 as performed by your Instructor/s in the real laboratory to be
posted on Google class as scheduled.

MODULE 7
The Aromatic Hydrocarbons
7. Drawn structures of aromatic compounds;
8. Named common aromatic compounds;
9. Identified the sources and the practical and medical applications/significance of aromatic compounds;
10. Explained the preparations of aromatic compounds by using chemical equations;
11. Discussed the physical properties of aromatic compounds;
12. Determined the correct products of the chemical reactions of aromatic hydrocarbons.
LESSON INTRODUCTION
In 1825, Michael Faraday isolated a pure compound of boiling point 80 °C from the oily mixture that
condensed from illuminating gas, the fuel burned in gaslights. Elemental analysis showed an unusually small
hydrogen-to-carbon ratio of 1:1, corresponding to an empirical formula of CH. Faraday named the new
compound “bicarburet of hydrogen.” Eilhard Mitscherlich synthesized the same compound in 1834 by
heating benzoic acid, isolated from gum benzoin, in the presence of lime. As Faraday did, Mitscherlich found
that the empirical formula was CH. He also used a vapor-density measurement to determine a molecular
weight of about 78, for a molecular formula of C6H6. Because the new compound was derived from gum
benzoin, he named it benzin, now called benzene.
Many other compounds discovered in the 19th century seemed to be related to benzene. These
compounds also had low hydrogen-to-carbon ratios as well as pleasant aromas, and they could be converted
to benzene or related compounds. This group of compounds was called aromatic because of their pleasant
odors. Although over time, chemists discovered that many derivatives of benzene are, in fact, odorless.
Nevertheless, the term “aromatic” is still used to describe all derivatives of benzene, regardless of whether
they are fragrant or odorless. Other organic compounds without these properties were called aliphatic,
meaning “fatlike.” As the unusual stability of aromatic compounds was investigated, the term aromatic came
to be applied to compounds with this stability, regardless of their odors.

LESSON 1: BENZENE” THE BASIC STRUCTURE OF AROMATIC HYDROCARBONS
Aromatic Hydrocarbons – are the unsaturated organic compounds whose functional groups are
characterized by a stable cyclic (aromatic ring), six carbon compounds and sometimes depicted as having
alternating single and double carbon-to-carbon bonds. Aromatic term was proposed by August Wilhelm
Hofmann in 1855. Structurally, each member of this family contains an aromatic ring. The most common is
Benzene (C6H6), which has a variety of molecular structure. Aromatics are planar ring compounds with
conjugated pi-system in which single and double bond present in alternate manner. This arrangement of
alternating single and double bonds is called a conjugated system of double bonds. August Kekulé, J. J.
Thomson and Sir Robert Robinson played an important role in the explanation of the structure and bonding
of aromatic compounds.
The first aromatic compound considered is benzene and all other aromatic compounds are
derivatives of benzene, in which at least one benzene ring must be present in order to be considered as an
aromatic compound.
Benzene is a cyclic compound commonly written as a hexagon with alternating double and single
bonds, or with a circle drawn in the center of a hexagon. It was in 1865 that Friedrich August Kekule
proposed that the carbon atoms in a benzene molecule are arranged in a ring consists of six carbon atoms
joined in a planar hexagonal arrangement. Each carbon atom is bonded to one hydrogen atom and that
single and double bonds alternated around the ring (with three carbon-carbon double bonds). Kekule’s
formulas have one serious shortcoming: They represent benzene and related substances as highly
unsaturated compounds.
Resonance Hybrid Benzene

Structure of Benzene Kekule Structure
The chemical behavior of benzene resembles that of an alkane. Benzene does not react like a typical
alkene; it does not decolorize bromine solutions rapidly , nor does it destroy the purple color of permanganate
ions (Baeyer’s test). Its typical reactions are the substitution type, wherein a hydrogen atom is replaced by
some other group. Almost all aromatic compounds including benzene have characteristics aroma and are
highly flammable liquid. They are mainly used as a precursor for the synthesis of heavy chemicals and an
important component of gasoline.
Three Types of Aromatic Compounds or Arenes
1. Monocyclic arenes: Involves mainly benzene and its derivatives.

2. Polycyclic isolated arenes: They are composed of more than one benzene ring which is isolated
from each other. For example; Biphenyl.
3. Polycyclic condensed arenes: They have fused benzene rings for example; naphthalene

LESSON 2: NOMENCLATURE OF AROMATIC COMPOUNDS
Substituted Benzenes are the most common benzene derivatives because substitution is the most
common reaction type for benzene. A substituted benzene is derived by replacing one or more
hydrogen atoms of benzene by another atom or group of atoms. Thus a Monosubstituted benzene has
the formula C6H5G, where “G” is the group replacing a hydrogen atom.
A. MONOSUBSTITUTED BENZENES, (C6H5G):
Mono-substituted aromatic compounds are named as derivatives of benzene.Thus “benzene” is

the parent compound, and the name of any atom or group bonded is used as prefix or substituents. The name is
written as one word.
PREFIX (Substituents) BENZENE
TABLE 8.1. Common Substituents Found in Benzene Rings:

Structural Formulas Name Structural Formulas Name
– Cl Chloro – OCH3 Methoxy

O
– Br Bromo l Formyl
C–H or – COH
O
– NH2 Amino l Carboxy
C – OH or – COOH
– NO2 Nitro – CH = CH2 Vinyl
– OH Hydroxy – CΞN Cyano
NOTE: Some Monosubstituted benzenes have special names (based on history rather than logic).
These are used as “parent names” for further substituted compounds, so they should be memorized.
Derivatives of Benzene
TABLE 4 – 2: Names and Formulas of Some Monosubstituted Benzenes:
Structural Formulas IUPAC Name COMMON Name
CH3 Methylbenzene Toluene
OH Hydroxybenzene Phenol
NH2 Aminobenzene Aniline

O
l Carboxybenzene Benzoic Acid
C – OH
O
l Formylbenzene Benzaldehyde
C–H
OCH3 Methoxybenzene Anisole
CH=CH2 Vinylbenzene Styrene
SO3H Benzenesulfonic Acid None
NO2 Nitrobenzene None
Cl Chlorobenzene None
Br Bromobenzene None
B. DISUBSTITUTED BENZENES, (C6H4G) – are benzenes where two hydrogen atoms in its molecular ring
are replaced by two substituent groups.
In Disubstituted benzenes, when two substituents groups replace two hydrogen atoms in a benzene ring,
three (3) different isomeric compounds are possible, and they may be named by either the I.U.P.A.C.
Nomenclature System or the Common System of Nomenclature.
1. The prefixes ortho- , meta-, and para- (abbreviated o-, m-, p-) are the Common Nomenclature
Systems used to name these Disubstituted benzenes. Furthermore, Ortho designates 1,2 di-
substitution, metha represents 1,3 di-substitution, and para designates 1,4 di-substitution, in the
IUPAC Nomenclature System.
TABLE 4 – 3: The Three Isomeric Compounds of Disubstituted Benzene
General Formula Example IUPAC Name

(Common Name)
G CH3 1, 2 – Dimethylbenzene
G CH3 (ortho-dimethylbenzene)
or
(ortho – Xylene)

(meta-dimethylbenzene)
or
G CH3 (meta – Xylene)
(para – Dimethylbenzene)
or
(para – Xylene)
G CH3
2. When the two substituents are different and neither is part of a compound with a special name, the
names of the two substituents are given in the “alphabetical order”, followed by the word “benzene”. For
Example:
Cl NO2 CH2CH2CH3
Br
CH2CH3
CH2CH3
o–-bromochlorobenzene m– ethylnitrobenzene p–ethylpropylbenzene

(1–Bromo–2–chlorobenzene) (3–ethyl–1–nitrobenzene) (4-ethyl-1-propylbenzene)
3. When one of the substituents corresponds to a Monosubstituted benzene that has a special name, the
Disubstituted compound is named as a derivative of that parent compound.
OH CH3 NH2
NO2 NO2
Br
o - nitrophenol m - nitrotoluene p - bromoaniline

(1-hydroxy-2-nitrobenzene) (1-methyl-3-nitrobenzene) (1-amino-4-bromobenzene)
OH CH=CH3 O–CH3
CH3 Cl
Br
o - cresol m - chlorostyrene p – bromoanisole
or 2-methylphenol 3 – chlorostyrene 4 - bromoanisole
or 1-hydroxy-2-methylbenzene 1- chloro – 3 – vinylbenzene 4 – bromo – 1 – formylbenzene
4. When the compound is named as a derivative of one of the special parent compounds, the substituent
of the parent compound is considered to be on carbon 1 of the ring. Numbering may be either clockwise or

counterclockwise but must be done in the direction that gives the lowest possible numbers to the substituent
groups. (See previous examples above).
C. POLYSUBSTITUTED BENZENES, (C6H3G or C6G6):
1. When there are more than two substituents on a benzene ring, the carbon atoms in the ring are
numbered starting at one of the substituted groups. Numbering may be done clockwise or
counterclockwise in the direction that gives the lowest possible numbers to the substituent groups.
2. When the compound is named as a derivative of one of the special parent compounds, the substituent
of the parent compound is considered to be on carbon 1 of the ring. For example:
NH2 OH CH3
Br O2N NO2
O2N NO2
Br NO2
3,5 – dinitroaniline 2,4 – dibromophenol 2,4,6 – trinitrotoluene (TNT)
3. Aromatic compounds in which both the attached groups impart a common name to benzene, there is an
order of priority about with which of the substituents group forms the parent name.
TABLE 7.4. Order of Priority of Substituent Groups
ORDER OF PRIORITY NAME OF SUBSTITUENT FORMULA

GROUP
HIGHEST Carboxy – COOH
Formyl – COH
Hydroxy – OH
Methoxy – OCH3
Amino – NH2
Nitro – NO2
Cyano –C=N
Mercapto – SH
Halogens (Br, Cl, F, I) – Br, – Cl, – F, – I

Benzyl C6H5 – CH2–
Phenyl C6H5 –
Vinyl – CH = CH2
LOWEST (Alkyl groups) – CnH2n + 1

t-butyl
sec-butyl
iso-butyl
iso-propyl
propyl
ethyl
methyl
D. THE “PHENYL” and “ BENZYL” GROUPS:
Some benzene compounds are more conveniently named by considering the benzene itself to be the
substituents.
In the IUPAC nomenclature system, the –C6H5 group is known as the “phenyl group”. It is derived by
removing one hydrogen atom from benzene .
An aromatic hydrocarbon with an aliphatic side chain would be named as a phenyl substituted
hydrocarbon, and the name “phenyl” is used to name compounds that cannot be easily named as benzene
derivatives.
Examples: - Br
Biphenyl Bromobiphenyl
CH3CHCH2CH3 H3CHCH=CH2 CH3

l
CHCHCH2CH3
l
Cl
2 – Phenylbutane 3 – Phenyl –1– butene 3– Chloro –2– phenylpentane
One final special name that occurs frequently in aromatic compounds is the “Benzyl group”:
C6H5CH2 or CH2
The use of this group’s name is illustrated by:

CH3
CH2Cl CH2– CHCH2CH2CH3 CH2–CH2–CH2
Benzyl Chloride or 2 - Benzylpentane or Dibenzyl methane or

Chlorophenyl methane 2 – methyl –1– phenylpentane 1,3 – diphenylpropane
E. Polycyclic Aromatic Compounds (Fused Ring Aromatics)
Aromatic hydrocarbon can contain one or more than one benzene ring. These compounds which contain
more than one benzene ring are known as polynuclear or polycyclic aromatic hydrocarbon like naphthalene,
anthracene etc. These aromatic compounds are generally taken as derivatives of benzene and they are
often referred to as “fused-ring aromatics”.
Fused Ring Aromatics - are organic compounds that form when two (2) or more aromatic rings are joined
by two or more Carbon atoms.
Examples:
1.) Naphthalene, C10H8: – the simplest fused-ring aromatic, used in some moth balls
2.) Anthracene, C14H10:
3.) Phenanthrene, C14H10:
4.) 3,4 – benze(o)pyrene, C18H12:
➢ this polycyclic aromatic compound is one of the products of tobacco smoke and is one of the most potent
carcinogenic materials known. It is also produced from the incomplete combustion of coal.
Benzene and its derivatives are mainly used in synthetic organic chemistry. The main source of
polynuclear aromatic compounds is coal tar.
For example, naphthalene is the largest single constituent (6 - 10%) of coal tar. It is mainly found in
middle oil fraction of coal tar distillation.
Anthracene is mainly extracted from green oil fraction of coal tar. Generally polynuclear aromatic
compounds are carcinogenic and toxic in nature.

LESSON 3: PHYSICAL PROPERTIES OF BENZENE
1. Aromatic hydrocarbons like benzene are colorless and have characteristic odor.
2. Benzene is toxic and carcinogenic in nature.
3. It is a non-polar molecule and exists in the form of colorless liquid and highly inflammable in nature.
That is the reason, the bottle of benzene are marketed with the warning of toxic and flammable liquid.
4. Because of the high percentage of carbon atoms compared to alkanes, Benzene burns with sooty
flame and less denser than water.
5. The density of benzene is 0.8765 g/cm3 and melts at 278.7 K.
6. The boiling point of benzene is 353.3 K temperature.
LESSON 4: CHEMICAL PROPERTIES OF AROMATIC HYDROCARBONS
Benzene and other derivatives of benzene undergoes substitution reactions in spite of the high degree
of unsaturation. This behavior of benzene is called as aromaticity or aromatic character. Aromaticity of
benzene can be easily explained on the basis of resonance structure of benzene. During additional reactions
of benzene, it will lose its aromaticity, hence it’s preferred to undergo substitution instead of additional
reaction.
A. ELECTROPHILIC AROMATIC SUBSTITUTION RECATIONS: These are several reactions that

belong to this category.
1. NITRATION – is the reaction process where a nitro group can be introduced into benzene or other
aromatic hydrocarbon by using a nitrating mixture. The nitrating mixture is a mixture of
concentrated nitric acid (HNO3) and concentrated sulfuric acid. The sulfuric acid acts as catalyst
and responsible for the formation of electrophile that is nitronium ion (NO2+). When benzene is
treated with this nitrating mixture at a temperature below 50°C, it forms nitrobenzene.
2. SULFONATION – This is the replacement of hydrogen atom of benzene by a sulfonic acid group (-
SO3H). The reaction is carried out in the presence of concentrated sulfuric acid containing
dissolved sulfur trioxide which is also known as fuming sulfuric acid. The sulfonation of benzene
results the formation of benzene sulfonic acid.
3. FRIEDEL-CRAFTS ALKYLATION – an alkyl group from an alkyl halide (R – X) in the presence of

aluminum chloride (AlCl3), catalyst, substitutes for an – H atom on the benzene ring.
➢ In Friedel-Crafts Alkylation and Acylation, some other Lewis acids like FeCl3 or BF3 etc. is also
used for the generation of an electrophile.

AlCl3
Ex: C6H6 + CH3CH2Cl -----------> C6H5 – CH2CH3 + HCl
Benzene chloroethane ethylbenzene hydrogen chloride
4. FRIEDEL-CRAFTS ACYLATION – the replacement of an – H atom on the benzene ring by an alkyl

group from an acyl-halide (R- CO – X) in the presence of catalyst, AlCl3.
Examples: Benzene, C6H6

➢ Name of the product of the Friedel-Crafts acylation of benzene: Acetophenone
➢ Name of the product of the nitration of benzene: Nitrobenzene
➢ Name of the product of the halogenation of benzene: Chlorobenzene
B. OTHER AROMATIC SUBSTITUTION REACTIONS:
Benzene shows some of substitution reactions to form alkane, alkene and alkyne under more drastic
condition to form additional products. These additional products are more stable and behave as saturated
hydrocarbons. The most common substitution reactions of benzene are hydrogenation and halogenation which
results in the formation of Alicyclic compounds and polysubstituted halo-benzenes respectively.
1. HALOGENATION
➢ Iron (II); FeCl2 or Iron (III) Chloride; FeCl3 catalyzed halogenation of benzene gives a product
which is a halogenated benzene.
➢ In the presence of sunlight, benzene shows additional reaction with halogens like chlorine or
bromine to form additional products.
➢ For example, with chlorine, it forms benzene hexachloride which is also called as BHC or
“gamaxine” and used as insecticide. Since this halogenation takes place in the presence of
light without any catalyst, therefore reaction follows free radical mechanism.

2. HYDROGENATION – is an example of addition reaction of benzene which occurs only under
drastic condition like strong catalyst, high temperature or high pressure etc. This reaction is
exothermic in nature and furnished in three steps through the formation of 1,3-cyclohexadiene,
Cyclohexene and finally forms Cyclohexane.
➢ Hydrogenation of benzene also takes place in the presence of metal catalyst like nickel,
palladium or platinum at high temperature around 475 - 500 K.
➢ The selective hydrogenation of benzene results the formation of Cyclohexene in the presence
of Ru-based catalyst.
➢ Since Cyclohexene is more prone to hydrogenation to form Cyclohexane, the reaction is
carried out in the presence of water (H-OH) which slows down this conversion by dissolving
benzene.
C. OXIDATION
1. COMBUSTION OXIDATION – The combustion of benzene forms carbon dioxide and water
like other hydrocarbons. It burns with sooty flame due to high carbon content compare to
other hydrocarbons.
2C6H6 + 15O2 → 2CO2 + 6H2O + heat
2. NON-COMBUSTION OXIDATION
a.) Side-Chain Oxidation – the catalyzed oxidation of hydrocarbon chains (or alkyl group)
attached to an aromatic ring by catalysts such as KMnO4 or K2Cr2O7 with concentrated
H2SO4.
➢ No matter how long the side-chain is, the hydrocarbon atom attached to the aromatic
ring is oxidized to a “carboxylic acid” group (– COOH).
Examples:

1. C6H5 –CH3 → C6H5–COOH
Toluene Benzoic Acid
2. C6H5 –CH2CH3 → C6H5–COOH + CO2

Ethyl benzene Benzoic Acid carbon dioxide
3. C6H5 –CH2CH2CH3 → C6H5–COOH + CH3COOH

Propyl benzene Benzoic Acid Formic acid
b.) Controlled Oxidation – is the oxidation reaction in the presence of a catalyst like vanadium
pentaoxide (V2O5) at 725 K temperature which results in the formation of the product -
maleic anhydride.
Benzene Maleic anhydride
3. OZONOLYSIS – The addition of ozone (O3) to benzene forms Glyoxal through the formation of
Benzene Triozonide as an intermediate.
SUMMARY of Some Electrophilic Substitution Reactions with Electrophile, Products and Catalyst are
as follows:
Reaction Type Typical Equation Electrophile E(+)
Halogenation: C6H6 + Cl2 & heat ——> C6H5Cl + HCl Cl(+) or Br(+)
FeCl3 catalyst Chlorobenzene
Nitration: C6H6 + HNO3 & heat ——> C6H5NO2 + H2O NO2(+)
H2SO4 catalyst Nitrobenzene
Sulfonation: C6H6 + H2SO4 + SO3 ——> C6H5SO3H + H2O SO3H(+)
& heat Benzenesulfonic acid

Alkylation: C6H6 + R-Cl & heat ——> C6H5-R + HCl R(+)
Friedel-Crafts AlCl3 catalyst An Arene
Acylation: C6H6 + RCOCl & heat ——> C6H5COR + HCl RCO(+)
Friedel-Crafts AlCl3 catalyst An Aryl Ketone
LESSON 5: RISK, BENEFITS AND USES OF BENZENE
A. TOXICOKINETICS - involves the complete description of the dose of toxic substance uptake into the
body that is absorption of toxic substance, movement of substance in body.
➢ Example: The distribution, conversion of substance to toxic or non-toxic species by bio-
transformation and finally the removal of substances from the body by excretion process.
➢ The total amount of toxic substance which is known as dose of substance can be explained by
using the dose-response relationship.
➢ The high dose of substances can be toxic and poisonous for a body. The higher dose of
substance severs more response and exhibits the toxic effect. However, the effect of toxic
substances depends upon the reactivity of substance as well as on individuals.
➢ Like other aromatic compounds, benzene is also toxic in nature and cause adverse effect. It is
mainly present at automobile service stations, industrial emissions, in tobacco smoke and in
exhaust from motor vehicles.
➢ Out of these sources, tobacco smoke contributes about 50% of the entire exposure. The workers
employed in benzene production industries like storage or transport of benzene, coke and coal
chemical manufacturing, rubber tire manufacturing and petroleum refining are mainly exposed by
high level of benzene.
➢ Around 50% of the benzene in air is absorbed through lungs and absorbed through the
gastrointestinal tract. This absorbed benzene is rapidly distributed in the body and accumulates
in fatty tissues.
➢ The metabolism of benzene produces many reactive metabolites in liver. The low level of these
metabolites can rapidly excrete as conjugated urinary metabolites like muconic acid and S-
phenyl mercapturic acid.
➢ Hence the urinary benzene level is a sensitive bio-marker of low level of exposure of benzene.
The permissible level for benzene in blood is 0.06-0.05 μg/L.
➢ The acute exposure of benzene mainly affects the hematopoietic system, nervous system, and
immune system. Since it is carcinogenic in nature, it can also be responsible for acute
myelogenic leukemia.
B. ENVIRONMENTAL FATE OF BENZENE
Benzene is mainly found in crude oil, gasoline and cigarette smoke. Because of various
industrial processes like burning coal, tobacco smoke, gasoline leaks, it enters in air, water, and soil.
Many natural sources like crude oil seeps, volcanoes and forest fires are also responsible for
exposure of benzene.
Benzene is a degradable substance up to a level by volatilization, bio-degradation under
aerobic conditions or photo oxidation with hydroxyl radicals. In metropolitan areas, it is found around
0.58 ppb in air sample and less than 5 ppb in sediment sample. While the level of benzene found in

surface water samples is around 100 μg/L. The degradation of benzene in air, water and soil results
the formation of other aromatic compounds like nitro benzene, nitro phenols, dihydroxybenzene etc.
MECHANISM OF THE DEGRADATION OF BENZENE IN AIR, WATER AND SOIL:
LESSON 6: USES OF BENZENE
Benzene is the simplest aromatic compound and involves in preparation of many other aromatic
compounds like cumene, aniline, ethylbenzene which are further involve in preparation of resins and
polymers.

C. OTHER USES OF BENZENE:
• Benzene is mainly used as industrial solvent like for decreasing metal and as gasoline additive
which decreases the knocking and increases the octane rating.
• A small amount of benzene used for manufacturing of rubbers, dyes, insecticides, solvents,
fumigants, gasoline, paint removers, drugs, lubricants, detergents, explosives and pesticides.
• Benzene is also used in tire and rubber manufacturing processes as solvent.

➢ Chapters 14
➢ Chapters 15 & 16
I. Study the given structural formulas of some Mono and Di-substituted Aromatic compounds and give
their (a) IUPAC name, and (b) Special Name if there is.
1.
OCH3
2.
OH
3.
NH2

4. O
ll
C–H
5. O
ll
C – OH
6.
CH=CH2
7. CH3
l
CH
l
CH3
8. O
ll
C – CH3
9. OH
CH3
10.
CH3 CH3
II. Nomenclature of Polysubstituted Aromatic Compounds. Name the following aromatic compounds
by their (a) IUPAC, (b) Isomeric name (Ortho, Meta, Para), and (c) Common or Special name if
applicable.
CH = CH2
1.
CH3
CH3
C–OH
2.
CH3

COOH
CH2CH3
3.
CH3
OH
4.
CH3CHCH3
CH3
NO2 NO2
5.
NO2
OH
6.
COOH
NH2
7.
CH3 CH3
CH3
Cl
8.
Cl
OCH3
CH3
Cl F
9.
F Cl

Br Br
10.
OH
OH
11.
OH
CH3 CH3
12. C
H
CH3 CH3
CH2CH3
13. C – CH2 – CH3
CH2CH3
CH3 CH3
14. C – CH2 – C
CH3 CH3
III. REACTIONS OF AROMATIC COMPOUNDS. (a.) Determine the Type of Reaction (1 point); (b.)
Predict and Write the S.F. of the main PRODUCT/S formed by the given reaction (2 points); (c.)
Give the IUPAC name of the MAJOR Product/s formed.
AlCl3
A. + CH3CH2Cl (b.)
(a.) _______________________________ (c.) ______________________________________

CH2CH3 H2SO4, ∆
B. + [O2] (b.)
K2Cr2O7
(a.) ______________________________ (c.) _______________________________________
∆
C. + H2SO4 (b.)
H2SO4
(a.) _______________________________ (c.) _______________________________________
CH3 H2SO4
D. + HNO3 (b.)
∆
(a.) ______________________________ (c.) _______________________________________
FeBr2
E. + Br2 (b.)
(a.) ______________________________ (c.) ______________________________________
CH2CH2CH3
KMnO4
F. + [O2] (b.)
H2SO4, ∆
(a.) _____________________________ (c.) ______________________________________
H+
7.) + CH2 = CH2 (b.)
∆
(a.) ________________________________ (c.) ____________________________________
Ni
8.) + 2H2 (b.)
∆
(a.) _______________________________ (c.) ______________________________________

O
ll AlCl3
9.) + CH3CBr (b.)
(a.) ______________________________ (c.) _______________________________________
H2SO4
10.) + HNO3 (b.)
∆
(a.) ______________________________ (c.) _______________________________________
Experiment #9, #10, and #11

Note: Watch video of Experiment #9 as performed by your Instructor/s in the real laboratory to be posted on

MODULE 8
The Alkyl Halides
13. Named common alkyl halides;
14. Explained the basic physical properties of alkyl halides;
15. Predicted the products of the chemical reactions involving alkyl halides;
16. Recognized the importance and disadvantages of common alkyl halides;
LESSON INTRODUCTION
Our study of organic chemistry is organized into families of compounds classified by their functional
groups. In this lesson, we will consider the properties and reactions of alkyl halides. We use alkyl halides to
introduce substitution and elimination, two of the most important types of reactions in organic chemistry.
Stereochemistry will also play a major role in our study of these reactions. Many other reactions show
similarities to substitution and elimination, and the techniques introduced in this lesson will be used
throughout our study of organic reactions.
There are three major classes of halogenated organic compounds: the alkyl halides, the vinyl halides,
and the aryl halides. An alkyl halide simply has a halogen atom bonded to one of the sp3 hybrid carbon
atoms of an alkyl group. A vinyl halide has a halogen atom bonded to one of the sp2 hybrid carbon atoms of
an alkene. An aryl halide has a halogen atom bonded to one of the sp2 hybrid carbon atoms of an aromatic
ring. The chemistry of vinyl halides and aryl halides is different from that of alkyl halides because their
bonding and hybridization are different. The reactions of vinyl halides and aryl halides will not be discussed
in this lesson.
Halogen-containing organic
compounds are not very
common in nature.
Exceptions occur in ocean
plants and invertebrates,
where organic halides are
common in toxic plants and
venoms. The Cymbal bubble
snail Haminoea cymbalum
discharges kumepaloxane, a
toxic defense chemical
containing both chlorine and
bromine, when it is disturbed
by predatory fishes.

The carbon–halogen bond in an alkyl halide is polar because halogen atoms are more electronegative
than carbon atoms. Most reactions of alkyl halides result from breaking this polarized bond. This versatility
allows alkyl halides to serve as intermediates in the synthesis of many other functional groups.
LESSON 1: NOMENCLATURE OF ALKYL HALIDES
➢ ALKYL HALIDES, (R – X) – are the halogen-substituted aliphatic or alicyclic compounds of alkanes,

alkenes, or alkynes. They are organic halogen compounds in which one or more hydrogen of a
hydrocarbon have been replaced with a halogen (F, Cl, Br, I). They are also known as “organohalides”.
General Formula: R – X ; X = F, Cl, Br, I
Alkyl halides are named in the same way as alkanes, by considering the halogen as a substituent on the
parent chain. There are three steps:
STEP 1: Find the longest chain, and name it as the parent. If a multiple bond is present, the parent chain
must contain it.
STEP 2: Number the carbons of the parent chain beginning at the end nearer the first substituent,
regardless of whether it is alkyl or halo. Assign each substituent a number according to its position on the
chain. If there are substituents the same distance from both ends, begin numbering at the end nearer the
substituent with alphabetical priority.
CH3 Br Br CH3
I I I I
CH3CHCH2CHCHCH2CH3 CH3CHCH2CHCHCH2CH3
1 2 3 l4 5 6 7 1 2 3 l4 5 6 7
CH3 CH3
5 – Bromo – 2,4 – dimethylheptane 2 – Bromo – 4,5 - dimethylheptane
STEP 3: Write the name. List all substituents in alphabetical order and use one of the prefixes di-, tri-, and
so forth if more than one of the same substituent is present.
CH3 Br Cl Br CH3 Cl CH2CH3

I I I I I I I
Br – CH2 - CH – CH2CHCHCH2CH2 CH3 – CH – CH – CH – CH – CH - CH – CH2 - Cl
1 I2 3 4 5 6 7 8 7 I6 5 I4 3 2 1
CH3 CH3 Br
1,3 – Dibromo – 7 – chloro – 1,2 – dimethylheptane 4, 7 – Dibromo – 1,3 – dichloro – 2 – ethyl – 5,6 - dimethyloctane

In addition to their systematic names, many simple alkyl halides are also named by identifying first the alkyl
group and then the halogen.
Examples: CH3I - can be called either iodomethane (IUPAC) or methyl iodide (C.N.)
CH3Cl - chloromethane (IUPAC) or methylchloride (C.N.)
CH2Cl2 – dichloromethane (IUPAC) or methylenechloride (C.N.)
CHCl3 – trichloromethane (IUPAC) or chloroform (C.N.)
CCl4 – Tetrachloromethane (IUPAC) or tetrachlorocarbon (C.N.)
LESSON 2: PREPARATION OF ALKYL HALIDES
1. By addition reactions of Alkyl Halides (HX) and Halogens (X 2) with Alkenes.
Ex. CH2 = CH2 + HCl -------> HCH2 – CH2Cl

Ethene Hydrogen Chloride Chloroethane
CH2 = CH2 + Br2 -------> BrCH2 – CH2Br

Ethene Bromine Dibromoethane
2. By substitution reaction of Chlorine (Cl2) with Alkanes.
Ex. CH4 + Cl2 -------> CH3Cl + HCl

Methane Chlorine Chloromethane Hydrogen Chloride
3. By treating Alcohols with Alkyl Halides (HX).
Ex. Ether
--OH + HCl (g) ------------> --Cl + HOH
0°C
Cyclohexanol Hydrogen chloride Chlorocyclohexane water
Note: Reactions works best with tertiary alcohols. Primary and secondary alcohols react much slowly.
R – OH + H–X ---------> R–X + H – OH
Increasing Reactivity: 1° ROH -----> 2° ROH -------> 3° ROH ;
4. By treating Primary and Secondary Alcohols with either Thionyl Chloride (SOCl 2) or Phosphorus
Tribromide (PBr3)
Ex1.
--OH + SO – Cl2 ------> --Cl + SO2 + HCl
Cyclopentanol thionylchloride chlorocyclopentane sulfurdioxide hydrogenchloride

Ex2. OH Br
I Ether I
3 CH3CH2CHCH3 + PBr3 ---------> 3 CH3CH2CHCH3 + P(OH)3
35°C
2 – Butanol phosphorus tribromide 2 – Bromobutane Phosphorus hydroxide
LESSON 3: REACTIONS OF ALKYL HALIDES
1. Formation and Protonation of Grignard Reagents.
➢ Alkyl halides react with Magnesium metal in Ether solvent to yield Organo-magnesium halides,
called Grignard Reagents after their discoverer, Victor Grignard, Grignard reagents contain a
carbon-metal bond and are thus organometallic compounds.
Ether
R–X + Mg ---------> R – Mg – X
Where: R = 1°, 2°, 3° alkyl, aryl or alkenyl

X = Cl, Br, or I
Ex. Ether
--Cl + Mg ---------> --MgCl
Chlorobenzene Phenylmagnesium Chloride
CH3CH2CH2CH2CH2CH2Br + Mg ---> CH3CH2CH2CH2CH2CH2 – MgBr + HOH --->

1 – Bromohexane 1 – Hexylmagnesium bromide CH3CH2CH2CH2CH2CH3
Hexane (85%)
2. NUCLEOPHILIC SUBSTITUTION REACTIONS
➢ Are substitution reactions of alkyl halides where each step involves the substitution of one
nucleophile (chlorine ion, Cl-, or hydroxide ion, OH-) by another.
➢ It is one of the most common and versatile reaction types in organic chemistry.
➢ It was discovered by the German chemist Paul Walden in 1896.
➢ It occurs by two major pathways, named S N1 reaction and SN2 reaction, where the “SN” part of the
name stands for “substitution, nucleophilic”.
Regardless of mechanism, the overall change during all nucleophilic substitution reactions is the same:
A nucleophile (Nu: or Nu:-) reacts with a substrate , R – X and substitutes for a leaving group, X:- to yield
the product R – Nu.
If the nucleophile is neutral (Nu:), then the product is positively charged to maintain charge
conservation; if the nucleophile is negatively charged (Nu:-), the product is neutral.

Neutral Nu: Nu꞉ + R –-- X R –-- Nu+ + X: --
Negatively charged Nu: -- Nu꞉ -- + R –-- X R –-- Nu + X: --
Examples of Some Nucleophilic Substitution Reactions with Bromomethane:
Mechanism: Nu꞉ -- + CH3Br Nu–-CH3 + Br –
Attacking Nucleophile Products

Formula Name Formula Name
H: -- Hydride CH4 Methane

..
CH3S:-- Methanethiolate CH3SCH3 Dimethyl Sulfide
..
HS:-- Hydrosulfide HSCH3 Methanethiol
N Ξ C:-- Cyanide N Ξ CCH3 Acetonitrile

..
:I: - Iodide ICH3 Iodomethane
..
HO: -- Hydroxide HOCH3 Methanol
..
CH3O: -- Methoxide CH3OCH3 Dimethyl Ether
..
N Ξ N = N:-- Azide N3CH3 Azidomethane
..
:Cl:-- Chloride ClCH3 Chloromethane
CH3CO2:-- Acetate CH3CO2CH3 Methyl acetate
H3N: Ammonia H3N+CH3Br-- Methylammonium bromide
(CH3)3N: Trimethylamine (CH3)3 N+CH3Br-- Tetramethylammonium bromide
3. Formation of an Alkene By Nucleophile Elimination of Hydrogen Halide

R’ R’
I I
Mechanism: R –- C –- X + Nu: -- R = C –- H + H-Nu: + X: --
I
H

Ex.1. CH3 – CH2Br + KOH- CH2 = CH2 + H-OH + KBr –
Bromoethane Potassium hydroxide Ethene Water Potassium bromide
Ex.2. CH3 CH3

I I
H3C –- C –- Br + C=N -- CH2 = C + H–- C=N + Br --
I I
CH3 cyanide CH3 hydrogen cyanide bromide
2 – Bromo – 2 – methylpropane 2 – Methylpropene
LESSON 4: PROPERTIES OF ALKYL HALIDES
1. Physical Properties
Haloalkanes or Halogenated Alkanes – are alkanes that react with halogens in which a hydrogen
atom/s of the alkane is substituted by a halogen atom.
➢ Haloalkanes are liquids, except those with fluorine atoms which are gases.
➢ Those with molecules which have more than one Cl, Br, or I atoms are denser than most other
organic compounds even in water.
2. Chemical Properties
➢ Halogenated hydrocarbons resist combustion or are nonflammable. Their resistance serves as a

plus for the use of haloalkanes in situations where danger of fire would be a serious drawback.
➢ Some haloalkanes are also toxic or carcinogenic.
Examples are:
a. CCl4 – are toxic to liver and kidneys and can be absorbed thru the skin as well as inhalation of
vapors.
b. CHCl3 – Chloroform is carcinogenic (it causes cancer).
Other Chemical Properties of Halogens:
The first two halogens F and Cl are highly electronegative and highly reactive. They can react both in
free radical mechanism as well as ionic. These two are good oxidizing agents.
1. Bromine is moderately reactive and is a moderately strong oxidizing agent.
2. Iodine is weak oxidizing but acts as a reducing agent also.
With various organic functional groups halogens shows different reactive methods and producing
derivatives of the compounds. The types of reactions that halogens can undergo are substitution
reactions, addition reactions electrophilic and nucleophilic reactions.

Halogens react with compounds in two different mechanisms:
1. Free radical
2. Ionic
LESSON 5: USES AND EXAMPLES OF HALOALKANES
1. Used in Dry Cleaning Industry.

➢ Their lack of flammability and ability to dissolve dirt and grease make them very effective.
2. Used as Refrigerants and Propellants.
➢ Example: Freon – it contains chlorine and fluorine and has a number to identify it like Freon 12 –
dichlorodifluoromethane.
➢ Chlorine atoms from Freon molecules react with the ozone layer. Freons can escape from refrigerator
coils or other containers, reach the Stratosphere, and damage the ozone (O 3) layer. Freons in aerosol
propellants represent the most serious threat to the ozone since they are released into the air.
➢ At one time, CCl4 was used as fire extinguishers because of its resistance to combustion. However, in
the presence of oxygen, CCl4 can decompose upon heating to produce a highly toxic compound
known as Phosgene (COCl2) or Carbonyl Chloride.
PHOSGENE Poisoning - produces symptoms of pneumonia like coughing with fever, sore throat,
edema, inflammation of the lungs due to aspiration of foreign materials.
3. Used in the field of Medicine as topical or inhaled anesthetics.

a. Chloroethane or ethylchloride - are used when sprayed on the skin, it vaporizes rapidly drawing
heat from the skin and thus deadening the nerve endings.
b. Haloethanes and Halopropanes – are used as general anesthetics administered by inhalation.
CF3CHClBr – Haloethane CHF2CF2CH2F - Halopropane
4. Other Uses of Organohalides are as:

1. Solvents,
2. Insecticides, herbicides, pesticides,
3. Fire extinguishing chemicals, and
4. Polymers.
In the electronic industry, it relies on halogenated solvents such as “trichloroethylene” for

cleaning semiconductor chips and other electronic components.
Methylchloride (Chloromethane) – is used mainly in making silicone polymers.

Methylenechloride (Dichloromethane) – is a solvent used as a paint remover.
Chloroform (Trichloromethane) – also a solvent, was used as an anesthetic in earlier times , but
such use is now considered dangerous or lethal; Also, 80% of its production was used as
flavorings in cough medicines, but because of evidence of its carcinogenic properties, it was
banned by the U.S. FDA in July, 1978.
Carbon tetrachloride (Tetrachloromethane) – has been used as a dry-cleaning solvent and as a
solvent in fire extinguishers, but it is no longer recommended for either use because exposure to
it can cause severe damage to the liver. As a fire extinguisher, once it reacts with water, it forms
“Phosgene” (COCl2), an extremely poisonous gas that was used during WWI.
DDT (Dichlorodiphenyltrichloroethane) – was a well known insecticide used during WW-II to

combat typhus epidemics in Europe and malaria epidemics in the South Pacific ; it was
discovered by Paul Mueller who was awarded a Nobel Prize in 1948 for its insecticidal
properties. In the early 1970’s, DDT and other related organochlorine insecticides dieldrin, aldrin,
chlordane, and heptachlor were banned by the U.S. EPA (Environmental Protection Agency) due
to their detrimental effect to the environment, except for a few special uses.
➢ Because DDT is a cheap and effective mosquito control agent, underdeveloped countries in
Africa and Latin America have experienced a dramatic increase in malaria deaths following
its removal, and arguments are made for returning it to limited use.
2,4,5-T (Trichlorophenoxy acetic acid) and 2,4-D (Dichlorophenoxy acetic acid) - are common
herbicides that are sold by most garden stores.
PCB’s (Polychlorinated Biphenyls) – are derived from the hydrocarbon biphenyl (C12H10), they
were once widely used as plasticizers and as insulating materials in electric equipment because
of their high electrical resistance. PCBs are now banned because they pose as an environmental
hazard.
Tetrachloroethylene and Triclene – are other chlorinated hydrocarbons used as excellent dry
cleaning agents because of their ability to dissolve fats, oils, and greases. They are relatively
flammable, have no effect on fabrics, and, because of their volatility, they are easily removed.
However, they are hazardous air and water pollutants, and are subject to regulations.
Chloroethene or Vinyl Chloride ( CH 2 = CHCl) – a polymer unit of PVC (Polyvinyl chloride) a

plastic, which are used in the manufacture of such products as floor tiles, raincoats, fabrics, and
furniture coverings. Evidence has shown that several workers exposed to vinyl chloride during
their work have died from a very rare form of liver cancer. In addition, exposure to vinyl chloride
is suspected to be responsible for certain types of birth defects.
Allyl Chloride or 3 – Chloropropene ( CH2 = CHCH2Cl) – a haloalkene with industrial uses.

https://www.academia.edu/42751716/Get_a_Better_Grade_in_Chemistry
➢ Chapter 8 - Haloalkanes, Halogenation, and Radical Reactions
➢ Chapter 10 – Organohalides
I. Properties of Alkyl Halides

A. TRUE OR FALSE. Write the word “TRUE” if the given statement is correct or the word “FALSE” if
the given statement is not correct or erroneous, after each question.
1. The halogen Bromine is moderately reactive and is also a moderately strong oxidizing agent.
2. The halogen Iodine on the other hand is a weak oxidizing agent but acts as a strong reducing
agent.
3. The halogens Fluorine and Chlorine are highly reactive halogens that can react both in a free
radical mechanism as well as ionic.
4. Halogens can react with alkanes under the influence of U.V. or at an elevated temperature by
free radical mechanism.
5. N-Propane on chlorination gives a mixture of 2 – isomers of chloropropanes.
6. N-Butane on chlorination gives a mixture of 3 – isomers of chlorobutanes.
7. Primary carbon atoms has a faster rate of halogenation reaction than tertiary carbon atoms.
8. Iodination is carried out in the presence of an oxidizing agent like H2SO4, or mercuric oxide.
9. Halogenation of aromatic hydrocarbons is much faster than their corresponding alkanes.
10. The carbon-halogen bond in aryl halides are stronger than the C – halogen bond in alkyl
halides.
II. Nomenclature of Alkyl Halides
B. Name the given Organohalides by using the IUPAC Rule.
CH3 Br Br CH3
l l l l
1. CH3 – CH–CH–CH–CH2-CH–CH3
I
l
2. CH3CH=CH–CH2–CH–CH3
Br Cl CH3
l l l
3. CH3 –C–CH2 –CH–CH–CH3
l
CH3
CH2Br
l
4. CH3–CH2–CH–CH2–CH2–CH3
Cl
l
5. Cl–CH2–CH–CH2–CΞC–CH2–Br

III. Structural Formula Writing: Draw structures corresponding to the following IUPAC names:
(a) 2,3-Dichloro-4-methylhexane
(b) 4-Bromo-4-ethyl-2-methylhexane
(c) 3-Iodo-2,2,4,4-tetramethylpentane
(d) cis-1-Bromo-2-ethylcyclopentane
(e) trans-1-Bromo-3-isopropylcyclohexane

MODULE 8
Alcohols, Ethers and Thiols
1. Drawn and created structures of alcohols, ethers and thiols;
2. Enumerated the homologous series of alcohols and thiols;
3. Classified the different types of alcohols and explained the differences;
4. Named alcohols, ethers and thiols by the IUPAC rules and by their common or alternative names;
5. Explained by using chemical equations the synthesis or preparations of alcohols, ethers and thiols;
6. Identified the sources as well as the practical and medical applications of the common alcohols, ethers,
and thiols
7. Simulated the preparation and reactions of alcohols in the laboratory;
8. Differentiated and explained the physical and chemical properties of alcohols, ethers and thiols.
LESSON INTRODUCTION
Alcohols are organic compounds containing hydroxy (¬OH) groups. They are some of the most
common and useful compounds in nature, in industry, and around the house. The word alcohol is one of the
oldest chemical terms, derived from the early Arabic al-kuhl. Originally it meant “the powder,” and later “the
essence.” Ethyl alcohol, distilled from wine, was considered to be “the essence” of wine. Ethyl alcohol (grain
alcohol) is found in alcoholic beverages, cosmetics, and drug preparations. Methyl alcohol (wood alcohol) is
used as a fuel and solvent. Isopropyl alcohol ( rubbing alcohol) is used as a skin cleanser for injections and
minor cuts.
Alcohols are important because they can be converted into many other types of compounds, including
alkenes, haloalkanes, aldehydes, ketones, carboxylic acids, and esters. Not only can alcohols be converted
to these compounds, but these compounds can also be converted to alcohols. Thus, alcohols play a central
role in the interconversion of organic functional groups.
https://anguishedrepose.wordpress.com/tag/rubbing-alcohol/

Alcohols are synthesized by a wide variety of methods, and the hydroxy group may be converted to most
other functional groups. For these reasons, alcohols are versatile synthetic intermediates. In this lessons, we
discuss the nomenclature of alcohols, the physical and chemical properties of alcohols, and summarize the
methods used to synthesize them. In the succeeding lessons, we continue our study of the central role that
alcohols play in organic chemistry as reagents, solvents, and synthetic intermediates.
LESSON 1: GENERAL STRUCTURE AND FORMULA
Alcohols are organic compounds which has the “hydroxyl” (OH) group as their functional group. Alcohols are
present naturally in many products like ethanol and methanol.
General formula of alcohol: R-OH, where R can only be an alkyl group.
LESSON 2: CLASSIFICATION OF ALCOHOLS
A. Nature of the Alkyl Group
Depending on the nature of alkyl group (R) the alcohol are classified as primary, secondary, tertiary, vinyl,
allyl and benzyl alcohol.
1. Primary alcohol
➢ Here the functional group is attached to a primary carbon atom - a carbon atom which is connected to
exactly one carbon atom. Ethanol is an example for primary alcohol.
2. Secondary alcohol
➢ Here the functional group is attached to a secondary carbon atom which is exactly connected to two
carbon atoms. 2-propanol is an secondary alcohol.
3. Tertiary alcohol
➢ Here the functional group is attached to a tertiary carbon atom which is exactly connected to three
carbon atoms. 2-methyl-2-propanol is an example for tertiary alcohol.
4. Vinyl alcohol
➢ It is an alcohol where the functional group is directly attached to a carbon containing double bond. 1-
Ethen-1-ol is an example for vinyl alcohol.

5. Allyl alcohol
➢ It is an alcohol where the functional group is directly attached to a carbon which is connected to
unsaturated carbon. 2 - Propen-1-ol is an example for allyl alcohol.
6. Benzyl alcohol
➢ Here the functional group is attached to a carbon chain containing the benzene ring. The structure of
benzyl alcohol is given below.
B. Hydroxyl Classification
Alcohols can also be classified with the number of OH groups attached.
1. Monohydric or Monohydroxy Alcohol
➢ When the alcohol contains only one OH it is called as mono hydric alcohol.
Example: Ethanol – H3CH2OH
2. Dihydric or Dihydroxy Alcohol
➢ When the compound contains two OH group it is called as di hydric alcohol.
Example: Ethylene glycol – CH2OH-CH2OH
3. Trihydric or Trihydroxy Alcohol
➢ An alcohol is called as tri hydric alcohol when there are three OH group attached in the compound.
Example: Glycerol – CH2OH-CHOH-CH2OH

LESSON 3: SYNTHESIS AND PREPARATION OF ALCOHOLS
1. Hydration of Alkenes
a. Alkenes on hydration in the presence of dilute acids give alcohols.
Example1: ethylene on hydration gives ethyl alcohol.
CH2=CH2 + H2O → CH3-CH2-OH
Example2: Hydration of propene gives 2-propanol in according to Markovnikov's rule. The reaction
involves protonation of alkene followed by addition of water.
2. Reduction of Aldehydes, Ketones, or Acyl Chlorides

a. Alcohols are synthesized by reduction of aldehyde with lithium aluminum hydride. Reduction of
aldehyde generally gives primary alcohols.
Example: acetaldehyde ---- ethyl alcohol
CH3-CHO → CH3-CH2-OH
b. Similarly ketones on reduction give secondary alcohols .
Example: acetone on reduction gives 2-propanol.
c. Acetyl chloride on strong reduction gives ethyl alcohol.
CH3-COCl → CH3CHO → CH3-CH2-OH
LESSON 4: NOMENCLATURE: IUPAC AND COMMON/ALTERNATIVE
1. Alcohols are named after the parent alkane chain by replacing ‘ane’ in the parent alkane chain with
‘ol’.
Example: CH3 –OH methanol
2. If the compound contains branches then the longest chain is selected as parent chain and other alkyl
groups are treated as substituents.

Example:
2 methyl Butanol
3. If the compound contains more than two carbon atoms then the position of attachment of OH group
should be indicated.
Example:
2-Butanol
4. In case of compounds containing more than one functional group, the order of priority should be
followed. The halogens will have least priority than alcohols and other functional groups like acids will
have more priority than alcohol.
5. For polyhydroxy alcohols, give the numbers of the carbon atoms to which the – OH groups are
attached (separated from each other by a coma) hyphenated, then give the name of the
corresponding alkane followed by the prefix based on the number of –OH groups (di-, tri-, ect.) and
end with the suffix –ol.
Example: OH – CH2CH2 – OH 1,2 – Ethanediol
6. For alcohols derived from cycloalkanes, simply attach the prefix cyclo– before the name of the parent
alcohol name.
OH
Example: H3C CH3 4,4 – Dimethylcyclohexanol
Other Examples of Alcohols and their Classifications:

7. The common name of alcohols is usually formed by giving the name of the alkyl group that is
attached to the –OH group followed by the word alcohol.
Chemical IUPAC Name Common Name Other Common

Formula Name
Monohydric alcohols
CH3OH Methanol Methyl alcohol Wood alcohol
C2H5OH Ethanol Ethyl alcohol Grain alcohol
C3H7OH n-Propanol Propyl alcohol Rubbing alcohol
C5H11OH n-Pentanol Pentyl alcohol Amyl alcohol
C16H33OH n-Hexadecanol Hexadecyl alcohol Cetyl alcohol
Polyhydric alcohols
C2H4(OH)2 Ethane-1 ,2-diol none Ethylene glycol
C3H5(OH)3 Propane-1 ,2,3-triol none Glycerin
C4H6(OH)4 Butane-1 ,2,3,4-tetraol none Erythritol
C5H7(OH)5 Pentane-1 ,2,3,4,5-pentol none Xylitol
C6H8(OH)6 Hexane-1 ,2,3,4,5,6-hexol none Mannitol, Sorbitol
C7H9(OH)7 Heptane-1 ,2,3,4,5,6,7-heptol none Volemitol
Unsaturated aliphatic alcohols

C3H5OH Prop-2-ene-1-ol none Allyl alcohol
C10H17OH 3,7-Dimethylocta-2,6-dien-1-ol none Geraniol
C3H3OH Prop-2-in-1-ol none Propargyl alcohol
Alicyclic alcohols
C6H6(OH)6 Cyclohexane-1 ,2,3,4,5,6-geksol none Inositol
C10H19OH 2 - (2-propyl)-5-methyl-cyclohexane-1-ol none Menthol
LESSON 5: PHYSICAL PROPERTIES

• Alcohols are colorless liquids with characteristic smell.
➢ Alcohols with C1 to C4 are colorless liquids
➢ Alcohols with C5 to C11 are semisolids to solids.
➢ Low molecular weight alcohols have flowery odors;
➢ Heavier alcohols are odorless solids,
➢ For polyhydroxy alcohols – sweetness increases as the number of –OH groups increases.

• They are soluble in water
➢ Alcohols with one to three carbon atoms are infinitely soluble in water.
➢ Alcohols with four or more carbon atoms have limited solubility in water (except tert. Butyl
alcohol).
• Relatively high boiling points. They are high boiling liquids due to presence of hydrogen bonding.
➢ Normal alcohols - their boiling point increases with increase in the length of carbon chain and
increase in the number of hydroxyl groups. So, ethylene glycol will have a higher boiling point
that ethanol.
➢ Branched chain alcohols have lower boiling points than the corresponding straight-chain
alcohols.
LESSON 6: CHEMICAL PROPERTIES
Alcohol are polar molecules due to the presence of OH functional group. The OH functional group
can release proton in solution and hence alcohol are slightly acidic. In the second case the OH functional
group can altogether be replaced. So the reaction of alcohols are classified as:
1. Reactions involving acidic hydrogen

2. Reactions involving hydroxyl functional group
LESSON 6A: REACTIONS OF ALCOHOLS
1. Reaction with Sodium

➢ Alcohols react with sodium to give sodium alkoxide and hydrogen. This is the characteristic reaction
of alcohol and is often used in organic analysis to identify the alcohol.
2CH3-CH2-OH + 2Na → 2CH3-CH2-ONa + H2
2. Reaction with Acids (Esterification Reaction)

➢ Alcohols condense with acids in the presence of concentrated sulfuric acid to give ester. For example
ethyl alcohol condense with acetic acid to give ethyl acetate.
CH3-CH2-OH + CH3-COOH → CH3-CH2-O-CO-CH3 + H2O
3. Reaction with Acidified Potassium Permanganate (Oxidation Reaction)

➢ Primary alcohols on oxidation give aldehyde which easily undergoes oxidation to give carboxylic acid
with same number of carbon atoms.
➢ Secondary alcohols on oxidation gives ketone which is difficult to oxidize further.
CH3-CH2-OH → CH3-CHO → CH3-COOH
4. Reaction with PCl5, PCl3, SOCl2

➢ Alcohols react with chlorinating agents like phosphorus pentachloride, phosphorus trichloride and
thionyl chloride to give chloroalkanes.
➢ Examples:
CH3-CH2-OH + PCl5 → CH3-CH2-Cl + POCl3 + HCl
CH3-OH + SOCl2 → CH3-Cl + SO2 + HCl
5. Reaction with Ammonia

➢ Alcohols react with ammonia to give a mixture of amines.
➢ The reaction yields depend on the concentration of ammonia and alcohol.
CH3-OH + NH3 → CH3-NH2 + H2O

CH3-NH2 + CH3-OH → CH3-NH-CH3 + H2O
CH3-NH-CH3 + CH3-OH → CH3-N-(CH3)2 + H2O
6. Dehydration Reaction
➢ Alcohols undergo intra-molecular dehydration with concentrated sulfuric acid to give alkene.
➢ For example, ethanol on dehydration gives ethene and propanol on dehydration give propene.
CH3-CH2-OH → CH2=CH2 + H2O

CH3-CH2-CH2-OH → CH3-CH=CH2 + H2O
➢ At elevated temperature alcohols undergo intermolecular dehydration to give ethers.

CH3OH + CH3OH → CH3-O-CH3 + H2O
7. Oxidation of Alcohols (Combustion Reaction)

➢ Alcohols readily undergo oxidation.
➢ Low molecular mass alcohols like methanol and ethanol undergo oxidation with the atmospheric
oxygen initial ignition and completely get oxidized.
➢ This process is called combustion.
C2H5OH + O2 → CO2 + H2O + Heat
LESSON 6B: CATALYZED OXIDATION OF ALCOHOLS
A. Primary Alcohol to Carboxylic Acid

➢ Primary alcohols can easily be converted in to carboxylic acids by complete oxidation process using
oxidizing agents.
➢ Oxidation of the primary alcohol can be done by the reduction of chromate ion or dichromate ion or
permanganate ion or by oxygen from nitric acid decomposition.
➢ Both cyclic and acyclic primary alcohols undergo this reaction.

With HNO3 or taking in to account the oxygen only the equation will be
RCH2OH + 2[O] → RCOOH + H2O
The overall reaction with dichromate ion is given below.
3RCH2OH + 2Cr2O72- + 16H+→ 3RCOOH + 4Cr3+ + 11H2O
LESSON 7: USES, IMPORTANCE AND FUNCTIONS OF SOME COMMON ALCOHOLS
A. METHANOL, CH3OH
➢ Simplest compound of alcohol
➢ It is a colorless and odorless liquid that is used as a solvent and a starting material for the synthesis
of “methanal or formaldehyde”.
➢ Also called “wood alcohol” because it was formerly produced by the destructive distillation of wood (in
the absence of air to prevent ignition).
➢ Etymology of its name can be traced to this process. In Greek, “methe” means “wine” and “hyle”
means “wood”; methyl alcohol was the “wine of wood”.
➢ The “reduction of CO2 with Hydrogen” is the source of large scale production of methanol since the
early 20th century up to the present.
➢ Potential Sources:
❖ Coal
❖ Burnable materials such as wood, agricultural wastes,
❖ Sewage sludge
➢ A very volatile liquid (b.p. 65°C),
➢ Highly flammable liquid
➢ Very poisonous when ingested in small quantities and capable of causing blindness since it damages
the optic nerve; death can also result.
➢ Uses:
❖ Conversion of formaldehyde (methanal), primarily for use in the manufacture of polymers

❖ Manufacture of other chemicals, especially various kinds of esters
❖ Denaturing ethyl alcohol rendering it unfit as a beverage
❖ An industrial solvent
❖ Added to gasoline (in 10% solution known as gasohol) to reduce the amount of CO 2 emissions in
air
❖ Also used as a gasoline solvent especially for racing cars
B. ETHANOL, CH3CH2OH
➢ Is a colorless and odorless to quite flowery smell liquid and is the alcohol in alcoholic beverages.
➢ It is the 2nd compound in the homologous series of alcohols.
➢ The earliest and most widely known alcohol.
➢ Commonly called as “ethyl alcohol”, “grain alcohol” or “beverage alcohol” or “spirits”, because it can
be produced by the fermentation of natural sugars and hydrolyzed starches (for legal use in
beverages) which are found in grapes and grains;
➢ Large part of ethanol for industrial uses is made by the acid catalyzed Hydration of Ethylene (made
from petroleum).
➢ Pure ethanol is highly hygroscopic
➢ Acts physiologically as:
❖ Food – the body is able to metabolized it to CO2 and H2O with the production of energy.
❖ Drug – a depressant (hypnotic or sleep producer). It depresses activity in the upper brain even
though it gives the illusion of being a stimulant.
❖ Poison – ethanol is also toxic, but it is much less toxic than methanol. In rats the lethal dose of
ethanol is 13.7 g kg-1 of body weight. In larger quantities, ethanol causes nausea, vomiting,
impaired perception, and incoordination. If a very large amount is consumed, unconsciousness
and ultimately death may occur.
• Excessive consumption of ethanol (from liquor) damages the liver (Cirrhosis) and causes
obesity.
[O]
• Ethanol --------> Ethanal (Acetaldehyde) ; a very toxic substance
[O]
• Ethanal --------> Ethanoic Acid (Acetic Acid) ; a source of biochemical energy
• Our bodies secrete enzymes called “alcohol dehydrogenase” which helps in oxidizing
ethanol to acetaldehyde.
• It is the acetaldehyde that causes the “hang-over” symptoms that we experience everytime
we consume a large amount of alcohol.
❖ Most cases of mentally retarded babies are born from alcoholic mothers, the effect of FAS (Fetal
Alcohol Syndrome).
➢ Uses:
❖ An intermediate in the manufacture of other chemicals such as acetaldehyde (ethanol), acetic
acid, ethyl acetate and diethyl ether.

❖ A solvent for many organic substances (tincture of iodine – a disinfectant, which is a mixture of
iodine solution and ethyl alcohol).
❖ Is often used as a solvent for perfumes, varnishes and some medicines like antiseptics and
mouthwashes.
❖ Solutions of 70% ethanol are also used to sterilize surgical equipment because it destroys
bacteria by coagulating protein.
❖ An essential component in alcoholic beverages
➢ Sources of Ethanol: yeast
Fermentation process: C6H12O6 (Glucose) ---------> 2C2H5OH (Ethanol) + 2CO2 (Carbon dioxide)
(enzyme)
• This is commonly thought of as the process for the natural production of ethanol. Yet it is a
much more universal process, encompassing a metabolic change caused by living
microorganism acting on organic materials.
• It is one of the oldest chemical processes used by humans.
• Fermentation is responsible for the aging of meat and cheese, and also the production of
bread, foods, animal feeds, drugs, antibiotics, hormones, and other materials.
• In 1857, Louis Pasteur, proved that alcoholic fermentation is caused by living cells (yeast).
• Beverages produced by the fermentation process are: Beers, Wines (natural, sparkling,
aromatic), and Distilled Spirits (Whiskey, Rum, Gin, Vodka, Scotch, Bourbon, etc.)
• The ethanol content of distilled spirits is expressed in terms of “Proof” = 2 x (% Volume
Ethanol).
➢ Other uses:
❖ To produce “Absolute Alcohol” – pure ethanol form that is often found in laboratories or in the form
of a solution containing 5% H2O (or 95% Ethanol).
❖ To prepare “Denatured alcohol” – ethanol that has been made unfit to drink by the addition of
small quantities of a poison such as “methanol” or “benzene” for use in some laboratories (as fuel
in alcohol lamps) and factories.
C. 2 – PROPANOL (ISOPROPYL ALCOHOL), CH3CH(OH)CH3
➢ It is a colorless and has a very slight aromatic odor liquid.

➢ It is not a potable alcohol since it is very toxic when ingested.
➢ Commonly called “Rubbing Alcohol” because patients with high fevers were often given baths of this
alcohol to reduce body temperature, where rapid evaporation of this alcohol results in fast skin
cooling. This practice is no longer commonly used.
➢ It is made from the “Hydration of Propene” derived from petroleum:
H+
CH3CH=CH2 + HOH ---------> CH3CHCH3
l
OH

➢ Uses:
❖ to manufacture other chemical – like acetone
❖ to make industrial solvents
❖ principal component in rubbing alcohol formulations
❖ as disinfectants
❖ to make an astringent (skin–drying agents)
❖ a raw material in the synthesis of organic materials
D. 1,2 – ETHANEDIOL (Ethylene Glycol); HO – CH2CH2 – OH

➢ The simplest polyhydroxy alcohol, containing 2 – OH groups.
➢ It is commercially derived from petroleum
➢ Very soluble in water, has low freezing point, and high boiling point
➢ Uses:
❖ In the preparation of the synthetic polyester fiber “Dacron” and the film “Mylar”
❖ As major ingredient in “permanent-type” antifreeze agents for automobiles and cooling systems
like air-conditioning units.
❖ As solvents in the paints and plastics industries
❖ In the formulations of printing ink and ink for ballpoint pens
➢ It has a very slight flowery odor and “sweet” taste (1/6 as sweet as sugar) but is extremely poisonous.
For this reason, color additives are used in anti-freeze to ensure that it is properly identified.
E. 1,2 – PROPANEDIOL (Propylene Glycol); HO – CH2CH(OH)-CH3

➢ It is a dihydroxy alcohol, containing 2 – OH groups also similar to ethanediol.
➢ is used as an environmentally friendly engine coolant because it is biodegradable, has a high boiling
point, and is miscible with water.
➢ Propylene glycol is now widely used as a low-toxicity alternative to ethylene glycol.
F. 1,2,3 – PROPANETRIOL (Glycerol); HO – CH2CH(OH)CH2 – OH

➢ It is also called “Glycerine”
➢ It is a viscous sweet tasting nontoxic liquid. It is about 6/10th (six-tenths) as sweet as cane sugar
➢ It is a hygroscopic substance
➢ It is very soluble in water
➢ It is obtained as a by-product of the processing of animal and vegetable fats to make soap and other
products
➢ It is also synthesized commercially from propene
➢ Uses:
❖ Raw material in the manufacture of polymers and explosives
❖ Emollient in cosmetics and pharmaceuticals
❖ Lubricant
❖ As a “humectant” – an agent that attracts and retains moisture; to preserve moistness in tobacco
products, cosmetics and the like because of its ability to H-bond with water molecules.
❖ Sweetener

❖ As ingredients in shaving creams and in cough drops and syrups because of its soothing
qualities.
❖ Can be converted into “Nitroglycerin” by treatment with concentrated Nitric and Sulfuric acids.
• “Nitroglycerin” or Glyceryl Trinitrate – is a very powerful liquid explosive which can decompose
into a hot gas that can expand 10,000 to 20,000 times its original volume.
• It is a “shock sensitive” explosive.
• Medically, nitroglycerine can also be used as a “vasodilator” – a medication taken by heart
patients to relieve angina pain; because of its ability to expand.
G. POLYHYDROXY ALCOHOLS
➢ Are alcohols with more than one hydroxyl group per molecule. Two of the most important examples
are ethylene glycol and glycerol.
➢ Are very important molecules in living cells.
➢ Many important biological molecules, including sugars (carbohydrates), fats (lipids), and proteins,
contain hydroxyl groups, thus they are also considered as polyhydroxy alcohols.
❖ Examples: O OH OH OH OH OH
ll l l l l l
1. Glucose – also called “Blood sugar” has the formula: HC – CH – CH – CH – CH – CH2
O
ll
2. Monolaurin – a “lipid” with the structural formula: CH2 – O – C – (CH2)10 – CH3
l
CH2 – OH
l
CH2 – OH
3. Lysine Vasopressin – a “protein”, with a partial structure of:
O O
ll ll
NH2 – C – CH2 – NH –-- CH –--- CH – NH – C – CH – NH2
l l l
(CH2)3 CH2 CH2 – SH
l l
NH2 C6H5–OH
4. Albuterol – used in some commonly prescribed respiratory medications (an asthma

medication).

➢ Chapters 11, pages 489 – 508

➢ Chapter 10, pages 437 - 477
CHEMICAL CONNECTIONS: Blood Alcohol Screening
Potassium dichromate oxidation of ethanol to acetic acid is the basis for the original breath alcohol
screening test used by law enforcement agencies to determine a person’s blood alcohol content. The test is
based on the difference in color between the dichromate ion (reddish orange) in the reagent and the
chromium(III) ion (green) in the product. Thus, color change from reddish orange to green can be used as a
measure of the quantity of ethanol present in a sample of a person’s breath.
In its simplest form, a breath alcohol screening test consists of a sealed glass tube containing a
potassium dichromate-sulfuric acid reagent impregnated on silica gel. To administer the test, the ends of the
tube are broken off, a mouthpiece is fitted to one end, and the other end is inserted into the neck of a plastic
bag. The person being tested then blows into the mouthpiece until the plastic bag is inflated. As breath
containing ethanol vapor passes through the tube, reddish orange dichromate is reduced to green
chromium(III). The concentration of ethanol in the breath is then estimated by measuring how far the green
color extends along the length of the tube. When the green color extends beyond the halfway point, the
person is judged to have a sufficiently high blood alcohol content to warrant further, more precise testing.
O
H2SO4 ll
CH3CH2OH + K2Cr2O7 CH3C – OH + Cr3+
H2O
Ethanol Potassium Acetic acid Chromium (III) ion
Dichromate (green)
(reddish orange)
The Breathalyzer, a more accurate testing device, operates on the same principle as the simplified
screening test. In a Breathalyzer test, a measured volume of breath is bubbled through a solution of
potassium dichromate in aqueous sulfuric acid and the color change is measured spectrophotometrically.
These tests measure alcohol in the breath. The legal definition of being under the influence of alcohol,
however, is based on blood alcohol content, not breath alcohol content. The chemical correlation between
these two measurements is that air deep within the lungs is in equilibrium with blood passing through the
pulmonary arteries, and an equilibrium is established between blood alcohol and breath alcohol. It has been
determined by tests in a person drinking alcohol that 2100 mL of breath contains the same amount of
ethanol as 1.00 mL of blood.

Copyright 2018 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part. WCN 02-200-203
Thiols and Ethers
LESSON INTRODUCTION
Ethers are the organic compounds having two alkyl or aryl groups bonded to an oxygen atom, as in the
formula R1–O–R2. The oxygen of an ether has “single bonds” to two different (or similar) carbons, which
maybe either aliphatic or aromatic carbons or both. The oxygen atom in ether, like alcohols and phenols, use
sp3 – hybrid orbitals in forming bonds.
Like alcohols, ethers are related to water, with alkyl groups replacing the hydrogen atoms. In an
alcohol, one hydrogen atom of water is replaced by an alkyl group. In an ether, both hydrogens are replaced
by alkyl groups. The two alkyl groups are the same in a symmetrical ether and different in an unsymmetrical
ether.
A thiol is a compound which contains an SH functional group . The -SH group itself is called a mercapto
group. A disulfide is a compound containing an -S-S- linkage. (Organic) sulfides have the structure R-S-R′,
and are therefore the sulfur analogues of ethers. The nomenclature of sulfides can be easily understood if
one understands the nomenclature of the corresponding ethers. Notice that the term “thio” is also used in
inorganic chemistry. For example, SO42− is the sulfate ion; while S2O32−, in which one of the oxygen atoms of
a sulfate ion has been replaced by a sulfur atom, is called thiosulfate. Thiolate anions, RS-, are analogous to
alkoxy anions, RO-. Thiolate anions are better nucleophiles than are alkoxy anions.
LESSON 1: NOMENCLATURE OF ETHERS
The two Structural Formulas of Ethers are shown below:
R – O – R’ = RO – R’
Lewis Structure Common Structural Formula
Where: R and R’ = both aliphatic, aromatic or a combination of aliphatic and aromatic HC’s.
The functional group in ethers is called the “Alkoxy” group, (RO–) consists of either an alkyl or aryl group
and an oxygen atom. Any ether is a “constitutional isomer” of an alcohol containing the same Molecular
Formula (M.F.), C2H6O, but differ in their formulas and possess very different properties.

Example: CH3 – O – CH3 - Dimethyl Ether (Methoxy Ether)
CH3CH2 – OH - Ethyl Alcohol (Ethanol)
M. F. : C2H3O
A. IUPAC NOMENCLATURE
The ether functional group does not have a characteristic IUPAC nomenclature suffix, so it is necessary to
designate it as a substituent. To do so the common alkoxy substituents are given names derived from their
alkyl component,
Alkyl Alkoxy
Name Name
Group Group
CH3– Methyl CH3O– Methoxy
CH3CH2– Ethyl CH3CH2O– Ethoxy
(CH3)2CH– Isopropyl (CH3)2CHO– Isopropoxy
(CH3)3C– tert-Butyl (CH3)3CO– tert-Butoxy
C6H5– Phenyl C6H5O– Phenoxy
a. Select the longest carbon continuous chain and label it with the name of the corresponding alkane.
b. Change the – yl ending of the other hydrocarbon group to – oxy to obtain the “alkoxy” name.
c. Combine the two names in steps a and b, giving the alkoxy name and its position on the longest carbon
chain to form the ether name.
Examples:
CH3CH2 – O – CH2CH3 Ethoxyethane
CH3CH2CH2 – O – CH2CH2CH2CH3 1 – Propoxybutane
CH3 CH3 CH3

l l l
CH3CH – O – CHCH2CHCH3 2 – Isopropoxy – 4 – methylpentane
CH3CH – O – CH2CH3 2 – Ethoxypropane

l
CH3
–O– Phenoxybenzene
–O–CH2CH2CH2CH3 Butoxycyclohexane
B. COMMON AND MISCELLANEOUS NAMES
➢ Simple ethers are given common names in which the alkyl or aryl groups bonded to the oxygen are named
in alphabetical order followed by the word "ether".
➢ Many simple ethers are symmetrical, in that the two alkyl substituents are the same. These are named as
"dialkyl ethers".
Examples:
CH3 – O – CH3 Dimethyl ether Methoxymethane
CH3CH2 – O – CH2CH3 Diethyl ether Ethoxyethane
CH3 – O – CH2CH3 Ethylmethyl ether Methoxyethane
–O– Diphenyl ether Phenoxybenzene
CH3
l
– O – CH – CH3 Isopropylphenyl ether Isopropoxybenzene
CH3 – O – CH2CH2 – O – CH3 Ethylene glycol dimethyl ether (glyme)
Other examples below show the common name and IUPAC name of some complex ethers.

LESSON 2: PROPERTIES OF ETHERS
➢ The oxygen atom causes the ether molecule to have a bent shape somewhat like that of water and alcohol
molecules.
➢ Ethers are somewhat more polar than alkanes and much less polar than alcohols.
➢ Boiling point is somewhat above that of the HC’s, but much lower than that of the more polar alcohol of the
same molecular mass.
➢ b.p. increases with increasing molecular mass, however diethyl ether has the same b.p. as pentane (35°C)
➢ They are almost soluble in water as are alcohols because Hydrogen bonding with water is more limited
because there are no – OH groups in ethers. Ethers cannot Hydrogen bond with themselves, but they can
H – bond with water.
➢ Ethers are mainly used as solvents for many organic compounds (especially diethyl ether).
➢ Ethers are unreactive towards acids, bases, and oxidizing agents, and for this reason, are often used as
solvents or catalysts to carry out chemical reactions.
➢ Like alcohols, ethers are extremely volatile and highly flammable .
➢ Ethers have little reactivity, but their use can be dangerous since low molecular weight ethers are “volatile”
and their “highly flammable vapors” form explosive mixtures with air called – “peroxides” – that are subject
to explosive decomposition when it reacts with oxygen in air.
➢ Ethers also produces unconsciousness by depressing the activity of the central nervous system.
LESSON 3: PREPARATION OF ETHERS
A. INTERMOLECULAR DEHYDRATION OF PRIMARY ALCOHOLS
➢ Ethers are usually prepared from alcohols or their conjugate bases by heating in the presence of an acid
catalysts (H2SO4 @ 140°C).
H2SO4, 140°C
R–O–H R – O – R’ + R = R’ or H2O
1° Alcohol – H2O Ether (major) Alkene (minor)
Examples:
CH3CH2 – OH CH3CH2 – O – CH2CH3 + CH2 = CH2

Ethanol Diethyl ether Ethylene
CH3CH2CH2 – OH CH3CH2CH2 – O – CH2CH2CH3 + H2O

1 – Propanol Dipropyl ether water
➢ 2°ROH and 3°ROH “DO NOT” form ethers when heated with an acid catalyst. “Intramolecular
dehydration” to alkenes is the major product at all temperatures.
B. WILLIAMSON “ETHER” SYNTHESIS
➢ A substitution reaction done by reacting “Alkyl Halides” and “Sodium Alkoxides” or “Sodium Phenoxides”.
➢ It proceeds by an SN2 reaction of an alkoxide nucleophile with an alkyl halide.
➢ Williamson Ether Synthesis, discovered more than 100 years ago, is still the best method for preparing
both symmetrical and unsymmetrical ethers.
➢ The alkoxide ion needed in the reaction is usually prepared by reaction of an alcohol with sodium or
potassium metal.
STEP 1: R–O–H + 2 Na+ 2 R – O- Na+ + H2

Alcohol Sodium metal Sodium alkoxide Hydrogen gas
STEP 2: 2 R – O- Na+ + R–X R – O – R’ + Na+X-

Sodium Alkoxide Alkyl Halide Ether Sodium Halide
Examples: CH3CH2 – O – Na + CH3CH2 – Cl CH3CH2 – O – CH2CH3 + NaCl

Sodium Ethoxide Ethyl Chloride Diethyl ether Sodium Chloride
LESSON 4: IMPORTANCE AND USES OF SOME COMMON ETHERS
1. Diethyl Ether – the most commonly known ether. It is used mainly as a solvent because it dissolves many
organic substances that are insoluble in water.
It boils at 36°C, and so it evaporates readily (highly volatile), making it easy to recover dissolved materials.
It is highly flammable to explosive.
It was introduced in 1842 by Charles Jackson, a Boston chemist, who anesthetized himself with Diethyl
ether; who also persuaded a dentist, William Morton, to use it – who discovered its anesthetic properties.
Subsequently, they persuaded a surgeon, John Warren, to give a public demonstration of surgery under
anesthesia, where the operation was a complete success, and soon a general anesthesia for surgery by
diethyl ether was routine for gen. surgery because it slows down the operation of the central nervous
system.

It was once the most widely used anesthetic for surgery but it is rarely used in humans today because of
its undesirable side-effects, such as post-anesthetic nausea and vomiting, and its irritating effect on the
respiratory passages. Furthermore, when mixed with air in the right proportions, it is explosive.
2. Divinyl Ether (or Vinethene®) and Methoxyflurane or Penthrane® (CHCl 2CFOCH3) – are ethers that were
eventually used as general inhalation anesthetics. But are no longer used today because it causes irritation
of the respiratory passages, which causes nausea and vomiting after its use.
3. Methylpropyl Ether (CH3 – O – CH2CH2CH3) – is an anesthetic known as Neothyl® (brand name).
4. Enflurane – is an inhalation anesthetic used toady and is a halogenated ether also known as Enthrane®
(the Merck Index. 12th ed., #3621), CHF2 – O – CF2 – CHClF.
5. Isoflurane – another inhalation anesthetic that is also a halogenated ether which is also known as Forane®
(the Merck Index. 12th ed., #5191), CHF2 – O – CHCl – CF3.
6. Methyl Tert-Butyl Ether (MTBE), (CH3)3COCH3 – an ether that was once produced in large volume, and it
is added to gasoline as an “antiknock agent” to increase the octane rating and reduce the emission of
carbon monoxide in automobile exhaust gas .
7. Ethylene Oxide – a cyclic ether produced in the largest amount commercially, is used to sterilize medical
instruments and as an intermediate in the synthesis of non-ionic surfactants (soaps & detergents).
It is a toxic gas used to make ethylene glycol, an antifreeze agent.
O H2 OH OH
+ H2O l l
CH2 – CH2
Ethylene Oxide Water Ethylene glycol
It is also used in the manufacture of polyester fibers and other plastics.
8. Tetrahydrofuran and Dioxane – are used as important solvents in the laboratory since they are inert and do
not react with most reagents like DEE.
LESSON 5: THIOLS NOMENCLATURE AND PROPERTIES
Thiols – are the sulfur analogs of alcohols, also called “ mercaptans” (R –SH).
The functional group of thiols (– SH) is called the “sulfhydryl” which are also referred to as the
“mercapto group”.
Thiols are named in the same way as alcohols, with the suffix – thiol used in place of – ol.
The prefix thio denotes replacement of a functional oxygen by sulfur. Thus, – SH is a thiol and C=S a
thione.

➢ Nomenclature of Thiols:
a. CH3–SH methanethiol (IUPAC) methyl mercaptan (C.N.)

b. CH3CH2SH ethane thiol ethyl mercaptan
c. CH3CHCH3 2 – propanethiol isopropyl mercaptan
l
SH
d. CH3CH2CHCH3 2 – butanethiol sec-butyl mercaptan

l
SH
Thiols have a higher molar mass than their corresponding alcohols, but boil at a lower temperature
than alcohols.
Thiols have “foul” odors
They are oxidized to “disulfides”
Thiols are stronger acids than their equivalent alcohols and phenols.
Importance in the Living System:

1. The disulfide structure often binds proteins into biologically useful three-dimensional shapes.
2. It is also a key part of a molecule (CoA – Coenzyme A) that plays a central role in the metabolism
of carbohydrates, lipids and proteins.

➢ Chapter 11, pages 491 – 497
➢ Chapter 10, pages 437 - 477
I. Nomenclature of Alcohols: Write the Correct IUPAC Name of the given Alcohols below.
Structural Formula of Alcohol IUPAC NAME
1. CH3CH-CH2CH2-CH-CH3
l l
CH2 OH
l
CH3
2. CH3CH-CH2CH–CH-CH3
l l l
CH2 OH OH
l
CH3
3. CH3CH–CH–CH2-CH2
l l l
CH3 OH CH3
4. HO OH
CH2CH3
5. CH3CH-CH2CH=CH-CH2OH
l
OH
Br Cl
6. l l
CH3–C–CH–CH2-CH2–Cl
l
OH
7.
OH
OH
8. l
CH–CH3
9. OH CH3
l
CH – CH3
OH
9.
HO
II. CLASSIFICATION OF ALCOHOLS. Determine if the given structural formulas is (a) primary, (b) secondary,
or (c) tertiary alcohol.
1. CH3CH-CH2CH2CH2CH2OH
l
OH

2. CH3CH2CH2CH2CH2OH
Br Cl
l l
3. CH3–C–CH–CH2-CH2–OH
l
Br
4. OH
OH Cl
l l
5. CH3–C–CH2–CH–CH2–OH
l
OH
CH3
6. OH
OH
CH3
III. STRUCTURAL FORMULA WRITING: Write a structural formula for each of the following compound.
(1) 5-Methyl-2-hexanol
(2) 2-Methyl-2-propyl-1,3-propanediol
(3) cis-3-Isobutylcyclohexanol
(4) 2,2-Dimethyl-1-propanol
(5) Allyl alcohol
(6) trans-2-Vinylcyclohexanol
(7) 5-Methyl-2-hexen-1-ol
(8) 2-Propyn-1-ol
(9) 3-Chloro-1,2-propanediol
(10) cis-3-Pentene-1-ol
IV. SYNTHESIS OF ALCOHOL

1. Starting with each of the following organic compounds, outline a practical synthesis or the preparation
of 1-Butanol.
(a) 1-Butene
(b) 1-Chlorobutane
(c) 2-Chlorobutane
(d) 1-Butyne
V. CHEMICAL REACTION OF ALCOHOLS
(A.) Give the IUPAC NAME of the REACTANT/S; (B) Predict and Write the S.F. of the MAJOR PRODUCT/S
formed by the reaction; (C.) Give the IUPAC name of the PRODUCT/S formed. (D.) Determine the Specific
TYPE of REACTION.
K2Cr2O7
1. CH3 – CH – CH3 -----------------> (B.)
l concd. H2SO4; Δ
OH
(C.) ________________________________
(A.) ___________________________ (D.) ________________________________
OH
l 96% H2SO4
2. CH3 – OH + CH3CH2CHCH3 -----------> (B.)
140°C; Δ
(C.) _______________________________
(A.) ___________________________ (D.) _______________________________
CH3
l ZnCl 2
3. CH3 – C – OH + HBr -------> (B.)
l Heat
CH3 (C.) _______________________________
(A.) __________________________ (D.) _______________________________
concd. H2SO4
4. CH3CH2CH2CH – CH3 -------------> (B.)
l 180°C; Δ
OH (C.) _________________________________

(A.) __________________________ (D.) _________________________________
K2Cr2O7
5. CH3CH2CH2CH2 – OH -----------------> (B.)
concd. H2SO4; Δ
(C.) __________________________________
(A.) ___________________________ (D.) ________________________________
O
ll concd. H2SO4
6. CH3CH2– C–OH + CH3CH2OH ------------> (B.)
(C.) _________________________________
(A.) _______________________________ (D.) _______________________________
EXPERIMENT NO. 12: PROPERTIES AND SPECIFIC TESTS FOR ALCOHOLS & PHENOLS
MODULE 9
Phenols
1. Drawn the structures of common phenolic compounds;
2. Named the common phenolic compounds using IUPAC rules and their corresponding common or
alternative names;
3. Identified the sources and the practical and medical applications of phenols;
4. Described and the physical properties of phenols;
5. Illustrated the chemical reactions of phenols.
LESSON INTRODUCTION
Phenols (“Feenols”) – are the aromatic compounds containing the one or more hydroxyl groups
bonded on a benzene ring, and all other derivatives of phenol are called as phenolic compounds. Phenol
was first isolated from coal tar in 1834 and found naturally in coal and decaying dead organic matter like
rotting vegetables. In 1867, Sir Joseph Lister (1827 – 1912), who learned from Louis Pasteur’s research
on bacteria, discovered that solutions of “phenol” kill bacteria. In the laboratory, phenol is prepared by
prolonged sulphonation of benzene which produces a benzene sulphonic acid. The molecular formula of
phenol is C6H5OH with molecular mass 94.11 g mol−1. Phenol is a white crystalline compound with a
melting point 182° C and boiling point 41° C. Phenol is also called as benzenol, phenylic acid, carbolic
acid, hydroxybenzene or phenic acid and it has a sweet odor and is widely used as in low cost, versatile
resins - mainly thermoset resins like in construction, plywood adhesion and the motorcar industry.
LESSON 1: NOMENCLATURE OF PHENOLS
➢ The simplest derivative of benzene is phenol, which is also accepted by IUPAC system.
➢ In IUPAC nomenclature, phenol is named as benzenol.
➢ If in a compound the hydroxyl group presents as a principal functional group, it must be considered as
a derivative of phenol and can be named as a substituted phenol in which the hydroxy group numbered
as one.
➢ For example, the systematic name for thymol is 5-methyl-2-isopropylphenol.
Thymol Vanillin
➢ In the presence of other principal functional groups, phenols can be named with the hydroxyl group as a
hydroxy substituent. For example, vanillin is named as 4-hydroxy-3-methoxybenzaldehyde.
TABLE 11.1. SOME PHENOLIC COMPOUNDS WITH THEIR COMMON NAME
Common name IUPAC name

Phenol Benzenol
o-cresol 2-Methyl benzenol
m-cresol 3-Methyl benzenol
p-cresol 4-Methyl benzenol
Pyrocatechol Benzene-1,2-diol
Resorcinol Benzene-1,3-diol
Hydroquinone Benzene-1,4-diol
n-Hexyl resorcinol 4-Hexyl resorcinol
Methyl salicylate Methyl-2-hydroxy benzoate
Vanillin 4-Hydroxy-3-methoxybenzaldehyde
Eugenol 4-Allyl-2-methoxyphenol
Thymol 5-Methyl-2-isopropylphenol

Picric acid 2,4,6-Trinitro phenol
o-Bromophenol 2-Bromophenol
p-Hydroxybenzoic acid 4-Hydroxybenzoic acid
LESSON 2: CHEMICAL PROPERTIES OF PHENOLS
A. ACIDITY OF PHENOLS
➢ Compared to alcohols, phenols are stronger acids than alcohols. Because of their acidic nature,
phenols can turn blue litmus paper to red and react with aqueous alkali to form phenoxide ion or
phenate.
➢ Compared to carboxylic acids, phenols are weaker acid.
➢ Electron donating groups like amino (-NH2) and alkyl (-R) decreases the acidity of phenol.
➢ For example, cresol or methylphenols are less acidic compared to phenol due to positive
inductive effect as well as hyperconjugation of the methyl group.
B. REACTIONS OF PHENOLS
1. Reactions that Involve the Cleavage of Oxygen-Hydrogen Bond
(a) Reaction with Metal: Phenol reacts with metals like sodium metal to form sodium phenoxide and
releases hydrogen gas.
(b) Reaction with Acid Chloride and Anhydrides: Phenol reacts with acid chloride (RCOCl) and acid
anhydride (RCOOCOR) to form esters. Reaction is catalyzed by pyridine or any acid like concentrated
sulfuric acid.
C6H5OH + RCOCl → C6H5 OCOR + HCl
C6H5 OH + RCOOCOR → C6H5 OCOR + RCOOH
The reaction of phenol with benzoyl chloride (C6H5 COCl) in the presence of aqueous sodium hydroxide
yields phenyl benzoate (C6H5OCOC6H5 ) and reaction is called as Schotten-Baumann reaction.
C6H5 OH + C6H5COCl → C6H5 OCO C6H5 + HCl
(c) Reaction with Grignard Reagent: Phenol reacts with Grignard reagent (RMgX) to form alkane.
C6H5 OH + RMgX → RH + Mg(OC6H5)X
2. Reactions that Involve the Cleavage of Carbon-Oxygen Bond.

(a) Reaction with Phosphorus Halide: Phenols reacts with phosphorus halide like PCl5 to form
chlorobenzene with triphenylphosphate (C6H5 O)3P=O).
C6H5 OH + PCl5 → C6H5 Cl + (C6H5O)3P=O
(b) Reaction with Ammonia: Phenol reacts with ammonia at 573 K temperature and high pressure in the
presence of ZnCl2 to form aniline (C6H5NH2) and water.
C6H5 OH + NH3 → C6H5 NH2+ H2O
(c) Reaction with Zinc Dust: This reaction is used for the preparation of benzene as phenol forms benzene in
the presence of zinc dust at high temperature.
∆
C6H5OH + Zn → C6H6 + ZnO
3. MISCELLANEOUS REACTIONS
A. SUBSTITUTION REACTIONS: Phenol undergoes electrophilic substitution reactions readily and forms
polysubstitution products.
(1.) Bromination: Phenol forms polyhalogen derivatives with chlorine or bromine water.
Example: with bromine water, it forms 2,4,6-tribromophenol which is precipitated as white precipitate.
(2.) Nitration: Phenol forms –o and –p-nitrophenol with dilute nitric acid, while with concentrated nitric acid, it
forms picric acid (2,4,6-trinitrophenol).

(3.) Friedel Craft’s Alkylation: Phenol undergoes alkylation with alkyl halide in the presence of anhydrous AlCl3
and forms alkyl substituted phenol.
C6H5OH + CH3Cl → C6H5OH(CH3) + HCl
(4.) Friedel Craft’s Acylation. This is also possible with phenol to form –o and –p-hydroxyacetophenone.
LESSON 3: TEST FOR PHENOLS
There are several tests for phenol like:

Phenol solutions turn blue litmus paper to red.
Phenols react with ferric chloride solution to give blue, violet or green coloration due to the formation
of ferric phenoxide.
Phenols react with diazonium salts in weak alkaline medium to form yellow or orange colored azo-
dyes.
Phenol forms white precipitate with bromine water
LESSON 4: PHENOLIC DERIVATIVES

A. RESORCINOL
Resorcinol is an aromatic diol with two hydroxy groups at meta position and named as m-
dihydroxybenzene or 1,3-benzenediol. Another common name used for resorcinol is resorcin .
➢ Resorcinol is a white solid which crystallized as colorless needles from benzene.
➢ It is easily soluble in water as well as in ethene and alcohol but insoluble in chloroform and carbon
disulfide.
➢ This diol is an essential component of an adhesive system which is widely used in the tire
manufacturing process and other fiber-reinforced rubber mechanical goods.
➢ Resorcinol is used to manufacture agricultural chemicals, pharmaceuticals, explosive
primers, dyestuffs, flame retardants, fungicidal creams, lotions and antioxidants.
➢ It is also used to improve the mechanical and chemical resistance of paper machine fabrics.
B. THYMOL
• Another name for Thymol is 2-isopropyl-5-methylphenol (IPMP) with molecular formula C10H14O (molar
mass 134.24 g/mol).
➢ It is in a colorless, translucent crystalline, also exists in flake form at room temperature.
➢ It is found in Thyme oil and can be extracted from various plants like Thymus vulgaris (chemotype
thymol), Thymus (chemotype carvacrol), and Thymus serpyllum (Wild thyme or mother of thyme).
➢ Other common names of Thymol are mint flavouring, 3-hydroxy-p-cymene, isopropyl cresol, 6-isopropyl
m-cresol and 4-methyl-2-hydroxyisopropylbenzene.
➢ m.p. of Thymol is 49°C and b.p. is 233°C.
➢ It is a stable molecule and less reactive to strong oxidizing agents, organic materials and strong bases.
➢ It is extremely soluble in alcohols and other organic solvents while slightly soluble in water, also soluble
in strongly alkaline aqueous solutions.
➢ Thymol has shown antibacterial activity against bacterial strains like Aeromoans hydrophila and
Staphylococcus aureus, thus it is widely used in mouthwash, toothpaste, breath freshener, body powder
and household cleaners.
➢ Because of its degradable nature it is widely used as pesticide agent and offers a safe alternative
compare to other more persistent chemical pesticides which can be dispersed in runoff and responsible
for subsequent contamination.

C. CRESOL
➢ Cresols are also called Methylphenols. Cresols are mainly found in coal tar.
➢ Cresol can be considered as methyl derivative of phenol or hydroxy derivative of phenol.
IUPAC Name of the 3 – Structural Isomers of Cresols:
1. o-cresol: 2-methylphenol or 2-hydroxytoluene – a colorless crystals; density is 1.05g/cm3
2. p-cresol: 4-methylphenol or 4-hydroxytoluene – thick and viscous liquid; density is 1.03g/cm3

3. m-cresol: 3-methylphenol or 3-hydroxytoluene – greasy-looking solid; density is 1.02g/cm3
➢ Cresols show almost the same chemical and physical properties. Hence it’s difficult to separate them
from their mixture which is obtained from coal tar and known as cresylic acid.
➢ Cresols act as precursor in the manufacture of disinfectants and synthetic resins.
➢ They are highly corrosive in nature and can injure eye, skin, mouth and gastrointestinal tract.
➢ Some common adverse effects of cresols are nausea, diarrhea, hypotension, vomiting, neurological
changes, myocardial failure, liver and renal toxicity, pulmonary edema, hemolysis and
methemoglobinemia.
D. PHENYL ACETATE
Esterification of phenol in the presence of acetic anhydride yields phenyl acetate. It can also be
produced by decarboxylation of aspirin or by reaction of phenol with acetic acid.
➢ Phenyl acetate is a clear colorless liquid with a sweetish solvent odor.

➢ Boiling point of phenyl acetate is 196 °C, density 1.073 g/mL at 25 °C.
➢ It is a quite stable, combustible compound and incompatible with strong acids and base as well as with
strong reducing agents and strong oxidizing agents.
➢ It is slightly soluble in water and mainly used as a laboratory reagent in the production of some organic
chemicals.
➢ Inhalation or contact with phenyl acetate may irritate or burn skin and eyes.
➢ Phenyl acetate is corrosive in nature and vapors of phenyl acetate may cause dizziness or suffocation.
E. XYLENOL
Aromatic compounds with two methyl group and one hydroxyl group are known as
Xylenol or dimethylphenol. Xylenol is a trivial name made up of the combination of Xylene and phenol.
Six positional isomers of Xylenol:

• 2, 3 – dimethylphenol, 2, 4 – dimethylphenol, 2, 5 – dimethylphenol, 2, 6 – dimethylphenol, 3, 4 –
dimethylphenol, and 3, 5 – dimethylphenol

➢ Xylenols are used to manufacture for a number of pesticides and other compounds like antioxidants.
➢ One of the derivatives of Xylenol – Xylenol orange is a redox indicator and 2,6-Xylenol acts
as monomer for an engineering resin like poly (p-phenylene oxide).
F. ETHYLPHENOL
Ethylphenol have three position isomers; 2-ethylphenol, 4-ethylphenol and 3-ethylphenol.
4-ethylphenol is more common and also abbreviated as 4-EP.
Biochemically Ethylphenol is produced by p-coumaric acid .
➢ Ethylphenols are naturally-occurring phenolic compounds like para-ethylphenol which is produced at

low concentrations by yeast in beer and wine.
➢ The mixture of all isomers of Ethylphenol is called as cresylic acids.
➢ Ethylphenol mainly involves in the manufacturing of resins and plastics for circuit boards, can coatings
and laminates.
LESSON 5: OTHER PHENOLIC COMPOUNDS OF IMPORTANCE
Generally phenolic compounds have strong antiseptic and antibacterial properties and act as nerve
stimulants and immunostimulants. They can cause hepatotoxicity as well as irritating for the skin.
A. SOME OTHER PHENOLIC COMPOUNDS WITH THEIR USES AND STRUCTURES
Phenolic Compound Structure Application

Used to produce other organic compounds
Bisphenol A
like ketones and phenol / cresol
Butylated Hydroxy Toluene

An antioxidant and food additive
(BHT)
Capsaicin Main component of chili peppers
A good solvent, disinfectants and

deodorizers. Also used in the preparation of
Cresol
other phenolic compounds. Found in coal
tar and creosote.
Estradiol A component of hormones
Eugenol the main component of oil of clove
Present in galls or cecidia. Galls are a kind

of swelling growth on the external tissues of
plants, fungi, or animals. Like plant galls are
Gallic acid
abnormal outgrowths of plant tissues,
similar to benign tumors or warts in
animals.
Present in in roasted coffee ,whisky, and

Guaiacol
smoke with smoky flavor,
4-Nonylphenol A product of detergents and nonoxynol-9
A good fungicide which is used for waxing

Orthophenyl phenol
citrus fruits

An explosive, main component of burn
Trinitrophenol or Picric acid
ointments
Phenolphthalein An indicator used in acid-base titration
Polyphenol A flavonoids and tannins
Propofol Used as an anesthetic
Serotonin A natural neurotransmitters
Adrenaline or Epinephrine A natural neurotransmitters
Thymol or (2-Isopropyl-5-
Used as an antiseptic in mouthwashes
methyl phenol)
Tyrosine An amino acid
Xylenol Used in antiseptics & disinfecticides

A synthetic form of the female hormone
Diethylstilbestrol (DES)
estrogen.
A dopamine pro-drug.
It is used to treat hypotension (low blood
L-DOPA pressure), low cardiac output, and reduced
perfusion of body organs due to shock,
trauma, and sepsis.
A major component of the essential oil of

Methyl salicylate
wintergreen
Used in preparation of different drugs but

Salicylic acid mostly used in the preparation of ASA
(Acetyl Salicylic Acid) or Aspirin.
An ingredient in Lysol.
2-Benzyl-4-chlorophenol They are currently used as disinfectants,
bacteriostats, sanitizers and microbiocides.
A nonirritating topical antiseptic and

4-Chloro-3,5- disinfectant which is used in a number of
dimethylphenol antibacterial soaps.
( or Chloroxylenol) It is used for skin disinfection and cleaning
(also known as para-chloro- surgical instruments, and also used in a
meta-xylenol, PCMX) number of household disinfectants and
wound cleaners.
The primary use for BHA is as an
antioxidant and preservative in food, food
Butylated Hydroxy Anisole packaging, animal feed, cosmetics, rubber,
(BHA) or 2-tert-butyl-4- and petroleum products. It is also
methoxyphenol commonly used in medicines, such as
isotretinoin, lovastatin, and simvastatin,
among others.
Present in skin irritants like in poison ivy
Catechol, or 1,2-
plants.
benzenediol, or 2-
It is a common building block in organic
hydroxyphenol,
synthesis.
Resorcinol, or 3- An antiseptic and disinfectant which used in
Hydroxyphenol, or m- the treatment of psoriasis, eczema, and
Dihydroxybenzene other skin conditions.
It is used in medicine as a topical and
urinary antiseptic, anthelmintic, cleanser for
4-Hexylresorcinol skin wounds, and anesthetic for throat pain.
Components in mouthwashes, throat
lozenges, and some skin medications.

It is also used to lighten the dark patches of
skin (also called hyperpigmentation,
melasma, "liver spots," "age spots,"
Hydroquinone, or 1,4-
freckles) caused by pregnancy, birth control
benzenediol, or 4-
pills, hormone medicine, or injury to the
hydroxyphenol,
skin. This medicine works by blocking the
process in the skin that leads to
discoloration.
Used as a precursor to a variety of
insecticides including carbaryl and
1-Napthol, or 1-
pharmaceuticals including nadolol as well
Hydroxynaphthalene
as for the antidepressant sertraline and the
anti-protozoan therapeutic atovaquone.
4-tert-Butylcalix[4]arene or capable of forming coordination complexes

Calixarenes with a wide variety of metal ions
LESSON 6: ANTIOXIDANT PROPERTIES OF PHENOLIC COMPOUNDS
Antioxidant action of phenolic compounds is due to their high tendency to chelate metals with heavy metals
like iron and copper. In human body as well as in plant system, free radicals are main component which can
easily damage cell due to the presence of free electrons.
Some phenolic compounds like vitamin-E and polyphenols are good antioxidants.
1. Vitamin-E
Vitamin-E is a fat soluble vitamin which are generally found in nuts, vegetables and fish oils.
➢ It is not a single molecule but a family of molecule in which four are called as tocopherols and the rest
of the four are known as tocotrienols.
➢ This vitamin is involved in the transportation of lipids and cholesterol in the blood which has high
concentration of polyunsaturated fatty acid and prone to oxidation.
➢ In this case Vitamin-E attacks itself by free radicals and become a shield over blood system to
protect oxidation.

2. Polyphenols
These phenolic compounds have one or more hydroxyl groups which are bonded with an aromatic ring.
➢ Around more than 8000 naturally occurring polyphenols are known.
➢ They have great tendency to bond with metal ions to form complexes.
➢ They generally form bond with iron (Fe) which exist as free radicals.

`https://www.academia.edu/34592551/Solomons_Fryhle_Organic_Chemistry_10_Edition
➢ Chapter 14, pages 641 – 650
Google class as schedul
MODULE 10
ALDEHYDES & KETONES
1. Named aldehydes and ketones by their IUPAC names, as well as their corresponding common or
alternative names;
2. Illustrated and explained the common preparations or syntheses of aldehydes and ketones;
3. Enumerated and discussed the uses and functions of common aldehydes and ketones
4. Identified the sources, the practical and medical applications of hydrocarbons;
5. Simulated the preparation and reactions of aldehydes and ketones in the laboratory;
6. Differentiated and explained the physical properties of aldehydes and ketones;
7. Categorized the different chemical reactions of aldehydes and ketones.
LESSON INTRODUCTION
This module begins with the study of carbonyl compounds—compounds containing the carbonyl group,
C=O. Aldehydes, ketones, carboxylic acids, and the carboxylic acid derivatives (esters, amides, anhydrides,

and acid chlorides) are all carbonyl compounds. The following lessons will focus on the nomenclature,
properties, and characteristic carbonyl group reactions of aldehydes and ketones.
Carbonyl compounds are everywhere. In addition to their uses as reagents and solvents, they are
constituents of fabrics, flavorings, plastics, and drugs. Many biologically important molecules like proteins,
carbohydrates, and nucleic acids that make up all plants and animals, contain carbonyl groups, and carbonyl-
group reactivity plays an important role in many biological reactions. In the succeeding lessons, we’ll consider
a number of these reactions and how they relate to the laboratory reactions that you will learn later.
Aldehydes and Ketones are characterized by the presence of the “carbonyl group” (–C=O), perhaps the
most important functional group in organic chemistry. The carbon atom of a carbonyl group must form two (2)
other bonds in addition to the carbon oxygen double bond in order to have four bonds. The nature of these two
additional bonds determines the type of carbonyl containing compound it is.
1. Aldehyde – have a carbon group (R-) as one of the two attached bonds to the carbonyl group and at
least one hydrogen atom. The other group may be to another hydrogen atom, an alkyl or cycloalkyl
group, or an aromatic ring system.
➢ The –CH=O group characteristic of aldehydes is often called a “formyl group”.
2. Ketone – are the organic compounds that have two other carbon groups connected to the carbonyl
carbon atom. The two other carbon atoms must be a part of an alkyl, cycloalkyl or aromatic group.
Note: The carbonyl group of an aldehyde is flanked by a hydrogen atom, while the carbonyl group of a
ketone is flanked by two carbon atoms. For example:

LESSON 1: NOMENCLATURE OF ALDEHYDES AND KETONES
A. NOMENCLATURE OF ALDEHYDES
1. The IUPAC name for an aldehyde is obtained from the parent alkane by removing the final -e and
adding “-al”. The parent chain must contain the –CHO group, and the –CHO carbon is always numbered
as carbon 1. For example:
O O O O O
ll ll ll ll ll
CH3CH2 – C – H CH3CH2CH2CH2 – C – H CH3CH2CH=CHCH2CH2 – C – H HC–CH2 –CH
3 2 1 5 4 3 2 1 7 6 5 4 3 2 1 1 2 3
Propanal Pentanal 4 – Heptenal Propanedial
2. For substituted aldehydes, we number the chain starting with the aldehyde carbon. For example:
CH3 O Cl Cl O O CH2CH3 O
l ll l l ll ll l ll
CH3CH – C – H CH3CH-CH-CH2 – C – H H–C–CH2CH=CH-CH-CH2 – C – H
3 2 1 5 4 3 2 1 7 6 5 4 3 2 1
2–Methylpropanal 3, 4 – Dichloropentanal 3–Ethyl – 4 – Hepten-dial
3. For more complex aldehydes in which the –CHO group is attached to a ring, the suffix “carbaldehyde” is
used:
–CHO H3 C – – CHO
Cyclohexanecarbaldehyde 3 – Methyl -2-cyclobutenecarbaldehyde

(Formylcyclohexane) (3 – Formyl – 1 – methylcyclobutene)
4. Some simple and well known aldehydes also have common names as shown by the table below.
Condensed Structure IUPAC Common Name

H-CHO Methanal Formaldehyde
CH3CHO Ethanal Acetaldehyde
CH3CH2CHO Propanal Propionaldehyde
CH3CH2CH2CHO Butanal Butyraldehyde
CH3CH2CH2CH2CHO Pentanal Valeraldehyde
CH3CH2(CH2)2CH2CHO Hexanal Caproaldehyde
CH3CH2(CH2)3CH2CHO Heptanal Enanthaldehyde
CH3CH2(CH2)4CH2CHO Octanal Carpryllaldehyde
CH3CH2(CH2)5CH2CHO Nonanal Pelargonaldyhyde
CH3CH2(CH2)6CH2CHO Decanal Capraldehyde
CHO Benzaldehyde Benzenecarbaldehyde
➢ In the common system of nomenclature, substituted aldehydes are named as derivatives of the
straight-chain parent compound (see above table). Greek letters are used to indicate the position of
the substituents. The carbon atom bonded to the carbonyl group is the α-carbon the next is the β-
carbon, and so on.
Examples:
CH3 O Cl Cl O
l ll 5 l 4 l 3 2 1ll
CH3CH – C – H CH3CH-CH-CH2 – C – H
γ β α δ γ β α
β – methyl propionadehyde γ, δ – Dimethyl valeraldehyde
CH2CH3 O
7 6 5 4 3 l 2 1 ll
CH3–CH2CH-CH2-CH-CH2 – C – H γ – ethyl, ε – methyl enanthaldehyde
lε δ γ β α
CH3
B. NOMENCLATURE OF KETONES
1. For ketones the final -e is replaced by -one, and a number indicates the position of the carbonyl group
wherever necessary. Examples:
O O O O
ll ll ll ll
CH3CH2 – C – CH2CH3 CH3CH2CH2CH2 – C- CH3 CH3CH2 – C– CH CH2–C–CH2CH2CH3
1 2 3 4 5 6 5 4 3 2 1 1 2 3 4 5 6 7 8 9
3 – Pentanone 2 – Hexanone 3,6 – Nonadione

(Diethyl ketone) (Butylmethyl ketone)

2. The carbon chain in ketones is numbered such that the carbonyl carbon gets the lowest possible
number. For example:
O O O O
ll ll ll ll
HC Ξ C – C – CH2CH3 CH3 – C – CH=CH – C – CH3 CH3CH2CH=CHCH2 – C – CH2CH2CH3
1 2 3 4 5 6 5 4 3 2 1 9 8 7 6 5 4 3 2 1
1– Pentyn – 3 – one 3 – Hexen – 2,5 – dione 6 – Nonen – 4 – one
3. The positions of the other substituents are specified by numbers as usual. The following examples
illustrate these principles.
5 6
CH3 O CH2CH3 Br Cl O OH O O O OH
l ll l l l ll l ll ll ll l
CH3CH – C – CHCH3 CH3CHCHCH2 – C – CH3 CH2C – C– CH=CH– C– CH2CH2
1 2 3 4 6 5 4 3 2 1 1 2 3 4 5 6 7 8
2,4–Dimethylhexanone 5–Bromo–4–chloro–2–hexanone 1,8-Dihydroxy-4-octen-2,3,6-trione
CH3
HO
=O =O =O
Cyclohexanone 4 – Hydroxy – 2 – cyclopentenone 2 – Methylcyclohexanone
4. In still other cases, traditional or common names are used.
O O O O
ll ll ll ll
– C –CH3 –C – -–C–- CH3-C-CH3
Acetophenone Benzophenone Acetone

(Methylphenyl ketone) (Diphenyl ketone) Dicyclopropyl ketone Dimethyl ketone
➢ The common name or alternative system for naming ketones are formed by adding the word ketone
to the names of the alkyl or aryl groups (the substituents) attached to the –C=O group. For example,
the compound below is 2-butanone in the IUPAC system as described.
➢ However, this molecule also can be named methyl ethyl ketone (or ethyl methyl ketone) and is
commonly referred to in industry as MEK (methyl ethyl ketone).

LESSON 2: SYNTHESIS OR PREPARATIONS OF ALDEHYDES AND KETONES
1. By Ozonolysis of Alkenes. Alkenes react with ozone to form ozonides which on subsequent reductive
cleavage with zinc dust and water or H2/Pd give aldehydes, Ketones or a mixture of both depending on
the substitution pattern of the alkene.
➢ Zinc dust removes H2O2 formed, which otherwise can further oxidize the aldehyde formed to acids.
Using a suitable alkene, the desired aldehyde or ketone can be formed.
➢ Example:
2. By Hydration of Alkynes. Ethynes adds water in the presence of H2SO4 and HgSO4 to give
acetaldehyde.
➢ Hydration of other alkynes under similar condition gives ketones.
3. By Oxidation of Methylbenzenes. Oxidation of an aromatic compound leaving a methyl group at the

benzene ring with CrO3 in the presence of acetic anhydride followed by hydrolysis gives the
corresponding benzaldehyde.

➢ Further oxidation of the benzaldehyde to benzoic acid is prevented as the aldehyde is trapped by acetic
anhydride as a non-oxidizable benzylidene diacetate derivative. This reaction is called the “Etard
Reaction”.
4. From Nitriles. Partial reduction of nitriles with acidified stannous chloride SnCl2/HCl at room
temperature gives aldehydes. In the first step imine hydrochloride is obtained which on subsequent
hydrolysis with boiled water gives aldehyde. This specific type of reduction of nitriles is called
“Stephen's reduction”.
SnCl2 + 2HCl → SnCl4 + 2 [H]
➢ Similarly, Benzonitrile gives Benzaldehyde.
LESSON 3: PROPERTIES OF ALDEHYDES AND KETONES
1. Aldehydes and Ketones are polar compounds and, as a result, have higher boiling points than
ethers, hydrocarbons, and non-polar compounds of comparable molecular weight.
2. There is No H-bonding between aldehyde or ketone molecules, and this lack of Hydrogen bonding
is why these compounds have lower boiling points than alcohols and carboxylic acids, compounds
in which there is H-bonding between molecules.
Name Structural Formula Molecular Weight Boiling Point (bp), °C

Diethyl ether CH3CH2OCH2CH3 74 34
Pentane CH3CH2CH2CH2CH3 72 36
Butanal CH3CH2CH2CHO 72 76
2-Butanone CH3CH2COCH3 72 80
1-Butanol CH3CH2CH2CH2OH 74 117
Propanoic acid CH3CH2COOH 72 141
Formaldehyde HCHO 30 – 21
Acetaldehyde CH3CHO 44 21
Propanal CH3CH2CHO 58 49
Acetone CH3OCH3 58 56
Pentanal CH3CH2CH2CH2CHO 86 103
2-Pentanone CH3COCH2CH2CH3 86 102
3-Pentanone CH3CH2COCH2CH3 86 102
3. Because the oxygen atom of the carbonyl groups of aldehydes and ketones are hydrogen bond
acceptors, the low molecular weight aldehydes and ketones are more soluble in water than are
nonpolar compounds of comparable M.W.
4. As the number of hydrocarbons increases, aldehydes and ketones become less soluble in water.
Name (IUPAC) Structural Formula Molecular Weight Solubility (g/100 g. water)
Formaldehyde HCHO 30 Infinite
Acetaldehyde CH3CHO 44 Infinite
Propanal CH3CH2CHO 58 16
Butanal CH3CH2CH2CHO 72 7
Hexanal CH3CH2 (CH2)3CHO 129 Slight
Acetone CH3OCH3 58 Infinite
2-Butanone CH3CH2CH2COCH3 72 26
3-Pentanone CH3CH2COCH2CH3 86 5
5. Most aldehydes and ketones have strong odors. The odors of ketones are generally pleasant, and
many are used in perfumes and as flavoring agents. The odors of aldehydes vary from foul odor to
pleasant ones. Many higher aldehydes, however, have pleasant odors and are also used in
perfumes.
Examples of Aldehydes found in Nature:

a. 2-Methylbutanal – nutty flavor of cheddar cheese
b. Benzaldehyde - oil of almonds, used as food flavoring
c. Cinnamaldehyde - oil of cinnamon, used as food flavoring
d. Citronellal - citronella oils; used as flavoring
e. Citral - lemon grass oil, used as flavoring
f. Vanillin - vanilla bean, used as food flavoring

Examples of Ketones in Nature:
a. Muscone - from the musk of deer used in perfumes
b. ß-Ionone – oil of violets, used in perfumes
c. Butanedione (Biacetyl) – flavoring for margarine
d. Carvone – oil of spearmint, used as flavoring
e. Cortisone – hormone used in protein metabolism; inflammation reducer
f. Progesterone – female sex hormone
g. Testosterone – male sex hormone
LESSON 4: REACTIONS OF ALDEHYDES AND KETONES
1. Oxidation
Aldehyde are oxidized to carboxylic acids by a variety of oxidizing agents, including potassium
dichromate. Aldehyde are also oxidized to carboxylic acids by the oxygen in the air.
➢ Ketones in contrast resist oxidation by most oxidizing agents, including potassium dichromate and
molecular oxygen. The fact that aldehydes are so easy to oxidize and ketone does not. To distinguish
between these types of compounds simple chemical tests are carried out.
➢ Suppose that we have a compound we know is either an aldehyde or a ketone. To determine which it is
we can treat the compound with a mild oxidizing agent. If it can be oxidized it is a aldehyde otherwise its
a ketone.
➢ One reagent which has been used for this purpose is Tollens reagent.
2. Reduction
Aldehydes are reduced to primary alcohols and ketones are reduced to secondary alcohols .
The reduction of a C = O double bond under these conditions is slower than the reduction of a C = C
double bond. Thus if the same molecule contains both C = O and C = C double bonds, the C = C double
bond is reduced first.

3. Formation of Acetals
It is well known that distilled alcoholic beverages contain a group of aroma compounds called acetals.
Acetals are formed by a reaction in which an aldehyde molecule adds a molecule alcohol to form a
labile hemiacetal. This combines with a second molecule of the alcohol and yields a stable acetal.
The reaction is catalyzed by acids but it is reversible , and consequently acetals are hydrolyzed in dilute
alcoholic solution when acids are present. Ketones react in a similar way to form ketals.
A. What is an Acetal?
Acetal is defined as "A molecule containing two OR groups bonded to the same carbon".
The acetal group serves as a good "protecting group". That is since the acetal is inert to most
substances, this "protects" the molecules in question from undergoing unwanted reactions.
B. Acetal Formation
Aldehydes and ketones undergo a reversible reaction with alcohols in the presence of an acid catalyst
to yield acetals, R2C(OR)2, compounds that have two ether like -OR groups bonded to the same carbon.
Acetal formation involves the acid catalyzed nucleophilic addition of an alcohol to an aldehyde or
ketone in a process analogous to that of the acid catalyzed addition of water.
Before elaborating some of the specific methods for cyclic acetal formation we might first consider a few
general principles which apply to acyclic as well as cyclic acetal formation.
1. Acetals are more easily prepared from aldehydes than from ketones.
2. Cyclic acetals are easier to form than acyclic acetals.
3. Conjugation deactivates the carbonyl group towards acetalization.
4. Sterically hindered carbonyls react more slowly.
5. In aromatic aldehydes and ketones electron donating substituents on the arene ring retard acetal
formation whereas electron withdrawing substituents facilitate it.
6. Gem-dialkyl substitution as in 2,2-dimethylpropan-1,3-diol, promotes cyclic acetal formation.
C. Acetal Hydrolysis

Acetal can be hydrolyzed to regenerate the aldehyde or ketone from which it was made. Protonation of
one oxygen atom occurs as the first step, and then a molecule of alcohol is displaced to produce the
resonance stabilized carbocation intermediate.
The carbocation is subsequently intercepted by a molecule of water and deprotonation yields the
hemiacetal.
4. Cannizzaro’s Reaction
Cannizzaro’s reaction is named after Stanislao Cannizzaro. In cannizzaro reaction, the following takes
place in the presence of base.
HCHO + HCHO ----> HCOOH + CH3OH
The characteristic features of Cannizzaro reaction are:

1) It is a disproportionate reaction.
2) It involves a reaction with aldehydes which have no alpha hydrogen atoms.
3) The products are an alcohol and a carboxylic acid.
A. Importance of Cannizaro’s Reaction

1.) Importance of the Solvent
This reaction can be done with KOH pellets with benzaldehyde in mortar and pestle which clearly
indicates the lesser important role of the solvent in the mechanism of the reaction resulting in the
formation of carboxylic acid and an alcohol. Thus, the role of the base becomes more important in
Cannizzaro reaction.
2.) Importance of the Reaction
Cannizzaro reaction is observed in aldehydes undergoing hydrolysis and not having an alpha hydrogen
atom. It can be used to prepare alcohols and carboxylic acids . Though, it is economically not a sound
method, this reaction can be used for preparation of alcohols for study purposes.
LESSON 5: USES AND FUNCTIONS OF SOME IMPORTANT ALDEHYDES AND KETONES

1. Formaldehyde (Methanal), H-CHO
➢ It is a gas at room temperature.
➢ It is soluble in water and so is normally found in laboratories as a 37% aqueous solution
called “formalin”.
Formalin – is a preservative for biological specimens. It does this by denaturing proteins, thus,
hardening them.
➢ It is used to embalm cadavers. But its use as a preservative and as an embalming liquid
has declined, because it has been determined that it is carcinogenic.
➢ It is toxic to both humans and microorganism, therefore, it is used to sterilize surgical
instruments.
➢ Industrially, formaldehyde is the most important aldehyde. Its principal use is in the
production of polymers.
Bakelite or Phenol-formaldehyde, urea-formaldehyde, and melamine-formaldehyde polymers
are not used only as plastics but even more importantly as adhesives and coatings.
Besides Bakelite, the trade names Formica and Melmac are also well-known fiber-boards
made from combining formaldehyde resins with wood chips or sawdust.
Also, some formaldehyde polymers are produced as porous foams and are used for building
insulation. However, in recent years, many of these products have been removed from the
market because they contain tiny amounts of free formaldehyde, which can get into the air
and possibly cause cancer.
➢ Acetaldehyde (Ethanal), CH3CHO

➢ Has a boiling point of 21°C, which is close to room temperature, because of this, acetaldehyde is
not easy to handle, either as a liquid or as a gas. For this reason, it is often converted to a cyclic
trimer (a molecule made of three units) called “paraldehyde”.
➢ Paraldehyde – was once used as a hypnotic or sleep-producer medication, but because of its
disagreeable taste and odor it is seldom used today.
➢ Acetaldehyde is the common intermediate in alcohol production by fermentation and a key
component in alcoholism.
➢ It is the key component in the symptoms of “alcoholic hangover”.
➢ The lethality of aldehyde is somewhere between NaCl and arsenic (As). Its LD50 value is 1900
mg/kg.
➢ USDA regulations set the acetaldehyde exposure limit by inhalation to 200 ppm over an 8-hr
exposure period. The regulatory limit for Formaldehyde exposure is even lower: 1.5 ppm.
2. Acetone (2-Propanone), CH3COCH3

➢ A liquid with a moderately low boiling point (56 °C).
➢ It is one of the few organic compounds that is infinitely soluble in water and also dissolves a great
deal of many organic compounds.
➢ It is one of the most important industrial solvents.
➢ It is used in paints, varnishes, resins, coatings, and nail polish, among other things.
➢ Acetone is produced in the body as a product of one pathway of lipid metabolism. Normally it
does not accumulate because the small amount produced is oxidized to CO 2 and H2O. However,
in diabetic patients a larger quantity of acetone is produced than the body can oxidize completely,
so much of it is excreted in the urine. A positive test for acetone in the urine is one way in which

diabetes is diagnosed. In severe cases of diabetes, acetone is exhaled, and its sweet odor can be
detected in the patient’s breath.
3. α-Chloroacetophenone
O
ll
– C –CH2 – Cl
➢ Lachrymators – are chlorine and bromine containing organic compounds that cause the eyes
to tear.
➢ α-Chloroacetophenone has long been used as a tear gas, by police and other government
officials to control unruly mobs.
➢ In recent years, this compound has been used as the active ingredient in “Mace” – a handheld
aerosol tear gas projector, used by individuals to protect themselves from an attacker. Mace
has a range of about 15 feet.

Chapter 16, pages 652 – 699
I. Give a structural formula and another acceptable name for each of the following compounds:
1.) Phenylacetaldehyde
2.) 3-methylpentanal
3.) Benzophenone
4.) Salicylaldehyde
5.) 4,4-Dibromo-2-methylpentanal
6.) Ethyl isopropyl ketone
7.) Diisopropyl ketone
8.) Dibutyl ketone
9.) Dipropyl ketone

10.) 2,3-dichlorobutanal
II. Synthesis and Preparation of Aldehydes and Ketones.
A. Show how “benzaldehyde” could be synthesized from each of the following:
(1) Benzyl alcohol
(2) Benzoic acid
(3) Phenylethene or Styrene
(4) C6H5CO2CH3
(5) C6H5C≡N
B. Show how “ethyl phenyl ketone, (C6H5COCH2CH3)” could be synthesized from each of the following:
(a) Benzene
(b) Benzonitrile, C6H5CΞN
(c) Benzaldehyde
III. Properties of Aldehydes and Ketones.

A. Which compound in each of the following pairs would be more soluble in water? Explain.
1. Acetone or 2-Pentanone
2. Propanal or Pentanal
3. CH3–CH2–CH3 or CH3–CH2–CHO
4. Propanone or 3-Hexanone
5. Butanal or Hexanal
IV. CHEMICAL REACTIONS: Illustrate and predict the products of the given chemical reactions below including
the correct catalyst for each given reactions.
1. Oxidation of Pentanal by an oxidizing agent and a concentrated acid.

2. Reduction or Hydrogenation of 2-butanone by a metal catalyst.
3. Hydration of Propanal.
4. Formation of a Ketal by the addition of Methanol to Acetone.
5. Formation of a Cyanohydrin by the reaction of HCΞN with Diethyl ether.
Experiment #13 Properties and Specific Tests for Aldehydes and Ketones
MODULE 11
CARBOXYLIC ACIDS, ESTERS AND AMIDES

1. Named carboxylic acids, ketones and amides by their IUPAC names, as well as their corresponding
common or alternative names;
2. Illustrated and explained the common preparations or syntheses of carboxylic acids, esters and amides;
3. Enumerated and discussed the uses and functions of common carboxylic acids, esters and amides;
4. Identified the sources, the practical and medical applications of carboxylic acids, esters and amides;
5. Simulated the preparation and reactions of carboxylic acids, esters and amides in the laboratory;
6. Differentiated and explained the physical properties of carboxylic acids, esters and amides;
7. Categorized the common chemical reactions of carboxylic acids, esters and amides;
LESSON INTRODUCTION
The most important chemical property of carboxylic acids, another class of organic compounds
containing the carbonyl group, is their acidity. Furthermore, carboxylic acids form numerous important
derivatives, including esters, amides, anhydrides, and acid halides. Carboxylic acids and their derivatives
rank with aldehydes and ketones among the most important organic compounds because they occur widely
in living organisms and because they serve important roles in organic synthesis.
This module or unit is concerned with the structures, properties, acidities, and carbonyl-group
reactions of carboxylic acids themselves, including some biologically important reactions. One reaction in
particular will allow us to understand how aspirin works. We will study many similar reactions, which will also
enable us to understand the life-saving properties of penicillin antibiotics.
This module is also devoted to a study of two carboxylic acid derivatives – esters and amides, where
their structures, properties, and carbonyl-group reactions will also be considered.
This module is peppered with dozens of reactions, but don’t be discouraged. By learning a few
mechanistic principles, we will see that nearly all of these reactions are examples of a type of reaction called
nucleophilic acyl substitution. Nucleophilic acyl substitution involves the creation of a new bond by a
nucleophilic addition and elimination at a carbonyl group . This process is utilized industrially in the synthesis
of complex polymers, such as nylon and polyesters used in sports like climbing. It also occurs in metabolism,
in the synthesis of proteins, fats, and steroid precursors, as well as in the breakdown of food for energy and
for other biosynthetic raw materials. Its versatility is truly amazing. By studying the mechanistic principles
that guide this process, we will be able to unify the reactions presented in this module and greatly reduce the
need for memorization.

LESSON 1: CARBOXYLIC ACID
LESSON 1.1. INTRODUCTION TO CARBOXYLIC ACID
The carbonyl compounds in which the carbonyl group (>C=O) is bonded with one hydroxyl group (-
OH) and another gets attached with either hydrogen or aryl/ alkyl group are called as carboxylic acid group.
Carboxyl group – is a carbonyl group (– C=O) with a hydroxyl group (– OH) bonded to the carbon atom. A
carboxyl group must occupy a terminal position in a carbon chain.
The generic formula for carboxylic acid compounds is RCOOH. Since these are acidic compounds, therefore
they easily lose H+ ion and covert in carboxylate ion (RCOO -).
General Formula:
A. Aliphatic C. A.: R – COOH; where: R – Alkyl or cycloalkyl groups

B. Aromatic C. A.: Ar – COOH ; where: R – Aryl (phenyl or benzyl) group
LESSON 1.2. STRUCTURE OF CARBOXYLIC ACID
The carboxyl group is made up of a carbonyl group joined with a hydroxyl group.
➢ C=O + -OH → -C(=O)OH
➢ The carbon atom in carboxyl group is bonded with two oxygen atoms; one by a double bond and another
by single bond. The remaining valency can be satisfied either by hydrogen or by alkyl group in aliphatic
carboxylic acids and by aryl group in aromatic carboxylic acids.

Carboxylic acids can be represented by two resonance structures.
Because of this resonance in carboxylic acid group, the >C = O bond length becomes 123 pm which is
lesser compared to alcohols (143 pm) and more than ketones (120 pm).
The Carbon-oxygen bond length on hydroxyl group side is around 136 pm which is more than >C = O
due to lack of double bond.
A. Carboxylic Acid Derivatives
The functional group of carboxylic acids is the carboxyl group; -C(=O)OH. If the hydroxyl group of carboxyl
group gets replace by other functional groups like halogen(-X), -OCOR’, -OR’ and-NH2, they are called
as acid halide, anhydrides, esters and amide respectively.
These compounds are collectively called as acid derivatives or functional derivatives of carboxylic acids
as hydrolysis of all these compounds again form parent carboxylic acid.

Carboxylic acid derivatives have wide applications like esters are found in fats and cell membranes.
Amides are involved in the manufacturing of synthetic fibers and bio molecules like proteins. Acyl
chloride and acid anhydride are mainly involved in the preparation methods for other carboxyl
derivatives.
Table 14.2. Some acid derivatives with their property are as follows:
LESSON 1.3. SYNTHESIS OR PREPARATION OF CARBOXYLIC ACID
A. Aldehyde to Carboxylic Acid

Aldehydes can be easily oxidized to carboxylic acids which have same number of carbon atoms as in
Aldehydes. The oxidation of aldehyde involves the cleavage of Carbon-hydrogen bond which is not the
same as the carbon-carbon bond in ketones.

Hence oxidation of aldehyde can occur with strong as well as weak oxidizing agents. Strong oxidizing
agents like chromic acid, potassium chromate, potassium permanganate, potassium dichromate and
concentrated nitric acid can oxidize Aldehydes to carboxylic acid containing the same number of carbon
atoms. Oxidation of aldehyde can be done under acidic and alkaline medium. In acidic conditions,
Aldehydes get oxidize to form carboxylic acid while in alkaline medium carboxylate salt is formed.
RCHO +H2O → RCOOH +2H+ +2e-

RCHO +3OH- → RCOO- +2H2O +2e-
❖ Oxidation of Aldehydes with different Oxidizing Agents
1. Oxidation with Potassium Dichromate Salt in Acidic Medium

A small amount of acidified potassium dichromate solution acts as good oxidizing agent for aldehyde to
convert it in carboxylic acid. The orange color of dichromate solution turns to green after oxidation due
to the formation of chromium sulfate in solution. During oxidation, dichromate ion (VI) gets reduced to
Cr3+ ion and oxidized aldehyde to carboxylic acid.
Cr2O72- +14H+ +6e- → 2Cr3+ +7H2O
RCHO+H2O → RCOOH +2H+ +2e-
The overall oxidation of aldehyde in the presence of dichromate salt is as follows;
3RCHO + Cr2O72- +8H+ → 3RCOOH + 2Cr3+ +4H2O

2. Oxidation with Tollen’s Reagent
Tollen’s reagent is an ammonical solution of silver nitrate contains diaminesilver (I) ion, [Ag(NH3)2]+.
It is prepared by the addition of ammonium hydroxide (NH4OH) solution in silver nitrate solution till gray
precipitate of Ag2O gets re-dissolved. By heating this solution with aldehyde, Ag2O is reduced to
metallic silver and deposited on the inner wall of test tube and aldehyde is oxidized to carboxylic acids.
2AgNO3 + 2NH4OH → Ag2O + 2NH4NO3 + H2O
Ag2O + 4NH4OH → 2[Ag(NH3)2]+OH- + 3H2O
RCHO + 2[Ag(NH3)2]+OH- + 3OH- → RCOO- + 2Ag + 4NH3 + 2H2O
3. Oxidation with Fehling's Solution or Benedict's Solution

Fehling’s solution and Benedict’s Solution are weak oxidizing agents that can oxidize aldehyde to
carboxylic acid also. Both oxidizing agents contain complexed copper (II) ions in an alkaline solution.
The only difference is that Fehling's solution contains copper (II) ions with tartrate ions in sodium
hydroxide solution while Benedict's solution contains copper (II) ions with citrate ions in sodium
carbonate solution.

In both solutions the presence salt ions prevent the precipitation of copper (II) hydroxide. With
these oxidizing agents, aldehyde is oxidized to carboxylic acid and copper (II) ion is reduced to copper
(I) ion which precipitates as a brick-red color ppt.
RCHO + 2Cu2+ + 5OH- RCOOH + Cu2O + 3H2O
Aldehyde Cupric ions Fehling’s/Benedict’s Carboxylic acid Copper (I) oxide water
(blue solution) (brick-red ppt.)
B. Reduction of Carboxylic Acid
Carboxylic acids and their salts undergo many reactions which involve either the elimination or
the decomposition of the carboxyl group. Reduction of carboxylic acid is one of them. Carboxylic acids
can be reduced to either alkane or alcohols depends upon the reducing agent involve in reaction.
1. Reduction of Carboxylic Acid to Alcohols

When the carbonyl group of carboxyl acid is reduced to >CH2 group, it gets converted to carboxylic
acid. Lithium aluminium hydride (LiAlH4) and sodium borohydride (NaBH4) are good reducing for this
conversion. For example, propanoic acid is reduced to propanol and benzoic acid to benzyl alcohol.
Reduction of carboxylic acid to alcohols follows nucleophilic acyl substitution followed by nucleophilic
addition.
4RCOOH+3LiAlH4 → Ether 4H2 + 4RCH2OM + metal oxides H2O + 4RCH2OH + Metal hydroxides
2. Reduction of Carboxylic Acid to Alkanes
Carboxylic acid reduced to alkanes in the presence of reducing agent red phosphorus at 473 K
temperature.
RCOOH + 6HI RCH3 + 2H2O + 3I2
LESSON 1.4. NOMENCLATURE OF CARBOXYLIC ACID
I. IUPAC NOMENCLATURE SYSTEM
1. Select the parent carbon chain which is the longest carbon chain that includes the carbon atom of the
carboxyl group.
2. Name the parent chain by changing the –e ending of the corresponding alkane to – oic acid.
3. Number the parent chain by assigning the number 1 to the carboxyl group.
4. Determine the identity and location of any substituent groups attached to the parent chain in the usual
manner, and attach this information to the parent name.
EXERCISES:
O
ll
1. CH3CH2CH2CH2C – OH Pentanoic acid (IUPAC)
Valeric acid (C.N.)
CH3O
l ll
2. CH3CH2C – C – OH 2,2 – Dimethyl butanoic acid (IUPAC)
l α,α – dimethtyl butyric acid (C.N)
CH3
Br CH3 O
l l ll
3. CH3CH-CHCH2–C–OH 4 – Bromo, 3 – methyl pentanoic acid (IUPAC)
β – Bromo, γ – methyl valeric acid (C.N.)
O
ll
4. CH3CH2CH–C–OH 2 – Ethyl pentanoic acid (IUPAC)
l α – Ethyl valeric acid (C.N.)
CH3CH2CH2
5. * Uncontrolled diabetics have high blood levels of the following carboxylic acid:
OH O
l ll
CH3CHCH–C–OH 3 – Hydroxy butanoic acid (IUPAC)
β – Hydroxy butyric acid (C.N.)
A. Dicarboxylic Acids
➢ Contains two (2) carboxyl groups both located at the terminal carbons.
➢ To name: attach the suffix – dioic acid to the corresponding alkane name.
➢ Both carboxyl carbon atom must be part of the longest parent carbon chain.
Examples:
O O
ll ll
1. HO–C–CH2CH2CH2CH2C–OH Hexadioic acid (IUPAC)
O CH3 O
ll l ll
2. HO – C – CH2CCH2C – OH 3,3 – Dimethyl pentadioic acid (IUPAC)
l
CH3
❖ Important Dicarboxylic Acids and their Functions:
1. Oxalic Acid – is the simplest dicarboxylic acid. It is found in the plants of the genus oxalic as well as in
rhubarb, cabbage and spinach.

2. Malonic Acid – one of the major compounds used in the manufacture of the class of drugs known as
“barbiturates” and the biological precursor for the synthesis of fatty acids.
3. Succinic Acid – including its derivatives play important roles in biological reactions that occur in the human
body.
❖ Common Names for the First Six (6) Dicarboxylic Acids
Length of Carbon Condensed Common Names IUPAC Names

Chain Structural Formula
C2 HOOC-COOH Oxalic acid Ethanedioic acid
C3 HOOC – CH2 – COOH Malonic acid Propanedioic acid
C4 HOOC– (CH2)2 – COOH Succinic acid Butanedioic acid
C5 HOOC – (CH2)3 – COOH Glutaric acid Pentanedioic acid
C6 HOOC – (CH2)4 – COOH Adipic acid Hexanedioic acid
C7 HOOC – (CH2)5 – COOH Pimelic acid Heptanedioic acid
❖ Simple dicarboxylic acids having the general formula HO2C–(CH2)n–CO2H (where n = 0 to 5) are known by
their common names. Common names, such as these can be troublesome to remember, so mnemonic
aids, which take the form of a catchy phrase, have been devised.
❖ For this group of compounds one such phrase is: "Oh My Such Good Apple Pie".
B. Aromatic Carboxylic Acids

O
➢ The carboxyl group is bonded to a benzene ring. ll
➢ The simplest is: Benzoic acid, C6H5OH –C–OH
Other simple aromatic carboxylic acids are derivatives of benzoic acid.
Examples: Salicylic Acid OH

O
–C – OH also called 2 – Hydroxybenzoic acid
Methyl benzoic acid go by the name “toluic acid”

CH3
l
COOH
C. Common Names for Carboxylic Acids

The common names of carboxylic acids indicate the natural sources from which these were isolated as
given in the table below.

Common Melting Boiling
Formula Source IUPAC Name
Name Point Point
HCO2H formic acid ants (L. formica) methanoic acid 8.4 ºC 101 ºC
CH3CO2H acetic acid vinegar (L. acetum) ethanoic acid 16.6 ºC 118 ºC
CH3CH2CO2H propionic acid milk (Gk. protus prion) propanoic acid -20.8 ºC 141 ºC
CH3(CH2)2CO2H butyric acid butter (L. butyrum) butanoic acid -5.5 ºC 164 ºC
CH3(CH2)3CO2H valeric acid valerian root pentanoic acid -34.5 ºC 186 ºC
CH3(CH2)4CO2H caproic acid goats (L. caper) hexanoic acid -4.0 ºC 205 ºC
CH3(CH2)5CO2H enanthic acid vines (Gk. oenanthe) heptanoic acid -7.5 ºC 223 ºC
CH3(CH2)6CO2H caprylic acid goats (L. caper) octanoic acid 16.3 ºC 239 ºC
CH3(CH2)7CO2H pelargonic acid pelargonium (an herb) nonanoic acid 12.0 ºC 253 ºC
CH3(CH2)8CO2H capric acid goats (L. caper) decanoic acid 31.0 ºC 219 ºC
The IUPAC names of the homologous series of carboxylic acids with the their similar common names are given
below. These two nomenclatures are illustrated in the following table, along with their melting and boiling points.
D. COMMON NOMENCLATURE
Designate the positions of substituents by using the letters of the Greek alphabets (α, β, ɣ, δ, ε, etc.)
rather than number, similar to the common nomenclature of Aldehydes.
Examples:
ɣ β α
1. CH3CHCH2CH2C-OH γ – Methylvaleric acid
l ll
CH3 O
δ ɣ β α
2. CH3CH2CHCH2CHCH2C-OH β, δ – Dimethyl enanthic acid
l l ll
CH3 CH3 O
ɣ β α
3. CH2CHCH2C-OH γ – Chloro - β – methyl butyric acid
l l ll
Cl CH3 O
E. Polyfunctional Carboxylic Acids

These are carboxylic acids that contain one or more additional functional groups besides the
carboxyl acid. They have uses in cosmetics and prescription drugs. They are important in the functioning
of the human body.
Examples:
1. Fumaric acid – an unsaturated c.a.
2. Pyruvic acid – a keto acid
3. Oxaloacetic acid – a keto acid
4. α-ketoglutaric acid – a keto acid
5. Lactic acid – a hydroxyl acid
6. Malic acid – a hydroxyl acid
7. Glyceric acid – a dihydroxyl acid
8. Citric acid – a carboxyhydroxy acid
❖ Structures of Polyfunctional Carboxylic acids that are Important in Metabolic Reactions in the Human
Body:
Derivatives of Propionic Acid Derivatives of Stearic Acid Derivatives of Glutaric Acid

(CH3CH2COOH) (HOOC- CH2CH2COOH) (HOOC–CH2CH2CH2–COOH)
Hydroxy Unsaturated (trans) Keto
CH3CHCOOH
H COOH O
l
ll
OH C=C HOOC-C-CH2CH2COOH
Lactic Acid – produced by
skeletal muscles during HOOC H
α – Ketoglutaric acid – an
strenuous exercises and causes Fumaric acid – an intermediate intermediate of ketoglutaric
muscle cramps. in the citric acid gels. acid
Dihydroxy Keto Carboxyhydroxy
OH
CH2CHCOOH O l
l l ll HOOCCH2CCH2COOH
OH OH HOOC-C-CH2COOH l
COOH
Glyceric acid – and its derivatives
are very important in glycolysis,
Oxaloacetic acid – begins and
ends the citric acid cycle . Citric acid – forms part of the
the initial reactions in the
breakdown of glucose free citric acid cycle; has many
energy. commercial uses; produces
the sharp taste of Citrus fruits.
Keto Hydroxy
O
ll OH
CH3CCOOH l
HOOC-CH-CH2COOH
Pyruvic acid – end product of
glycolysis, further broken down in
Malic acid – an intermediate in
the citric acid cycle.
the citric acid cycle.

F. Saturated and Unsaturated Carboxylic Acids
➢ Carboxylic acids are widespread in nature, often combined with other functional groups.
➢ Simple alkyl carboxylic acids, composed of four to ten carbon atoms, are liquids or low melting
solids having very unpleasant odors.
➢ The fatty acids are important components of the biomolecules known as lipids, especially fats and
oils.
➢ These long-chain carboxylic acids are usually referred to by their common names, which in most
cases reflect their sources.
➢ A mnemonic phrase for the C10 to C20 natural fatty acids is: "Curly, Larry & Moe
Perform Silly Antics".
➢ Interestingly, the molecules of most natural fatty acids have an even number of carbon atoms.
➢ Analogous compounds composed of odd numbers of carbon atoms are perfectly stable and have
been made synthetically.
➢ Since nature makes these long-chain acids by linking together acetate units, it is not surprising that
the carbon atoms composing the natural products are multiples of two.
➢ The double bonds in the unsaturated compounds listed on the right are all cis (or Z).
FATTY ACIDS
Saturated
Unsaturated
Common Melting
Formula Common Melting
Name Point Formula
Name Point
lauric
CH3(CH2)10CO2H 45 ºC palmitolei
acid CH3(CH2)5CH=CH(CH2)7CO2H 0 ºC
c acid
myristic
CH3(CH2)12CO2H 55 ºC CH3(CH2)7CH=CH(CH2)7CO2H oleic acid 13 ºC
acid
linoleic
palmitic CH3(CH2)4CH=CHCH2CH=CH(CH2)7CO2H -5 ºC
CH3(CH2)14CO2H 63 ºC acid
acid
CH3CH2CH=CHCH2CH=CHCH2CH=CH(CH2)7 linolenic
stearic -11 ºC
CH3(CH2)16CO2H 69 ºC CO2H acid
acid
arachidon
arachidic CH3(CH2)4(CH=CHCH2)4(CH2)2CO2H -49 ºC
CH3(CH2)18CO2H 76 ºC ic acid
acid
The following formulas are examples of other naturally occurring carboxylic acids. The molecular structures
range from simple to complex, often incorporate a variety of other functional groups, and many are chiral.

G. Other Unsaturated Carboxylic Acids
➢ Propenoic acid (Acrylic acid) – simplest unsaturated monocarboxylic acid

Used in the manufacture of several polymeric materials..
CH2=CCOOH
➢ 3 – Methyl – 2- hexenoic acid – unsaturated monocarboxylic acid responsible for body odor.
CH3CH2CH2C=CHCOOH
l
CH3
Butenedioic acid – simplest unsaturated dicarboxylic acid. It has two (2) isomers:
1. Fumaric acid (trans – isomer; lower left) – a metabolic acid.
H COOH HOOC COOH
C=C C=C
HOOC H H H
2. Malic acid (cis – isomer; upper right) – some antihistamines are marketed as salts of malic
acid.
H. Polyunsaturated Carboxylic Acids
➢ Tretinoin – has an all trans double bond configuration.

▪ It is used in the treatment of severe acne.
➢ Accutane – also used in the treatment of severe acne.

▪ Has a – cis bond in the position closest to the carboxyl group with the rest of the double bonds
in – trans configuration.

I. Hydroxy Acids
These are carboxylic acids that contains a hydroxyl aside from the carboxyl groups in their structural
formula.
Examples:
1. Glycolic acid – the simplest hydroxyl acid
▪ Finds use in cosmetic products
2. Malic acid and Tartaric acid – occur naturally in fruits
3. Lactic acid – present in sour milk and dill pickles
4. Citric acid – best known carboxylic acids
▪ Gives citrus fruits their “sharp taste”
▪ Used widely in beverages and foods
▪ Prevents enzymatic browning reactions
▪ Retards microbial growth in sea foods by lowering the pH.
II. FORMULA WRITING OF CARBOXYLIC ACIDS
1. 2 – Methyl propanoic acid
2. Β – Chlorocaproic acid
3. α – Phenylsuccinic acid
4. Phenylacetic acid
5. 3 – Chloropentanoic acid
6. The food additive Monosodium Glutamate (MSG) is derived from 2 – aminopentanedioic acid. Write the
structural formula of this acid.
LESSON 1.5. CHEMICAL PROPERTIES OF CARBOXYLIC ACID
A. Carboxylic Acid Reactions

Carboxylic acid is considered as a compound composed of two main parts; an alkyl or aryl group and a
carboxyl group. Therefore, the reactions of carboxylic acids can be due to carboxyl group or because of
alkyl group.

➢ Overall all reactions of carboxylic compounds can be classified in Four types:
1. Reactions involve the cleavage of –O-H bond in hydroxyl group.
2. Reactions involve the cleavage of C-O bond in carboxyl molecule.
3. Reaction involving whole carboxyl group
4. Reactions involve the alkyl group of carboxyl compounds.
1. REACTIONS INVOLVING THE CLEAVAGE OF “-OH” BOND IN HYDROXYL GROUP
(a) Acidity of Carboxylic Acids

Carboxylic acids can be easily ionized and exist in a dynamic equilibrium between the carboxylate
ion and hydronium ion. Hence they show acidic nature.
R COOH + H2O ⇌ RCOO- + H3O+
Some reactions will show the acidic nature of carboxylic compounds are as follows:
1. Reaction with metal-Carboxylic acids react with active metals like; K, Ca, Mg to form their respective
salts and release hydrogen gas.
2RCOOH + 2Na → 2RCOONa +H2
2. Similarly carboxylic acids react with alkalis like sodium hydroxide to form salts and water and show
simple acid-base neutralization reaction.
RCOOH +NaOH → RCOONa + H2O
3. Carboxylic acids are weaker than mineral acids like sulphuric acid or nitric acid and able to react with
weaker bases like carbonates and bicarbonates to evolve CO2 with water.
RCOOH + NaHCO3 → RCOONa + CO2 +H2O
The carbon dioxide gas evolved with brisk effervescence, thus reaction can be used to detect the
presence of carboxyl group in a compound and differentiate between carboxylic acids and phenols as
they cannot give effervescence with aqueous solution of NaHCO3.
2. REACTIONS INVOLVING THE CLEAVAGE OF “C–O” BOND IN CARBOXYL MOLECULE
These reactions involve the replacement of hydroxyl group by some other groups like; -Cl, -OR, -NH2 to
form acyl chloride, ester and acid amide.
(a) Ester Formation.

Carboxylic acids react with alcohols to form esters which have a general structural formula of COOR.
Reaction involves the replacement of hydroxyl group by –OR group of alcohol or phenol and also
known as Fischer-Speier Esterification. In Fisher esterification an alcohol and an acid are reacted in
an acidic medium such as concentrated sulfuric acid or dry HCl gas.
Example:
(b) Amide Formation

Carboxylic compounds react with ammonia to form ammonium salts which upon heating lose water
molecule to form amide.
RCOOH + NH3 RCOO-NH4+ RCONH2 + H2O
Example: CH3COOH + NH3 CH3COONH4 CH3CONH2 + H2O

Acetic acid Ammonia Ammonium Acetate Ethylamide water
(c) Acid Halide Formation
Carboxylic acids can react with a number of halide derivatives; phosphorous trichloride (PCl3),
phosphorous pentachloride (PCl5), thionyl chloride (SOCl2), and phosphorous tribromide (PBr3) to
form acyl halides.
(d) Acid Anhydride Formation
The dehydration of carboxylic group in the presence of a strong dehydrating agent likes phosphorus
pentoxide or concentrated sulfuric acid forms acid anhydrides. For example, two molecules of acetic
acid forms acetic anhydride in the presence of concentrated sulfuric acid.

CH3COOH + HOOCCH3 CH3COOCOCH3 + H2O
Acetic acid Acetic acid Acetic Anhydride water
3. REACTIONS OF WHOLE CARBOXYL GROUP
a. Decarboxylation Reaction
Sodalime that is a mix of sodium hydroxide with calcium oxide is a best reagent used for
decarboxylation and forms alkanes. Simple copper salts such as copper chromate, copper hydroxide or
copper carbonate are also good in decarboxylation of aliphatic and aromatic acids.
4. REACTIONS INVOLVING THE ALKYL GROUP OF CARBOXYL COMPOUNDS: HALOGENATION

The alkyl group of carboxylic acids can involve in halogenation to form haloacids. Halogenation
takes place with chlorine or bromine in the presence of small quantities of red phosphorus which form α-
halo or β-haloacids. The reaction is called as “Hell-Volhard-Zelinsky” Reaction.
RCH2-COOH + X2 H2O; Red Phosphorus R-CH(X)-COOH + HX

Carboxylic acid halide Halogenated C.A. hydrogen halide
Bromination of carboxylic acids is more selective in nature and exclusively occurs at alpha position to
form α-bromocarboxylic acids.

Example: Br
l
CH3CH2COOH + Br2 CH3CHCOOH + HBr
Propanoic acid Bromide 2 – Bromopropanoic acid Hydrogen bromide
Chlorination of carboxylic acid first occurs at alpha position, but when all alpha position gets occupied, it
occurs further along the chain.
Example: Cl
l
CH3CH2CH2COOH + Cl2 CH3CH2CHCOOH + HCl
Butanoic acid Chloride 2 – Chlorobutanoic acid Hydrogen chloride
LESSON 2. ESTERS
Esters are a class of compounds widely distributed in nature. The simple ester tend to have pleasant
odors. In many cases although not exclusively so the characteristic flavors and fragrances of flowers and
fruits are due to compounds with the ester functional group. An exception is the case of the essential oils.
Esters – are the organic compound derivatives of carboxylic acid in which the hydroxyl group (– OH) has been
replaced with an “– OR” group.
These are organic compounds whose characteristic functional group is also the “carboxy” group (– COO).
O
ll
General Formulas: R – C – OR’ or R- COOR’
Where: R and R’ – Alkyl, Aryl or Cyclic groups

Have an acid part and an alcohol part.
“R – C=O” – is the acid part while the – O – R’ is the alcohol part.
LESSON 2.1. NOMENCLATURE OF ESTERS
1. Esters are commonly prepared from carboxylic acids and alcohols.

2. Esters names have two words, the first word comes from the alcohol portion, and the second word is
derived from the acid portion.
3. The first word is the carbon group named as a substituent. The second word has the ester ending -oate.
Some examples are shown below:
• The alcohol portion is named as 3-methylbutyl. The acid portion is ethanoic acid, which is changed to
ethanoate. Therefore the IUPAC name is 3-methylbutyl ethanoate.
• This is the major odor producing chemical in bananas.

• The alcohol portion is simply a methyl group. The acid portion would be 2-hydroxybenzoic acid. The
ester name is methyl-2-hydroxybenzoate.
• This is the major odor producing chemical in oil of wintergreen.
• This ester is 2-chloropropyl propanoate.
➢ This ester is propyl-2-chloropropanoate. It is important to put the substituent in the proper part of the
name.
Table 14.7. Common Names of Selected Esters
IUPAC NAME STRUCTURAL FORMULA CHARACTERISTIC

FLAVOR/ODOR
O
ll
Ethyl Ethanoate CH3C–OCH2CH3 Plastic Balloon
O
ll
Ethyl Methanoate CH3C–OCH3 Rhum or Rum
O CH3
ll l
Isobutyl Methanoate H–C –OCH2CHCH3 Raspberries
O
ll
Pentyl Ethanoate CH3C–O(CH2)4CH3 Ripe Banana/ Peach

O
ll
Octyl Ethanoate CH3C–O(CH2)7CH3 Orange
O
ll
Pentyl Propanoate CH3CH2 –C–O(CH2)4CH3 Apricot
O
ll
Methyl Butanoate CH3(CH2)2C–OCH3 Apple
O
ll
Ethyl Butanoate CH3(CH2)2C–OCH2CH3 Pineapple
O
ll
C – OCH3
Methyl – 2 – aminobenzoate Grape
NH2
LESSON 2.2. SYNTHESIS OF ESTERS
1. Esters are prepared by the acylation of alcohols or phenols.
The formation of esters is known as esterification. Esterification of carboxylic acids with alcohols
requires a mineral acid such as concentrated H2SO4 or HCl gas a catalyst.
2. Fischer Esterification

The esterification of carboxylic acids with alcohols is a kind of nucleophilic acyl substitution. The
above mechanism is supported by the using isotopically labeled methanol (CH3O18H) with acetic
acid to give methyl acetate (having labeled oxygen) and water not containing any isotopic oxygen.
Esters of phenols are prepared by reversible acylation of phenols with acyl chloride or
anhydrides rather than the reaction with carboxylic acid in which all the steps are reversible.
LESSON 2.3. PROPERTIES OF ESTERS
A. PHYSICAL PROPERTIES OF ESTERS

1. Esters cannot form hydrogen bonds to each other.
2. The boiling point of esters is lower than those of alcohols and acids of comparable mass.
3. Esters are more like ethers in properties.
4. Low molecular weight esters are soluble in water.
5. Solubility rapidly decreases as the carbon chain length increases.
6. Low and intermediate molecular mass esters are usually colorless liquids at room temperature.
7. Most esters have pleasant odors or aromas.
B. CHEMICAL PROPERTIES
1. Hydrolysis of Ester
Esters hydrolyzed by boiling water slowly to carboxylic acids and phenols. The hydrolysis is
accelerated in the presence of mineral acid on alkali.
The alkaline hydrolysis is known as saponification. This is because esters with high molecular
mass (C12 - C17) give soap on hydrolysis with a base. Soaps are sodium or potassium salts of
Carboxylic acids with high molecular mass (C12-C17). The carboxylic acid is obtained by
acidification of the salt with mineral acid (H2SO4 or HCl).

2. Alcoholysis of Ester
Esters react with alcohols in the presence of an acid catalyst to undergo exchange of alcohol i.e.,
alkoxy parts. The equilibrium mixture consists of the reactants and a new ester and a new alcohol.
The reaction involves acyl substitution of the alkoxy group of the ester with the alkoxy group of the
alcohol and is known as trans esterification.
3. Reaction with Ammonia and Amines to form Amides
4. Reduction of the Acyl Group of Ester with LiAlH4 (but not with NaBH4) to a Primary Alcohol
LESSON 2.4. USES AND IMPORTANCE OF SOME ESTERS
A. Flavoring Agents – esters are largely responsible for the flavor and fragrance of fruits and flowers.
B. Pheromones
1. Isoamyl Acetate – is the alarm pheromone for honey bees.
O CH3
ll l
H–C –OCH2CH(CH2)2CH3
2. Methyl – p – hydroxybenzoate – is the sexual attractant for canine species.

C. Medications
1. Benzocaine – is a local anesthesia
NH2
O
ll
C – OCH2CH3
2. Esters of Salicylic Acid
a. Aspirin – is produced from the reaction of acetic acid with the alcohol group of salicylic acid.
➢ A drug that has the ability to decrease pain, lower body temperature and to reduce
inflammation.
➢ When ingested, it undergoes hydrolysis to produce salicylic acid and acetic acid
b. Oil of Wintergreen (Methyl Salicylate) – is produced from the reaction of methanol with the
acid group of a salicylic acid.
➢ It is used in skin rubs and liniments to help decrease the pain of sore muscles.
➢ Absorbed through the skin when it is hydrolyzed to produce salicylic acid.
D. Polyesters
Are polymers in which the monomers are joined through a series of ester linkages.
➢ Dicarboxylic acids and dialcohols are the monomers used to form polyesters.
➢ A Monomer – is comprised of one (1) unit of a “molecule” or a “mer”.
➢ A Polymer – is composed of many “mers”.
1. Dacron – is a polyester produced from the monomers: terephthalic acid and ethylene glycol.
➢ It is used to produce synthetic artery grafts that replaces diseased arteries and also used in
the manufacture of heart valve replacements.
2. Degradable Polymers – are polymers that are degraded in the environment once they are no longer
useful.
a. Poly(hydroxyalkanoates) – are natural biopolymers that have been developed for use in the
manufacturing of degradable plastic containers.
Examples:
1. Poly(3–hydroxybutyrate), PHB and Poly(3–hydroxyvalerate), PHV – are naturally occurring
polyesters produced by certain bacteria.
❖ PHB has many physical properties in common with polypropelene.
❖ PHB-PHV copolymer (BIOPOL) has recently been used to manufacture plastic shampoo
bottles.
➢ It is of special interest because it is biodegradable.
➢ It is a naturally occurring polymer and it is easily degraded by enzymes produced by soil
microorganisms and therefore does not persists in the environment after disposal.
❖ Polyesters of ε-Caprolactone and Lactic acid – are also biodegradable polymers of
importance.

LESSON 3. AMIDES
Amides are another important nitrogen derivative of carboxylic acids. It contains an oxygen bonded to the
same carbon as nitrogen. Thus, an amine has the nitrogen atom attached directly to a carbonyl group:
O O O H O R”
ll ll ll l ll l
–C–N– R – C – NH2 R – C – N – R’ R – C – N – R’
Amide functional group (1) (2) (3)
The Three Classifications of Amides
Amides are neutral (nonbasic) molecular substances and exist as molecules (not ions) both in the
crystalline form and when dissolved in water.
LESSON 3.1. NOMENCLATURE of AMIDES
Like all derivatives of carboxylic acids, amide names are based on the name of the corresponding carboxylic
acid.
Rules For Naming Amide:
1. The ending of the name of the corresponding carboxylic acid is changed from –ic acid (common) or –oic
acid (IUPAC) to –amide.
2. The names of groups attached to nitrogen are placed first, using an N- prefix for each group.
To name an amide, we need to distinguish the acyl part from the amino part of the amide. The acyl part and
the amino part are those derived from the carboxylic acid and amine, respectively.
O R”
ll l
Acyl Part  R – C – N – R’ → Amino Part
Example Exercises:
O CH3
ll l
1.) CH3CH2CH2 – C – N – CH2CH3
O
ll
2.) CH3CH2C – CH2 – NH – CH3

H O
l ll
3. CH3CH2 – N – C – CH3
O
ll
4. CH3CHCH2 – C – N – CH2CH2CH3
l l
CH2CH3 CH3
O
ll
5. CH3CH2CH – C - NH – CH2CH3
l
CH2CH3
O H
ll l
6. – C –C – N –
O CH3
ll l
7. CH3CH – C – N –-
l
CH3
O
ll
8.) C – N – CH2CH3
l
CH2CH3
H O
l ll
9.) --N – C – CH2CH3
O
ll
10.) CH3 – CHCH2CH2 – C – NH2
l
NH2
LESSON 3.2. SYNTHESIS & PROPERTIES OF AMIDES
A. PREPARATIONS OF AMIDES
4. AMMONOLYSIS OF ESTER: Reaction of Ammonia with Esters to form an Amide and a 1°Alcohol
5. Reaction of Acyl Halides with Ammonia to form an Amide and Ammonium Salt

6. Reaction of Acetic Anhydride with Ammonia to form Acetamide and Acetic Acid
7. Heating Ammonium Salts of Acids to form an Amide and Water
B. PHYSICAL PROPERTIES
1. Amides are the least reactive of the common carboxylic acid derivatives.
2. They are neutral substances.
3. They occur widely in nature. The most important amides are the proteins.
4. They have exceptionally high boiling points for their molecular weight, although alkyl substitution on
the nitrogen lowers the boiling and melting points by decreasing the Hydrogen-bonding possibilities.
C. CHEMICAL PROPERTIES
1. HYDRATION REACTION: Hydrolysis of Amide to form Carboxylic acid and Ammonia
O O
ll ll
R – C – NH2 + HOH R – C – OH + NH4
Amide Water Carboxylic acid Ammonia
O O
ll ll
CH3 – C – NH2 + HOH CH3 – C – OH + NH4
Acetamide water Acetic acid ammonia

(Ethylamide) (Ethanoic acid)
2. REDUCTION TO AMINES
O
ll LiAlH4
R – C – NH2 R – CH2 – NH2
H2
Amide Amine
O
ll LiAlH4
CH3 – C – NH2 CH3 – CH2 – NH2
H2
Acetamide Acetamine
(Ethylamide) (Ethylamine)
LESSON 3.3. IMPORTANT AMIDES & THEIR USES
1. Formamide (Methanamide) – is the only amide that exists as a liquid at room temperature. It is the
simplest amide in the homolog series. All other unsubstituted amides are solids at room temperature.
Many are odorless and colorless.

2. Urea (H2NCONH2) – a diamide of carbonic acid, is a colorless, water soluble crystalline solid that melts
at 133C.
It is the normal end product of protein metabolism. Humans and other higher animals get rid of
their waste nitrogen by converting it to urea and excreting it in the urine. The normal adult excretes
about 30 g. of urea daily. It is produced commercially from CO2 + NH3 which is widely used in fertilizers
to add nitrogen to the soil, or as a starting material in the production of plastics and barbiturates.
Barbituric Acid (Barbiturates) – a derivative of amide made from the reaction of urea with diethyl
malonate. It was discovered by Adolph von Baeyer in 1864. It is a cyclic amide which was later
discovered that certain derivatives of it had powerful physiological effects. They could put people
to sleep. A number of its derivatives were made into important drugs such as:
Barbiturates – are the salt form of barbituric acid. These drugs are used as sedatives (tranquilizers)
in small doses; and in larger doses they induce sleep. Barbiturates are addictive. Because they act
as tranquilizers, they are called “downers” or “goof balls”. They are especially dangerous when
combined with alcohol, and are responsible for many deaths because of its combined effect (called
synergistic effect).
Complex Amides are of tremendous importance. Our body contains many kinds of proteins, all held
together by amide linkages. Nylon, silk, and wool molecules also contain hundreds of amide functional
groups.
Nylon 66 – is a very important synthetic polyamide. It is used to make shirts, dresses, stockings,
underwear, and other kinds of clothing, as well as carpets, tire cord, rope, and parachutes. It also has
nonfabric uses; for example, it is used in paint brushes, electrical parts, valves, gears, clips, and fasteners.
It is a very tough and strong, nontoxic, nonflammable, and resistant to chemicals.

I –TRUE or FALSE: Write the Letter “True” if the given statement is correct, and write the letter
“False if the given statement is not correct or erroneous.
1. The – COOH is called the carboxyl group

2. Acetic acid is a stronger acid than hydrochloric acid.

3. Oxalic acid is also known as ethanedioic acid.
4. The common name of Pentanoic acid is valeric acid.
5. Sodium Benzoate is more soluble in water than Benzoic acid.
6. Aromatic carboxylic acids contain six or more carbon atoms.
7. The IUPAC name for CH3(CH2)5COOH is Hexanoic acid.
8. The IUPAC name for CH3CH2CH2COOCH3 is 2 – Pentanoic acid.
9. CH2ClCH2CH2COOH is called β - Chlorobutyric acid.
10. Unsaturated carboxylic acids have lower melting points than saturated carboxylic acids of similar
molar mass.
11. Esters have higher boiling points than alcohols or acids of comparable molar mass.
12. Low and intermediate molar mass esters have characteristic, usually fragrant or fruity odors.
13. A compound of formula C6H12O can be both a carboxylic acid and an ester.
14. The IUPAC name for CH3CH2CH2CH2COOCH2CH3 is Ethyl Butanoate.
15. Methyl propanoate and propyl methanoate are isomers.
16. The reaction between phosphoric acid and ethyl alcohol is known as “esterification”.
17. CH3CH2COOCH2CH3 is commonly called Diethyl ester.
18. In polyesters, the monomers are joined by ester linkages between the carboxylic acid and alcohol
groups.
19. The reaction of an ester and aqueous sodium hydroxide will produce a carboxylic acid and s sodium
alkoxide salt.
20. When polymerized, glycerol and o-phthalic acid form a thermoplastic polymer.
II. Chemical Reactions of Carboxylic Acids:

a.) Write the Correct Structural Formula of the Reactant/s;
b.) Write the formula of the specific Catalyst/s of the reaction;
c.) Predict the Product/s of the given reactions.
1.) Illustrate the Synthesis or preparation of Benzoic Acid from the oxidation of Benzaldehyde with
Tollen’s reagent.
2.) Illustrate the catalyzed Reduction of Propanoic acid into Propanol.
3.) Illustrate the Ammonolysis of Butyric acid to Butanamide.
4.) Illustrate the Formation of Acetic Anhydride in the presence of a strong dehydrating agent
diphosphorus pentoxide.
5.) Illustrate the formation of the Acyl Halide Chlorobenzyl and its byproducts from the reaction of
Benzoic acid with phosphorus pentachloride.
6.) Illustrate the catalyzed decarboxylation reaction of Propenoic acid with Cupric Chromate.
Experiments #14

MODULE 12
AMINES
1. Drawn structures of amines;

2. Named amines using IUPAC rules and their corresponding common or alternative names;
3. Identified the sources and the medical applications of amines;
4. Explained the basic physical and chemical properties of amines;
5. Observed reactions of amines in the laboratory.
LESSON INTRODUCTION
Amines are organic derivatives of ammonia in the same way that alcohols and ethers are organic
derivatives of water. Like ammonia, amines contain a nitrogen atom with a lone pair of electrons, making
amines both basic and nucleophilic. We’ll soon see, in fact, that most of the chemistry of amines depends on
the presence of this lone pair of electrons.
Amines occur widely in all living organisms. Trimethylamine, for instance, occurs in animal tissues and
is partially responsible for the distinctive odor of fish; nicotine is found in tobacco; and cocaine is a stimulant
found in the leaves of the South American coca bush. In addition, amino acids are the building blocks from
which all proteins are made, and cyclic amine bases are constituents of nucleic acids.
Amine-containing compounds have an also an incredible range of biochemical properties. Some, like
acetylcholine, act as neurotransmitters, control muscle function, enhance sensory perceptions, and sustain
attention span. Others play far more sinister roles. Colombian poison dart frogs, for example, are tiny and
beautiful, but they are also deadly. They produce a compound known as histrionicotoxin, an amine that
causes paralysis and eventually death through suffocation. The respiratory muscles cease to function
because acetylcholine cannot act, preventing it from initiating the electrical signaling that makes the muscles
of our lungs function. Similarly, Amazon tribes have long used a mixture of compounds from a woody vine
called curare for hunting game and for self-protection; this material includes another paralytic neurotoxin
called d-tubocurarine, which also blocks acetylcholine function. As we shall see, these examples represent
just the tip of the iceberg for what amines do.
https://www.pinterest.ca/pin/42995371417011675/ www.pdf.woody

LESSON 1: AMINES STRUCTURE
Amines can be either alkyl-substituted (alkylamines) or aryl-substituted (arylamines). Although much of

the chemistry of the two classes is similar, there are also substantial differences. Amines are classified as
primary (RNH2), secondary (R2NH), or tertiary (R3N), depending on the number of organic substituents
attached to nitrogen. Thus, methylamine (CH3NH2) is a primary amine, dimethylamine [(CH3)2NH] is a
secondary amine, and trimethylamine [(CH3)3N] is a tertiary amine. Note that this usage of the terms primary,
secondary,and tertiary is different from our previous usage. When we speak of a tertiary alcohol or alkyl halide,
we refer to the degree of substitution at the alkyl carbon atom, but when we speak of a tertiary amine, we refer
to the degree of substitution at the nitrogen atom.
AMINES, (R–C–NH2) – are the organic substances that contain the elements carbon, hydrogen , and nitrogen.
Amines are derivatives of ammonia in which one or more of the hydrogens has been replaced by an alkyl or
aryl group.
A. CLASSIFICATION of AMINES
Amines are classified according to the number of carbons directly bonded to the nitrogen.
8. Primary (1º), Secondary (2º) & Tertiary (3º) amines have one, two or three carbons directly bonded to the
nitrogen.
9. Aromatic (Aryl) Amine – is an amine in which at least one benzene or other aromatic group is directly
bonded to nitrogen.
10. Aliphatic Amine – is an amine in which no benzene or other aromatic groups are directly bonded to
nitrogen.
Furthermore, the terms primary (1º), secondary (2º) & tertiary (3º) are used to classify amines in a completely
different manner than they were used for alcohols or alkyl halides.
When applied to amines these terms refer to the number of alkyl (or aryl) substituents bonded to the nitrogen
atom, whereas in other cases they refer to the nature of an alkyl group.
1. Primary (amino, NH2) - Primary amines have one alkyl group attached to the nitrogen atom.
2. Secondary (imino, NH) - Secondary amines have two alkyl groups attached to the nitrogen atom.

3. Tertiary (nitrile, N) - Tertiary amines have three alkyl groups attached to the nitrogen atom.
B. NOMENCLATURE OF AMINES
The nomenclature of amines is complicated by the fact that several different nomenclature systems exist, and
there is no clear preference for one over the others.
1. The IUPAC System names amine functions as substituents on the largest alkyl group. The simple -NH2
substituent found in 1º-amines is called an amino group. For 2º and 3º-amines a compound prefix (e.g.
dimethylamino in the fourth example) includes the names of all but the root alkyl group.
2. The Chemical Abstract Service has adopted a nomenclature system called Chemical Abstract. The CA for
short (Published by the American Chemical Society) is a journal that abstracts the world’s chemical literature.
The CA rules for naming amines are similar to the IUPAC rules for naming alcohols:
Select the longest continuous carbon chain that has the attached nitrogen.
Change the ending of the name of the Alkane from –e to –amine. The position of attachment of nitrogen
to the carbon chain is indicated by a number in front of the name. The carbon chain is numbered from the
end nearest the nitrogen.
Prefixes with numbers are used to indicate substituents attached to the longest chain.
Compounds with two NH2 groups are named as alkanediamines.
(1.) H2N – CH2CH2CH2CH2CH2 – NH2 (2.) H2N – CH2CH2CH2CH2CH2CH2 – NH2
Cadaverine or 1,5 - Pentanediamine 1,6 – Hexanediamine
A cyclic, non-aromatic compound containing an attached NH 2 group is named as a cycloalkanamine. The

ring carbon holding the nitrogen is always C1.

NH2 NH2 CH3
(3.) (4.) (5 .) N
NH2 CH3 CH3
1,2 – cyclohexadiamine 2 – methylcyclohexanamine N,N –Dimethylcyclohexanamine
or: __________________ or: ____________________ or: ____________________
Name 2º and 3º-amines on the basis of the group with the longest carbon chain attached to nitrogen. The
names of the other groups attached to nitrogen are placed in front of the alkanamine or cycloalkanamine
name. N- and N, N- prefixes are used to indicate that the other groups are attached to nitrogen.
3. Finally, a common system for simple amines names each alkyl substituent on nitrogen in alphabetical
order, followed by the suffix -amine. These are the names given in the last row.
4. Many aromatic and heterocyclic amines are known by unique common names, the origins of which are often
unknown to the chemists that use them frequently. Since these names are not based on a rational system, it
is necessary to memorize them (Refer to the diagram).
➢ The four compounds shown in the top row of the diagram below are all C4H11N isomers.

➢ The first two are classified as 1º-amines, since only one alkyl group is bonded to the nitrogen; however, the
alkyl group is primary in the first example and tertiary in the second.
➢ The third and fourth compounds in the row are 2º and 3º-amines respectively.
➢ A nitrogen bonded to four alkyl groups will necessarily be positively charged, and is called a 4º-ammonium
cation. For example, (CH3)4N(+) Br(–) is tetramethylammonium bromide.
C. AROMATIC AMINES EXAMPLES
D. NATURAL NITROGEN COMPOUNDS
Nature abounds with nitrogen compounds, many of which occur in plants and are referred to as alkaloids.
Structural formulas for some representative alkaloids and other nitrogen containing natural products are
displayed below, and many of the basic structural features listed above are recognized in their formulas. Thus,
Serotonin and Thiamine are 1º-amines, Coniine is a 2º-amine, Atropine, Morphine and Quinine are 3º-amines,
and Muscarine is a 4º-ammonium salt.

ALKALOIDS (“like alkalis”) – are heterocyclic amines that occur naturally in plants. Like other amines, these
compounds are basic. Many of these compounds exhibit physiological activity. Among the familiar alkaloids
are:
b. Coniine (2-propylpiperidine) – is very poisonous. It is found in the hemlock plant. The philosopher
Socrates committed suicide by drinking a cup of hemlock extract.
c. Caffeine - is the compound that is mainly responsible for the stimulating action of coffee and tea. It is
also present in chocolate, cocoa, colas, and “stay awake” pills (No-Doz).
d. Nicotine – is the alkaloid which is the active ingredient in tobacco. It is a stimulant in small doses. It is
not harmful in itself, but it is habit-forming and thus exposes smokers to harmful effects of the other
components of cigarette smoke (tars, CO, carcinogens, and other poisons).
e. Atropine – is found in poisonous plants such as Henbane and Belladonna. Dilute solutions of atropine
have been used for thousands of years to dilate the pupils of the eyes (make them larger). The name
“belladonna” – means “beautiful lady” – because Roman women in olden times used extracts from this
plant to make themselves more attractive.
f. Morphine – is an Opium from the dried latex of the Poppy plant. It is a valuable drug in medicine, being
one of the most effective pain-killers known. It is a narcotic drug, which means they are addictive.
Heroin – is not found in nature, but is made from morphine by esterification of the OH groups with
acetic anhydride. Heroin is more harmful than morphine because it enters the brain more rapidly
than morphine. Once there, it is converted back to morphine and is trapped in the brain cells. The
use of heroin is illegal, and morphine is restricted to hospital use only.
Demerol – is a synthetic drug substitute for the pain-killing effect of morphine.
g. Codeine – is the methyl ether component of morphine from the poppy plant. It is also a narcotic drug
sometimes used in cough syrups to decrease throat discomfort.
h. Cocaine – is extracted from the Coca bush found in Peru and Bolivia. It is used as a stimulant. Cocaine
reduces fatigue, permits greater physical endurance, and gives a feeling of tremendous confidence and
power. It is a narcotic drug. In the 19th century, it was used as a local anesthetic for tooth extractions.
Because of its toxicity and addictive effect, it was replaced by synthetic compounds.
i. Quinine – is the actual compound responsible for the treatment of malaria. It is extracted from the bark
of the Cinchona tree.
j. Strychnine – comes from the seeds of the plant Strychnos nux vomica, which has been used for many
years as a poison for rats and even humans . It is also used medicinally, in low dosage to counteract
poisoning by central nervous system depressants.
k. Reserpine – is extracted from the shrub called Indian Snake Root, is used as a tranquilizer for patients
in mental hospitals and as a drug that lowers blood pressure.

Of more immediate interest are Pyrimidine (C4H4N2), and Purine (C5H5N4). Compounds related to these two
are constituents of “nucleic acids” - the information and control centers in the cell.
E. USES & FUNCTIONS OF SOME IMPORTANT AMINES
1. Methylamine, (CH3NH2) and Ethylamine, (CH3CH2NH2) – are the first and second compounds in the
homolog series of amines and are flammable gases with a strong ammoniacal odor.
2. Trimethylamine – has a “fishy” odor. The higher-molar mass amines have obnoxious odors.
3. Aniline – is the amine with an NH2 group attached directly to a benzene ring . It is used in making dyes.
Aromatic amines tend to be toxic, and some are strongly carcinogenic (cancerous). It is easily absorbed
through the skin.
➢ Simple amines are similar to ammonia in odor, basicity, and other properties. It is the higher amines that
are most interesting like the following:
CH3 CH2NH2
CH3 – C – NH2 HO CH2OH
NH2
H3C
Aniline N
Amphetamine Pyridoxamine
H2N – CH2CH2CH2CH2CH2 – NH2 H2N – CH2CH2CH2CH2CH2CH2 – NH2
Cadaverine or 1,5 - Pentanediamine 1,6 - Hexanediamine

4. Amphetamine is a stimulant drug.
5. Cadaverine has the odor of decaying flesh .
6. 1,6 – Hexanediamine is used in the synthesis of nylon.
7. Pyridoxamine is a Vitamin B.
8. Glycine (H2NCH2COOH) – the simplest amino acid, also considered an amine because it contains an
amine functional group.
F. BASICITY OF AMINES
➢ The basicity of a compound is a measure of a compound's ability to accept a proton(H +).
➢ Amines are basic in nature. This is because they possess an unshared pair (lone pair) of electrons on
nitrogen. This lone pair of electrons is available for the formation of a new bond with a proton or Lewis
acids. Thus, amines react with acids to form salts.
Amine Alkyl ammonium chloride
➢ Strong bases like NaOH, KOH, etc completely ionize in aqueous solution. Amines are weak bases.
They are only partially ionized in aqueous solution and an equilibrium exists between the ionized and
unionized forms.
➢ Aliphatic amines are stronger bases than ammonia. This is because the alkyl groups are electron-
releasing. They increase the electron density around the nitrogen, thereby increasing the availability of
the lone pair of electrons.
" The greater the number of electron-releasing alkyl groups, the greater the availability of nitrogen's
lone pair and stronger the base."
Compound kb value
Ammonia (NH3) 1.8 x 10-5
Methyl amine (CH3NH2) 37 X 10-5
Di methyl amine (CH3-NH-CH3) 54 X 10-5
Tri methyl amine (CH3-N(CH3)2 6.7 X 10-5
➢ Basicity of aliphatic amines in increasing order

G. BOILING POINT & SOLUBILITIES OF AMINES
➢ The table illustrates differences associated with isomeric 1º, 2º & 3º-amines, as well as the influence of
chain branching.
➢ Since 1º-amines have two hydrogens available for hydrogen bonding , they have higher boiling points
than isomeric 2º-amines, which in turn should boil higher than isomeric 3º-amines (no bonding).
➢ The 3º-amines have boiling points similar to equivalent sized ethers ; and in all but the smallest
compounds, corresponding ethers; 3º-amines and alkanes have similar boiling points.
➢ In the examples shown here, it is further demonstrated that chain branching reduces boiling points by
10 to 15 ºC.
Compou CH3(CH2)2C CH3(CH2)2 CH3(CH2)2N CH3CH2NHC (CH3)3C (CH3)2CHO (CH3)2CHN (CH3)3

nd H3 OH H2 H3 H H H2 N
Mol.Wt. 58 60 59 59 58 60 59 59
Boiling -0.5º 97º 48º 37º -12º 82º 34º 3º
Point ºC
➢ The water solubility of 1º and 2º-amines is similar to that of comparable alcohols .

➢ The water solubility of 3º-amines and ethers is also similar . These comparisons, however, are valid only
for pure compounds in neutral water.
H. QUATERNARY AMMONIUM SALT
➢ When all the four hydrogen of the ammonium ion (NH 4 +) has been replaced by alkyl groups, the
compound is called Quaternary Ammonium salt.
➢ The amine salts are usually named as substituted ammonium salts.
Example
➢ Tetraalkylammonium halides are obtained by treating ammonia with excess of an alkyl halide or by
heating a tertiary amine with an appropriate alkyl halide.
➢ For example: (CH3)3N + CH3I → (CH3)4N+I-
➢ Tetraalkylammonium halides have properties very similar to the ionic inorganic salts. They are
crystalline solids. Their aqueous solutions conduct an electric current.

I. PREPARATION OF 1º-AMINES
➢ Although direct alkylation of ammonia by alkyl halides leads to 1º-amines, alternative procedures are
preferred in many cases. These methods require two steps, but they provide pure product, usually in
good yield. The general strategy is to first form a carbon-nitrogen bond by reacting a nitrogen
nucleophile with a carbon electrophile.
➢ The following table lists several general examples of this strategy in the rough order of decreasing
nucleophilicity of the nitrogen reagent. In the second step, extraneous nitrogen substituents that may
have facilitated this bonding are removed to give the amine product.
2nd
Nitrogen Carbon 1st Reaction 2nd Reaction Final
Example Initial Product Reaction
Reactant Reactant Type Type Product
Conditions
RCH2-
RCH2-X or RCH2-N3 or LiAlH4 or
1. N3(–) SN2 Hydrogenolysis NH2 or
R2CH-X R2CH-N3 4 H2 & Pd
R2CH-NH2
RCH2- RCH2-
RCH2-X or Na in
2. C6H5SO2NH(–) SN2 NHSO2C6H5 or Hydrogenolysis NH2 or
R2CH-X NH3 (liq)
R2CH-NHSO2C6H5 R2CH-NH2
RCH2-
(–) RCH2-X or RCH2-CN or CH2NH2 or
3. CN SN2 LiAlH4 Reduction
R2CH-X R2CH-CN R2CH-
CH2NH2
RCH2-
RCH=O or Addition / RCH=NH or H2 & Ni
4. NH3 Reduction NH2 or
R2C=O Elimination R2C=NH or NaBH3CN
R2CH-NH2
Addition /
5. NH3 RCOX RCO-NH2 LiAlH4 Reduction RCH2-NH2
Elimination
NH2CONH2
6. R3C(+) SN1 R3C-NHCONH2 NaOH soln. Hydrolysis R3C-NH2
(urea)

Experiments #14

LABORATORY ACTIVITIES

NAME:________________________ RATING:__________________
GROUP #:_____________________ DATE:____________________
LABORATORY ACTIVITY # 1
LABORATORY SAFETY PRECAUTIONS AND SYMBOLS
OBJECTIVE:
1. To be knowledgeable with regards to laboratory safety precautions
2. To be acquainted with warning signs and symbols seen in the laboratory
PROCEDURE:
1. Watch the link posted at your google classroom.
2. Draw the Personal Protective Equipment (PPE) on the space provided below
3. Draw and discuss the symbols and its precautions
RUBRICS FOR SCORING:

Drawing
3 – for a drawing with equal likeness Equipment and symbols (excellent)
2 – for a comparable likeness (good)
1 – for an apparent likeness (fair)
0 – for no likeness at all to the apparatus
A. Personal Protective Equipment (PPE)
1. DRAWING
Laboratory Gown (Lab gown) Laboratory Goggles

Laboratory Mask Laboratory Hand gloves
2.Give the Different types and the uses of the PPE enumerated above.
Laboratory Gown (Lab gown) Laboratory Goggles

Laboratory Mask Laboratory Hand gloves
3.Give ten (10) Safety precautions to be observe in the laboratory.
B. Signs and Symbols
1. Drawing

2. Discuss the safety precautions of the symbols above. (1 point each)

NAME:________________________ RATING:__________________
GROUP #:_____________________ DATE:____________________
LABORATORY ACTIVITY # 2
SOME SELECTED CHEMISTRY LABORATORY APPARATUS
AND ITS USES AND FUNCTIONS
OBJECTIVE:
1. To be acquainted with some selected laboratory apparatus and equipment used in the chemistry
laboratory by drawing an equal likeness of the apparatus and equipment.
2. To describe and identify the uses and function/s of the different laboratory apparatus and
equipment.
MATERIALS:
Erlenmeyer flask Graduated Pipette

Florence flask Volumetric Pipette
Distilling Flask Pasteur Pipette
Round Bottom Flask Serological Pipette
Volumetric Flask Microspatula
Condenser Lei-big pH Meter
Separatory funnel Centrifuge
Burette Hot Plate
Centrifuge Tubes Electronic Balance
PROCEDURE:
1. Watch link posted at your google classroom
2. Using the format given by your Instructor:
a. Draw the apparatus
b. Give the description (1 point)
c. Give the function/use each (1 point)
RUBRICS FOR SCORING:

Drawing
3 – for a drawing with equal likeness to the apparatus (excellent)
2 – for a comparable likeness (good)
1 – for an apparent likeness (fair)
0 – for no likeness at all to the apparatus

NAME:________________________ RATING:__________________
GROUP #:_____________________ DATE:____________________
EXPERIMENT NO. 1
COMMON LABORATORY OPERATIONS
OBJECTIVE:
1. To be familiar with the common laboratory operations regularly done in the chemistry laboratory
2. To perform the common laboratory operations competently.
INTRODUCTION
One of the aims of general chemistry laboratory is to teach and train students the proper laboratory working habits
and techniques. These laboratory techniques are best learned from actual demonstration and constant reminders.
Laboratory work can become more systematic and efficient through the application of useful procedures and techniques
that can lead to accurate analysis of experimental results. Nothing is more effective than proper and careful handling of
reagents and test solutions. Unnecessary waste of time, effort, and reagents are often avoided if experimental work is
conducted using the guidelines of laboratory procedures and techniques.
MATERIALS & REAGENTS
A. MATERIALS
Glass rod Watch glass

250 ml Beaker Erlenmeyer flask
3 – 4 test tubes with rack and brush Evaporation dish
Funnel Wire gauze
Filter paper Tripod
Iron stand and iron ring Pipette
Bunsen burner Pipettol (or aspirator)
B. REAGENTS
Sodium hydroxide solution; Ferric chloride solution; Sodium chloride solution
RUBRICS FOR SCORING
For Procedures:
➢ 2 points is given for every short procedure done that requires an immediate written observation
o 1 point for doing the procedure correctly
o 1 point for the answer
➢ An extra 3 points may be given for long procedures that requires 5 – 15 minutes to perform;
➢ An extra 5 points for procedures that require 16 – 30 min. to perform on the average
➢ An extra 8 points for procedures that require 31 – or more minutes to perform on the average
➢ 3 points is given for every generalization or conclusion made
o 1 point is to be deducted from the score for every mistake identified by the instructor
➢ 1 point is given for items that do not require performing a procedure
➢ 5 points is given for every illustration made
o 5 – outstanding – the illustration shows genuine effort on the part of the maker and all parts are labeled
with no misspelled words
o 4 – excellent – the illustration shows above average effort on the part of the maker, 1 or 2 parts are not
labeled and with misspelled words
o 3 – Good – the illustration shows average effort on the part of the maker, 3 to 4 parts are not labeled and
with misspelled words
o 2 – Fair – the illustration shows below average effort on the part of the maker, 5 or more parts are not
labeled and with misspelled words
o 1 – Poor – the illustration shows little effort on the part of the maker, and the illustration is not labeled
➢ 1 point is given for every correct chemical formula written
For Questions for Research:

➢ 5 points is given for each question
o 5 – outstanding – no mistakes identified
o 4 – excellent – 2 mistakes or missing concepts identified
o 3 – Good – 3 mistakes or missing concepts identified
o 2 – Fair – 4 mistakes or missing concepts identified
o 1 – Poor – 5 mistakes or missing concepts identified
o 0 – The answer is totally different from the expected response
PROCEDURES and OBSERVATIONS:
A. Pouring of Liquids.
In pouring from one container into another, care must be taken to prevent the liquid from running at the sides of the
container from which it is being poured. Fill a 150 mL beaker with 100 mL water. Hold a glass rod or a piece of glass
tubing against the lip of the beaker and pour the water very slowly into another empty beaker (as illustrated in Figures
– 2a & 2b below).
What is the purpose of the glass rod in pouring liquid?
_________________________________________________________________________
_________________________________________________________________________
Figure – 2a Figure – 2b
Often it becomes necessary to transfer an exact amount of a liquid from a bottle into another container by the use
of a pipette or a medicine dropper. In this case, let the pipette be filled by gravity or by the use of a rubber bulb or
aspirator similar to that on a medicine dropper.
B. Heating Liquids in Test Tubes.
Partially fill a test tube with water and grasp it with a test tube holder. Bring the water to a boil by holding the tube at
an angle of 45 and passing it back and forth over the tip of the flame. The heat should be applied to the upper portion
of the liquid but should not strike the tube above the level of the liquid. If the flame plays upon the glass above the
liquid, the glass becomes so hot that it cracks when the liquid touches it. On the other hand, if heat is applied only to
the lowest part of the test tube, the sudden formation of vapor sometimes causes the contents of the tube to be thrown
out.
(CAUTION: In Heating liquids, never point the test tube towards a person).
Why is heat not applied above the level of the liquid in the test tube?
_________________________________________________________________________
_________________________________________________________________________
C. Pipetting
Pipets are used as a tool for transferring fluids. Pipets can be graduated for measurements of small volumes of liquids.
1. Hold the pipette on one hand and a rubber bulb (or aspirator) with the other hand.
2. Squeeze the rubber bulb and touch it to the mouth of the pipette. Insert no more than ½ cm of the pipette’s mouth
into the bulb.
3. Dip the pipette into the liquid to be withdrawn or transferred.
4. Insert the squeezed rubber bulb into the pipette.
5. Slowly release your grip on the rubber bulb and the liquid will be sucked up into the pipette until you reached your
desired measured volume. Upon reaching the desired level of volume, quickly remove the bulb and replace with the
index finger, as shown in Figure 2c below. NEVER USE YOUR THUMB – your index finger will allow better control
and will also enable you to hold the other items with your free fingers when necessary. Touch the tip of the pipette
to the inside wall of the reagent bottle or container to remove any adhering drops.
6. Move your pipette into a receiving container, loosen the index finger slowly (but do not remove), and allow the
pipette to drain by gravity.

Figure 2c: How to use a pipet
D. Precipitation.
Place 2 mL of Sodium Hydroxide (NaOH) solution in a test tube and slowly add to this 2 mL of Ferric Chloride (FeCl3)
solution. Observe and describe the results.
Result:
____________________________________________________________________________________________
______________________________________________________
The solids which are formed in the interaction of two chemicals are known as a PRECIPITATE, and in this case it is
the insoluble Ferric Hydroxide, Fe(OH)3.
Allow the precipitate (Ferric hydroxide) to settle and then add a few more drops of ferric chloride solution. If more ferric
hydroxide is seen to form, it is an indication that the initial precipitation was not complete. Allow the newly formed
precipitate to settle again and add a few more drops of ferric chloride. Repeat this operation until no more precipitate
is produced. This indicates that complete precipitation has occurred.
Keep the mixture for the next laboratory procedure.
Show the finished result to your instructor. ____________________________________
E. Filtration.
Get a filter paper, about 6cm. square, then fold it in the middle into exact halves, then into quarters, and then into
another quarter. Open the last two folded sides so as to form a cone with one thickness on one side and three
thicknesses on the other sides. Place it in a funnel with the insides moisten with a little amount of water. Refer to
Figure – 2d for this procedure.
Figure – 2d Figure – 2e
Place the funnel with filter paper directly in an Erlenmeyer flask or to an Iron Ring attached to an Iron stand with the
Flask at the bottom (refer to Figure – 2e). Transfer the mixture formed in Part 3 by carefully pouring the mixture, with

the aid of a glass rod, into the filter paper. Set aside both the residue and the filtrate to be used in Procedure 6.
Compare the appearance of the original mixture with that of the filtrate.
The process of separating solid particles from a liquid by pouring the mixture through a filter paper is called
FILTRATION. The liquid that passes through the filter paper is called the FILTRATE. The solid that is left on the filter
paper is called the RESIDUE.
Results and Observations: __________________________________________________
_________________________________________________________________________
_________________________________________________________________________
Show the finished result to your instructor: ___________________________________
F. Decantation.
Put 25 ml of water in a small beaker. Transfer the residue retained in the filter paper from procedure 5 to the beaker
with water. Stir the solution then let it stand for five minutes (5) to allow the solid particles to settle to the bottom of the
beaker. Carefully raise the beaker (avoid shaking the beaker) and pour-off or decant the supernatant liquid without
disturbing the solid particles. The solid particles must be left in the beaker.
Based from the procedure that you did, define in your own words what decantation is.
_________________________________________________________________________
_________________________________________________________________________
Show the fished result to your instructor. _____________________________________
G. Evaporation.
Put 1 ml. of sodium chloride solution in a clean evaporating dish. Put the evaporating dish on top of a tripod with a
wire gauze to support it. Using a moderate non-luminous flame, heat the evaporating dish until all the water had
evaporated. Examine the dish and see if there is anything left in it. Describe the appearance of the residue in the dish.
Result and Observations: ___________________________________________________
_________________________________________________________________________
Show the finished result to your instructor: ___________________________________
H. Heating in a Water Bath.

Sometimes it is better to carry out evaporation by the use of a Water bath. If the residue to be recovered or the
reactants in a chemical reaction are easily decomposed by heat, then heating must be done in a water bath.
Fill a 250 mL beaker with water two-thirds (2/3) full, which will serve as a water bath. A solution to be evaporated is
placed in a watch glass, or a small beaker and any of these apparatus used is placed on top of the water bath.
If test tubes are used for heating, put the test tubes in the water bath but see to it that the level of liquid in the test tube
is lower than that of the water in the beaker which is used as a water bath.
1. Put 1 ml. of Sodium chloride solution in a watch glass. Put the watch glass on the water bath. Heat the water bath
to boiling until all the water in the watch glass has completely evaporated. Examine the watch glass and observe
for the presence of a residue. Describe the quality of the residue.
Results and Observations: _________________________________________________
________________________________________________________________________
Show finished result to your instructor: ___________________________________
CONCLUSION:
QUESTIONS
1. Define the following terms:

a. Precipitation f. Decantate
b. Precipitate g. Residue
c. Filtration h. Supernatant
d. Filtrate i. Centrifugation
e. Decantation j. Centrifugate
2. Name and describe three (3) laboratory apparatus used to transfer liquid from one container to another container.
3. Enumerate at least five (5) proper ways or safety procedures that should be done when handling laboratory glasswares?
4. What are the proper procedures or safety precautions that you should do when
a. Heating or cooling laboratory glasswares?
b. Cleaning and drying laboratory glasswares?
c. Disposing of contaminated and uncontaminated broken glasswares?
5. Name and describe five (5) Common Methods of Separating a Solid-Liquid Mixture.

NAME:________________________ RATING:__________________
GROUP #:_____________________ DATE:____________________
EXPERIMENT NO. 2
CHEMICAL REACTIONS
OBJECTIVES:
1. To demonstrate the different types of chemical changes through chemical reactions
2. To observe whether a chemical reaction has taken place
3. To use chemical equations to illustrate a chemical reaction
A. MATERIALS
Evaporating dish, 8 test tubes, 150 mL beaker, watch glass, test tube rack, test tube brush, test tube holder, Crucible
tong, Bunsen burner, tripod, wire gauze, 1 pcs. Scrap paper, 2 pcs. filter papers, 8-inch clean & polished glass tubing
or plastic straw
B. REAGENTS
Mg ribbon, Zinc moss, Sulfur Powder, Iron fillings, Aluminum fillings, 6M H2SO4, 3M NaOH, 3M FeCl3, 0.1M Fe(NO3)2
solution, 0.1M AgNO3 solution, 0.1M Na2CrO4 solution, Lime water, Ca(OH)2, Carbonated Drink (Coke in can)
RUBRICS FOR SCORING

For Procedures:
➢ 5 points is given for every chemical equation written

PROCEDURES & OBSERVATIONS
A. Synthesis or Direct Union
1. Mix 1.0 gram sulfur with 1.0 gram iron filings in a test tube and heat over a Bunsen flame.
Result: ______________________________________________________________
______________________________________________________________
Give the balanced chemical equation for the above reaction.
______________________________________________________________
2. Place a 2 cm piece of magnesium ribbon at the tip of your crucible tong and ignite it with the Bunsen burner
flame. Collect the ashes on a clean watch glass.
Result: ________________________________________________________________
_______________________________________________________________________
What substance reacted with magnesium ribbon during the burning process? _________
Give the balanced chemical equation for the reaction.
____________________________________________________________________
B. Decomposition or Analysis
1. Open an ice cold carbonated drink without shaking then taste the content. Next pour a small amount of the
carbonated drink in a small clean beaker and warm it over a moderate Bunsen flame. Taste the warm soft drink.
Is there a difference in taste between the ice cold soft drink and the warmed one?
______________________________.
What made the difference? Explain.

___________________________________________________________________
___________________________________________________________________
What was the gas that evolved during the heating of the soft drink?
___________________________________
Write the balanced chemical equation for the decomposition of Carbonic Acid, (H2CO3):
________________________________________________________

2. Crumple a small piece of paper, burn it in an evaporating dish and then hold a clean and dry watch glass over
the burning paper using a crucible tong. Examine closely the watch glass and note what are deposited in it.
Results: ______________________________________________________
______________________________________________________________
Name three substances obtained from the burning of paper.
______________________________________________________________
C. Single Replacement or Substitution
1. Put 1 small piece of Zinc metal in a test tube and add 3 ml of 6N Sulfuric acid solution. Observe what happens.
Results: ___________________________________________________________
___________________________________________________________________
What gas was evolved? _____________________
Give the balanced chemical equation for the reaction
____________________________________________________________________
2. Place 3 mL of Ferrous Nitrate, Fe(NO3)2 solution in a clean and dry test tube. Add a pinch of Aluminum fillings
in the solution. Observe what happens and record your results.
Result: ______________________________________________________________
____________________________________________________________________
Write the balanced chemical equation of the reaction.
____________________________________________________________________
3. Filter the solution and set aside the residue. Place the filtrate in an evaporating dish and evaporate to dryness.
Compare the residue in the evaporating dish with that of the residue in the filter paper.
Result: _____________________________________________________________
___________________________________________________________________
What substance is present in the residue? ______________________________
What compound is present in the filtrate? _______________________________
D. Double Replacement or Metathesis
1. Get 2 mL each of Sodium Hydroxide (NaOH) solution and Ferric Chloride, FeCl3. Mix the two solutions in a clean
test tube and observe.
Result: _______________________________________________________________
_______________________________________________________________
Give the chemical equation for the reaction.

_______________________________________________________________
2. Get 2 mL each of Silver Nitrate (AgNO3) solution and Sodium Chromate (Na2CrO4) solution. Mix the two solutions
in a clean and dry test tube and observe.
Result: _________________________________________________________
________________________________________________________________
_______________________________________________________________
3. Place 10 mL of filtered lime water in a 150 mL beaker. Put a straw or polished glass tubing in the beaker with
lime water then blow gently on the upper end of the straw or glass tubing. Make sure that the lower end of the
straw or glass tubing is immersed in the lime water. Blow several times until there is an observed change in the
lime water.
Result: ______________________________________________________________
____________________________________________________________________
What substance is responsible for the turbidity of the lime water? ________________
____________________________________________________________________
CONCLUSIONS
QUESTIONS
1. List at least three (3) evidences that a chemical reaction has taken place.
2. Give 5 examples of chemical changes you observe in your everyday activities.
3. Zinc metal, Zn, will react with 0.5 M HCl but copper metal, Cu, will not. Why?
4. From the following list of chemicals, write ALL combinations that would lead to a double replacement reaction. Write
the complete balanced equation for the reactions below.
CaCl2 H2CO3 KClO3 Fe(OH)3 Mg3(PO4)

NAME:________________________ RATING:__________________
GROUP #:_____________________ DATE:____________________
EXPERIMENT NO. 3
PROPERTIES OF SOLUTIONS
OBJECTIVE
1. To observe the various factors that affects the solubility of compounds

2. To explain expertly the effects of the factors that affects the solubility of solutions
3. To describe and compare the different properties of solutiions
4. To prepare and observe the properties of supersaturated solution
A. MATERIALS
50-ml beaker, thermometer, glass rod, triple beam balance, Bunsen burner, tripod, wire gauze (hot plate is more
preferable), crucible tong, applicator sticks, Test tubes with test tube rack, Test tube brush
B. REAGENTS
Potassium Permanganate crystals, Distilled water, NaCl crystals, Sodium Sulfate, Calcium Carbonate, Benzoic Acid,
Ethyl alcohol, Diethyl ether
RUBRICS FOR SCORING

For Procedures:


A. FACTORS AFFECTING THE SPEED OF DISSOLVING
1. Drop a crystal each of Potassium Permanganate into two separate test tubes half filled with water.
2. Shake the contents of one test tube until the solid is dissolved, but do not shake the other one.
3. Observe the layer of denser salt solution on the bottom of each test tube by tilting the test tubes back and forth slowly.
Compare also the color of the two solutions.
Result and Observations: _____________________________________________
___________________________________________________________________
What means of increasing the rate of solubility have just been demonstrated?
____________________________________________________________
B. FACTORS AFFECTING THE SOLUBILITY OF A SUBSTANCE
1. NATURE OF SOLUTE
a. Weigh 0.5 gram of each of the following: Sodium Chloride, Sodium Sulfate, Calcium Carbonate, and Benzoic
Acid. Place these separately into four (4) test tubes.
b. Add 3 ml of water to each test tube. Shake thoroughly and observe the solubility of these substances. Write your
observations in the table below.
Solutes: Solvent Solubility of Solute Type of Solute

(Soluble, Slightly soluble (Polar or Nonpolar)
or Insoluble)
Sodium Chloride, NaCl Water
Sodium Sulfate, Na2SO4 Water
Calcium Carbonate, Water

CaCO3
Benzoic Acid, Water
C6H5COOH
2. NATURE OF SOLVENT
a. Place about 0.5 gram of Sodium Chloride, NaCl in each of three test tubes.
b. To each test tube, add 3 ml of Ethyl Alcohol (Ethanol), Diethyl Ether and Water, respectively. Shake each solution
thoroughly and observe the solubility of the sodium chloride with each of the three solvents used. Record your
results in the table below.
Solute Solvent Solubility of Solute Type of Solvent

(Soluble, Slightly (Polar or Nonpolar)
soluble or Insoluble)
Sodium Chloride, NaCl Ethyl Alcohol,
C2H5OH

Sodium Chloride, NaCl Diethyl Ether,
C2H5OC2H5
Sodium Chloride, NaCl Water, H2O
c. Repeat the experiment, using Benzoic Acid instead of Sodium Chloride. Write your results and observations in
the given table below.
(Soluble, Slightly (Polar or Nonpolar)
soluble or Insoluble)
Benzoic Acid, Ethyl Alcohol,
C6H5COOH C2H5OH
Benzoic Acid, Diethyl Ether,
C6H5COOH C2H5OC2H5
Benzoic Acid Water, H2O
C6H5COOH
d. Repeat the experiment, using liquid solute. Dissolve 1 mL of water in 2 mL each of the given solvent in the table.
Write your results and observations in the table given on the next page.

(Miscible, Slightly (Polar or Nonpolar)
miscible or Immiscible)
Water, H2O Ethyl Alcohol,
C2H5OH
Water, H2O Diethyl Ether,
C2H5OC2H5
Water, H2O Hexane,
C6H14
What type of solutes dissolve in Polar solvents? _____________________________
What type of solutes dissolve in Non-polar solvents? _________________________
What type of solvents dissolve Polar solutes? _______________________________
3. EFFECT OF TEMPERATURE
a. Add a few drops of dilute hydrochloric acid to 1 ml of lead acetate solution.
Result: _______________________________________________________
______________________________________________________________
b. Heat the mixture and observe the effect on the precipitate.
Result: _______________________________________________________
______________________________________________________________

c. Cool this by allowing tap water to run over the outside of the tube.
Result: _______________________________________________________
______________________________________________________________
What is the effect of a rise of temperature upon the solubility of solid?
______________________________________________________________
______________________________________________________________
4. SUPER SATURATION
a. Weigh 5.0 grams of crystallized Sodium Thiosulfate and place it in a clean test tube.
b. Add 2 ml of water and heat gently until all of the salt has been dissolved. If, after continued heating, some of the salts
still remain un-dissolved, pour carefully the solution into another test tube. See to it that no undissolved particles will
transfer to the 2nd test tube. Cover the 2nd test tube with a piece of filter paper and set aside to cool.
c. Drop a small crystal of sodium thiosulfate into the solution and shake.
Result: _____________________________________________________________
Why is it necessary to dissolve all the salt before setting the solution aside to cool?
____________________________________________________________________
____________________________________________________________________
CONCLUSIONS
QUESTIONS FOR RESEARCH

1. What is a Solution?
2. Define unsaturated, saturated and supersaturated solution?
a. Unsaturated solution –
b. Saturated solution –
c. Supersaturated solution –
3. Differentiate Solubility from Concentration?
4. Enumerate three (3) factors that affect the speed of dissolving.
5. Enumerate three (3) factors that affect solubility of a solute.
6. One generalization which can be used for determining solubility is “like dissolves like”. Explain this statement. How was
this generalization illustrated in this activity?

NAME:________________________ RATING:__________________
GROUP #:_____________________ DATE:____________________
EXPERIMENT NO. 4
ACID AND BASE TITRATIONS
OBJECTIVES
1. To apply the procedures of titration with confidence

2. To observe the process of neutralization of an acid and a base
3. To analyze the neutralization reactions of acids and bases
4. To produce accurate data of neutralization reactions.
INTRODUCTION
It is sometimes necessary to determine experimentally the concentration of an acid solution or a base solution. In
an acid-base titration, a solution with a known concentration, called standard solution, is used to neutralize a solution with
an unknown concentration to which a few drops of an appropriate acid-base indicator is added. If the solution of unknown
concentration is acidic, a standard base solution is added to the acid solution drop by drop until it is neutralized, and vice
versa.
While doing an acid-base titration, you must be able to recognize when to stop adding the standard solution. A
sudden change in color indicates that neutralization has occurred. At this point, the number of hydronium ions from the acid
is equal to the number of hydroxide ions from the base. The point at which this happens is called the end point of the titration.
When this point is reached, the volume of the standard solution used must be carefully determined. Then, measured
volumes of the two solutions and the known concentration of the standard solution can be used to calculate the concentration
of the other solution.
MATERIALS AND REAGENTS
A. MATERIALS
2 - Burettes, Burette clamp, 3 - Erlenmeyer flask, 3 - beakers, Dropper/pipette, 100 mL graduated cylinder, Iron stand
B. REAGENTS
0.5M standard solution (NaOH); 0.5M HCl solution; Phenolphthalein indicator; Methyl Orange indicator, Distilled
water
RUBRICS FOR SCORING

For Procedures:

➢ 5 points is given for every correct value computed
o 5 points for every correct value with complete solution
o 3 points for every correct value without complete solution
o 1 point for every incorrect value computed

PROCEDURES AND OBSERVATIONS
A. ACIDIMETRY
Neutralization of an unknown concentration of an Acid with a Standard Solution of a Base.
1. Wash the burettes with detergent solution. Rinse them thoroughly, first using tap water, then finally with distilled
water.
2. Pour about 10ml of the prepared base solution in one burette (make sure that the stop cock is closed) and rinse
the inside surface of the burette thoroughly. Then open the stop cock and allow the base to run out the burette tip.
Next, close again the stop cock then fill the burette with the prepared standard NaOH solution.
3. Make adjustments so that the lower meniscus of the liquid level will coincide with the zero-mark of the burette.
Before recording this reading, make sure that there are no air bubbles entrapped in the tip end of the burette. If
there are, put a clean empty beaker underneath the burette then open the stopcock of the burette to fill up the
lower end of the burette. Check that there are no bubbles formed this time. Use the base collected in the beaker
to fill up again the burette until the lower meniscus of the solution is at zero.
4. Support the burette on an iron stand using a burette clamp as shown in Figure 1 below.

5. Measure 10 mL. of the prepared standard HCl solution into a 250 mL. Erlenmeyer flask. Dilute it with 20 mL.
distilled water, pouring it along the sides of the flask to wash down any adhering alkali droplets. Then, add three
drops of phenolphthalein indicator. Swirl the flask to mix all the reagents.
6. Place the Erlenmeyer flask under the burette filled with standard NaOH. Slowly open the stopcock to allow the
NaOH solution to drop – by drop into the Erlenmeyer flask containing the acid (HCl) solution. While adding the
NaOH solution, keep on rotating the Erlenmeyer flask with a swaying motion of the wrist. Continue the addition of
NaOH until the solution attains the first temporary light pink color. (Figure 2 above)
7. Continue the gradual addition of the base with continuous swirling of the flask until a permanent faint pink color
appears that does not fade for at least 1 minute with continuous swirling. If this happens, STOP adding the NaOH
standard solution. This is the end point of the titration.
8. Read accurately the volume used-up from the burette and record this as the exact final volume reading of the
NaOH used.
9. Confirm your results by performing 2 more trials.
TABLE 1: ACIDIMETRY – DATA AND RESULTS
Trial 1 (NaOH) Trial 2 (NaOH) Trial 3 (NaOH)
Initial reading (ml)
Final reading (ml)
Volume used(ml)
B. ALKALIMETRY.
Neutralization of an unknown concentration of a Base with a Standard Solution of an Acid.
1. Repeat procedures 2 to 4 above but use the Standard HCl solution to fill the other burette.
2. Measure 10 mL of the prepared standard HCl solution into a 250 mL. Erlenmeyer flask. Dilute it with 40 mL distilled
water, pouring it along the sides of the flask to wash down any adhering alkali droplets. Then, add three drops of
methyl orange indicator. Swirl the flask to mix all the reagents.
3. Place the Erlenmeyer flask under the burette filled with standard HCl solution. Slowly open the stopcock to allow the
HCl solution to drop – by drop into the Erlenmeyer flask containing the base (NaOH) solution. While adding the HCl
solution, keep on rotating the Erlenmeyer flask with a swaying motion of the wrist. Continue the addition of HCl until
the solution attains the first temporary light orange color. (Figure 2 above)
4. Continue the gradual addition of the base with continuous swirling of the flask until a permanent faint orange color
or peach color appears that does not fade for at least 1 minute with continuous swirling. If this happens, STOP
adding the HCl standard solution. This is the end point of the titration process.

5. Read accurately the volume used-up from the burette and record this as the exact final volume reading of the HCl
used.
6. Confirm your results by performing 2 more trials.
TABLE 2: ALKALIMETRY – DATA AND RESULTS
Trial 1 (HCl) Trial 2 (HCl) Trial 3 (HCl)
Initial reading (ml)
Final reading (ml)
Volume used(ml)
CALCULATIONS
1. For each trial in Table 1, calculate the concentration in Molarity of the unknown HCl solution using the relationship:
Macid x Vacid = M base x V base Equation (1)
Where: Macid = Concentration of acid (known or unknown), mol/L

Mbase = Concentration of base (known or unknown), mol/L
Vacid = Volume of Acid used = (Vfinal – Vinitial), mL
Vbase = Volume of Base used = (Vfinal – Vinitial), mL
1. For each trial in Table 2, calculate the concentration in Molarity of the unknown NaOH solution using the relationship
in equation 1 above
2. Write ALL your final answers in Table 3.
***Show ALL Computations at the Back of this page.
TABLE3: DATA OF COMPUTATIONS
TRIALS ACIDIMETRIC TITRATIONS ALKALIMETRIC TITRATIONS

Molarity of HCl Computed, mol/L Molarity of NaOH Computed, mol/L
Trial 1
Trial 2
Trial 3

CONCLUSIONS
QUESTIONS AND PROBLEMS
1. Define the following terms:
a. Standard solution
b. Titration
c. Endpoint
d. Indicator
e. Neutralization
2. Compare your results in each trial in the Acidimetric titration. Was there a difference? What was the reason for the
difference? Explain.
3. Compare your results in each trial in the Alkalimetric titration. Was there a difference? What was the reason for the
difference? Explain.
3. Give one importance of Neutralization reactions in the medical field and discuss briefly.
4. If 50.0ml of 0.5M KOH is needed to neutralize 10.0ml of H2SO4 solution of unknown concentration, what is the
concentration in (a) Molarity and (b) Normality of the H2SO4 solution?

NAME:________________________ RATING:__________________
GROUP #:_____________________ DATE:____________________
EXPERIMENT NO. 5
COMPARATIVE STUDY OF THE PROPERTIES OF
ORGANIC AND INORGANIC COMPOUNDS
OBJECTIVES
1. To compare the common differences between organic and inorganic compounds;
2. To identify the characteristics of Organic Compounds;
3. To apply simple laboratory techniques learned from previous experiments.
A. Materials
12-Test tubes, test tube rack, TT-Holder, test tube brush, evaporating dish, Watch glass, Bunsen Burner, wire gauze,
crucible tong, stop watch, tripod, crucible tong
B. Reagents
NaCl salt, NaCl solution, Solid K2SO4, Sucrose, Naphthalene, Benzoic acid, Diethyl ether, Ethanol, hexane, distilled
water
RUBRICS FOR SCORING

For Procedures:
➢ 3 points is given for every chemical equation written


A. Solubility.
Determine the solubility of the following substances in the different solvents indicated. Use only a pin head size of
each solute per 2 ml of each solvent.
Solutes Solvents
Water Diethyl Ether Ethanol
NaCl
K2SO4
Benzoic Acid
Naphthalene
Based on your observation, make a general statement as to the differences in the solubility of organic and
inorganic compounds.
____________________________________________________________________________________
_______________________________________________
B. Stability Towards Heat
Place a 0.5 gram of NaCl (Sodium chloride) in an evaporating dish and note its physical properties. Place another
small amount of NaCl in a test tube and heat strongly for 3 minutes. Cool and note the physical properties of the
heated NaCl.
Properties NaCl before heating NaCl after heating
Appearance
Color
Taste
Repeat the procedures above, this time make use of Sugar or Sucrose (C11H22O11) instead of Sodium Chloride or
NaCl.
Properties Sugar Before Heating Sugar After Heating

Appearance
Color
Taste
Compare the stability of organic and inorganic compounds toward heat.

C. Melting Point
Place a pinch of Sodium Chloride (NaCl) in a test tube. Heat the salt and note the time it takes to melt it. If after 3
minutes of heating, the substance does not melt, stop the heating.
Result and Observation:

_______________________________________________________________________
Repeat the same procedure above, this time use Benzoic Acid in place of Sodium Chloride.
Result and Observation:

_______________________________________________________________________
Based on your results, compare the melting point of an inorganic compound from an organic compound.
__________________________________________________________________________________________
____________________________________________________
D. Boiling Point.
Heat 2 ml of water in a test tube and note the number of minutes needed for it to start boiling. Repeat the above
procedure but this time, use Ethyl Alcohol in place of water. (CAUTION: ETHYL ALCOHOL IS FLAMMABLE!)
Result and Observations:

______________________________________________________________________
Repeat the above procedure but this time, use Ethyl Alcohol in place of water. (CAUTION: ETHYL ALCOHOL IS
FLAMMABLE!)
Result and Observations:
______________________________________________________________________
Based on your results and observations, make a generalization as to the boiling points of inorganic compounds
and organic compounds.
__________________________________________________________________________________________
____________________________________________________
E. Combustibility
Place 5 drops of Water in an evaporating dish. Ignite it with a lighted splinter. If combustible, note the color and
nature of the flame. Repeat this procedure using Ethanol and Hexane. Write your results and observations in
the table below.
Substances Tested Combustibility Color and Nature of Flame

Water
Ethanol
Hexane

Based on your results, which of the ignited compounds can be used as a good fuel/s and why?
___________________________________________________________________
___________________________________________________________________
CONCLUSIONS
1. Name and give the corresponding molecular or structural formula of all the Organic and Inorganic compounds
used in this experiment. Tabulate your answers.
2. Tabulate the observed differences between organic and inorganic compounds done in this experiment and give
three other differences.

NAME:________________________ RATING:__________________
GROUP #:_____________________ DATE:____________________
EXPERIMENT NO. 6
A SEPARATION TECHNIQUE USED IN ORGANIC CHEMISTRY: SOLVENT EXTRACTION
OBJECTIVE
1. To demonstrate the process of extraction;
2. To apply some of the common laboratory techniques in purifying and separating the components of organic
substances;
3. To manipulate the Separatory funnel correctly.
INTRODUCTION
When the organic compound is partially soluble in one solvent but the impurity is totally soluble, a purification
technique can be made by introducing another kind of solvent where the component is still soluble in the first and the
impurity soluble in the second solvent.
One of the most common methods of separating and purifying organic compounds from other substances is by
means of extraction. Extraction is a separation technique frequently employed in the laboratory to isolate one or more
components from a mixture. In the organic laboratory one of the more important applications of the extraction process has
been its use to remove an organic compound from a solution when distillation is not feasible or advantageous.
Extraction is based on the principle of solubility. The compound to be extracted is more soluble in a certain solvent
while the other components of the mixture are less soluble or insoluble. Extraction is a very general, highly versatile
technique that is of great value not only to the laboratory but in everyday life. The brewing of tea from tea leaves or the tea
bag and of coffee from the ground beans are excellent examples of extraction.
A. Materials
3 - 250 mL Beakers, 500 mL Beaker, Watch glass, Petri dish, 2 – 150 mL Erlenmeyer flask, Garduated cylinder,
Stirring rod, Separatory Funnel, Transfer funnel, Water through, Iron stand, Tripod, Iron ring, Bunsen burner, Wire gauze,
Crucible tong, Analytical balance, Filter papers
B. Reagents
Instant coffee, Benzoic acid, Sucrose, Sodium bicarbonate, Ethanol, Ethyl acetate, Sodium Sulfate (Anhydrous),
Distilled water, Ice
RUBRICS FOR SCORING

For Procedures:


➢ 1 point is given for each correct answer to an enumeration.
➢ 2 points is given to every correct definition answer.
➢ 4 points is given for other questions.
o 4 – excellent – 1 mistake or missing concept identified
A. FILTRATION
Filtration is a method of separating miscible or soluble substances from each other by passing the mixture on a filter
medium like a filter cloth or a filter paper. This is also a separation technique based on solubility differences.
1. Weigh 0.25 gram each of benzoic acid and sugar and note their physical appearance. Mix the two compounds
thoroughly and divide the mixture into two portions.
2. Put the first portion in a small test tube and add 2 mL of distilled water. Stir briskly using a stirring rod and filter.
3. Examine the residue and the filtrate. Which of the two organic compounds is soluble in the water?
4. Which substance is present in the filtrate? _____________________________
5. Which substance is present in the residue? _________________________________
6. Put the second portion in another test tube and add 2 mL of Ethanol (Ethyl alcohol).
7. Stir the solution briskly and filter.
8. Examine the residue and the filtrate.
Which substance is present in the filtrate? __________________________
Which is present in the residue? __________________________________
B. EXTRACTION OF CAFFEINE FROM INSTANT COFFEE
1. Preparing the Coffee Extract

a. Start heating 100 mL of distilled water in a 400 mL beaker and as soon as it starts to boil, lower the flame.
e. Weigh 2.0 grams of Sodium bicarbonate (NaHCO3) and stir into the beaker until it is dissolved.
f. In another container, weigh 5.0 grams of instant coffee and add to the mixture in procedure (b), stir until all the coffee
is dissolved.
g. Remove from the flame and cool.
2. The Extraction Process
a. Place a clean and dry Separatory funnel atop an iron ring clamped on an iron stand.
b. Using a transfer funnel, pour the coffee mixture from procedure 1 into the Separatory funnel. Ensure that the
Separatory funnel valve is closed (horizontal position).
c. Using a clean graduated cylinder, measure 30 mL of Ethyl acetate and add to the coffee mixture in the
Separatory funnel.
d. Mix the contents of the Separatory funnel by slowly rotating it. Avoid shaking the Separatory funnel too vigorously.
Release some of the pressure inside the funnel by removing the top cover of the Separatory funnel.
h. Observe the mixture.
What substance is found on the upper layer? ___________________________
What substance is found on the lower layer? ___________________________
i. Place an Erlenmeyer flask under the separatory funnel to catch the bottom layer. Gently open the valve to allow only
the bottom layer to pass through. Set aside this solution for reference purposes.
Reminders: When using a Separatory funnel, the lower layer should always pass thru the bottom while the upper
layer is thru the top to ensure proper separation of the two immiscible liquids.
j. Pour the upper layer in another Erlenmeyer flask. To this solution, add 2.0 grams of Anhydrous Sodium Sulfate
(Na2SO4) and stir.
Reminders: After the upper layer is removed from the separatory funnel, it must pass through a drying agent such
as Anhydrous Sodium Sulfate (Na2SO4). The purpose of the second filtration set-up is to remove any excess water
from the upper layer.
k. Filter the contents of the flask from procedure (g) in order to remove the Sodium Sulfate (Na2SO4). This filtrate now
contains the Caffeine.
2. Recovering the Caffeine
a. Place the filtrate from procedure 2(h) in an evaporating dish. Evaporate to dryness using a water bath. Eventually the
solvent will be driven off and a solid will be left behind which is the caffeine.
Precaution: Use the Fume hood during this operation. Use your Facemask to avoid inhalation of too much fumes
produced by the process of evaporation.
b. Determine the weight of the caffeine left in the evaporating dish using an Analytical Balance.
Weight of Caffeine: _____________________________________________

3. Calculating the % Yield
a. Calculate the % Yield of Caffeine by using the formula below. Show your calculations below.
% YIELD = Weight of Caffeine (g) X 100%

Weight of Coffee (g)
CONCLUSION
QUESTIONS
1. Enumerate five compounds that are good extracting solvents and give the specific substance they can extract. Write
your answers in a tabulated form.
2. Enumerate five characteristics of a good extracting solvent.
3. Enumerate four factors that can affect the process of extraction and explain how they can affect the results.

NAME:________________________ RATING:__________________
GROUP #:_____________________ DATE:____________________
EXPERIMENT NO. 7
PAPER CHROMATOGRAPHY:
SEPARATION TECHNIQUE USED IN ORGANIC CHEMISTRY
OBJECTIVES: To identify and apply some other methods of purifying and separating organic substances.
INTRODUCTION
Chromatography is another technique frequently employed to separate the components of a mixture. In its original
application the method was used for the separation of colored substances, but color need not be a required property for
compounds to be separated by chromatography. Colorless compounds may be rendered visible by other means. A mixture
to be resolved by paper chromatography is placed as a small spot on one end of a strip of paper and solvent is allowed to
move by capillary action through the spot and up the paper. The water adsorbed on the cellulose of the paper is the
“stationary phase” and the moving solvent is called the “mobile phase”. The ratio of the distance traveled by a compound
to that traveled by the solvent is called the Rf Value.
Rf Value = Distance the Compound Traveled__

Distance the Solvent Traveled
Note: The Rf value of a compound is a characteristic of the compound and the solvent used, and it serves to identify the
identity of each component in the mixture.
A. Materials
6 – Test tubes, 6 – Strips of Whatman Filter Paper, 6 – Corks, Glass tubing or Stirring Rod, Test Tube Rack, Pair of
scissors, Cutter, Foot rule, Hair Dryer, Pencil
B. Reagents
Distilled Water, 95% Ethanol, Isopropyl Alcohol, Methyl Red, Methyl Orange, Methylene Blue
RUBRICS FOR SCORING
For Procedures:


PROCEDURES & OBSERVATIONS:
1. Preparation of the Paper Chromatogram
a. Cut a rectangular piece of filter paper about 1.5 cm. wide and from 13 to 15 cm. long. Use a foot rule to
measure its dimensions. Make 6 strips.
b. Draw a line (use pencil) 2 cm. above the edge of the filter paper. In the center of the line draw a small circle,
about the size of the cross section of a glass tubing.
c. With the aid of a stirring rod or glass tubing, put a spot of Methyl Orange in the circle. Prepare another strip
with Methyl Orange spot. Dry the filter papers using a hair dryer.
d. Repeat the same process in procedure (c) but use Methylene Blue to spot the circle, then Methylene Red.
Make two spotted strips for each reagents. Again, dry the filter papers.
e. See to it that the dyes do not spread out to the edges of the filter paper. If this happens, change the filter
paper.
f. Get 6 corks, that should fit in the openings of the test tube to be used as developing chambers. Slit the bottom
of the cork carefully with a cutter then insert the paper chromatograms in the slits, securing the paper firmly.
2. Preparation of the Developing Chambers
a. Mix 1 mL each of 95% Ethyl alcohol and Water in a test tube. Label this as Test tube 1. In another test tube
mix 1 mL each of Isopropyl alcohol and Water and label it as Test Tube 2.
b. Prepare another 2 sets of the above mixtures and label them as Test Tube (TT) 3, TT4, TT5 and TT 6
respectively.
3. Development of the Spot
a. With careful handling insert each type of chromatogram in each of the six developing chambers using the cork
as handles.
b. Methyl Orange (MO) chromatogram in TT1 (Ethanol-water mixture) and TT2 (Isopropanol-water mixture)
respectively, Methyl Red (MR) chromatogram in TT3 and TT4, and Methylene Blue chromatogram in TT5 and
TT6 respectively.
c. Make sure that the chromatogram is vertical and does not touch the side of the test tubes or developing
chambers.
d. The solvent should be in contact with the lower end of the suspended filter papers but should not touch the
circle, which was spotted with the dyes!
e. Secure the corks on top of the test tubes and let it stand undisturbed for 30 minutes to allow the chromatogram
to develop.

f. After the given time is reached, carefully remove the filter papers (chromatogram) from the test tubes and
quickly mark the position of the solvent before it dries up.
g. But if the developing solvent had reached the point where the filter paper is attached to the cork in less than
30 minutes, remove the filter paper carefully from the cork and quickly mark that point with a pencil before the
solvent evaporates.
h. Dry the developed-chromatogram completely using a hair dryer.
i. Attach the dry developed-chromatogram on any space available on your manual with a scotch tape and label
them properly.
j. Draw the set-up of these procedures at the back of this page.
4. Calculation of the Rf Value
a. Measure in centimeters the distance traveled by each spot (MO, MR and MB) from their original positions.
Write your data on Table 1 below.
b. Measure in centimeters the distance traveled by each solvent (Ethanol-water mixture and the Isopropanol-
water mixture). Record your data in Table 2.
c. Calculate the Rf values for each chromatogram and solvents by using the formula given in the introduction
part.
d. Complete the required data in the Table 1 and 2.
e. Show your complete computations after the tables.
TABLE 1
Chromatograms Distance Traveled in Distance Traveled in

Ethanol – Water Mixture, Isopropanol – Water
(cm) Mixture, (cm)
1. Methyl Orange Spot
2. Methyl Red Spot
3. Methylene Blue Spot
TABLE 2:
DEVELOPING SOLVENTS Distance Traveled in
Filter Paper, (cm)
Ethanol – Water Mixture with:
2. Methyl Red Spot
Isopropanol – Water Mixture with:


2. Methyl Red Spot
ENRICHMENT QUESTIONS
1. Which of the three chromatograms has the farthest distance travelled in any of the solvents used? Why is this?
Reason out your answer.
2. Which of the three chromatograms has the shortest distance travelled in any of the solvents used? Again, why?
Explain your reasoning.
3. Which solvent-water mixture is the best to use in this type of chromatography and why?
4. Which combination of chromatogram and solvent gives the highest Rf value and why is this?
5. Which combination of chromatogram and solvent gives the lowest Rf value and why is this?
6. If you are going to perform paper chromatography effectively, what are the factors that you must consider in: (a)
choosing a good chromatogram; and (b) choosing a good developing solvent? Lists your answers in a tabulated
form.

CONCLUSION
QUESTIONS
1. What is the Rf value and its importance in chromatography?
2. Based on the Results of this Experiment:

a. Which dye has a Lesser affinity to the Filter paper?
b. Which has a Stronger affinity to the Filter paper?
3. Amino acids – the building blocks of proteins – are colorless compounds but they can be separated and
identified by Paper Chromatography. How is this possible?
4. Enumerate and give a brief description and discussion of the different types of chromatographic techniques.
5. What are the importance of Chromatographic techniques in the field of forensics and crime investigation? Cite
two (2) specific examples.

NAME:________________________ RATING:__________________
GROUP #:_____________________ DATE:____________________
EXPERIMENT NO. 8
PURIFICATION OF ORGANIC SOLIDS:
SUBLIMATION AND RECRYSTALLIZATION
INTRODUCTION
Once a product has been separated from a reaction mixture it must ordinarily be purified to remove any residual impurities.
Solids are usually purified by recrystallization, but solids with high vapor pressures can be purified by sublimation and a
few low-melting solids can be purified by distillation.
Sublimation is a phase change in which a solid passes directly into the vapor phase without going through an intermediate
liquid phase. Many solids that have appreciable vapor pressures below their melting points can be purified by (1) heating
the solid to sublime it (convert it to a vapor), (2) condensing the vapor on a cold surface, and (3) scraping off the condensed
solid. These processes are reversible and the vapors, when cooled, will condense directly to the solid. Sublimation work’s
best if impurities in the crude solid do not sublime appreciably. Sublimation is not as selective as recrystallization or
chromatography, but it has some advantages in that no solvent is required and losses in transfer can be kept low.
On the other hand, the simplest and most widely used operation for purifying organic solids is recrystallization.
Recrystallization is so named because it involves dissolving a solid that (in most cases) had originally crystallized from a
reaction mixture or another solution, and then causing it to again crystallize from solution. In a typical recrystallization
procedure, the crude solid is dissolved by heating it in a suitable recrystallization solvent.
Organic compounds which are more soluble in hot solvents than in cold solvents can easily be purified by re-crystallization.
If an impure organic solid is dissolved in an appropriate solvent at an elevated temperature and filtered before being allowed
to cool, most of the insoluble impurities will be removed. As temperature of the solution decreases, crystals will appear in
the solution. The crystals formed are more nearly pure than the starting material. Recrystallization is based on the fact
that the solubility of a solid in a given solvent increases with the temperature of the solvent.
A. Materials
Analytical balance or electronic balance, 2 – 250 mL Erlenmeyer flask, 2 – 250 mL beakers, 10 mL Graduated cylinder,
Watch glass, Petri Dish, Test tubes, Test tube rack, Test tube brush, Transfer funnel, Tripod, Wire gauze, Bunsen burner,
Applicator sticks, Glass chips, Filter papers, Water trough, Clean vials or containers, Stirring Rod, Medicine droppers
B. Reagents
Potassium Sulfate (K2SO4), Naphthalene, Benzoic acid, 1% BaCl2 Solution, Charcoal powder, or Activated Carbon,
Distilled Water, Ice Cubes
RUBRICS FOR SCORING

For Procedures:

A. SUBLIMATION
1. Weigh 1.0 gram each of Potassium Sulfate (K2SO4) and Naphthalene in a clean watch glass. Mix and pulverized
the two compounds into a homogeneous mixture using a mortar and pestle.
2. Transfer the mixture into a 250 mL beaker and cover the top of the beaker with a clean Petri dish filled with ice
cubes or ice cold water.
3. Place the beaker on a wire gauze placed on top of a tripod and gently heat the beaker until the bottom part of the
Petri dish is filled up with crystals.
4. Cool the entire set-up then carefully lift the Petri dish and scrape off the deposited crystals. Collect the crystals on
a clean sheet of paper. Compare the crystals to the original Naphthalene crystals used.
Result: ________________________________________________________________
_______________________________________________________________________
Note the odor of the collected crystals compare it with the original Naphthalene. Write your observations.
_______________________________________________________________________
5. Transfer half of the collected crystals in a test tube and dissolved in 1 mL of Chloroform. Add 10 drops of Barium
Chloride (BaCl2) Solution (Barium Chloride solution is a test reagent for the presence of Sulfates).

6. Scrape the remaining residue left in the beaker and transfer a small amount to a test tube. Dissolved the solid by
adding 1 mL of distilled water then test the solution with 10 drops of Barium Chloride (BaCl2) solution.
Result: ________________________________________________________________
______________________________________________________________________
______________________________________________________________________
What is the name and chemical formula of the substance deposited at the bottom of the Petri dish?
______________________________________________________________________
What is the name and chemical formula of the substance left in the beaker?
______________________________________________________________________
B. RECRYSTALLIZATION
1. Weigh 4.0 grams of Benzoic Acid (b.a). Put 1 gram in a watch glass and set aside.
2. To the remaining 4.0 grams of Benzoic acid, put it in an Erlenmeyer flask and add 20 mL of distilled water and boil
over a low flame using the Bunsen burner. Add the boiling sticks to prevent boiling over of the solution.
3. Heat the mixture to a gentle boil until no more solids appear to dissolve. If the Benzoic acid has not completely
dissolved after 30 seconds to 1 minute, add water in approximately 2 mL increments as needed (but should NOT
exceed 30 mL) until all the b.a. has dissolved and wiith constant stirring.
4. When all of the b.a. has dissolved, add 0.1 gram (or a pinch) of charcoal and continue heating with vigorous and
constant stirring.
5. Total the volume of water you have added in the original mixture and add an additional of 25% of the total volume
of water and continue heating to keep the solution hot. Let the solution boil.
6. Remove the flask from the flame using a crucible or wrap it with a towel then filter. (CAUTION: THE VAPOR from
the mixture can SCALD your hands or face! KEEP YOUR HANDS and FACE AWAY FROM THE VAPORS!).
7. Collect the filtrate in a small beaker using gravity filtration. The residue collected are impurities, you may discard
this. Keep the filtrate.
8. Cool the filtrate at room temperature to cool then later put the beaker containing the filtrate in an ice bath or water
trough containing ice cubes for 10 – 15 minutes to allow further recrystallization. You may enhance the
recrystallization process by stirring.
9. Collect the crystals formed by gravity filtration. Air dry them (or use the cool air from a hair dryer) then compare them
to the physical appearance of the original Benzoic acid.
Results and Observations: _______________________________________________
______________________________________________________________________

CONCLUSION
1. What principle is the process of extraction based? Explain briefly your answer.
2. Give two (2) important applications of the extraction process.
3. Enumerate three (3) properties of a good extracting solvent?
4. Give two (2) proofs that the crystals collected in the sublimation process are Naphthalene.
5. Give two (2) limitations of the Sublimation process as a general method of separation technique?
6. Glucose is soluble in hot water as well as in cold water. Can it be purified by the re-crystallization method used in
this experiment? Explain briefly.
7. What would be the behavior of Ethyl Alcohol (Ethanol) in an Ethyl Acetate –Water mixture? Explain your answer
briefly.

NAME:________________________ RATING:__________________
GROUP #:_____________________ DATE:____________________
EXPERIMENT NO. 9
DETERMINING THE PURITY OF ORGANIC SOLVENTS:
BOILING POINT BY CAPILLARY METHOD
INTRODUCTION
After a reaction product has been purified it is usually analyzed to find out whether it is, in fact the desired product, and how
pure it is. Another function of analysis is to determine the identity of a substance’s physical properties. A solid substance is
usually analyzed by measuring its melting point and a liquid substance is by measuring its boiling point.
In this experiment the capillary boiling point is determined. The boiling point of a liquid is defined as the temperature at
which the vapor pressure of the liquid is equal to the external pressure at the surface of the liquid, and also as the
temperature at which the liquid is in equilibrium with its vapor phase at that pressure. These definitions are the basis for
various standard scale and small–scale methods for measuring boiling points. For example, the boiling point of a liquid can
be determined by measuring the temperature at which the liquid/s vapor, trapped inside a capillary tube immersed in the
liquid, exerts a pressure equal to the external pressure.
Like the melting point of a solid, the boiling point of a liquid is a physical characteristic of a compound. Many factors go into
the estimation of the boiling point of a liquid such as the mass and most importantly, hydrogen bonding. The boiling point of
a pure liquid is constant and serves as an indication for its identity, just as the melting point does for a pure solid.
A. Materials
Barometric Thermometer (150° - 200°C), 250 mL Beaker, 8 pcs. Capillary tubes, 6 – pcs. Rubber bands, Pasteur
pipettes, 6 – Test tubes, Test tube holder, Test tube rack, Test tube brush, Iron Stand with iron Ring, Iron Clamp, Wire
Gauze, Cork with hole to fit Thermometer, Bunsen Burner, Tripod
B. Reagents
Glycerol oil, 95% Ethanol, Methanol, Acetic acid, Ethyl Acetate, Cyclohexane
RUBRICS FOR SCORING

For Procedures:

A. DETERMINATION OF BOILING POINTS OF ORGANIC SOLVENTS
1. Preparation of Boiling Point Capillary Method Set-up

(a) Get six (6) capillary tubes and heat one end of each over a Bunsen burner until it is completely sealed.
(b) Cool the capillary tubes, then put one in a test tube containing 1 mL of 95% Ethanol. Set-aside the other
capillary tubes for the solutions to be tested.
(c) The sealed-end of the capillary tube must be pointing upward and the open-end is the one touching the bottom
part of the test tube with the ethanol solvent.
(d) Insert a thermometer in a cork in such a way that the calibrations are visible.
(e) Use a rubber band to attach the thermometer to the test tube containing the ethanol and capillary tube.
(f) The bottom of the test tube and the mercury bulb of the thermometer must be at the same level.
(g) Clamp the entire set-up to an iron stand. Put a tripod with wire gauze and a 250 mL beaker half-filled with
Glycerol oil underneath the thermometer.
2. Verifying the Boiling Points of Alcohols

(a) Open the iron clamp and lower the thermometer into the beaker (set-up should not be touching the side or bottom
of the beaker).
(b) The level of glycerol in the beaker must be higher than the level of ethanol or other solvents in the test tube.
(c) Place the Bunsen burner under the beaker and heat (use moderate flame!) until a rapid and continuous stream
of bubbles are released from the open end of the capillary tube.
(d) Put-off the flame and note the moment bubbles cease to come out of the capillary tube and liquid in the test tube
enters the capillary tube.

(e) Read right away read the temperature in the thermometer. This is the boiling point of your test liquid. Record the
observed boiling point.
(f) Compare your experimental result and the literature boiling point of the liquid.
(g) Repeat the same procedures for the Methanol, Acetic acid, Ethyl Acetate, and Cyclohexane but use a different
test tube and capillary tube for each test liquid.
(h) For each liquid to be tested, the thermometer and oil bath must be cooled first before using it for the next test.
NOTE: Cool the glycerol used and return it to the Reagent Bottles.
(i) DRAW AND LABEL THE SET-UP FOR BOILING POINT CAPILLARY METHOD
TABLE2: DATA & RESULTS FOR BOILING POINTS
Test Liquids Observed Boiling Literature Boiling Difference in

Point, °C Point, °C Temperature, °C
95% Ethanol
Methanol
Ethyl Acetate
Acetic Acid
Cyclohexane
Which test liquid has the lowest experimental boiling point? ____________________________
Which test liquid has the highest experimental boiling point? ___________________________

Which of the test liquids have their boiling points almost near their literature boiling point?
______________________________________________________________________
And which of the test liquid/s have their boiling point/s almost very far from their literature boiling point? What do you think
caused the big difference? Explain.
______________________________________________________________________
______________________________________________________________________
______________________________________________________________________
CONCLUSIONS
QUESTIONS
1. Enumerate three (3) factors that affect the melting point of pure substances and explain the effect of each factor.
2. Enumerate three (3) factors that affect the boiling point of pure liquids and explain the effect of each factor.
3. Why is the Melting point of a sample which has been previously melted different from the melting point of the original
sample? Explain.
4. Aside from melting point and boiling point, what other simple test can you do to determine if a given solid or liquid is
pure or not? Explain briefly.

NAME:________________________ RATING:__________________
GROUP #:_____________________ DATE:____________________
EXPERIMENT NO. 10
PURIFICATION OPERATIONS IN ORGANIC CHEMISTRY:
FRACTIONAL DISTILLATION
OBJECTIVES:
1. To learn how to separate the components of an impure organic solvent.
2. To apply competently the process of fractional distillation
3. To identify some factors that affects the purity of fractionated liquid
INTRODUCTION
Most liquid products of reactions are purified by simple distillation. High boiling liquids that may decompose during ordinary
distillation can be purified by vacuum distillation. When a liquid product contains a substantial amount of liquid impurity
having a boiling point close to that of the product itself, it should be purified by fractional distillation. Both liquid and solid
products can sometimes be purified also by column chromatography.
Fractional distillation is the process of separating two or more liquids by making use of their differences in boiling points.
It also refers to a distillation process involving several concurrent vaporization-condensation cycles. A mixture of miscible
liquids with different boiling points can be separated satisfactorily by fractional distillation, where the liquid with the lowest
boiling point distilling over first. The first distillate produced from such a mixture is called the forerun. During a fractional
distillation process, the distillate is collected in several separate fraction collectors (receivers), the contents of each being
a different fraction. Each fraction is collected over a different temperature range, with the lower boiling fractions containing
a greater percentage of the more volatile component and the higher boiling fractions containing more of the less volatile
component. The middle fraction would be a mixture of the two, which could be redistilled if desired. If the initial distillate is
redistilled, the first vapor and condensate again will be richer with the lower boiling fraction. The process if repeated a great
many times will result in fairly clean separation of the mixture. The condensate becomes richer with the lower boiling point
fraction and the residual liquid in the distilling flask become richer with the higher boiling fraction.
A. Materials
Distilling Flask, Condenser Lei Big, Thermometer, Graduated Cylinder, Evaporating dish, 12 - Test tubes, Test tube
rack, Test tube brush, Cork with hole to fit Flask, Glass chips, 2 – Iron Clamps, 2- Iron Stand, Iron Ring, 2 – Rubber
Tubings, Transfer funnel, Pasteur pipettes, Water trough, Tripod, Applicator sticks, Wire Gauze, Bunsen Burner
B. Reagents
Table Sugar (sucrose) and 40% Ethanol Solution
RUBRICS FOR SCORING

For Procedures:

A. Fractional Distillation Set-up
1. Measure 100 mL of 40% Ethanol (Ethyl Alcohol)
2. Place 95 mL of ethanol in your previously cleaned and washed distilling flask taking care that no liquid enters the side
arm of the flask.
3. Place the remaining 5 mL ethanol in a labeled test tube and set aside for procedure B.
4. Add a few glass chips into the distilling flask to prevent bumping. Bumping is a term given to irregular boiling.
5. Assemble the rest of the apparatus for simple distillation set-up. Let your instructor check your set-up before proceeding.
6. Cover the top of the distilling flask with a cork fitted with a thermometer. Make sure that the tip of the thermometer bulb
is just below the side arm of the distilling flask.
7. Check all connections for tightness or possible sources of leaks.
8. Heat the contents of the flask to boiling using a moderate flame. Lower down the flame when the sample is already
boiling. Make sure that your ethanol solution does not boil to dryness.
9. Note the temperature of the appearance of the first drop: _______________________
10. Collect forty (40) drops of distillate in a test tube. Label this as the first fraction. Then collect five (5) more fractions
successively taking note of the temperature reading for each fraction collected. Do not forget to label your fractions.

11. Record all your results and data in the Table.
B. Comparative Tests of Original Solution and Fractions
1. Odor
Note the odor of each fractions and compare it with the 40% original Ethanol solution taking into consideration the
strength of the alcoholic smell. Write your observation in the data table.
2. pH
Divide each fractions into two equal parts and set aside the other half for procedure 4. To the other half portion,
dip a strip of pH paper into each fractions and take note of their pH readings. Write your results in the table.
3. Flammability
a. Place ten drops of fraction 1 in an evaporating dish and ignite using an applicator stick.
CAUTION: Be extra careful since you will be dealing with open flame if the fractions tend to be
flammable!!
b. Repeat the above procedure using the 2nd Fraction then the 3rd, and so on, until all the fractions have been
tested.
c. Test also the flammability of the 40% Ethanol solution.

d. Write all your results and observations in the Table.
4. Solubility
a. Test the solubility of a few crystals (0.10 gram) of sugar on the remaining half portion of fractions.
b. Similarly test also the solubility of a few crystals of sugar on the original solution of 40% Ethanol.
Note: Strictly follow the amount of sugar to be dissolved in each fractions as to prevent other factors such
as saturation in interfering with the correct interpretation of the results.
C. TABLE OF DATA AND RESULTS
Properties Temperature Odor pH Flammability Solubility of

(°C) Sugar
40% Ethanol
Original
Solution
1st Fraction
2nd Fraction
3rd Fraction
4th Fraction

5th Fraction
CONCLUSION
QUESTIONS
1. What is the main component of the condensate? ____________________
2. What is the main component of the residual liquid in the distilling flask? _________________
3. From the experimental results, which fraction has the highest % of Ethanol and why?
4. How can alcohol content of the distillate be increased? Discuss.
5. State one importance of the use of fractional distillation in the Chemical Industry and give a brief discussion on how it
is used.
6. Enumerate four (4) factors that can affect the purity of the fractions in a fractional distillation process and give a short
explanation for each.

NAME:________________________ RATING:__________________
GROUP #:_____________________ DATE:____________________
EXPERIMENT NO. 11
COMPARATIVE STUDY OF THE COMMON PROPERTIES OF HYDROCARBONS
OBJECTIVES
1. To prepare simple hydrocarbons from inorganic reactants
2. To observe and describe the common properties oh hydrocarbons
3. To identify the reactions of each hydrocarbon with different test reagents.
A. MATERIALS
12- Test tubes with TT-rack, TT-holder, Test Tube Brush, Water trough, Delivery tube, Cork stoppers, Medicine
dropper
B. REAGENTS
Calcium Carbide, Cyclohexane, Cyclohexene, Toluene, Bromine water, CCl4, KMnO4 solution, Ammoniacal sol’n of
AgNO3, conc. H2SO4
RUBRICS FOR SCORING

For Procedures:

A. Generation of Acetylene.
1. Fill-up to 2/3 full a water trough with water. Get five clean test tubes, fill it with water and using your thumb as cover
over each test tube, invert it and immersed each tube in the beaker with water. Hold the test tubes immersed in water
at one side of the beaker or trough.
2. Get a lump of calcium carbide and gently drop it in the middle of the beaker. Hold one test tube over the bubbles that
will result from the reaction between calcium carbide and water. When all the water in the tube is displaced, stopper
the test tube with a cork while the tube is still under the water. Repeat the procedure with the other remaining test
tubes. If no more bubbles are formed add another lump of calcium carbide and repeat the procedure until all test
tubes are filled up with acetylene gas.
3. Write the complete and balanced chemical reaction of Calcium carbide and water”
___________________________________________________________________________
B. Bromination of the Different Hydrocarbons.
1. Get 3 test tubes and place 1 ml of Cyclohexane to test tube 1, 1 ml of Cyclohexene to test tube 2, 1 ml of Toluene to test
tube 3, and get 1 test tube of Acetylene from procedure A.
2. To each test tube add 5 drops of bromine in CCl4; stopper the test tubes and shake thoroughly each test tube and allow
to stand for a few minutes before observing. Note what happens to the original color of bromine. If reaction is slow,
expose the test tubes to sunlight. Record your results in Table2.
3. Test all the test tubes containing the different hydrocarbons for the presence of a gas or HBr with a Blue Litmus Paper
(BLP) previously moistened with distilled water and held by forceps or tweezers placed on the mouth of the tubes.
Observe what happens to the BLPs and record your results in Table1.
4. Write all the chemical equations for the Bromination reactions of the four hydrocarbons tested.
C. Reaction with Potassium Permanganate, KMnO4 (Baeyer’s Test).
1. Add 5 drops of potassium permanganate acidified with a drop of conc. Sulfuric Acid (H2SO4) to 1 ml each of
Cyclohexane, Cyclohexene and Toluene and to a test tube containing Acetylene.
2. Stopper each test tube then shake thoroughly.

3. Note what happens to the color of potassium permanganate right after shaking. Record your observations in the table
1.
4. Write the chemical equation for ALL the reactions of the four hydrocarbons with KMnO4.
D. Reaction with Silver Nitrate (AgNO3).
1. Add 5 drops of ammoniacal solution of Silver Nitrate to 1 ml each of Cyclohexane, Cyclohexene, Toluene and to a test
tube of Acetylene.
2. Stopper each test tube then shake thoroughly.
3. Note in which test tube is a precipitate obtained. Get a small portion of the precipitate and spread it on a wire gauze
and heat. The Silver Acetylide salt is explosive, so if the precipitate does not produce a crackling sound when heated,
it is not a Silver Acetylide salt but just an impurity.
TABLE 1: Results and Observations:
TESTS
HYDROCARBON
Blue Litmus
Br2 Paper Test KMnO4 AgNO3
Cyclohexane
Cyclohexene
Acetylene
Toluene
Based from your observations, which reagent is:
(a) Positive to ALL groups of Hydrocarbons? ____________________________________

(b) Positive to Unsaturated Aliphatic Hydrocarbons only? __________________________
(c) Used to differentiate between Alkenes and Alkynes? ___________________________
(d) Negative to both Alkane and Toluene? ______________________________________
(e) In which hydrocarbon/s was the color of the BLP changed? ______________________
4. Write the complete and balanced chemical reaction of AgNO3 with Acetylene.
”
___________________________________________________________________________
CONCLUSION
QUESTIONS
1. What is the major structural feature that distinguishes a saturated hydrocarbon from an unsaturated hydrocarbon and
from an aromatic hydrocarbon? Discuss briefly.
2. What do you call the test for Unsaturated Hydrocarbons?
3. Give one simple chemical test that can be used to differentiate an Alkane from an Aromatic hydrocarbon? Discuss
briefly.
4. Is the un-saturation of toluene the same as that of alkenes and alkynes? Explain briefly.
5. What is the relationships of the (a) Boiling points, and (b) Melting points of hydrocarbon compounds with respect to the
lengths of their hydrocarbon chains?

NAME:________________________ RATING:__________________
GROUP #:_____________________ DATE:____________________
EXPERIMENT NO. 12
PROPERTIES AND SPECIFIC TESTS FOR ALCOHOLS AND PHENOLIC COMPOUNDS
OBJECTIVES
1. To describe and compare the properties of alcohols with phenolic compounds
2. To perform accurately the different tests for alcohols and phenolic compounds
3. To predict and write correctly the chemical equations of the different reactions involved.
4. To follow safety precautions while conducting the different experimental procedures.
A. Materials
Test tubes, Test tube Rack, Test Tube holder, Test tube brush, 2 – 250 mL Beakers, Pasteur pipettes, Evaporating
dish, Splinters, Bunsen Burner, Wire gauze, Tripod, pH papers
B. Reagents
Anhydrous K2CO3, 95% Ethanol, 95% Isopropanol, Tert. Butyl Alcohol, Glycerol, Methanol, 1% K2Cr2O7 Solution, 1 M
HCl, Bromothymol Blue, Conc. H2SO4, Iodine in KI Solution, Lucas Reagent, 10% NaOH Solution, Solid Phenol, 10%
Aqueous Solution of Phenol, 1% KMnO4 Solution, 5% Na2CO3 Solution, Bromine water, Resorcinol Solution,
Catechol, Salicylic Acid solution, Alpha Naphthol, Cresol, 1% FeCl3 Solution, 5% NaOH Solution, Millon’s Reagent,
Distilled water
RUBRICS FOR SCORING

For Procedures:


A. CHEMICAL PROPERTIES OF ALCOHOLS
1. Reaction with Oxidizing Agents
a. Get five (5) clean and dry test tubes and label them as test tube 1, 2, 3, and 4 respectively.
➢ To test tube 1 (TT1), put 1 mL of Ethanol
➢ To test tube 2 (TT2), put 1 mL of Isopropyl alcohol
➢ To test tube 3 (TT3), put 1 mL of Tert. Butyl alcohol
➢ To test tube 4 (TT4), put 1 mL of Glycerol
b. Add 10 drops of Potassium Dichromate (K2Cr2O7) solution into each solutions.

c. Acidify the solutions with 5 drops of concentrated Sulfuric acid (H2SO4).
(CAUTION: Concentrated H2SO4 is MORE CORROSIVE and MORE TOXIC than Concentrated HCl, so
HANDLE WITH CARE! ALWAYS WEAR YOUR PPE’s)
d. Stopper each test tube and shake each solution carefully then place them in a hot water bath (90°C – 96°C)
for three (3) minutes.
NOTE: Some of the alcohols may change color immediately even before being placed in the water
bath. Make sure that you take note of this as well.
e. While in the water bath, take note of the test tube that changed color first, then second, then third, and then
last.
f. Remove the test tubes from the water bath and further observe the alcohol solutions. Record your
observations in Table 1 below.
TABLE 1: Results and Observations
Alcohols
Ethanol
Isopropanol
Tert. Butyl
Glycerol
Based from your observations of the above procedures:
Which alcohol/s immediately changed color? _________________________________________
What class of alcohol is this? _____________________________________________________
Which alcohol/s was second to change color? ________________________________________
Which alcohol/s did not change color or the last one to change color? _____________________

Write the correct chemical equation for the Oxidation reaction of each of the Alcohols
Alcohols Complete Chemical Equations (Use Structural Formulas)
Ethanol
Isopropanol
Tert. Butyl
Glycerol
2. Iodoform Test
a. Get four (4) clean and dry test tubes and label them as test tube 1, 2, 3, and 4 respectively.
➢ To test tube 1 (TT1), put 1 mL of ethanol
➢ To test tube 2 (TT2), put 1 mL of isopropyl alcohol
➢ To test tube 3 (TT3), put 1 mL of tert. Butyl alcohol
➢ To test tube 4 (TT4), put 1 mL of glycerol
b. To each alcohol solutions in the test tubes, add 1 mL of water and 10 drops of Iodine in potassium Iodide
solution.
c. Add 10% sodium hydroxide solution drop by drop simultaneously to ALL the test tubes with alcohol solutions
with constant shaking until the Iodine color disappears and the solution is faintly yellow in one or two test
tubes.
I. In which alcohol was a light yellow color or precipitate was obtained?
_____________________________________________________________
II. Note the odor of the alcohol. ______________________________________
III. What class of alcohol is this? _____________________________________
d. Continue the addition of the 10% sodium hydroxide solution drop by drop until another of the remaining
alcohol solutions turns yellow.
I. Which alcohol is the next to turn yellow? ____________________________
II. What class of alcohol is this? _____________________________________
III. For what class of alcohol/s is the Iodoform Test for?
_____________________________________________________________
3. Lucas Test
➢ To test tube 1 (TT1), put 1 mL of ethanol
➢ To test tube 2 (TT2), put 1 mL of isopropyl alcohol

➢ To test tube 3 (TT3), put 1 mL of tert. Butyl alcohol
➢ To test tube 4 (TT4), put 1 mL of glycerol
b. Place 2 mL of Lucas reagent to each alcohol solutions in each test tubes

c. Shake the test tubes gently and allow to stand for a few minutes
I. In which test tube is a cloudy layer formed? __________________________
II. What class of alcohol is this? _____________________________________
d. Let the test tubes containing the alcohols stand for another 15 minutes
I. Which of the alcohol solutions in the test tubes turned cloudy?
_____________________________________________________________
II. Lucas test therefore is a test for what class of alcohols?
_____________________________________________________________
4. Salting – Out Process

The process of salting-out is the separation of an organic phase from an aqueous phase by the addition of salt. This
method is commonly used by biochemists in the purification of proteins. Weak intermolecular forces (e.g. hydrogen
bonds) between organic molecules or nonelectrolytes and water are easily disrupted by the hydration of electrolytes.
a. Add 1 drop of Bromothymol blue to the remaining solutions of alcohols in procedure A.1.
b. Add 1 drop of 1.0M HCl.
c. Saturate the mixtures with anhydrous potassium carbonate (APC). Shake the mixture for every addition of the
APC.
NOTE: To saturate the solutions, add pinch by pinch of anhydrous K2CO3 one at a time with vigorous
shaking after each addition until no further K2CO3 dissolves.
d. Prepare another test tube and place 1 mL of the Phenol solution and repeat procedures “a” to “c” above for this
solution.
e. Let the solutions stand for a few minutes (3-5 minutes) and observe what happens.

Test Original Color of Color After Addition of Results and Observations
Solutions Solutions Bromothymol Blue After Addition of K2CO3
Ethanol
Isopropanol
Tert. Butyl
Glycerol
Phenol

B. CHEMICAL PROPERTIES of PHENOL & PHENOLIC COMPOUNDS
1. Oxidation Reaction
a. Place 1 mL of aqueous solution of phenol in a clean and dry test tube
b. Add 3 drops of 1% KMnO4 solution.
c. Acidify with 3 drops of conc’d. H2SO4
Observations: __________________________________________________________
_______________________________________________________________________
d. Write the chemical equation for the above reaction.
2. Bromination
a. Place 1 mL of aqueous phenol solution in a clean and dry test tube.
b. Add 10 drops of Bromine water.
c. Shake the solution and let it stand for a few minutes before observing.
Observations: __________________________________________________________
_______________________________________________________________________
d. Write the chemical equation for the above reaction.
3. Acidity Test
a. Get three (3) clean and dry test tubes and label them as test tube 1, 2, and 3.
➢ To test tube 1 (TT1), put 1 mL of Ethanol
➢ To test tube 2 (TT2), put 1 mL of Phenol solution
➢ To test tube 3 (TT3), put 1 mL of 1M Acetic acid
b. Add one small pellet of NaOH to each solution in the test tube. In which test tube is the NaOH dissolved?
_________________________________
c. Repeat procedures 1 and 2 above but replace the NaOH with powdered Na2CO3. In which test tube are bubbles
produced? _________________________________
C. TEST FOR PHENOLIC COMPOUNDS
1. Ferric Chloride (FeCl3) Test

a. Prepare six (6) clean and dry test tubes and label them as test tube 1, 2, 3, 4, 5, and 6 respectively.
➢ To test tube 1 (TT1), put 1 mL of aqueous solution of phenol
➢ To test tube 2 (TT2), put 1 mL of alcoholic solution of resorcinol

➢ To test tube 3 (TT3), put 1 mL of alcoholic solution of cathecol
➢ To test tube 4 (TT4), put 1 mL of alcoholic solution of salicylic acid
➢ To test tube 5 (TT5), put 1 mL of α – naphthol
➢ To test tube 6 (TT6), put 1 mL of σ – cresol
b. Add drop by drop 1% FeCl3 solution to each solution in the test tubes
c. Shake the test tube after each addition of the FeCl3 reagent until a permanent color is produced in each of the
phenolic solutions.
d. Describe the color produced in each mixtures and record your results and observations in the Table below.

Phenolic Structural Original Color of Color of Phenolic Solutions
Compound Formula Phenolic Solutions After addition of 1% FeCl3
Phenol
Resorcinol
Cathecol
Salicylic Acid
α – Naphthol
σ – Cresol
What structure is common to all the phenolic compounds above? ___________________
CONCLUSIONS

1. Based on the different chemical tests done, identify if the substance is Methanol, Ethanol, Phenol, or Acetic acid.
a. Organic substance formed a violet color after treatment with FeCl3. It dissolved NaOH pellet but not Na2CO3 powder.
What is the organic substance? ____________________________
b. Organic substance formed a yellow color after treatment with Iodoform reagent. It did not dissolve both the NaOH
pellet nor the Na2CO3 powder. What is the organic substance?
____________________________________
c. Organic substance did not form a violet color after treatment with FeCl3. It dissolved both the NaOH pellet and the
Na2CO3 powder. What is the organic substance?
____________________________________
2. Cite two (2) methods of preparing alcohols. Describe each method briefly and illustrate the complete equation for the
synthesis of each method.
3. Arrange the rate of reaction of primary, secondary, and tertiary alcohol with sodium metal from the slowest to the
fastest.
4. Cite at least one medical application of the following alcohols: (a) Ethyl alcohol, (b) Isopropyl Alcohol, (c) Glycerol,
and (d) Nitroglycerol.
5. What is the Victor-Meyer Test for alcohols? Describe how it is performed including the reagents used and their results.
Use chemical equations to illustrate their reactions.
6. Enumerate two (2) phenolic compounds that are important natural “neurotransmitters”. Write their structural formula.
7. Devise a simple chemical test to differentiate ethyl alcohol from phenol. Include steps and results.

NAME:________________________ RATING:__________________
GROUP #:_____________________ DATE:____________________
EXPERIMENT NO. 13
PROPERTIES AND TESTS FOR ALDEHYDES AND KETONES
OBJECTIVES
1. To observe the chemical properties of both aldehydes and ketones

2. To compare the properties of aldehydes and ketones with other hydrocarbons
3. To prepare other hydrocarbon derivatives from specific reactions of aldehyde and ketone
4. To work safely and efficiently in the laboratory
A. Materials
Test tubes, Test tube Rack, Test Tube holder, Test tube brush, Pasteur pipettes, Watch glass, Evaporating dish, 250
mL Beaker, Splinters, Bunsen Burner, Wire gauze, Tripod, pH papers, Litmus papers
B. Reagents
Formaldehyde, Acetaldehyde, Bezaldehyde, Methanol, 95% Ethanol, 95% Isopropanol, Acetone, K2Cr2O7 Solution,
Conc. H2SO4, 2,4 – DNPH in Methanol, Sat. Sol’n of NaHSO3, Conc. NaOH, Benedict’s Reagent, Fehling’s A & B
Reagents, Schiff’s Reagent, 0.5% Sodium Nitroprusside Solution, Distilled water, Ice cubes
RUBRICS FOR SCORING
For Procedures:


A. CHEMICAL TESTS FOR ALDEHYDES AND KETONES
1. Reaction with Strong Oxidizing Agent

➢ To test tube 1 (TT1), place 1 mL of Formaldehyde
➢ To test tube 2 (TT2), place 1 mL of Acetaldehyde
➢ To test tube 3 (TT3), place 1 mL of Benzaldehyde
➢ To test tube 4 (TT4), place 1 mL of Acetone
b. Cautiously add 3 drops of 1% potassium dichromate solution to each carbonyl solutions.
c. Acidify with each solution with 3 drops of conc’d sulfuric acid with caution.
d. Observe and write your results if there are changes in the color of each of the carbonyl solutions.
____________________________________________________________________
____________________________________________________________________
____________________________________________________________________
e. Write the equation for the reactions in the boxes below.
2. Brady’s Test
a. Get four (4) clean and dry test tubes and label them as test tube 1, 2, 3, and 4 respectively:

b. Add 1 mL of 2, 4 – Dinitrophenyl Hydrazine solution to each test tube containing the carbonyl solutions.
c. Acidify each solution with 3 drops of conc’d sulfuric acid with caution (check acidity using BLP).

d. Observe if there are any changes in the color of each carbonyl solutions. Write your results below.
____________________________________________________________________
____________________________________________________________________
____________________________________________________________________
____________________________________________________________________
e. What is Brady’s test for? ________________________________________________
____________________________________________________________________
3. Benedict’s Test
a. Get four (4) clean and dry test tubes and label them as test tube 1, 2, 3, and 4 respectively:
b. Add 2 mL of Benedict’s reagent to each test tube containing the carbonyl solutions
c. Place the test tubes in a boiling water bath for 3 minutes
d. Observe for any color change or formation of a precipitate in each of the carbonyl solutions.

Carbonyl Color of Solution Upon addition Results after the Hot water
Solutions of Benedict’s Reagents bath
Formaldehyde
Acetaldehyde
Benzaldehyde
Acetone
4. Fehling’s Test
a. Get two (2) clean and dry test tubes and label them as test tube 1, and 2 respectively.

b. Add 1 mL of Fehling’s reagent A and 1 mL of Fehling’s reagent B respectively to each of the solutions in the
test tubes. Carefully shake the test tubes to completely mix the contents.
c. Place the test tubes in a boiling water bath for 3 minutes
d. Observe for any color change or formation of a precipitate.

Color of Solution Upon addition Results after the Hot water
Test Solutions of Fehling’s Reagents A & B bath
Acetaldehyde
Acetone
Based on the results and observations of the above procedures:
In which solution was the Fehling’s test positive? ______________________________
What is the positive results for Fehling’s test? _________________________________
In which solution was the Fehling’s test came-out negative? Why? Explain your answer.
_______________________________________________________________________
_______________________________________________________________________
What can you say about the Benedict’s Test and Fehling’s test as to their results with both aldehydes and
ketones?
_______________________________________________________________________
_______________________________________________________________________
Can you use these test to differentiate between an aldehyde and a ketone? __________
B. SPECIFIC TESTS FOR ALDEHYDES AND KETONES
1. Schiff’s Test
i. Get two (2) clean and dry test tubes and label them as test tube 1 and 2 respectively.
➢ To test tube 1 (TT1), place 5 drops of Acetaldehyde and 1 mL of ethanol
➢ To test tube 2 (TT2), place 5 drops of Acetone and 1 mL of ethanol
ii. Add 10 drops of Schiff’s reagent. Let the solutions stand for a minute then observe.
Observations: __________________________________________________________
_______________________________________________________________________

2. Legal’s Test
e. Place 2 mL of acetone in a clean and dry test tube

f. Add 5 drops of 0.5% Sodium Nitroprusside and note all changes that occurred
Observation: ___________________________________________________________
_______________________________________________________________________
g. Add 10 drops of concentrated NaOH solution (check alkalinity using RLP).

h. Observe for further changes in the solution and write your observations below.
Note: This test may also be used to detect the presence of ketone bodies in urine.
Observations: __________________________________________________________
_______________________________________________________________________
3. Reaction of Aldehydes with Strong Bases
a. Get two (2) clean and dry test tubes and label them as test tube 1 and 2 respectively:

b. Add 1 mL of concentrated solution of NaOH in each solutions of aldehyde. Shake to mix the contents.
c. Place the test tubes in a boiling water bath for 2-3 minutes.
d. Observe in which test tube was a brown resinous substance formed?
________________________________________________________________
e. What do you call the reaction between formaldehyde and concentrated NaOH or KOH?
________________________________________________________________
f. Write the equation for this reaction
g. What do you call the reaction between acetaldehyde and concentrated NaOH or KOH?
_______________________________________________________________
h. Write the equation for this reaction

CONCLUSIONS
1. Aside from the oxidation of primary alcohols, give another method of preparing an aldehyde. Discuss and illustrate
the mechanism of formation.
2. What are acetals and hemiacetals? Illustrate their formation and cite their importance in biological processes.
3. What is chloral hydrate? How is it formed? What is its importance? Discuss.
4. Write the structural formula of (a) diphenyl ketone and (b) dibenzyl ketone. What are their IUPAC name? and what
are their uses or importance? Discuss each.
5. What are ketals and hemiketals? Explain briefly. Illustrate their mechanism of formation.
6. Cite two methods of preparing Ketones aside from the oxidation of secondary alcohols. Show by using equations
their mechanism of formation.
7. Describe the expected positive result of (a) Benedict’s test, (b) Fehling’s test, and (c) Tollen’s test? Discuss also their
applications.

NAME:________________________ RATING:__________________
GROUP #:_____________________ DATE:____________________
EXPERIMENT NO. 14
PREPARATIONS AND PROPERTIES OF CARBOXYLIC ACIDS AND ESTERS
OBJECTIVES
1. to successfully prepare solutions of carboxylic acids and esters

2. to observe the chemical properties of carboxylic acids and esters
3. to compare the acidity of organic acids with other hydrocarbon derivatives
4. to describe and evaluate the different reactions of carboxylic acids and esters
A. MATERIALS
Test tubes, TT holder, TT rack, TT brush, Pasteur pipettes, Watch glass, Beakers, Erlenmeyer flask, 10 mL Graduated
Cylinder, Stirring Rod, 6 – inch Copper wire, pH papers, Water trough, Bunsen burner, Tripod, Wire gauze, Electronic
balance,
B. REAGENTS
Formic acid, Acetic acid, Propionic Acid, Butyric Acid, Benzoic acid, Salicylic acid, Bromothymol blue, Methyl Red,
Diethyl Ether, 10% NaOH solution, 1M HCl, conc’d H2SO4, Litmus Papers, pH Papers, FeCl3 Solution, Formaldehyde,
Acetaldehyde, K2Cr2O7 solution, Tollen’s reagent, Methanol, Ethanol, Isopropyl Alcohol, Tert. Butyl Alcohol, Isoamyl
alcohol, Methyl acetate, Ethyl butyrate, Isoamyl acetate, Methyl salicylate, Ethyl acetate, Ferric Chloride Solution,
0.5% Resorcinol, Distilled water
RUBRICS FOR SCORING

For Procedures:


A. PREPARATION OF CARBOXYLIC ACIDS (C.A.’s)
1. Oxidation of Aldehydes
a. Get two (2) clean and dry test tubes and label them as test tube 1 (TT1) and test tube 2 (TT2) respectively:
➢ To test tube 1 (TT1), place 1 mL of formaldehyde

➢ To test tube 2 (TT2), place 1 mL of acetaldehyde
b. Add 3 drops of K2Cr2O7 solution to each solution in the test tube

c. Acidify with 3 drops of conc’d. H2SO4 and with constant swirling of the test tubes to mix the contents (check
acidity with BLP)
d. Heat in a boiling water bath for 3 minutes
e. Observe the reactions and note the odor that is produced.
Observations: __________________________________________________________
_______________________________________________________________________
f. Write the equation for the reaction
B. CHEMICAL PROPERTIES OF CARBOXYLIC ACIDS
1. Test for Acidity of C.A.’s with Different Indicators
a. pH Paper
➢ Prepare two (2) test tubes and place 2 mL of formic acid in one test tube and 2 mL of acetic acid in the
second test tube
➢ Dip a strip of pH paper into each test tube of the acids
➢ Remove the strips of pH papers and take the pH readings
➢ Write your observations in Table1
➢ Save the contents for procedure b.
b. Methyl Red
➢ Prepare two (2) test tubes and place 2 mL of formic acid in one test tube and 2 mL of acetic acid in the
second test tube
➢ Add 3 drops of Methyl Red in each solutions.

➢ Shake the test tubes and observe the colors of the solutions
➢ Write your observations in Table1 below

Acid-Base Indicators Formic Acid Acetic Acid
pH Paper
Methyl Red
2. Reaction with Sodium Bicarbonate

a. Get two (2) clean and dry test tubes and label them as test tube 1 and 2 respectively.
➢ To test tube 2 (TT1), place 1 mL of Glacial acetic acid
➢ To test tube 3 (TT2), place 1 mL of 1M HCl
b. Add 1 mL of 10% NaHCO3 solution in each test tube
c. Observe what happens and record your results in Table 2 below.

Test Solutions Results and Observations
Glacial Acetic Acid
1M HCl
What gas is released during the reactions above? _______________________________

d. Write the chemical equations for the above reactions below:
3. Reaction with Strong O.A.’s
a. Get four (4) clean and dry test tubes and label them as test tube 1, 2, 3 and 4 respectively:
➢ To test tube 1 (TT1), place 1 mL of formic acid

➢ To test tube 2 (TT2), place 1 mL of acetic acid
➢ To test tube 3 (TT3), place 1 mL of propionic acid
➢ To test tube 4 (TT4), place 1 mL of butyric acid
b. Add 3 drops of K2Cr2O7 solution to each solution in the test tube

c. Acidify with 3 drops of conc’d. H2SO4 and with constant swirling of the test tubes to mix the contents (check
acidity with BLP)
d. Heat in a boiling water bath for 5 minutes

e. Observe the reactions and write all the results in table 3.
4. Tollen’s Test
a. Prepare the same solutions of acids used in procedure 3a.

b. Add 2 mL of Tollen’s reagent to each of the acid.
c. Heat in a boiling water bath for 5 minutes, cool the solutions and observe. Write the results in the table below.
Carboxylic Acids Reaction with K2Cr2O7 Reaction with Tollen’s

Reagent
Formic Acid
Acetic Acid
Propionic Acid
Butyric Acid
Based on the results of the above reactions:
Make a general statement about the susceptibility of carboxylic acids to a strong oxidizing agents and compare it
with that of alcohols and aldehydes.
_______________________________________________________________________
_______________________________________________________________________
_______________________________________________________________________
Which of the above acids gave a different result? Why is this so? Explain briefly.
_______________________________________________________________________
_______________________________________________________________________
_______________________________________________________________________
5. Hydrolysis of Acid Functional Derivatives

a. Prepare 2 test tubes and place 1 mL of water in each test tube.
➢ Add 1 mL of ethyl acetate to the first test tube
➢ Add a pinch of acetanilide to the second test tube
b. Place in a boiling water bath for a few minutes until the solution is homogeneous
c. Cool the solutions over running water under a tap
d. Test for the presence of free acids using Blue Litmus Paper

Solutions Results After Hot Water Bath Results with BLP
Ethyl Acetate
Acetanilide
e. Write the equation for the hydrolysis of Ethyl Acetate and Acetanilide
C. PREPARATION of ESTERS
1. Esterification Reactions
a. Prepare a set-up for a hot water-bath. While waiting for the water to boil
b. Get five (5) clean and dry test tubes and label them as test tube 1, 2, 3, 4, and 5 respectively:
➢ To test tube 1 (TT1), mix 3 mL of Ethanol with 1 mL Acetic acid and 2 drops of conc’d. H2SO4
➢ To test tube 2 (TT2), mix 3 mL of Isoamyl alcohol with 1 mL of acetic acid and 2 drops of conc’d. H2SO4
➢ To test tube 3 (TT3), mix 3 mL of Ethanol with 1 mL Formic acid and 2 drops of conc’d. H2SO4
➢ To test tube 4 (TT4), mix 3 mL of Tert. Butyl alcohol with 1 mL Acetic acid and 2 drops of conc’d. H2SO4
➢ To test tube 5 (TT5), mix 3 mL of Methanol with 1 mL Salicylic acid and 2 drops of conc’d. H2SO4
c. Place the test tubes containing in the boiling water bath for 5 minutes and observe for a distinct odor from
emanating from each solution.
d. Identify the respective odors by associating them with common odors or flavors of substances. Record your
observations in the table below.
TABLE 1: Data and Results

Alcohol’s Name Carboxylic Acid’s Name of Ester Formed Odor Observed
Name

e. Write all the esterification equations involved in the above procedures.
A. CHEMICAL PROPERTIES OF ESTERS
1. Hydrolysis of an Ester
❖ Procedure for Hydrolysis

a. Dissolve 5 pellets of NaOH in 5 mL of Methyl Salicylate in an Erlenmeyer flask. Shake to mix.
b. Heat gently in a hot water bath (use a low flame so as not to evaporate the contents of the flask) until the
mixture becomes homogeneous.
c. Remove the flask and cool the solution
d. Add 2 mL of concentrated H2SO4 and cautiously shake the mixture
e. Put the acidified mixture in an ice bath with constant stirring to precipitate the solids.
f. Filter the solids formed and save it including the filtrate for the next procedure.
Based on the above equation, what is the chemical name of the residue?
____________________________________________________________________
On the other hand, what compound is in the filtrate? __________________________
❖ Test for the Solids Formed

Dissolved a pinch of the solids obtained with 1 mL of ethyl alcohol then add a few drops of Ferric Chloride
solution.
Result: _____________________________________________________________
____________________________________________________________________
❖ Test for the Filtrate
i. Get 2 mL of the filtrate and place it in a test tube

ii. Wind a piece of copper wire around a stirring rod or glass tubing to make a coil – 2cm. long. Insert the other
end of the wire in a cork stopper to make a handle.
iii. Heat the copper coil in the upper part of the blue flame of a Bunsen burner.
iv. Plunge the coil while still red hot in the filtrate
v. Withdraw the spiral, and cool the mixture under running water from a tap.
vi. Repeat procedures c, d, and e two more times to oxidize the filtrate.
Into what compound was the filtrate oxidized? _______________________________
vii. Add two drops of 0.5% Resorcinol after cooling the mixture.
viii. Incline the test tube and cautiously add 2 mL of concentrated H2SO4. DO NOT SHAKE the mixture with
acid. This will form two layers.
ix. Observe the color formed at the junction of the two liquids.
__________________________________________________________________
CONCLUSIONS

1. Explain and discuss the acidity of carboxylic acids.
2. Enumerate five (5) functional derivatives of carboxylic acid and their formation or mechanism of synthesis.
3. Explain or discuss the rule of Citric acid in the Citric acid cycle or Kreb’s Cycle.
4. Illustrate the formation of Acetyl salicylic acid. Cite its function or uses and discuss how it is hydrolyzed in the human
body.
5. What are lactones? Give three examples of lactones and write their structural formulas.
6. “Dexon” is a polyester that is spun into fibers. Write the structural formula of Dexon and discuss its use or importance
in the medical field.
7. What is “Dacron”? Illustrate the formation of dacron and enumerate some of its uses in the chemical industry and in the
field of medicine?

NAME:________________________ RATING:__________________
GROUP #:_____________________ DATE:____________________
EXPERIMENT NO. 15
COMPARATIVE STUDY OF THE PROPERTIES OF AMINES AND AMIDES
OBJECTIVES
2. To determine the properties of amides and amines

3. To compare the properties of amides and amines
4. To perform simple tests to identify amides from amines
A. MATERIALS
Beakers, Test tubes, TT Rack, TT Holder, Pasteur pipettes, Watch glass, Bunsen burner, Wire gauze, tripod,
tweezers, Litmus papers
B. REAGENTS
Urea, Acetamide, Distilled water, 10% HCl, 10 & NaOH, Dilute Sol’n of CuSO 4, Aniline, Ethylamine, Ninhydrin
reagents, Alcoholic KOH, Chloroform
RUBRICS FOR SCORING

For Procedures:


A. PHYSICAL PROPERTIES
1. Solubility of Amines and Amides in Water

g. Get four (4) clean and dry test tubes and label them as test tube 1, 2, 3, and 4 respectively.
➢ To test tube 1 (TT1), place 10 drops of Aniline
➢ To test tube 2 (TT2), place 10 drops of Ethylamine
➢ To test tube 3 (TT3), place a pinch of Acetamide
➢ To test tube 4 (TT4), place a pinch of Urea
b. Add of 2 mL of distilled water to each of the acid solution and shake the mixture very well.
c. Let the solutions stand for 2 minutes.
d. Observe the solubility of amines and amides in water and record your observations in table1 below.
2. Solubility of Amines and Amides in Acids

a. Prepare a hot water bath before proceeding.
b. Get four (4) clean and dry test tubes and label them as test tube 1, 2, 3, and 4 respectively.
➢ To test tube 1 (TT1), place 10 drops of of Aniline
c. Add 1 – 2 mL of 10% HCl in each test tubes and until acidic and shake the mixtures to mix well (check acidity
with BLP’s)
d. Observe any color changes, odor changes and solubility of amines and amides in HCl and record your
observations in table1 below.
e. Stopper the test tubes containing acetamide and urea and place them in the boiling water bath for 2 minutes
f. Remove the test tubes from the water bath
g. Using forceps or tweezers, hold a moistened RLP on the mouth of the test tubes one at a time and take note if
there’s any change in the color of the RLP.
h. Record your observations in table2.
i. Return the test tubes in the water bath and continue heating for another 3 minutes.
j. Remove the test tubes and carefully detect the odor of each solution by wafting it towards your nose. Write
your observations in table2
3. Solubility of Amines and Amides in Basic Solutions
➢ To test tube 1 (TT1), place 10 drops of of Aniline
b. Add 1 – 2 mL of 10% NaOH solution in each test tubes until basic and shake the mixtures to mix well (check
alkalinity with RLP’s).
c. Let the solutions stand for 2-3 minutes.
d. Observe any color changes, odor changes and solubility of amines and amides in NaOH and record your
observations in table1 below.
e. Stopper the test tubes containing acetamide and urea and place them in the boiling water bath for 2 minutes
f. Remove the test tubes from the water bath
b. Using forceps or tweezers, hold a moistened RLP on the mouth of the test tubes one at a time and take note if
there’s any change in the color of the RLP.
c. Record your observations in table2.
d. Return the test tubes in the water bath and continue heating for another 3 minutes.
e. Remove the test tubes and carefully detect the odor of each solution by wafting it towards your nose. Write
your observations in table2
TABLE 1: Results and Observations for Solubilities
Test Samples Solubility in Water Solubility in 10% HCl Solubility in 10%

Solution NaOH Solution
Aniline
Ethylamine
Acetamide
Urea
TABLE 2: Results and Observations for Amides
Test Color in 10% Odor in 10% Color 10% Odor 10%

Samples HCl HCl NaOH NaOH
Aniline Reactions
with RLP
Ethylamine
Acetamide
Urea
B. CHEMICAL PROPERTIES
1. pH Test for Amines

a. Place two sets of RLP and BLP in a watch glass
b. Place a drop of Aniline on the first set of litmus papers
c. Place a drop of Ethylamine on the second set of litmus papers
d. Write your results below
Observations: _________________________________________________________________
_____________________________________________________________________________
2. Ninhydrin Test for Amines and Amides

➢ To test tube 1 (TT1), place 1 mL of Aniline
➢ To test tube 2 (TT2), place 1 mL of Ethylamine
➢ To test tube 3 (TT3), place a pinch of Acetamide in 1 mL of water
➢ To test tube 4 (TT4), place a pinch of Urea in 1 mL of water

b. Add 1 mL of Ninhydrin reagent in each test tubes
c. Stopper the test tubes and place them in a boiling water bath for 4 – 7 minutes
d. Observe for any changes in color.
e. Record your results in table 3
Test Samples Color of Solutions Upon Addition Color of Solutions After Hot Water
of Ninhydrin Reagent Bath
Aniline
Ethylamine
Acetamide
Urea
3. Biuret Test for Diamides
a. Place a pinch of urea in a test tube

b. Hold a piece of moistened RLP at the mouth of the test tube while heating. Write your observations below.
Observations: __________________________________________________________
What do you think was the gas evolved? ______________________________________
c. Cool the residue and add 10 drops of NaOH solution and heat it again.
d. Cool once more and add 5 drops of CuSO4 solution. Write your observations below
Observations: __________________________________________________________
_______________________________________________________________________
What is the Biuret test for? _________________________________________________
4. Carbylamine Reaction for Aniline
a. Mix together 5 drops of aniline with 5 drops of chloroform in a clean and dry test tube
b. Add 1 mL of alcoholic KOH (made by dissolving KOH in hot alcohol, the hot alcohol on the other hand may be
prepared by heating it in a water bath)
c. Cautiously smell the odor of the mixture by wafting it towards your nose.
WARNING: The odor could get disagreeable, DO NOT INHALE DEEPLY!
d. Describe the odor and write your observations below.
Observations: _________________________________________________________
______________________________________________________________________

CONCLUSIONS

1. Describe the following reactions of amines and include chemical equations.
a. Hinsberg Reaction
b. Diazotization
2. What is ammonolysis reaction? Discuss and give an example using chemical equations.
3. Enumerate four (4) biologically important amines and their uses.
4. Aside from the tests done in this experiment, cite another test for Amides. Discuss its processes and its positive results.
5. How are amide bonds formed? Discuss. Give its importance in biochemical systems.

REFERENCES
A. BOOKS
Main Textbook: Hein, M., Best, L., Pattison, S. and Arena, S. (2009). Introduction to General,
Organic and Biochemistry (9th Ed). New York: John Wiley & Sons, Inc.
Brown, T. et. al. (2009). Chemistry: The Central Science (11th ed). New Jersey: Prentice Hall Inc.
Burdge, J. (2009). Chemistry. New York, N.Y.: McGraw.
Committee on Chemistry Laboratory (2010). Laboratory Manual: General Chemistry. Intramuros,
Manila: Mindshapers
Hill, R. and Finster, D. (2010). Laboratory Safety for Chemistry Students. Hoboken, N.J.: Wiley
Hein, M., Peisen, J. and Miner, R. (2011). Foundations of College Chemistry in the Laboratory . (13th
ed). Hoboken, N.J. : Wiley
House, J. (2008). Inorganic Chemistry. Amsterdam: Elsevier
Landesberg, J. (2012). Basic Laboratory Experiments General, Organic, and Biochemistry . Australia:
Brooks/Cole
Middlecamp, C. et.al. (2012). Chemistry in Context: Applying Chemistry to Society. (7th ed.) New
York, N.Y.: McGraw.
Miessler, G. and Tarr, D. (2011). Inorganic Chemistry. (4th ed.) Boston: Prentice Hall
Miessler, G. and Tarr, D. (2008). Inorganic Chemistry. (3rd ed.) Singapore: Pearson Education Asia
O'Connell, John P., and J. M. Haile.(2005) "Properties Relative to Ideal Gases. " Thermodynamics:
Fundamentals for Applications. Cambridge: Cambridge UP
Rosenberg, J. and Epstein, L.(2011). Schaum's Easy Outline College Chemistry. 2nd ed. New York:
McGraw.
Seager, S. and Slabaugh, M. (2008). Chemistry for Today: General, Organic, and Biochemistry . (6th
ed.) Australia: Thomson
Slowinski, E.J. et. al. (2002). Chemical Principles in the Laboratory. (7th ed.). Singapore: Brooks/Cole
Thomson Learning.
Smith, J. (2012). Principles of General, Organic, & Biological Chemistry. New York, N.Y.: McGraw
Stoker, H. (2011). Introduction to Chemical Principles. (10th ed). Boston: Prentice Hall
Stoker, H. (2010). General, Organic, and Biological Chemistry. (5th ed.) Australia: Brooks, Cole,
Cengage Learning
B. MAGAZINES/JOURNALS
Sutton,C.(2020) The Particle Connection and Spaceship Neutrino.
C.ONLINE RESOURCES
http://scitechconnect.elsevier.com/importance-inorganic-chemistry-todays-world/
https://www.shutterstock.com/image-vector/classes-inorganic-compounds-142417303
https://www.sigmaaldrich.com/technical-documents/articles/biology/periodic-table-of-elements-names.html
http://www.qrg.northwestern.edu/projects/vss/docs/propulsion/1-what-is-an-
ion.html#:~:text=An%20ion%20is%20a%20charged,of%20protons%20in%20the%20atom.
https://chem.libretexts.org/Bookshelves/Introductory_Chemistry/Book%3A_Introductory_Chemistry_(CK-
12)/11%3A_Chemical_Reactions/11.4%3A_Combination_Reactions
https://www.google.com/search?q=matter&tbm=isch&ved=2ahUKEwijqqHHoN7qAhUHapQKHe2DD-QQ2-
cCegQIABAA&oq=matter&gs_lcp=CgNpbWcQAzIHCAAQsQMQQzIECAAQQzIECAAQQzIECAAQQzIECAAQQzIECAAQQzI
ECAAQQzIECAAQQzIECAAQQzIECAAQQzoCCAA6BggAEAcQHlCUiDdYiZc3YJicN2gAcAB4AoABsgiIAfAWkgEPNC4yLj
EuMS4wLjEuMC4xmAEAoAEBqgELZ3dzLXdpei1pbWfAAQE&sclient=img&ei=P9MWX-
OOMYfU0QTth76gDg&bih=740&biw=1440#imgrc=HHSGYSy7TKr7BM
https://www.britannica.com/science/chemistry
http://www.columbia.edu/itc/chemistry/chem-c2507/navbar/chemhist.html
https://chem.libretexts.org/Courses/UWMilwaukee/CHE_125%3A_GOB_Introductory_Chemistry/11%3A_Ene
rgy_and_Chemical_Processes/11.02%3A_Energy_and_Its_Units
https://www.infoplease.com/encyclopedia/science/chemistry/concepts/chemistry/history-of-chemistry
https://chem.libretexts.org/Bookshelves/Physical_and_Theoretical_Chemistry_Textbook_Maps/Supplemental_
Modules_(Physical_and_Theoretical_Chemistry)/Atomic_Theory/The_Atom/Sub-Atomic_Particles
https://www.chem.fsu.edu/chemlab/chm1045/e_config.html
http://chemed.chem.purdue.edu/
https://opentextbc.ca/introductorychemistry/chapter/kinetic-molecular-theory-of-gases-2/
https://byjus.com/chemistry/gay-lussacs-law/

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SCHOOL OF CRIMINAL JUSTICE AND PUBLIC SAFETY

Inorganic and Organic Chemistry

A Self-regulated Learning Module

A Self-regulated Learning Module 1

For the Use of University of Baguio

Compiled and Prepared by:

MS. MIROMA R. VILLACRUSIS

MS. RACHELLE B. ROBERTO

A Self-regulated Learning Module 1

A Self-regulated Learning Module 2

G. Live lecture/Video conferencing guidelines:

Teresa N. Villanueva, RMT, MACT

A Self-regulated Learning Module 4

WEEK TOPIC ACTIVITIES

2 Unit 2: Nomenclature and Writing Chemical Formulas of Lecture:

3 Unit 3: Chemical Equations and Reactions Lecture:

4 Unit 4: Solutions Lecture:

6 FIRST GRADING EXAMINATION

A Self-regulated Learning Module 5

8 Unit 6: Hydrocabons: Alkanes and Cycloalkanes, Lecture:

1. Homologous Series Laboratory:

10 Unit 7: Aromatic HC Lecture:

11 Unit 8: Alkyl Halides Lecture:

12 MIDTERM GRADING EXAMINATION

A Self-regulated Learning Module 6

14 Unit 11: Aldehydes and Ketones Lecture:

16 Unit 12: Carboxylic Acids, Esters and Amides

A Self-regulated Learning Module 7

18 Unit 13: Amines Lecture:

FINAL GRADING EXAMINATION

A Self-regulated Learning Module 8

Unit 1: Introduction to Inorganic Chemistry…………………………………………………………………………………………….. 11

Unit 2: Nomenclature and

Writing Chemical Formulas of Chemical Compounds………………………………………………….……. 18

Unit 3: Chemical Equations and Reactions……………………………………………………………………………………………. 33

Unit 4: Solutions and Electrolytes ………….…………………………………………………………………………………………………. 43

Unit 5: Introduction to Organic Chemistry…………………………………………………………………………………..………… 49

Unit 6: Hydrocabons: Alkanes and Cycloalkanes, Alkenes, Cycloalkenes, Alkynes…………. 71

Unit 7: Aromatic Hydrocarbons…………………………………………………………………………………………………………………… 112

Unit 8: Alkyl Halides………………………………………………………………………………………………………………………………………… 132

Unit 9: Alcohols, Ethers and Thiols…………………………………………………………………………………………………………… 142

Unit 10: Phenols……………………………………………………………………………………………………………………………………………….. 166

Unit 11: Aldehydes and Ketones………………………………………………………………………………………………………………. 178

Unit 12: Carboxylic Acids, Esters and Amides………………………………………………………………………………….… 192

Unit 13: Amines………………………………………………………………………………………………………………………………………………... 218

Activity #1 Laboratory Safety Precautions and Symbols……………………………………………………………….. 230

Experiment #1 Common Laboratory Operations………………………………………………………………………………… 235

Experiment #2 Chemical Equation……………………………………………………………………………………………………………. 242

Experiment #3 Properties of Solutions…………………………………………………………………………………………………... 249

Experiment #4 Acid Base-Titration…………………………………………………………………………………………………………… 242

A Self-regulated Learning Module 9

Compounds …………………………………………………………………………………………………………………………….... 254

Experiment #4 A Separation Technique Used in Organic Chemistry:

Solvent Extraction ……………………….……………………………………………………………………………………… 258

Experiment #5 Paper Chromatography: A Separation Technique Used in

Organic Chemistry ……………………………………………………………………………………………..…………..… 262

Experiment #6 Purification of Organic Solids: Sublimation and Recrystallization ………. 267

Experiment #7 Determination of the Purity of Organic Solvents:

Boiling Point Determination by Capillary Method……………………………………………..... 271

Experiment #10 Purification operations in Organic chemistry: Fractional Distillation…… 275

Activity #11 Comparative Study of the Common Properties of Hydrocarbons………………… 279

Module Evaluation Questionnaire……………………………………………………………………………………………………. 310

A Self-regulated Learning Module 10