Senior High School

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General Chemistry 1
Quarter 2 - Module 3
Organic Compounds
General Chemistry I- Grade 11
Alternative Delivery Code
Quarter 2 - Module 3: Organic Compounds
First Edition, 2020

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 Senior
Senior High
High School
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General
Chemistry 1
Quarter 2 - Module 3
Organic Compounds

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 Table of Contents

What This Module is About ................................................................................................................... i

What I Need to Know .............................................................................................................................. i
How to Learn from this Module ............................................................................................................ii
Icons of this Module ................................................................................................................................ii

What I Know ........................................................................................................................................... ..iii

Lesson 1:
Hydrocarbons and Functional Groups ........................................................1
What I Need to Know ....................................................................................1
What’s New ...................................................................................................1
What Is It ......................................................................................................2
What’s More : …............................................................................................6
What I Have Learned: ...................................................................................6

Lesson 2:
Structural Isomerism and Organic Reactions .......................................7
What’s In........................................................................................................7
What’s New ...................................................................................................7

What Is It ......................................................................................................8
What’s More A …. .........................................................................................13
What’s More B:..............................................................................................13
What I Have Learned ....................................................................................14
What’s I Can Do (A) ......................................................................................14
What’s I Can Do (B) ......................................................................................15

Summary ......................................................................................................................................16
Assessment: (Post-Test) ............................................................................................................17
Key to Answers............................................................................................................................18
References ...................................................................................................................................19
Module 3

What This Module is About

Organic compounds are considered as carbon-containing chemical compounds

of living things because of their association with organisms and life processes. Their
structure, properties, reactions, compositions and preparation are the core topics of
organic chemistry.

About 200 years ago, it is believed that organic compounds needed a ‘life force’
to be produced. Other compounds like rock that were from nonliving things were
referred to as inorganic. The synthesis of urea (an organic compound) from amonium
cyanate (an inorganic compound) as an experiment of Friedrich Wöhler in 1828
dispelled the belief that organic compounds could only be formed by nature. The range
of application of organic compounds includes, but is not limited to petrochemicals,
food, pharmaceuticals, explosives, fragrances, paints and cosmetics.

In this module, we describe the structures, properties and reactions of

hydrocarbons and organic functional groups. Moreover, the preparation of selected
organic compounds is introduced for you to have a gist of the complexity of organic
synthesis.

What I Need to Know

At the end of this module, you should be able to:

1. Describe the different functional groups (STEM_GC11OCIIg-j-87);
2. Describe structural isomerism and give examples (STEM_GC11CBIId-g-89);
3. Describe some simple reactions of organic compounds: combustion of organic
fuels, addition, condensation, and saponification of fats (STEM_GC11CBIId-g-
90);
4. Describe the preparation of selected organic compounds (STEM_GC11CBIId-
g-97)

i
How to Learn from this Module
To achieve the objectives cited above, you are to do the following:
• Take your time reading the lessons carefully.
• Follow the directions and/or instructions in the activities and exercises
diligently.
• Answer all the given tests and exercises.

Icons of this Module

What I Need to This part contains learning objectives that

Know are set for you to learn as you go along the
module.

What I know This is an assessment as to your level of

knowledge to the subject matter at hand,
meant specifically to gauge prior related
knowledge.
What’s In This part connects previous lesson with that
of the current one.

What’s New An introduction of the new lesson through

various activities, before it will be presented
to you

What is It These are discussions of the activities as a

way to deepen your discovery and under-
standing of the concept.

What’s More These are follow-up activities that are in-

tended for you to practice further in order to
master the competencies.

What I Have Activities designed to process what you

Learned have learned from the lesson

What I can do These are tasks that are designed to show-

case your skills and knowledge gained, and
applied into real-life concerns and situations.

ii
 What I Know

Pretest: MULTIPLE CHOICE:

Directions: Read and understand each item and choose the letter of the correct
answer. Use separate answer sheet of paper.

1. Which element is present in all organic compounds?

A. Helium C. Carbon
B. Nitrogen D. Oxygen

2. What products are obtained with CH4(g) burns completely in an excess of oxygen?
A. CO2 C. Hydrogen gas
B. CO2 and H2O D. Explosion

3. A hydrocarbon molecule is saturated if the molecule contains ___________

A. Single covalent bonds, only C. A double covalent bond, only
B. A triple covalent bond D. Single and double covalent bonds

4. A functional group with a carbonyl group functionality is _________________.

A. Alcohol C. Ester
B. Amine D. Ketone

5. Choose the incorrect option regarding Isomerism:

A. They differ in both physical and chemical properties
B. They have the different molecular formula
C. Chain isomers differ in the arrangement of their skeleton
D. They have the same molecular formula

6. Which among the following is formed when an alcohol is dehydrated?

A. Aldehyde C. Alkene
B. Ketone D. Amine

7. The reaction of water with alkene to produce an alcohol is a/an ______ reaction.
A. Addition C. Combustion
B. Condensation D. Saponification

8. The organic starting materials for the preparation of an ester could be_________
A. a ketone and alcohol C. an acid and alcohol
B. water and oxygen D. alkane and aldehyde

9. Hydrolysis (saponification) of a fat would yield_____________.

A. water and alkene C. ethanol and acid

B. ketone and aldehyde D. glycerol and soap

10. This type of isomerism occurs when different compounds are formed due to the
different arrangements of their atoms leading to different functional groups.

A. chain C. positional
B. functional D. geometric

iii
 Hydrocarbons and Functional
1 Groups

What I Need to Know

Organic compounds are carbon-containing compounds which do not only

pertain to hydrocarbons but also compounds with any number of other elements,
including hydrogen (most compounds contain at least one carbon–hydrogen bond),
oxygen, nitrogen, phosphorus, halogens, silicon, and sulfur. In this lesson, you should
be able to familiarize and describe the structures and properties of hydrocarbons and
organic functional groups.

What’s New

Activity 1: Matching Type

Directions: Match column A with the corresponding item in column B. Write the
letter of your answer for each number.

1
 What Is It

From the discussion on the bonding models in the previous module, it can be
seen that carbon has a unique nature. Carbon completes its octet by sharing electrons
with other carbon atoms forming single, double, and triple bonds. It also readily forms
bonds with atoms of other elements like H, O, N, and the halogens. Carbon can form
millions of different compounds and can form more compounds than any other element
in the periodic table.

Organic Compounds: Hydrocarbons

A hydrocarbon is a compound composed of only carbon and hydrogen atoms

and is considered as one of the major groups of organic compounds. Based on
structure, hydrocarbons are divided into two main classes—aliphatic (those that do not
contain a benzene ring) and aromatic (those that contain a benzene ring).

HYDROCARBONS

ALIPHATIC AROMATIC

ALKANES CYCLOALKANES ALKENES ALKYNES

Figure 1. Classification of hydrocarbons

a. Alkanes- are aliphatic, saturated hydrocarbons and has only single carbon-
carbon bonds in the molecule. They are referred to as saturated
hydrocarbons because they hold the maximum number of hydrogen atoms
that can bond to the carbon atoms present. Some alkanes are gases and
are used directly as fuels. Saturated hydrocarbons that forms a single ring
are called cycloalkanes. Alkanes are nonpolar, not very reactive, insoluble
in water and have little biological activity. They are all colorless and
odorless.

Figure 2. Some common alkanes and cycloalkanes

2
 b. Alkenes- also called as olefins. These are unsaturated hydrocarbons that
contain at least one carbon-carbon double bond. They are all colorless and
odorless in nature except ethene. They are insoluble in water due to their
nonpolar feature but are more reactive than alkanes.

Figure 3. Short chain alkenes

c. Alkynes- contain at least one carbon-carbon triple bond, hence

unsaturated. They have physical properties similar to alkanes and alkenes.
They dissolve in organic solvents, slightly soluble in polar solvents, and are
insoluble in water. Alkynes are more reactive and have slightly higher boiling
points compared to alkanes and alkenes.

Ethyne Propyne Butyne

Figure 4. Short chain alkynes

Organic Compounds: Functional Groups

A group of atoms that is mainly responsible for the chemical behavior of the
parent molecule is called functional group. Organic compounds may also be classified
according to the functional groups they contain. Compounds with the same functional
groups undergo like reactions.

a. Alcohols- (R-OH; R=hydrocarbon)

All alcohols contain the hydroxyl functional group, -OH. Ethyl alcohol, or
ethanol, which is produced biologically by the fermentation of sugar or starch,
is by far the best known. The alcohols are very weakly acidic and are soluble in
water because of their polar nature. Most alcohols are highly flammable.
Methanol is highly toxic.

Methanol Ethanol Propanol Phenol

Figure 5. Some common alcohols

3
b. Ethers- (R-O-R’; R, R’=hydrocarbon)

Ethers contain the R-O-R’ linkage, where R and R’ are hydrocarbon.

They are slightly polar and slightly soluble in water, but they are extremely
flammable. They tend to slowly form explosive peroxides when left standing in
air. Diethyl ether, one of the common ethers, was used as an anesthetic for
many years but also known for its irritating effects on the respiratory system
and the incidence of postanesthetic vomiting and nausea.

Figure 6. Some common ethers

c. Aldehydes and Ketones – ( , )

The functional group in aldehydes and ketones is the carbonyl group

( ). At least one hydrogen atom is bonded to the carbon in the carbonyl
group in an aldehyde. The carbon atom in the carbonyl group is bonded to two
hydrocarbon groups in a ketone. Aldehydes and ketones are highly polar
molecules. The small aldehydes and ketones are soluble in water, but solubility
falls with chain length. They also have slightly higher boiling and melting points
than alkanes. Formaldehyde, the simplest aldehyde, is used in the laboratory
to preserve animal specimens. Acetone, the simplest ketone, is primarily used
as solvent for organic compounds and as nail polish remover.

Figure 7. Some common aldehydes and ketones

d. Carboxylic acids- ( )

The functional group in carboxylic acids is the carboxyl group,

These acids are weak in nature and are widely found in both plant and animal
kingdoms. Carboxylic acids are polar and are soluble in water. Acetic acid, one
of the common carboxylic acids, is also known as vinegar.

4
 Figure 8. Some common carboxylic acids

e. Esters- ( )

Esters have the general formula R’-COOR, where R’ can be a

hydrocarbon group or Hydrogen and R is a hydrocarbon group. They are
used in the production of perfumes and as flavouring agents. The smell and
flavour of many fruits come from the presence of small quantities of esters.
Oranges contain octyl acetate (CH3COOCHCH3C6H13), and apples contain
methyl butyrate (CH3CH2CH2COOCH3). Esters are polar and water soluble.

Figure 9. Esters in some common fruits

f. Amines – ( )

Amines are organic bases having the general formula R3N, where R
may be Hydrogen or a hydrocarbon group. When amines are allowed to
react with acids, they form colourless and odourless salts. When all Rs are
hydrogens, the resulting compound is ammonia, NH3.

Methylamine Diethylamine Purine Pyrimidine

Figure 10. Some common amines

5
 What’s More

Activity 2: Identification
Directions: Identify the functional group each compound represents. If the compound
represents two or more functional groups, list all groups being represented. If the
compound is a hydrocarbon, write the specific type of hydrocarbon class it belongs.
Write your answer on the space provided below each item.

1. ____________ 2. ____________ 3. _____________

4. _____________ 5. ____________ 6. ______________

7.______________ 8. ____________ 9. ______________

What I Have Learned

Activity 3: Take your pick!

Directions: Identify which functional group interests you the most and explain why
you find it the most interesting. Fill out the table below with the needed details.

Sample Why I find it the Products/things

The most
Structure of a most interesting Special where this this
interesting
compound with among other Properties and functional
functional
functional functional Common Uses group is present
group:
group: groups:

6
 Structural Isomerism and
2 Organic Reactions

What’s In

In lesson 1, we have learned that organic compounds are carbon-containing

compounds which do not only pertain to hydrocarbons but also compounds with any
number of other elements. Moreover, we also examined the structures and properties
of hydrocarbons and some functional groups. In this lesson, we study the structural
isomerism and simple reactions and preparation pathways of selected organic
compounds.

What’s New

Activity 1: Clones or isomers?

Directions: Identify if the two structures are the same compounds or isomers. Write
“isomers” if the compounds have the same chemical formula but exactly different
structure or compound and write “clones” if the compounds are exactly the same.

1.

2. .

3.

4.

7
 What Is It

I. Structural Isomerism

When two or more organic compounds have the same molecular formula but
different properties due to their difference in arrangement of atoms along the carbon,
they are called structural isomers. There are six forms of structural isomerism and
the most common are chain, positional and functional isomerism.

STRUCTURAL ISOMERISM

CHAIN POSITIONAL FUNCTIONAL METAMERISM TAUTOMERISM RING-CHAIN

Figure 1. Forms of Structural Isomerism

a. Chain Isomerism

Chain isomers are organic compounds with the same formula, but the
arrangements of their carbon skeleton are different.

FORMULA: C4H10

Figure 2. Example of chain isomerism

b. Positional Isomerism
Positional isomerism occurs when the same functional groups are
attached to different positions on a carbon chain.

FORMULA: C4H8
FORMULA: C3H7OH

Figure 3. Examples of positional isomerism

8
 c. Functional Isomerism
Functional isomerism occurs if different compounds are formed
due to the different arrangements of their atoms leading to different
functional groups. As functional groups are usually the reactive centre of
a molecule, functional isomers have entirely different properties.

FORMULA: C2H6O

FORMULA: C3H6O

FORMULA: C2H4O2

Figure 4. Examples of positional isomerism

II. Simple Reactions of Organic Compounds

a. Combustion Reactions

When a substance reacts with oxygen gas, releasing energy in the form
of light and heat, a combustion reaction occurs. This type reaction must involve
O2 or oxygen gas as one reactant. One of the most notable combustion
reactions is the combustion of organic fuels. Fuels rapidly react with oxygen to
produce energy. These fuels include: coal, high molecular weight
hydrocarbons, methane, propane, and butane.

1.

Reaction 1. Complete combustion of butane

b. Addition Reactions

Multiple bonds, such as a double or a triple bond, can be converted into

other functional groups using addition reactions. Other elements such as
hydrogen, halogens, compounds like water and functional groups such as the
hydroxyl group can be attached or added to one or both of the carbons involved
in the multiple bond.

2. 3.

4.

Reactions 2,3 and 4. Addition reactions of alkenes and alkynes

9
 c. Condensation Reactions

A condensation reaction takes place when two or more molecules

combine to form a larger and new molecule, with the simultaneous loss of a
small molecule such as water and a formation of a new bond.

6.

ketone aldehyde

5.

Water is lost as a product

New oxygen-carbon bond is formed

Loss of water

Reactions 5 and 6. Examples of condensation reactions

d. Saponification Reactions

Saponification reaction takes place when a fat, oil or lipid is cleaved and
converted into soap and alcohol by the action of heat and with the presence of
water and a base. Fats are typically in the form of esters. When esters undergo
saponification, carboxylate (soap) and an alcohol (glycerol) functional groups
are produced.

Reaction 7. Saponification reaction of a fat

10
 III. Preparation of Selected Organic Compounds

Organic compounds are usually synthesized from other groups of organic

compounds. Two or more organic compounds react to form a new organic compound
with characteristic properties. Sometimes, a single type of organic compound
undergoes a certain reaction, producing a new compound as a product. Heat,
temperature and pressure, acids, bases and water are some of the essentials needed
to make a chemical reaction feasible. There are several ways to prepare a certain
organic compound; the examples given below are the most common and just few of
the many preparation routes.

1. Preparation of Alkanes

1a. Catalytic Cracking- large hydrocarbon molecules are broken or

fragmented into smaller and more useful bits of hydrocarbons using high pressures
and temperatures. Heat, pressure

Reaction 8. Catalytic cracking of a large alkane

1b. Alkanes from Unsaturated Hydrocarbon

Alkane can be prepared from alkene and alkyne through addition of H2

gas or the process called hydrogenation. In this process, dihydrogen gas is
added to alkynes and alkenes in the presence of a catalyst - substance that
makes the reaction proceed faster.

Reaction 9. Hydrogenation of an alkyne to produce an alkane

2. Preparation of Alkenes

2a. Alkenes from the Dehydration of Alcohols

Alkenes are generally prepared through dehydration of an alcohol

or removal of water from an alcohol compound. Water is removed from
the alcohol compound and is freed as a product.

acid

Reaction 10. Removal of water from an alcohol to produce an alkene

11
 3. Preparation of Alcohols

3a. Alcohols from the Hydration of Alkenes

Alcohols are usually obtained by the net addition of water across

the double bond of an alkene. This reaction uses an acid as a catalyst.

acid

Reaction 11. Acid-catalysed hydration of an alkene to produce an alcohol

4. Preparation of Esters

4a. Esters from the Reaction of Alcohol and Carboxylic acid

Esters are produced when carboxylic acids are heated with

alcohols in the presence of a catalyst, specifically an acid, .in the process
called esterification.

Heat,acid

Reaction 12. Esterification reaction of ethanoic acid and ethanol to produce an

ester named ethyl ethanoate

5. Preparation of Carboxylic Acids

5a. Carboxylic acids from the Oxidation of Primary Alcohols

The oxidation of primary alcohols is a common method for the synthesis of

carboxylic acids which requires a strong oxidizing agent. Primary alcohols are those
alcohols. Primary alcohols are those alcohols where the carbon atom of the hydroxyl
group (OH) is attached to only one single hydrocarbon or R group like ethanol,
propanol and etc.

Strong
oxidizing
agent

Heat

Ethanol, primary alcohol

Reaction 13. Oxidation of ethanol to ethanoic acid (carboxylic acid)

12
 What’s More (A)

Activity 2.1: Structural Isomerism Identification

Directions: Identify what type of structural isomerism is being exhibited by each pair
of compounds. Choose from the three most common types of isomerism (e.g. chain,
position and functional isomerism).

1. 3.

2. 4.

What’s More (B)

Activity 2.2: Organic Reaction Identification

Directions: Identify what type of organic reaction is being represented by each item.
Choose from the basic types of organic reactions (e.g. combustion, addition,
condensation and saponification reaction).

_____________1. Hydrocarbons reacts with oxygen gas producing water and

carbon dioxide as products.

_____________2. Reaction of water to an alkene leading to the removal of the

double bond and production of an alcohol.

_____________3. A carboxylic acid and an alcohol react forming a new bond

with the simultaneous loss of water molecule, hence the formation
of a new compound.

_____________4. The production of soap from fats

_____________5. The production of esters from alcohol and carboxylic acid

13
 What I Have Learned

Activity 3: Think Like a Chemist!

Directions: Level up your way of thinking and put yourself in a chemist’s
perspective. Answer and explain each item briefly and concisely.

1. Structural isomers have the same molecular formula but have different
properties. How is this possible?
2. How are positional and functional isomerism different from each other?
3. Ethanol and dimethyl ether have the same molecular formula C2H6O.
Ethanol is liquid at room temperature while dimethyl ether is gas. How is this
possible?
4. Why are short-chain alkanes like methane and butane serve as good fuels?

5. Does the compound below undergo saponification reaction? Why?

6. Describe how will you prepare an alcohol from an alkene.

7. Describe how will you prepare an alkene from an alcohol.
8. Describe how will you prepare an ester.

What I Can Do (A)

Activity 4.1: Meet My Isomers

Directions: Research about the structural isomers of the compound with a formula
C4H10O. Identify at least three structural isomers, provide their structures and their
individual properties and uses. Write your answers in each cell of the table below.

STRUCTURAL ISOMERS OF C4H10O

Name of the isomer Structure of the isomer Properties and uses

1.

2.

3.

14
 What I Can Do (B)

Activity 4.2: The Grandma Ester Corporation

Directions: The goal is to convince an investor to invest in your company so that you
can build a factory to make ester compounds. For example, you could make hexyl
pentanoate, and sell it for use in perfumes and make the investor money. You must
come up with a compound that you can make and sell. You can use your textbooks
and the internet as resources. You can also access the link:
https://jameskennedymonash.wordpress.com/2013/12/13/infographic-table-of-esters-
and-their-smells/ to look at an infographic of the ester compounds responsible for the
smell of different fruits, perfumes and flowers. At the end of your research, you must
have the compound table filled out.

Ester How to
Compound Structure prepare the Properties Uses
Name compound?

15
SUMMARY

Organic compounds are carbon-containing compounds which do not only pertain to

hydrocarbons but also compounds with any number of other elements,
Carbon completes its octet by sharing electrons with other carbon atoms forming
single, double, and triple bonds. It also readily forms bonds with atoms of other
elements like H, O, N, and the halogens.
A hydrocarbon is a compound composed of only carbon and hydrogen atoms and is
considered as one of the major groups of organic compounds.
Alkanes are aliphatic, saturated hydrocarbons and has only single carbon-carbon
bonds in the molecule.
Alkenes are also called as olefins. These are unsaturated hydrocarbons that contain
at least one carbon-carbon double bond.
Alkynes contain at least one carbon-carbon triple bond, hence unsaturated.
A group of atoms that is mainly responsible for the chemical behavior of the parent
molecule is called functional group.
All alcohols contain the hydroxyl functional group, -OH.
Ethers contain the R-O-R’ linkage, where R and R’ are hydrocarbon.
The functional group in aldehydes and ketones is the carbonyl group. At least one
hydrogen atom is bonded to the carbon in the carbonyl group in an aldehyde. The
carbon atom in the carbonyl group is bonded to two hydrocarbon groups in a ketone.
The functional group in carboxylic acids is the carboxyl group.
Esters have the general formula R’-COOR, where R’ can be a hydrocarbon group or
Hydrogen and R is a hydrocarbon group.
Amines are organic bases having the general formula R3N, where R may be Hydrogen
or a hydrocarbon group.
When two or more organic compounds have the same molecular formula but different
properties due to their difference in arrangement of atoms along the carbon, they are
called structural isomers.
When a substance reacts with oxygen gas, releasing energy in the form of light and
heat, a combustion reaction occurs.
Multiple bonds, such as a double or a triple bond, can be converted into other functional
groups using addition reactions.
A condensation reaction takes place when two or more molecules combine to form a
larger and new molecule, with the simultaneous loss of a small molecule such as water
and a formation of a new bond.
Saponification reaction takes place when a fat, oil or lipid is cleaved and converted into
soap and alcohol by the action of heat and with the presence of water and a base.
Organic compounds are usually synthesized from other groups of organic compounds.
Two or more organic compounds react to form a new organic compound with
characteristic properties. Sometimes, a single type of organic compound undergoes a
certain reaction, producing a new compound as a product. Heat, temperature and
pressure, acids, bases and water are some of the essentials needed to make a
chemical reaction feasible. There are several ways to prepare a certain organic
compound.

16
 Assessment: (Post-Test)

Multiple Choice. Answer the questions that follow. Choose the best answer
among the given choices for each item.

1. Which of the following compounds is a functional group isomer of C2H5OH, ethanol (ethyl
alcohol)?
A. ethanal, CH3CHO C. acetic acid, CH3COOH
B. dimethyl ether, (CH3)2O D. diethyl ether, (C2H5)2O

2. Two isomeric forms of a saturated hydrocarbon _____________

A. have the same structure.
B. have different compositions of elements.
C. have the same molecular formula.
D. react vigorously with one another.

3. The reaction of water with alkene to produce an alcohol is a/an ______ reaction.
A. Saponification C. Combustion
B. Condensation D. Addition

4. The organic starting materials for the preparation of an ester could be_________
A. an acid and alcohol C. a ketone and alcohol
B. water and oxygen D. alkane and aldehyde

5. What is the product of the following reaction?

A. ester C. alcohol
B. aldehyde D. alkyne

6. The isomerism shown is _____________.

A. chain C. positional
B. functional D. geometric

7. The isomerism shown is _____________.

A. chain C. positional
B. functional D. geometric

8. Short chain alkanes are prepared through __________.

A. Saponification C. Catalytic cracking
B. Hydration D. Oxidation

9. Saponification of fats needs a strong __________ to proceed to completion.

A. halogen C. acid
B. catalyst D. base
10. Fruits have pleasant odors because of the presence of _______________.
A. ethers C. ethyl
B. esters D. aldehyde

17