Week 12-13 Module

38
LEARNING GUIDE
Week No.: __12-13__
TOPICS/SUBTOPICS:
INTRODUCTION TO ORGANIC CHEMISTRY AND HYDROCARBONS
o Introduction to Organic Chemistry

o Classification of Hydrocarbons
o Nomenclature of Hydrocarbons
o Industrial Applications of Hydrocarbons
EXPECTED COMPETENCIES
At the end of the lesson, you must have:
• defined Organic Chemistry;
• classified the different hydrocarbons;
• distinguished between molecular formula and structural formula;
• defined isomers;
• distinguished among alkanes, alkenes, alkynes, and cyclic hydrocarbons;
• learned the nomenclature of hydrocarbons;
• determined the correct IUPAC names of hydrocarbons;
• written/drawn correct hydrocarbon structures based on their IUPAC names and
• identified the industrial applications of hydrocarbons.
CONTENT/TECHNICAL INFORMATION
Introduction
Organic Chemistry is defined as the study of carbon and

its compounds. The element carbon forms a vast number of
compounds. Over 10 million carbon-containing compounds
are known, and about 90% of the new compounds synthesized
each year contain carbon.
A unique feature of carbon is its ability to bond to other

carbon atoms to give chains and rings of various lengths. Several elements have limited
ability to form such chains or rings of like atoms, but only carbon does this with more
than a few atoms.
The term “organic” means living. The term arose from an 18th century concept that
organic compounds could be formed only by living systems. This idea was disproved in
1828 by Friedrich Wohler, a German chemist who synthesized urea (an organic
substance found in the urine of mammals) from inorganic substances ammonium chloride
and silver cyanate.
𝑁𝐻4 𝐶𝑙 + 𝐴𝑔𝑂𝐶𝑁 → 𝐴𝑔𝐶𝑙 + 𝑁𝐻2 𝐶𝑂𝑁𝐻2

ammonium silver silver urea
chloride cyanate chloride
This module is a property of Technological University of the Philippines Visayas and intended
for EDUCATIONAL PURPOSES ONLY and is NOT FOR SALE NOR FOR REPRODUCTION.
39
Today, several organic compounds have been prepared artificially such as synthetic
rubber, plastics, textiles, dyes, and medicines. Some of the carbon compounds which
occur naturally are gasoline, coal, sugar, carbohydrates, natural rubber, etc.
Bonding in Organic Compounds
A carbon atom has four electrons in its valence shell. As a result of 𝑠𝑝2 hybridization,
each of these four electrons forms an equivalent covalent bond. For example, in the compound
methane, 𝐶𝐻4 , each of the four hydrogen atoms is attached to the carbon atom by the same
kind of covalent bond. The structural formula for methane is shown below:
Each dash is a covalent bond.
In methane, each hydrogen atom shares its one electron with the carbon atom. A total of
four bonds are formed, each bond consisting of a pair of electrons. As shown in the structural
formula of methane, the carbon atom has a hold on eight electrons in its valence shell while
each hydrogen atom is associated with the two electrons. Thus, the carbon and hydrogen
atoms resemble the stable structures of noble gases neon and helium, respectively.
The bonds of carbon atoms usually extend into three-dimensional space at equal angles
to each other. Such bonding produces a tetrahedral structure. In this structure, the carbon
atom is at the center, and the atoms bonded to the carbon atom are at the corners.
109.5°
Carbon forms an unusually large number of compounds because of its exceptional ability
to catenate. Catenation is the bonding of atoms of the same element into a series called a chain.
In addition, the carbon atom can form four very stable single covalent bonds; it also has the
ability to form double or triple bonds with other carbon atoms or with atoms of other elements.
40
single bond
double bond
triple bond
The nature of the bonds between each pair of carbon atoms in an organic compound
determines whether the compound is saturated or unsaturated. Saturated compounds are those
in which the bonds between the carbon atoms are all single bonds. Unsaturated compounds
have at least one double bond or one triple bond between carbon atoms.
Molecular Formulas, Structural Formulas and Isomerism
A molecular formula is a chemical formula which tells the number of atoms of each
element in a molecule of the compound. It uses chemical symbols of elements that make up a
molecule, followed by subscripts to show the number of atoms of each type in the molecule. A
subscript is used only when more than one atom of a given type is present.
A structural formula is a chemical formula which shows the arrangement of the atoms
in a molecule by the use of connecting lines, called valence bonds, between atoms. Single lines
mean single bond; two lines mean double bond; and three lines mean triple bond.
Compounds that have the same molecular composition but different structures are
called isomers. Butane and isobutene are example of isomers. Both have the same molecular
composition (82.8% carbon and 17.2% hydrogen by mass); and both have the same
molecular mass (58 atomic mass units). But each substance has its own unique structure and
hence its own unique set of properties.
41
The number of possible isomers that an organic compound can form increases greatly as
the number of carbon atoms increases. The compound whose molecular formula is
𝐶15 𝐻32 could have over 400 isomers. In fact, many of these isomers have been prepared.
Classifications of Hydrocarbons
Because carbon compounds are so numerous, it is convenient to organize them into

families that exhibit structural similarities. The simplest class is the “hydrocarbons”,
compounds composed only of carbon and hydrogen.
Alkanes
HYDROCARBONS
Aliphatic or Acyclic
Alkenes
hydrocarbons
Alkynes
Aromatic Cycloalkanes
Cyclic
hydrocarbons
Alicyclic Cycloalkenes
Cycloalkynes
Figure 1. Classifications of Hydrocarbons
I. Aliphatic or acyclic hydrocarbons – are ones that have an open-chain structure, either
straight or branched.
42
Examples of straight chains:
(a) (b) (c)
Examples of branched chains:

Carbon atoms outside the red box are branches.
A. Alkanes – are hydrocarbons

(a) in which all the carbon-carbon
(b) bonds are single bonds
B. Alkenes – are hydrocarbons which have a carbon-carbon double bond somewhere
in their molecular structure
C. Alkynes – are hydrocarbons which contain a carbon-carbon triple bond in their
structure
alkane alkene alkyne

II. Cyclic hydrocarbons – are hydrocarbons in which the carbon atoms join to form closed
chain structures (rings).
A. Aromatic hydrocarbons – are hydrocarbons that contain benzene ring or similar
features. Benzene is a compound made up of 6-carbon atoms in a ring with
alternating single and double carbon-carbon bonds.
benzene
B. Alicyclic hydrocarbons – are cyclic hydrocarbons which do not contain a benzene
ring.
43
a. Cycloalkanes – are ones in which all the carbon-carbon bonds in the rings are
single bonds
b. Cycloalkenes – contain a double bond between two of the carbon atoms in the
ring structure
c. Cycloalkynes – contain a triple carbon-carbon bond in their ring structure
or
cycloalkane cycloalkene
or
THE ALKANES cycloalkyne
The alkanes are saturated hydrocarbons that conform to the general formula 𝑪𝒏 𝑯𝟐𝒏+𝟐 ,
where n is the number of carbon atoms in the compound. The alkane series is sometimes called
the paraffin series. Paraffin comes from the Latin parum affinis, meaning “little affinity”. As
a result of their saturation, paraffins do not react readily and are unaffected by many reagents.
Paraffin wax is a mixture of compounds from this series.
The names of alkanes are composed of a prefix, which denotes the number of carbon
atoms, and the suffix –ane which signifies that the compound contains only single bonds, and
is thus saturated.
Number of Carbon Prefix
atoms
1 meth
2 eth
3 prop
4 but
5 pent
6 hex
7 hept
8 oct
9 non
10 dec
44
The first ten members of the alkane series are:
Molecular
No. of C No. of H
Formula Structural Formula IUPAC Name
atoms atoms
(𝑪𝒏 𝑯𝟐𝒏+𝟐 )
1 4 𝑪𝑯𝟒 methane
2 6 𝑪 𝟐 𝑯𝟔 ethane
3 8 𝑪 𝟑 𝑯𝟖 propane
4 10 𝑪𝟒 𝑯𝟏𝟎 butane
5 12 𝑪𝟓 𝑯𝟏𝟐 pentane
6 14 𝑪𝟔 𝑯𝟏𝟒 hexane
7 16 𝑪𝟕 𝑯𝟏𝟔 heptane
8 18 𝑪𝟖 𝑯𝟏𝟖 octane
9 20 𝑪𝟗 𝑯𝟐𝟎 nonane
10 22 𝑪𝟏𝟎 𝑯𝟐𝟐 decane
The Alkyl Groups
If a hydrogen atom is removed from a terminal carbon atom of any alkane compound, the
remaining portion of the alkane is called an alkyl group or alkyl radical. The general formula
of such a group is 𝐶𝑛 𝐻2𝑛−1 . Alkyl groups are named by replacing the –ane ending of the alkane
compound with the ending –yl. Examples of alkyl groups are given below:
45
Alkyl groups show up in many organic compounds. They are merely parts of compounds.
Two examples of compounds that contain the methyl group, 𝐶𝐻3 , are methyl alcohol and
methyl amide.
IUPAC SYSTEM OF NAMING ALKANE DERIVATIVES
As more and more isomers were discovered and isolated, the need for greater precision
and uniformity in naming these compounds became greater. In 1982, a group of chemists met
in Geneva, Switzerland, and developed a simplified system for naming organic compounds.
This conference produced the Geneva System of nomenclature, which was then modified
somewhat and adopted by the International Union of Chemistry in 1930. The present name of
this organization is the International Union of Pure and Applied Chemistry. The rules are
now referred to as the IUPAC System of nomenclature.
To understand the IUPAC System, the rules are applied first on the alkanes. Later,
similarities in the rules and their application will simplify the naming of other types of organic
compounds.
Rules:
1. Find and name the longest continuous carbon chain. This chain is called the parent
chain.
The parent chain

has 5 carbon
atoms, so it is
pentane.
46
2. Identify and name the branches attached to this chain.
The branch is an alkyl with 1

carbon atom, so it is methyl.
3. Number the chain starting at the end nearest the first branch and specify the carbon
atoms on which the branches are located. Use the lowest possible numbers.
If numbering starts from
left to right, the branch
falls on the 2nd carbon. If
it’s from right to left, the
branch is on the 4th
carbon. 2 is lower than 4,
so the correct numbering
is from left to right.
4. Assemble the name, starting with the number of the position of the branch, followed by
a dash, the name of the branch, and finally the name of the parent chain. There should
be no space between the names of the branches and the parent chain. If there is more
than one type of branch, list the branches in alphabetical order.
This compound is 2-methylpentane, not 4-methylpentane.
5. If two (or more) of the same branch are attached to the same carbon atom, the number
of the carbon atom is repeated (separated by a comma). In addition, the number of times
the branch occurs is indicated by a prefix (di, tri, tetra, penta, hexa, etc.). These prefixes
are not considered when alphabetizing.
47
Examples:
1. Name the following compound.
Solution:
branch
branch
parent chain
branch
This compound is a derivative of pentane because the longest chain contains five carbon
atoms. There are three identical methyl (CH3) groups on the backbone. Two of these methyl
groups are on the second carbon, and one is on the fourth. This compound is therefore 2,2,4-
trimethylpentane.
Solution:
branch branch
parent chain
The longest continuous chain in the skeleton structure of this compound contains seven
carbon atoms, not six. It is therefore a derivative of heptane. The heptane chain contains two
branches, a methyl group on the second carbon atom and an ethyl group on the fourth carbon
48
atom. Because the branches are listed in alphabetical order, the systematic name for this
compound is 4-ethyl-2-methylheptane.
Solution:
Although this looks at first glance to be a heptane, the methyl group at the left of the chain
can be viewed as part of the parent chain. The longest chain has eight carbon atoms, so it is
an octane. The molecule has two branches: one methyl and one ethyl. Both branches are
attached to the fourth carbon atom. The full name is 4-ethyl-4-methyloctane.
THE ALKENES
The alkene series is a family of unsaturated hydrocarbons. Each member of the series has
a structure in which one pair of carbon atoms is connected by a double bond. Such a bond
indicates the sharing of two pairs of electrons. The general formula for the alkenes is 𝐶𝑛 𝐻2𝑛 .
The first member of this series is commonly called ethylene. Its IUPAC name is ethene and its
formula is 𝐶2 𝐻4 .
or
The following equation shows that ethene can add atoms, such as chlorine atoms, directly to
its structure:
The reaction above is called an addition reaction. Notice that it involves the double-
bonded carbon atoms. One bond of the double bond is broken, and each of the carbon atoms
then forms a covalent bond with a chlorine atom. The halogen compounds formed by addition
49
reactions with alkenes are usually oily liquids. Thus, the alkene series is also known as the
olefin (oil-former) series. Ethene serves as the starting point for the production of the plastic
polyethylene and the antifreeze ethylene glycol.
The formulas of the higher members of the alkene series are obtained by the addition of
the increment −𝐶𝐻2 −, just as in the alkane series. The second member has the formula 𝐶3 𝐻6 ,
and has an IUPAC name of propene.
The first four members of the alkene series are:
No. of C No. of H Molecular

Structural Formula IUPAC Name
atoms atoms Formula (𝑪𝒏 𝑯𝟐𝒏 )
2 4 𝑪 𝟐 𝑯𝟒 ethene
3 6 𝑪 𝟑 𝑯𝟔 propene
4 8 𝑪 𝟒 𝑯𝟖 butene
5 10 𝑪𝟓 𝑯𝟏𝟎 pentene
IUPAC rules state that the names of the alkenes must end in –ene and that the position of
the double bond must be shown by a number preceding the name. This number indicates the
first carbon atom in the double bond pair. The carbon atoms are numbered from the end of the
chain nearest the double bond. The rules for naming derivatives are similar to those used form
naming alkanes.
50
Examples:
Solution:
This molecule has a double bond, so it is an alkene with a name ending in -ene. The double
bond is between the first and second carbon atoms, so it is a 1-butene. Full name is 3,3-
dimethyl-1-butene.
Solution:
When a halogen is substituted into a hydrocarbon, the halogen is treated as a functional group
(prefixes are fluoro-, chloro-, bromo- and iodo-). The carbon atoms are numbered from right
to left such that the double bond is on the first carbon atom. This molecule is 1-chloro-1-
butene.
51
Solution:
If the chain is numbered from the left this molecule would be called 1-bromo-4-methyl-3-
pentene. If the chain is numbered from the right it would be 5-bromo-2-methyl-2-pentene.
The chain is numbered in the direction that gives any multiple bonds the lowest possible
number, so the correct name is 5-bromo-2-methyl-2-pentene.
The Alkadienes
As implied by the –diene ending, alkadienes are unsaturated hydrocarbons with two
double bonds between two pairs of carbon atoms. Alkadienes are isomeric with alkynes, with
the general formula of 𝑪𝒏 𝑯𝟐𝒏−𝟐 . The double bonds in alkadienes do not occur consecutively
in the molecule. Thus, the minimum number of carbon atoms in an alkadiene is generally four.
The first, and most important member of the series is butadiene, 𝐶4 𝐻6 . To emphasize the
locations of the double bonds, it could be named 1,3-butadiene. However, the name butadiene
is usually used and is sufficient because it does not have an isomer in the –diene family. The
next higher alkadiene has the molecular formula 𝐶5 𝐻8 .
THE ALKYNES
Members of the alkyne series are unsaturated hydrocarbons that contain a triple bond.
Such bonds represent the sharing of three pairs of electrons by two neighboring carbon atoms
in the hydrocarbon chain. Compounds in this series are, therefore, more unsaturated than those
in the alkene series. The general formula for the alkyne series is 𝑪𝒏 𝑯𝟐𝒏−𝟐 .
The common name for the alkyne series is the acetylene series, named after its first
member, acetylene, 𝐶2 𝐻2 . Acetylene burns with a hot flame and is used in the oxyacetylene
blowtorch for cutting and welding metals.
In accordance with IUPAC rules, alkynes are named by adding the suffix –yne to the
usual hydrocarbon prefixes. Thus, the IUPAC name for acetylene, with its two carbon atoms,
is ethyne. Some of the other compounds in this series are propyne, butyne, and pentyne.
The first four members of the alkyne series are:
52
No. of Molecular
No. of C IUPAC
H Formula Structural Formula
atoms Name
atoms (𝑪𝒏 𝑯𝟐𝒏−𝟐 )
2 2 𝑪 𝟐 𝑯𝟐 ethyne
3 4 𝑪 𝟑 𝑯𝟒 propyne
4 6 𝑪 𝟒 𝑯𝟔 butyne
5 8 𝑪 𝟓 𝑯𝟖 pentyne
The first two alkynes (ethyne and propyne) have no isomers. The two structural formulas
for propyne are the same. They are simply written with the methyl group at opposite ends.
or
The next higher alkyne, butyne, has two isomers. As with the alkenes, IUPAC rules state
that the position of the triple bond must be shown by a number preceding the name. This
number indicates the first carbon atom in the triple bond pair. The two isomers of butyne are
1-butyne and 2-butyne.
ALICYCLIC HYDROCARBONS
Hydrocarbons in which the carbon atoms are arranged in a closed, or ring, structure are
called cyclic hydrocarbons. The two main groups of cyclic hydrocarbons are the alicyclic
hydrocarbons and the aromatic hydrocarbons.
In alicyclic hydrocarbons, the carbon atoms are linked by single or double bonds and are
arranged in a closed structure. These hydrocarbons are also classified into cycloalkanes,
cycloalkenes, cycloalkynes, and other more complex groups. Their names consist of the prefix
cyclo- attached to the names of different series of aliphatic hydrocarbons.
53
Like the alkanes, cycloalkanes are saturated hydrocarbons, i.e. they contain only single
bonds between carbon atoms. Since the minimum number of carbon atoms that can form a
closed structure is three, the first member of this series is cyclopropane. The names and
structure formulas of the first three members of the cycloalkane series are shown below.
Similarly, cycloalkenes contain one double bond between a pair of carbon atoms in the
ring structure. Cycloalkadienes contain two double bonds between two different pairs of
carbon atoms.
cyclopentene 1,3-cycloheptadiene
AROMATIC HYDROCARBONS
Aromatic hydrocarbons are by far the widely studied class of hydrocarbons. The name
aromatic indicates that many of the compound sin this series have pleasant and/or distinctive
odors. The general formula for member of this series is 𝐶𝑛 𝐻2𝑛−6 .
All of the aromatic hydrocarbons have structures that are related to or derived from that
of benzene. The molecular and structural formulas of benzene are shown below. It contains a
ring of six carbons with alternating single and double bonds.
54
Benzene is an excellent solvent and is widely used as such. It is also used as the starting
point for the synthesis of dyes, explosives, and drugs such as aspirin and sulfa drugs. It is one
of the products obtained in the fractional distillation of coal tar. The explosive TNT is produced
by the reaction of toluene with nitric acid in the presence of concentrated sulfuric acid.
In its reactions, benzene displays properties that are typical of both saturated and
unsaturated hydrocarbons. To indicate the equivalency of the carbon-carbon bonds, the
structural formula for benzene is often written as a hexagon with a circle inside.
The radical formed from benzene by the removal of a hydrogen atom:
is called a phenyl radical. The phenyl radical is an example of an aryl radical, a group that is
produced by the removal of a hydrogen atom from a carbon of the benzene ring of an aromatic
compound.
The second member of the benzene series is toluene, 𝐶7 𝐻8 . The IUPAC name of
toluene is methylbenzene and its structure is shown below.
The IUPAC rules for naming benzene derivatives are similar to those used in naming
chain compounds. Prefixes are attached to the parent name, benzene. The prefixes identify the
group(s) that haven substituted for hydrogen atoms on the benzene ring. Thus, in the
methylbenzene (toluene) molecule, one methyl group has been substituted from a hydrogen
atom.
55
As with chain compounds, the IUPAC system of naming benzene derivatives involves
numbering the carbon atoms in the ring in order to pinpoint the locations of the side chains.
However, if only two groups are substituted in the benzene ring, the compound formed will be
a benzene derivative having three possible isomeric forms. In such cases, the prefixes ortho-,
meta- and para- may be used to name the isomers. The three prefixes are abbreviated o-, m-
and p-, respectively. In the ortho- structure, the two substituted groups are located on adjacent
carbon atoms. In the meta- structure, they are separated by one carbon atom. In the para-
structure, they are separated by two carbon atoms. The figure below shows the structural
formulas and the common and IUPAC names for the three isomers of xylene, 𝐶8 𝐻10.
ortho-xylene meta-xylene para-xylene

(1,2-dimethylebenzene) (1,3-dimethylebenzene) (1,4-dimethylebenzene)
Here are the names and structural formulas of several benzene derivatives.
bromobenzene 1-bromo-2-nitrobenzene
1,3,5-trinitrobenzene 2,4,6-trinitro-methylbenzene
Industrial Uses of Hydrocarbons
One of the most important sources of hydrocarbons is petroleum or crude oil. Most of
the gaseous and liquid fuels such as LPG, gasoline, kerosene, etc., are obtained from this
source. These gaseous and liquid fuels are obtained by fractional distillation of petroleum. In
this process, successive distillations are carried out at increasingly higher temperatures. The
distillate is collected in several portions or fractions. The first fraction is the richest in the
petroleum components that have the lowest boiling points. The later fractions have components
with the higher boiling points. The fractions include such substances as gasoline, kerosene,
furnace oil, naphthas, and lubricating oils. These fractions are usually purified before they are
distributed commercially. Below are the petroleum fractions at different temperatures.
56
FRACTIONS FROM DISTILLATION OF PETROLEUM
Boiling Range Name Range of Use

in 0C Carbon Atoms
Heating and
Below 20 LPG C1 to C4 cooking
20-200 Naphtha, C5 to C12 Fuel and solvents as

Gasoline petroleum ether
200-300 Kerosene C12 to C15 Fuel
300-400 Fuel oil C15 to C18 Diesel fuel
Lubricating oil, greases,

Over 400 ------- Over C18 paraffin,
wax, asphalt
One of the most important products of fractional distillation is gasoline; it is widely

used as fuel for cars. In order for gasoline to function properly in an engine, it should not
begin to burn before it is ignited by the spark plug. If it does, it gives the engine “knock”.
The antiknock characteristics of gasoline are rated by the octane number scale. This scale
is based on two reference substances, heptane which is given an octane number of 0, and
isooctane (2,2, 4-trimethylpentane) which is given an octane number of 100. The higher
the octane number, the better the antiknock characteristics. Substances such as tetraethyl
lead maybe added to gasoline to raise the octane rating number.
Cracking is the process in which higher molecular mass hydrocarbon molecules,

which are unsuitable for direct use in gasoline, are broken down into smaller molecules
that are more easily evaporated and, therefore, more suitable for gasoline. The two chief
cracking processes are thermal cracking and catalytic cracking. In thermal cracking,
the higher molecular mass molecules are heated under pressure. These molecules,
containing 10-16 carbon atoms each, are decomposed chiefly into alkanes and alkenes of
lower molecular mass. The alkenes are present in larger quantities than the alkanes and
are superior in antiknock qualities. Catalytic cracking usually uses high temperatures and
some increase in pressure in addition to a catalyst. The product of catalytic cracking is
superior to that obtained by thermal cracking because it produces not only alkenes but a
greater amount of branched-chain and ring compounds. These compounds increase
octane ratings and improve the antiknock qualities of the gasoline.
57
PROGRESS CHECK
Answer the following problems.
1. (a) Write the structural formula of an organic compound whose molecule has 2 chlorine
atoms, 4 hydrogen atoms, and 2 carbon atoms. (b) If you are able, write another structural
formula for a different organic molecule composed of 2 chlorine atoms, 4 hydrogen atoms,
and 2 carbon atoms. (c) Why is it necessary to use structural formulas to represent most
organic compounds rather than molecular formulas?
2. Why was it important to develop a standard system of nomenclature for organic
compounds?
3. Name the following compounds according to IUPAC rules:
a)
____________________________________________
b)
____________________________________________
c)
__________________________________________
d)
Cl
CH CH2
H2C CH Cl
CH2 CH2 _________________________________________________
58
4. Write the structural formulas of the following:
a) 3-ethyl-2,4-dimethylpentane
b) 2,2,3-trimethylbutane
c) 4-ethyl-2,3-dimethylhexane
d) 2,4,4-trimethyl-2-pentene
e) 4-bromo-3-methyl-1-pentyne
f) 2,3-dimethyl-1,3-butadiene
g) 1,3-cyclopentadiene
59
REFERENCES
Balacuit, G. G., Hermosura, A. J., Dingcong, M. G., Ralios, M. C., Tortosa, H. L., &
Andres, J. (1990). Handbook of General Chemistry I (1st ed.).
Brown, T. L., Jr., H. E., Bursten, B. E., Murphy, C., Woodward, P., Langford, S., Sagatys,
D., & George, A. (2013). Chemistry: The central science. Pearson Higher Education
AU.
Dorin, Henry (1982). Chemistry, The Study of Matter. Allen and Bacon, Inc.
Mortimer, Charles E. (1986). Chemistry, Sixth Edition. Wadsworth Publishing Company
60
LEARNING GUIDE
Week No.: __13__
TOPICS/SUBTOPICS:
Other Classes of Organic Compounds: Nomenclature, Properties and Uses
Organic halides
Alcohols
Aldehydes
Ketones
Carboxylic acids
Esters
Ethers
EXPECTED COMPETENCIES
At the end of the lesson, you must have:
1. classified other groups of organic compounds;
2. identified the functional groups for organic halides, alcohols, aldehydes, ketones,
carboxylic acids, esters and ethers;
3. learned the nomenclature of other classes of organic compounds based on IUPAC
rules;
4. drawn structures based on the IUPAC names of organic halides, alcohols, aldehydes,
ketones, ethers, carboxylic acids, and esters names and name based on their structures
and
5. identified the properties and uses of organic halides, alcohols, aldehydes, ketones,
ethers, carboxylic acids, esters and ethers.
CONTENT/TECHNICAL INFORMATION
Introduction
This lesson guide is devoted to a number of important classes of organic compounds,

other than the hydrocarbons. These classes of compounds include alcohols, aldehydes, halides,
ketones, ethers, carboxylic acids, esters, and other derivatives.
FUNCTIONAL GROUPS
There are various groups of atoms, called functional groups, which give organic
compounds characteristic properties. For example, the –OH group in alcohols gives certain
properties that are common to alcohols. Although the IUPAC system names these compounds
as though they were hydrocarbon derivatives, they are not necessarily prepared from
hydrocarbons. Some of the functional groups are listed in the table below.
61
FUNCTIONAL GROUP
Name of Group Structure Examples of the Group in a Compound
halides (where X represents

(occurs in organic a halogen: Cl, Br,
halides) I, or F) fluoromethane trichloromethane
hydroxyl, or
alcohol group
(occurs in ethanol
alcohols) methanol (ethyl alcohol)
(methyl alcohol)
aldehyde group
(occurs in
methanal ethanal
aldehydes)
(formaldehyde) (acetaldehyde)
carbonyl group
(occurs in
ketones) propanone 2-pentanone
(methyl ketone) (methylpropyl ketone)
ether group
(occurs in ethers)
dimethyl ether diethyl ether
carboxyl group
(occurs in
carboxylic acids) methanoic acid ethanoic acid
(formic acid) (acetic acid)
ester group
(occurs in esters)
methyl methanoate ethyl ethanoate
(methyl formate) (ethyl acetate)
62
OTHER CLASSES OF ORGANIC COMPOUNDS
I. Organic Halides
An organic halide is formed when one or more hydrogen atoms of the hydrocarbon is
replaced by an atom or atoms of any halogen. The general formula for an organic halide is
RX, where R represents an alkyl.
Nomenclature:
Organic halides are named by placing the name of the halogen first followed by the
name of parent hydrocarbon. The location of the halogen is shown by the smallest possible
number.
Examples:
Structural Formula IUPAC Name Use
chloroethane local anaesthetic
dichlorodifluoromethane (freon
refrigerant
12)
as starting material to make

2 – bromopropane
other chemicals, drugs and
dyes
II.Alcohols
Alcohols are formed when a hydrogen atom in a hydrocarbon is replaced by an –OH

group. The general formula for an alcohol is ROH, where R represents an alkyl group and
OH is the functional group. R, for example, represents 𝐶𝐻3 in methanol (𝐶𝐻3 𝑂𝐻); and
𝐶𝐻3 𝐶𝐻2 in ethanol (𝐶𝐻3 𝐶𝐻2 𝑂𝐻).
63
The alcohol group in an alcohol does not function the same way as the 𝑂𝐻 − ion in an
inorganic base. In an inorganic base, the hydroxide group is ionically bonded. In alcohols, the
hydroxyl group is covalently bonded. Thus, alcohols do not dissociate to form hydroxide ions
in water solution as inorganic bases do.
Nomenclature:
The –e ending of the name of the parent hydrocarbon is replaced by –ol. The
location of –OH is shown by the smallest number.
Classification of Alcohols:
1. Monohydroxy alcohols – contain only one hydroxyl group per molecule. (e.g.
methanol, ethanol)
Monohydroxy alcohols can either be primary, secondary or tertiary alcohols, depending

upon the number of carbon atoms directly bonded to the carbon atom holding the –OH
group.
a. Primary alcohol – one in which the carbon holding the –OH group is bonded
to only one other carbon atom at the end of the hydrocarbon chain.
1-propanol
b. Secondary alcohol – one in which the carbon holding the –OH group is
bonded to two other carbon atoms.
2-butanol
c. Tertiary alcohol – one in which the carbon holding the –OH group is bonded
to three other carbon atoms.
2-methyl-2-propanol
64
Methanol and Ethanol.
The simplest alcohol is methanol, and it can be obtained from wood by the process
called destructive distillation. Since methanol was originally prepared this way, it was
given the name wood alcohol, a name that is still used today. Methanol is now prepared
by the catalytic combination of carbon monoxide and hydrogen.
Methanol tastes like ethanol, but is extremely poisonous when swallowed. It attacks
the nervous system, especially the optic nerves, and may result to blindness and even
death. Methanol is commercially used as a solvent in lacquers and varnishes, and as a fuel
and in the manufacture of formaldehyde.
Ethanol, or ethyl alcohol, is the most common

and familiar of the alcohols. It is also known as grain
alcohol because it can be prepared from corn or other
grain plants, and also from any sweet fruit juice. The
starch in the grains is first converted into a sugar, and
then fermented to produce ethanol. The ethanol is
then removed from the fermented mixture by
distillation. The term proof is used in the liquor trade
to indicate the proportion of ethanol in a beverage.
The proof is equal to twice the percentage of alcohol by volume. Thus, 90 proof means
45% alcohol by volume. Pure alcohol is 200 proof and is called absolute alcohol. Ethanol
intended for commercial use is often “denatured”, or rendered unfit to drink, by the
addition of methanol.
Ethanol is a volatile, colorless, flammable liquid with

a pleasant odor. It is an excellent solvent and fuel. Besides
its use in alcoholic beverages, ethanol is used as a solvent
for lacquers, and in the preparation of extracts, ether,
drugs, and perfumes.
2. Dihydroxy alcohols – commonly called glycols, contain two hydroxyl groups per
molecule
The IUPAC names for dihydroxy alcohols end with –diol , indicating that there are
two hydroxyl groups in a molecule. The best known dihydroxy alcohol is 1,2-ethanediol,
commonly known as ethylene glycol. It is used as antifreeze for car radiators.
1,2-ethanediol (ethylene glycol)
65
3. Trihydroxy alcohols – have three hydroxyl groups per molecule
The most important trihydroxy alcohol is glycerine. It is a viscous, sweet-tasting

liquid obtained as a by-product in the manufacture of soap. It is used to make plastics,
drugs, cosmetics, foods, and nitroglycerine. Glycerine’s IUPAC name is 1,2,3-
propanetriol.
1,2,3-propanetriol
III.Aldehydes
An aldehyde is formed when a primary alcohol undergoes oxidation, and it has a general
formula of RCHO.
𝑹𝑪𝑯𝟐 𝑶𝑯 + 𝑶 → 𝑹𝑪𝑯𝑶 + 𝑯𝟐 𝑶
primary alcohol aldehyde
Nomenclature:
The IUPAC names of aldehydes are obtained by replacing the –e ending of the
related hydrocarbon with –al. For example, the aldehyde 𝐶𝐻2 𝑂 is related to the
hydrocarbon 𝐶𝐻4 . By removing the –e ending from methane and replacing it with –al, the
name methanal is obtained. By the same reasoning, the IUPAC name of acetaldehyde is
ethanal. The position of the aldehyde group in all aldehydes is at the end of the carbon
chain.
Examples:

germicide and disinfectant;
methanal
used to preserve dead animal
(formaldehyde)
specimens
used to make dyes, synthetic
ethanal
rubber, and many important
(acetaldehyde)
organic compounds
propanal
anaesthetic
66
IV. Ketones
A ketone is formed by the oxidation of a secondary alcohol, and it has a general formula
of RCOR.
𝑹𝑪𝑯𝟐 𝑶𝑯𝑹 + 𝑶 → 𝑹𝑪𝑯𝑶𝑹 + 𝑯𝟐 𝑶

secondary alcohol ketone
Nomenclature:
The IUPAC system names ketones by replacing the –e ending of the related
hydrocarbon with –one. Where necessary, a number is used to show the position of the
carbonyl group. Carbonyl groups are always found in the interior part of a chain, never at
either end, with hydrocarbon radicals to either side. Take for example the ketone related to
pentane. Removing the final –e from pentane and replacing it with –one gives pentanone.
The number of the carbon atom to which the oxygen is doubly bonded is indicated,
as in the cases of 2-pentanone and 4-methyl-3-hexanone. Note that the carbonyl carbon is
given the lower number in relation to substituted groups.
Examples:

as solvent to remove nail
propanone polish; to dissolve
(acetone) varnishes, plastics and
paints
as solvent to replace
propanone; synthetic food
2-pentanone
flavoring agent; in organic
synthesis
4-methyl-3-hexanone to dissolve oil and waxes
V. Carboxylic Acids
Carboxylic acids are derivatives of hydrocarbons which possess the carboxyl group –
COOH. The compounds are acidic because they yield hydrogen ion. Their general formula is
RCOOH.
𝑹𝑪𝑶𝑶𝑯 → 𝑹𝑪𝑶𝑶− + 𝑯+
67
Nomenclature:
The IUPAC system names organic acids by replacing the final –e of the parent
hydrocarbon with –oic and then adding the word acid. For example, the simplest organic
acid is the methanoic acid (commonly known as formic acid). This acid is related to
methane. The two-carbon acid is related to ethane and so its IUPAC name is ethanoic acid.
Many fruits and vegetables contain carboxylic acids. One such acid is the familiar citric
acid found in lemons, oranges, and other citrus fruits. Oxalic acid is found in rhubarb.
Tartaric acid is found in grapes.
The three common carboxylic acids are:
ethanoic acid (acetic acid) oxalic acid
citric acid
68
VI. Esters
Esters are formed when a carboxylic acid reacts with an alcohol. They can also be
formed when an inorganic acid reacts with alcohol. Their general formula is RCOOR.
𝑹𝑪𝑶𝑶𝑯 + 𝑹𝑶𝑯 → 𝑹𝑪𝑶𝑶𝑹 + 𝑯𝟐 𝑶
carboxylic acid alcohol ester water
Nomenclature:
The name of the radical coming from the alcohol is named first followed by the
name of the carboxylic acid where the –oic ending is replaced by – oate.
Examples:
methyl ethanoate ethyl ethanoate
ethyl butanoate propyl propanoate
Esters made from alcohols and organic acids of low molecular mass are colorless
liquids that have agreeable, fruity odors. Many of the odors in flowers come from esters. Thus,
esters are used in preparation of perfumes and synthetic flavors. Methyl ethanoate gives nail
polish its odor. Ethyl butanoate gives the pineapple its flavor.
Fats are glyceryl esters of carboxylic acids of relatively high molecular mass. At room
temperature, saturated fats are solids while unsaturated fats are liquids.
69
VII. Ethers
Ethers are organic oxides with the general formula ROR’, where R and R’ are alkyl
groups that may be the same or different.
Nomenclature:
The –yl ending of the radical with the least number of carbon atoms is replaced by –
oxy. This radical is named first followed by the name of the hydrocarbon with the most
number of carbon atoms.
Examples:
methoxy methane (dimethyl ether)
methoxy ethane (methyl ethyl ether)
ethoxy ethane (diethyl ether)
The best known ether is ethoxy ethane, also called diethyl ether or just plain ether. Ether
was commonly used in surgery as a general anaesthetic. Because of its several drawbacks, ether
is seldom used in surgery today except with laboratory animals. Some of its major drawbacks
are its great flammability, the irritation it causes the respiratory tract, and the nausea many
people feel as they awake from ether. Industrially, ether is used as a solvent for gums, fats and
waxes.
70
PROGRESS CHECK
I. Write structural formulas for the following molecules:
1. 3-hexanol
2. butanal
3. 2-butanone
4. 3-methylhexanoic acid
5. 2-methylpentanal
6. 4,5,6-triiodo-3-hexanol
II. Name each of the following compounds:
1.
__________________________________________
2.
___________________________________________
3.
___________________________________________
4.
___________________________________________
71
REFERENCES
Balacuit, G. G., Hermosura, A. J., Dingcong, M. G., Ralios, M. C., Tortosa, H. L., &
Andres, J. (1990). Handbook of General Chemistry I (1st ed.).
Brown, T. L., Jr., H. E., Bursten, B. E., Murphy, C., Woodward, P., Langford, S., Sagatys, D.,
& George, A. (2013). Chemistry: The central science. Pearson Higher Education AU.
Dorin, Henry (1982). Chemistry, The Study of Matter. Allen and Bacon, Inc.
Mortimer, Charles E. (1986). Chemistry, Sixth Edition. Wadsworth Publishing Company

Week 12-13 Module

Uploaded by

Document Information

Copyright

Available Formats

Share this document

Share or Embed Document

Sharing Options

Did you find this document useful?

Is this content inappropriate?

Copyright:

Available Formats

Week 12-13 Module

Uploaded by

Copyright:

Available Formats

38

Week No.: __12-13__

o Introduction to Organic Chemistry

Organic Chemistry is defined as the study of carbon and

A unique feature of carbon is its ability to bond to other

𝑁𝐻4 𝐶𝑙 + 𝐴𝑔𝑂𝐶𝑁 → 𝐴𝑔𝐶𝑙 + 𝑁𝐻2 𝐶𝑂𝑁𝐻2

Bonding in Organic Compounds

Molecular Formulas, Structural Formulas and Isomerism

Because carbon compounds are so numerous, it is convenient to organize them into

Figure 1. Classifications of Hydrocarbons

Examples of straight chains:

(a) (b) (c)

Examples of branched chains:

A. Alkanes – are hydrocarbons

alkane alkene alkyne

THE ALKANES cycloalkyne

The first ten members of the alkane series are:

10 22 𝑪𝟏𝟎 𝑯𝟐𝟐 decane

The Alkyl Groups

IUPAC SYSTEM OF NAMING ALKANE DERIVATIVES

The parent chain

2. Identify and name the branches attached to this chain.

The branch is an alkyl with 1

This compound is 2-methylpentane, not 4-methylpentane.

1. Name the following compound.

2. Name the following compound.

3. Name the following compound.

The first four members of the alkene series are:

No. of C No. of H Molecular

2. Name the following compound.

3. Name the following compound.

The first four members of the alkyne series are:

The radical formed from benzene by the removal of a hydrogen atom:

ortho-xylene meta-xylene para-xylene

Industrial Uses of Hydrocarbons

FRACTIONS FROM DISTILLATION OF PETROLEUM

Boiling Range Name Range of Use

20-200 Naphtha, C5 to C12 Fuel and solvents as

200-300 Kerosene C12 to C15 Fuel

300-400 Fuel oil C15 to C18 Diesel fuel

Lubricating oil, greases,

One of the most important products of fractional distillation is gasoline; it is widely

Cracking is the process in which higher molecular mass hydrocarbon molecules,

CH2 CH2 _________________________________________________

4. Write the structural formulas of the following:

Mortimer, Charles E. (1986). Chemistry, Sixth Edition. Wadsworth Publishing Company

Week No.: __13__

This lesson guide is devoted to a number of important classes of organic compounds,

halides (where X represents

OTHER CLASSES OF ORGANIC COMPOUNDS

Structural Formula IUPAC Name Use

chloroethane local anaesthetic

as starting material to make

Alcohols are formed when a hydrogen atom in a hydrocarbon is replaced by an –OH

Monohydroxy alcohols can either be primary, secondary or tertiary alcohols, depending

Methanol and Ethanol.

Ethanol, or ethyl alcohol, is the most common

Ethanol is a volatile, colorless, flammable liquid with

1,2-ethanediol (ethylene glycol)

3. Trihydroxy alcohols – have three hydroxyl groups per molecule

The most important trihydroxy alcohol is glycerine. It is a viscous, sweet-tasting

Structural Formula IUPAC Name Use

𝑹𝑪𝑯𝟐 𝑶𝑯𝑹 + 𝑶 → 𝑹𝑪𝑯𝑶𝑹 + 𝑯𝟐 𝑶

Structural Formula IUPAC Name Use

Week No.: 12-13

Week No.: 13