MUFULIRA COLLEGE OF EDUCATION

SECONDARY TEACHERS DIPLOMA BY DISTANCE

LEARNING

CHEMISTRY MODULE 7
THE CHEMISTRY OF CARBON AND ITS COMPOUNDS
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All rights reserved. No part of this module may be reproduced, stored in retrieval system or
transmitted in any form or by any means electronic or mechanical including photocopying, recording
or otherwise without permission from Mufulira College of Education.
 CHEMISTRY MODULE 7
P.O. Box 40400
Mufulira
Zambia
E-mail: mucestudents@yahoo.com
Website: http://sites.google.com/site/muce2009/

Acknowledgements
Mufulira College of Education wishes to thank those below for their contribution to this module:

Writers
Banda A

Moono K.C.

Tebeka J.

Instructional Designers
Dr. Chifwepa V.
Mr Nkosha D.C
Mr Mwewa G.

Contents

1
 CHEMISTRY MODULE 7

About this Module

How this Module is structured....................................................................................................

Module overview
Welcome to Chemistry Module 7: Organic Chemistry...............................................................
Module outcomes........................................................................................................................
Timeframe...................................................................................................................................
Study skills..................................................................................................................................
Need help?...................................................................................................................................
Assessments................................................................................................................................

Getting around this Module

Margin icons................................................................................................................................

ORGANIC CHEMISTRY
Introduction…………………………………………………………………………………….9
Hydrocarbon…………………………………………………………………………………………..10

Homologous series…………………………………………………………………………………....10

Functional groups……………………………………………………………………………………10

Nomenclature of unbranched akly groups…………………………………………………………….11

Nomenclature of branched alky groups………………………………………………………………11

Functional groups…………………………………………………………………………………..

Isomerism…………………………………………………………………………………………..

Alkanes………………………………………………………………………………………………..14

Fuels: Natural gas, crude oil (Petroleum) and derivatives…………………………………………….16

Cracking………………………………………………………………………………………………17

Alkenes………………………………………………………………………………………………18

Nomenclature of alkenes…………………………………………………………………………….19

Addition reactions…………………………………………………………………………………...21

Condensation polymers………………………………………………………………………………23

Alkynes………………………………………………………………………………………………23

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 CHEMISTRY MODULE 7

Preparation of alkynes……………………………………………………………………………….23

Chemical properties of alkynes……………………………………………………………………...23

Alcohols…………………………………………………………………………………………….24

Nomenclature of alcohols…………………………………………………………………………..25

Preparation of alcohols……………………………………………………………………………..25

Reaction of alcohols………………………………………………………………………………..25

Carboxylic acids……………………………………………………………………………………26

Nomenclature of carboxylic acids…………………………………………………………………27

Chemical properties of carboxylic acids…………………………………………………………..27

Saponification…………………………………………………………………………………….28

Unit summary……………………………………………………………………………..29
References………………………………………………………………………………………...30

About this Module

Organic Chemistry Module 7: The outline of this Module is structured in the same way as the
previous ones.

5
 CHEMISTRY MODULE 7

How this Module is structured

This overview gives you a general introduction to the module. It will help you determine:
 If the module is suitable for you.
 What you will already need to know.
 What you can expect from the course.
 How much time you will need to invest to complete the module.
 The overview also provides guidance on:
o Study skills
o Where to get help
o Activity icons

We strongly recommend that you read the overview carefully before starting your study.

The Module content

 The module has one unit only
 An introduction to the unit content
 Unit outcomes
 Core content of the unit with a variety of learning activities
 A unit summary

Resources
For those interested in learning more on this subject, we have provided you with a list of additional
resources at the end the unit.

Your comments
After completing this Module we would appreciate if you would take a few moments to give us
your feedback on any aspect of this Module. Your feedback might include comments on:
 Module content and structure.

7
 CHEMISTRY MODULE 7

 Subject reading materials and resources.

 Module activities.
 Module duration.
 The Diploma Course or Module support

Your constructive feedback will help us to improve and enhance this course.

9
Module overview

WELCOME TO MODULE 7: ORGANIC CHEMISTRY

This is the seventh and last Module in the third year of the Secondary Teachers’ Diploma
Course that you are doing. This module looks at Organic Chemistry. The knowledge you shall
obtain after studying this module will help you teach science effectively either at Upper Basic
School level or at High School level. You will enjoy going through this module.

Outcomes

Upon completion of this module you will be able to:

1. Define an organic compound

2. Define a hydrocarbon
3. Define a homologous series
4. Classify homologous series and name each using the IUPAC system
5. Give an account of structural isomerism
6. Describe the chemical properties of alkanes, alkenes, alcohols and
carboxylic acids
7. Describe the process of purifying crude oil (distillation, cracking)

How long? Timeframe

For you to complete the third year of your study, you need to cover this
module. You are therefore expected to spend about three months to
complete studying this module. You can manage to cover the whole
module if you plan your study time very well and spend an hour per day
studying it.
 Study skills
You may need more hours to read through other suggested readings
and websites. Timetabling yourself may help you to work through
this module easily. Here are some learning tips you can use to work
through this module:
 Schedule your time table and stick to it. Select days and times in
a week when you can study.
 Make sure that you have all necessary materials.
 Studying requires a little or no disturbance. Try to find a quiet
place in your house or somewhere else where you can study well.
 Identify students doing the same course living within your area.
You may arrange study times with them whenever possible.
 Family and other social related challenges may make you fail to
write or complete the assignments within the scheduled time.
This should not make you abandon the course. Try to contact
your lecturers to see how best they can help you.

Help Need help?

For any help, use the College website or email address. The website and
email address are found on the first preliminary page after the cover.

Assessment
Both summative and formative assessments will be given based on this module. We are now
preparing you for your final diploma examination. Hence, ensure that you develop your
Continuous Assessment (CA) before then.
 Getting around this Module

Margin icons
While working through this Module you will notice the frequent use of margin icons. These
icons serve to “signpost” a particular piece of text, a new task or change in activity; they have
been included to help you to find your way around this Module.
A complete icon set is shown below. We suggest that you familiarize yourself with the icons
and their meaning before starting your study.

Activity Assessment Assignment Case study

Discussion Group activity Help Note it!

Outcomes Reading Reflection Study skills

Summary Terminology Time Tip

 ORGANIC CHEMISTRY

1.0 INTRODUCT ION

1.1 What is organic chemistry?
Organic Chemistry is the study of carbon and its compounds or the study of chemistry
of life. All organic compounds contain carbon in association with hydrogen, oxygen,
nitrogen, and other elements such as phosphorus. There are over 600 million
compounds known today, but more than 90% of those compounds contain the element
carbon, why?

Carbon is contained in most of these compounds because of its ability to form chains
with itself, a property called catenation. Carbon is a tetravalent element, that is, it is
bonded to four other atoms in compounds.

Outcomes

Upon completing this module you will be able to:

1. Define what an organic compound is
2. Define a hydrocarbon
3. Define a homologous series
4. Classify homologous series and name each using the IUPAC system
a) Alkanes
b) Alkenes
c) Alkynes
d) Alcohols
e) Carboxylic acids
f) Esters
8. Give an account of structural isomerism
9. Describe the chemical properties of alkanes, alkenes, alkynes, alcohols
and carboxylic acids

10. Describe the process of purifying crude oil (distillation, cracking)

1.2 RATIONALE
Organic Chemistry is important because it is the study of life and all chemical
reactions related to life. Several carriers apply an understanding of organic chemistry
such as Doctors, veterinarians, Dentists, Pharmacologists, chemical engineers, e.t.c.
Organic chemistry plays an a part in the development of common household
chemicals, foods, plastics, drugs fuels, e.t.c

1.2 HYDROCARBON
A hydrocarbon is a compound that contains carbon and hydrogen, only. Hydrocarbons
are the simplest organic compounds containing only the elements carbon and
hydrogen (C-H). A hydrocarbon has the molecular formula C xHy ; where x and y are
whole numbers.
e.g. CH4, CH3CH2CH3, H2C=CH2
All the above are organic compounds called hydrocarbons.

1.4 HOMOLOGOUS SERIES

A homologous series is a group of substances that share the same general formula or it
is a series of compounds in which each member differs from the one preceding by a
constant unit of -CH2-, e.g., CH4, CH3CH3, CH3CH2CH3, CH3CH2CH2CH3, e.t.c. each
member of the series is called a homologue. Examples of homologous series include
alkenes, alkenes, alkynes, alcohols, esters, ethers, carboxylic acids, e.t.c.

1.5 CHARCTERISITCS OF HOMOLOGOUS SERIES

1. Members conform to a same general formula.
2. Members differ in molecular formula from one by the same unit-CH2-.
3. Their physical properties change gradually as the chain length increases.
4. General methods of preparation are known and can be applied to any member of
the series.

1.6 FUCNTIONAL GROUPS

A functional group is a substance (atom, radical, word) that identifies a particular

homologous series, e.g. alcohols are identified by the presence of the hydroxyl (-OH)
group. The functional group is responsible for the properties of an organic compound.
HOMOLOGOUS SERIES FUNCTIONAL GROUP SYMBOL
ALKANES Saturated single bonds C-C
ALKENES Unsaturated double bond C=C
ALKYNES Unsaturated triple bond CC

ALCOHOLS Hydroxyl group -OH

CARBOXYLIC ACIDS Carboxyl group

ESTERS Carboxyl group derivative

1.7 NOMENCLATURE OF ORGANIC CHEMICALS

Alkanes are used as the basis for naming the majority of organic compounds.
Nomenclature is a term use to fro naming organic compounds. The convention of
naming is called the International Union of Pure and Applied Chemistry (IUPAC). The
development of a formal system for naming organic compounds did not come about
until the end of the nineteenth century (@ 1892), but it has undergone a lot of
revision. The latest revision was done in 1993.

Before then, organic compounds were given names based on the source of that
compound, e.g. Acetic acid obtained from vinegar, (Latin word for vinegar is
Acetum). Formic acid from ants from the Latin word formicae.

The older names for organic compounds are called common names or Invial names.
The IUPAC names are the ones used to name organic compounds correctly.

The basic rules for this nomenclature (system of naming the compounds) are as
follows:

1. Various homologous series have a characteristic ending, e.g, -ane for all alkanes.
2. Straight carbon chain molecules are just called butane, hexane, e.t.c.

1.8 NOMENCLATURE OF UNBRACHED AKLYL GROUPS

Alkane Alkyl Group

Abbreviation
CH3-H (Methane) becomes CH 3- (methyl)
Me

CH3CH2-H (Ethane) ,, CH 3CH2- (Ethyl)

Et

CH3CH2 CH2-H ,, CH 3CH2 CH2-(Propyl)

Pr

CH3CH2 CH2 CH2-H ,, CH 3CH2 CH2 CH2-(Butyl)

Bu

1.9 NOMENCLATURE OF BRACHED AKLYL GROUPS

3. Branched carbon chains are displayed so that the longest chain shown is used as
the parent hydrocarbon.
(a) Choose the longest chain, then
(b) Look for a functional group. And choose the shortest distance from either end
of the parent chain. Put numbers 1, 2, 3…along the parent hydrocarbon. Each
group attached to the parent hydrocarbon is identified by its radical, -CH 3(the
methyl group; abbreviated Me), -C 2H5(the ethyl group), -C3H7(the propyl
group), -OH (the hydroxyl group), e.t.c.

Use the numbers obtained by application of rule number 3 to designate the location
of the substituent group. The parent name is placed last, the substituent group,
preceded by the number designating its location on the chain, is placed first. In
short, the order is: number of substituent group-substituent group-parent name.

4. When two or more substituents are present, give each substituent a number
corresponding tot its location on the longest chain. The substituent groups should
be listed alphabetically, i.e, ethyl before methyl.

5. When two substituents are present on the same carbon atom, use that number
twice.
6. When two or more substituents are identical, indicate this by the use of prefixes di,
tri, tetra, and so on.

2, 3-Dimethylbutane 2, 3, 4-Trimethylpentane 2, 2, 4, 4-
Tetramethylpentane

7. When two chains of equal length complete for selection as parent chain, choose
the chain with a great number of substituents.

2, 3, 5-Trimethyl-4-propylheptane

8. When branching first occurs at either distance from either end of the longest chain,
choose the name that gives the ‘lower number’ at the first point of difference.

2, 3, 5-Trimethylhexane not 2, 4, 5-Trimethylhexane

Activity 1.1

1.1. Give the systematic names to each of the

following:
(a) CH3(CH2)CH3
 (b) (CH3)2CHCH2CH3
(c) (CH3)3C(CH2)6CH3
(d) C(CH3)4
(e) CH3CH(CH3)CH2CH2CH(CH3)2

(f)

1.2 The line formula for a branched alkane is shown below:

(a) (b)

(c ) (d) (e)

For each f the above (a) to (e),

(i) How many carbon atoms are there in the longest chain?
(ii) What are the molecular formulae of the compounds?
(iii) Howe many alkyl substituents are attached to each of the compounds?

1.3 Give the correct structural formulae of

(a) 2,2,3-Trimethylhexane
(b) 1,1,2,2-Tetrachloropropane
(c) 2,5-Dimethyl-3-ethylhexane
(d) 2,2,3-Trimethylpentane

2.0 ALKANES (ENDING WITH -ANE)

Alkanes are saturated hydrocarbons that contain single bonds (σ-bonds) between their
carbons. Each carbon atom forms four bonds and each hydrogen forms a single bond

with carbon. All alkanes have a general molecular formula: , where n

=1,2,3,4…..

Examples:

1.0 Methane, n =1CH4 (gas, fuel) 2.0 Ethane, n =2, C2H6 (gas, fuel)
 Structural formula Structural formula

Activity 2.1

Complete the table below by filling in the missing items;

# OF CARBON NAME STRUCTURAL MOLECULAR STATE

ATOMS FORMULA FORMULAR
1 Methane CH4 Gas (fuel)

2 Ethane
3 Propane Gas (fuel)
4
5
6
7
8
9
10 Decane C10H22

All alkanes form a homologous series because each member of the group differs
from the one preceding by a unit if the methylene group (-CH2-).

Alkanes are:

i. Hydrocarbons and have the same general formula,

ii. Form a homologous series, and
iii. Saturated ( or contains single bonds).
iv. Burn in oxygen with a non-luminous flame to form carbon dioxide and
water,e.g:
 Methane is a gas and a fuel. It can burn completely in oxygen (with a blue
flame) to form carbon dioxide and water.

Insufficient supply of oxygen leads to incomplete combustion, and poisonous

carbon monoxide is produced instead of carbon dioxide.

From Pentane to Decane, Petrol or Gasoline is formed as liquid fuel. Then,

Kerosene, Diesel, Vaseline, Grease and form as one goes down the group.

v. Reaction with chlorine. In diffuse light, methane reacts with Chlorine by

giving a series of products by successive replacement of hydrogen atoms.
Each of the reactions is a substitution reaction.

2.1 FUELS: NATURAL GAS, CRUDE OIL (PETROLEUM) AND

DERIVATIVES

Natural gas and Petroleum are some of the most important organic minerals in the
world. Petroleum is a complex mixture of organic compounds, mostly alkanes. It also
contains small amounts of oxygen, nitrogen and sulphur containing compounds.
Some of the molecules in petroleum are clearly of biological origin. Most scientists
believe that both natural gas and petroleum originated from decayed matter buried
underground, that is, plants and animals under conditions of heat and high pressure
over millions of years. They are found deep underground in a porous formation of
rocky layers and also below the sea bed. Wells are sunk into the earth or sea bed and
the oil rises under high pressure to the surface.

2.2 CRUDE PETROLEUM REFINING

Since crude oil is a complex mixture of gases, liquids and solids, it must be refined
into its components of fractions. The fractions are separated by virtue of their different
boiling and melting points. The crude oil is first heated by gas or electricity in a
separate furnace to about 400C. The heated liquid is then passed into the
fractionating column or tower.

The tower consists of trays and bubble caps, placed at different levels or temperatures.
Each tray is a little cooler than the one below it. As the hot mixture of gases and
vapours passes up the tower, the various vapours condense at different levels,
according to their boiling pints. The fraction collected at each level is tapped off and
redistilled. Heavier fractions remain at the bottom of the fractionating column.

Activity 2.2

1. (a) Draw a well-labelled diagram that shows the fractional distillation of crude
oil.
(b) Draw a table under the following subheadings and fill in the missing items.

FRACTION USE BOILING POINT OF

FRACTION (C)

Methane(Natural gas)
Petroleum ether
Petrol (Gasoline)
Kerosine (Paraffin)
Diesel(Gas oil)
Grease (Lubricating oils, waxes)
Heavy asphalt(Bitumen)

2.3 CRACKING
Due the increasing demand for gasoline (petrol) to much greater extent than that
supplied by the gasoline fraction of petroleum led scientist to devise new ways or
techniques of producing it from long chain alkanes.
 Cracking is a process of breaking down long- chain hydrocarbons (alkanes) by heat
into shorter-chain molecules. The breaking down of long-chain alkanes can be done in
two ways:

(i) THERMAL CRACKING

Hydrocarbon fractions of long carbon chains (C12-C18) are broken down into
shorter chains of petrol by heating under very high pressure (up to 200 atm) to
temperatures of about 500C.

(ii) CATALYTIC CRACKING

Long chain hydrocarbons are heated in the presence of a catalyst, aluminium oxide
(Al2O3). Hence, cracking is done at lower pressures though the temperatures still
remain around 500C.
The cracking of long-chain alkanes always leads to the formation of, at least, one
unsaturated product.

3.0 ALKENES (ENDING WITH –ENE)

These are unsaturated hydrocarbons that contain a double bond (π-bond) between any
two carbon atoms. The first member of this homologous series is ethene. The general

formula is:

e.g. for n =8 , General formula: CnH2n. Molecular formula is equal to C8H2x8 = C8H16

All Alkenes are:

i. Hydrocarbons and have the same general formula,
ii. Form a homologous series, and
iii. Unsaturated ( or contains double bonds)
iv. Burn in oxygen with a smoky flame giving carbon dioxide and water. As in
alkenes, carbon monoxide is produced in insufficient oxygen accompanied by
water.
v. Addition reaction
 Activity 3.1

Complete the table below by filling in the missing items:

# OF CARBON NAME STRUCTURAL FORMULA MOLECULAR

ATOMS FORMULAR
2 Ethene H2C=CH2

3 Propene
4 Butene
5 Pentene
6 Hexane
7 Heptene
8 Octene

3.1 NOMENCLATURE OF ALKENES

Alkenes are named in the same way as alkanes. Here are some of the rules for naming
alkenes.

1. Determine the parent name by selecting the longest chain.

2. Start numbering he chain from the end closer to the double bond.

1-Butene or But-1-ne (not 3- Butene)2-Hexene or Hex-2-ene(not 4-hexene)

3. Indicate the locate on for the substituent groups by the numbers of carbon atoms
to which they are attached.
 2-methyl-2-butene (not 3-methyl-2-butene) 2,6-dimethylheptene (not 2,6-methyl-
5-heptene)

4. Number substituted cycloalkenes in the way that gives the carbon atoms of the
double bond the 1 and 2 positions and also that gives the substituent groups low
numbers at the point of difference.

1- Methylcyclopentene 3,5-
dimethylcylohexene

5. When naming an alkene with an alcohol (OH), give the alcohol carbon the lower
number.

4-Methyl-3-penten-2-ol 2-methyl-2-cylohexen-
1-ol
 or 4- methylpent-3-en-2-ol or 2-methyl cyclohex -2-
en-1-ol

6. If two identical groups are on the same side of the double bond, the compound can
be designated as cis; if on the opposite sides can be designated as trans.

Cis-1,2-dichloroethene Trans-1,2-
dichloroethene

Note that if there are two double bonds within a parent name then the compound will
end with diene; if three, triene and so on, e.g:

2-Methylbuta-1,3-diene 2-chlorobuta-1,3-diene

Activity 3.2

1.1 Use the IUPAC system to name the following compounds:

(a) CH3CH(CH3)CH2CH2OH (b)

CH3CH(CH3)CH2CH(OH)CH3

(c) H2C=CHCH2CH3 (d)

(e) (f)
 2.0 Write the structural formula of the following:

(a) 2,4-diethyl-2-pentene

(b) 4,5-dibromo-2-hexene

(c) 1,2-dichlorocyclohexene

(d) Cis-3-octene

(e) Trans-2-hexene

(f) 3,5-dimethylhex-4-ene

(g) 1,2-dimethyl-3-ethylcyclobutane

3.2 ADDITION REACTIONS

(a) These are common with all unsaturated compounds. In such a reaction, two
substances combine to produce a new substance. The reaction between ethane and
bromine in typical of such reactions. Ethene reacts rapidly with bromine vapour
(reddish-brown) to form colourless oily drops of 1,2-dibromoethane. The
decolourization of bromine water is the test for unsaturated hydrocarbons.
C2H4 (g) + Br2 (g)  BrCH2CH2Br(g)
(b) Reaction with hydrogen. Ethene reacts with hydrogen at 200C, in the presence of
finely divided nickel or platinum black catalyst to form ethane.
C2H4 (g) + H2 (g) C2H6 (g)

(c) Reaction with water

The preparation of lower molecular alcohols such as ethanol proceeds by the acid
catalyzed addition of water to the alkene. The acids mostly used are dilute H 3PO4
and dilute H3SO4 at 300C.

(d) Reaction with hydrogen halides

When a hydrogen is added across a double bond of an alkene, the hydrogen joins
to the carbon that has more carbon atoms bonded to it. Compare the reactions
below:
(i) Addition of Hydrogen iodide to ethene
 (ii) Addition of Hydrogen Chloride to 2-Butene

(e) Reaction with concentrated sulphuric acid. At room temperature, ethane undergoes
addition reaction with concentrated sulphuric acid. An oily liquid, ethyl hydrogen
sulpahte is formed.
C2H4 (g) + H2SO4 (l) CH3CH2HSO4 (g)
The oily liquid is hydrolyzed when boiled with water to ethanol and sulphuric
acid.
CH3CH2HSO4 (g) + H2O  CH3CH2OH + H2SO4
(f) Acidified potassium manganate (VII) solution (pink) in colour is rapidly
decolourized when shaken with ethane gas, and alkaline potassium manganate
(VII) solution turns green.

C2H4 + H2O + [O]  CH2(OH)CH2OH Ethane-1,2-diol (Glycol)


From KMnO4
(g) Polymerization (Addition reaction )
Ethane becomes a liquid under pressure and when liquefied ethane is heated in the
presence of a trace of oxygen, a special kind of addition reaction occurs.
Ethene(monomers) molecules combine to form one long chain of as many as 1000
carbon atoms called polythene (from poly ethene).

Polythene is a white plastic solid which is relatively unreactive and is unaffected by

acids and alkalis. Polymerization is a process by which molecules (monomers) of a
compound are combined to form a complex giant molecule (polymer ) of very high
relative molecular mass.

3.3 CONDENSATION POLYMERS

 These are also another group of broad polymers which are also called step-growth
polymers. They are prepared by condensation reactions, in which monomer units are
joined through the elimination of small molecules like water. Among condensation
polymers are polyesters.

Polyvinyl Chloride (PVC)

4.0 AKYNES (ENDING WITH –YNE)

Alkynes, like alkenes are unsaturated hydrocarbons that contain a triple bond between
any two carbon atoms. The first member of this homologous series is ethyne. The
general formula is:

CnHn

e.g. for n = 6 , General formula: C nH2n-2. Molecular formula is equal to C6H2x6-2 =

C8H10

All Alkynes are:

i. Hydrocarbons and have the same general formula,
ii. Form a homologous series, and
iii. Unsaturated ( or contain triple bonds)
iv. Burn in oxygen with a smoky flame giving carbon dioxide and water. As in
alkenes, carbon monoxide is produced in insufficient oxygen accompanied by
water.
v. Addition reaction

4.1 PREPARATION

The simplest alkyne is ethyne, C2H2. This is prepared by adding water to metal carbide
such as calcium carbide, CaC2.

CaC2 (s) + H20 (l) → Ca (OH) + C2H2 (g)

4.2 CHEMICAL PROPERTIES OF ALKYNES

a) Oxidation

H-C≡C-H → CO2 + H20 Very sooty flame

b) Addition reaction

c) Polymerization

5.0 ALCOHOL (ENDING WITH –OL)

Alcohols are saturated organic compounds that contain a hydroxyl (-OH) group. They
are named by replacing the final ‘e’ of the parent name with ‘ol’, e.g:

Methane (CH3-H) becomes methanol (CH3-OH); Ethane (CH3CH3) becomes ethanol

(CH3CH2OH).

General formula: CnH2n+1OH, where n =1,2,3,….

For n =1, molecular formula is C1H2x1 +1OH

C1H3+1OH = CH3OH (methanol)

Activity 5.1

Complete the table below by filling in the missing items:

# OF CARBON NAME STRUCTURAL FORMULA MOLECULAR

ATOMS FORMULAR
1 Methanol CH3OH
2 Ethanol CH3CH2OH
3 Propanol
 4 Butanol

5.1 NOMENCLATURE OF ALCOHOLS

The nomenclature of alcohols is the same as the other homologous series we have
looked at. The parent name will end with –ol, e.g.

5.2 PREPARATION OF ALCOHOLS

Alcohols are formed by basically two major processes:

 Addition reaction of alkenes with steam

 Fermentation

a) Addition reaction of alkenes with steam (refer to notes under alkenes)

b) Fermentation

This gives brief description of the manufacture of ethanol from glucose by

fermentation. Yeast cells are added to a solution of glucose at a temperature
between 18 ◦C and 20 ◦C under anaerobic conditions. Glucose is broken down by
the enzyme (Zymase) found in yeast cells to form ethanol and carbon dioxide. The
ethanol if obtained by fractional distillation of the mixture.

Zymase

C6H12O6 2C2H3COOH

18 ◦C - 20 ◦C
5.3 REACTIONS OF ALCHOLS

Alcohols undergo basically three types of reactions:

 Combustion

 Oxidation (with acidified K2Cr2O7)

 Reaction with carboxylic acids

a) Combustion

Alcohols burn in oxygen to produce carbon dioxide and water. Alcohols are
actually good fuels.

2C2H5OH + O2 → CO2 + H2O

b) Oxidation (with acidified K2Cr2O7)

Ethanol can be oxidized to form ethanoic acid using acidified potassium

dichromate.

K2Cr2O7

2C2H5OH CH3COOH

Ethanol Conc. H2SO4 180 ◦C Ethanoic Acid

[O]

c) Reaction with carboxylic acids

Ethanol reacts with carboxylic acids to produce esters and water. For example,
ethanol reacts with ethanoic acid to produce a sweet smelling liquid called ethyl
ethanoate, an ester and water.

This reaction is a condensation reaction type, but the reaction that produces an
ester is called an esterification reaction.
Activity 5.2

1.0 What is the IUPAC name for each of the following molecular formulae:

a) CH3CH(CH3)CH2CH(OH)CH3

b) C6H5OH

c) CH3CH2C(CH3)2CH2OH

d)

2.0 Write structural formulae of the following compounds:

a) Cyclohexan-1,2-diol

b) Pentan-2,2,3-triol

6.0 CARBOXYLIC ACIDS (ENDING WITH –IOC)

Organic or Carboxylic acids are saturated organic compounds that contain the

carboxyl (-COOH) group or ( ).

The general formula is CnH2n + 1COOH. All the name of carboxylic acids end with
‘oic’ and the carboxyl group is assigned number one (1), Methane Methanoic acid
(HCOOH); Ethane  Ethanoic acid(CH3COOH)

6.1 NOMENCLATURE OF CARBOXYLIC ACIDS

It is the same as for alkanes except for the addition of ‘oic’ at the end of the name. All
the rules for naming still apply.

6.2 CHEMICAL PROPERTIES OF CARBOXYLIC ACIDS

a) Reaction with alcohols (see esterification under alcohols)

b) Reaction with Sodium hydroxide (NaOH) at room temperature

 Carboxylic Acids react with aqueous sodium hydroxide forming sodium
ethanoate.

Activity 6.2

1.0 Draw a table showing the name, molecular formula and the structural formula for
carboxylic acids with n = 3,4,5,6.

2.0 What is the IUPAC name for each of the following compounds?

a) CH3CH2CH(CH3)CH2CH2COOH

b) CH3CH=CHCH2CH2COOH

c) C6H5CH2(CH2)3COOH

d) Br(CH2)3COOH

7.0 ISOMERISM

1 Isomerism is the occurrence of two or more compounds with the same molecular
formula, but different structures, e.g. C4H10 has four isomers:

2 There are basically two main types of isomerism ,i.e. structural (constitutional)
and stereo isomerism as summarized below:
 Figure 1: ISOMERISM

3 The number of isomers increases rapidly with increasing number of carbon atoms
in a given homologous series, e.g. for alkanes as few as 12 carbon atoms, there are
about 355 possible forms the molecule can take.

Activity 7.1

1.0 (a) How many alcohols can you find with the formula C4H9OH?
(b) Name the alcohols and draw their structures.
2.0 The halogen alkene of the formula C 4H9Br can exist in a number of isomeric
forms.
3.0 Determine the isomers of the compounds with the following molecular
formulae:
a) C4H8
b) C2H6O
c) C6H4Cl2

8.0 SAPONIFICATION
Saponification comes from the Latin word “Sapon” which means “Soap”. Animal
fat/vegetable oil is boiled with a base, e. g. Sodium hydroxide. Animal fat or vegetable
oil is an ester of glycerol with other long-chain carboxylic acids called fatty acids.

Summary

Having gone through this module you must have developed confidence in how to
apply Organic Chemistry to real life situation. You should be able to apply the general
formulae for the various homologous series in order to correctly name a given organic
compound with confidence. You should have realized, also that the compounds in
each homologous series have similar chemical reactions. This makes it much easier
for us to predict the products of a given chemical reaction. Although widely used,
Organic Chemistry is not easily appreciated by society due to limited knowledge on
its usefulness.

REFERENCES
1. Banda and Kumar, (1995): Introductory Chemistry, Lusaka, University of Zambia
Press
2. Mathews Philip, (1992): Advanced Chemistry, Cambridge, Cambridge University
Press

3. Michael Clugstone and Rosalind, (2000): Advanced Chemistry, Oxford, Oxford

Univeristy, Press

4. Kotz etal (2003): Chemistry Chemical Reactions, 5th ed. London, Brooks/Cole

5. Madan R.D (2008): Modern Inorganic Chemistry, 16th ed. New Delhi, S.Chand
& Co. Ltd

6. Susan McMurray (2000): Organic Chemistry, 5th ed. London, Brooks/Cole

7. Peter Atkins, etal ( ): CHEMISTRY: Molecules, Matter and Change, 3rd

ed. Oxford,

Freeman