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 Learn the Rules,
Master the Facts
with More Than
Enough Examples!

OLANREWAJU, ADEBAYO BAMIDELE

(B.Sc (Hons) Chem Engr. (Ife), ASM)
ORGANIC CHEMISTRY
MADE EASY

OLANREWAJU B. ADEBAYO
(B.Sc (Hons) Chem Engr. (Ife), ASM)
 TABLE OF CONTENTS
Dedication i
Acknowledgment ii
The Secrets of Academic Success iii
Introduction iv

CHAPTER ONE
HYDROCARBONS
1.1 Introduction 1
1.2 Classification of Hydrocarbons 1
1.2.1 Alkanes 2
1.2.2 Alkenes 3
1.2.3 Alkynes 3
1.2.4 Comparison between Alkanes, Alkenes and
Alkynes 4
1.2.5 Cyclic Hydrocarbons 4
1.2.6 Aromatic Hydrocarbons 5
1.2.7 Haloalkanes 6
1.3 Terms Associated with Hydrocarbons 6
1.4 Reactions Involving Hydrocarbons 8
1.4.1 Substitution Reaction 8
1.4.2 Combustion Reaction 9
1.4.3 Addition Reaction 9
1.4.4 Polymerization 9
1.5 Isomerism (Structural, Geometrical & Optical
Isomerism, Calculation of Isomers) 10
1.6 Formation & Refining of Crude Oil 13
Take-Away 14
CHAPTER TWO
ALKANOLS
2.1 Introduction 18
2.2 Classification of Alkanol 18
2.2.1 Monohydric Alkanols 19
2.2.2 Polyhydric Alkanols 19
2.3 Properties of Alkanols 20
2.3.1 Physical Properties 20
2.3.2 Chemical Properties (Including all the Reactions
Involved) 20
2.4 Production of Ethanol (via Fermentation Reactions) 23
2.5 Phenomenon Associated with Alkanols 25
2.6 Phenols 25
2.6.1 Differences between Alkanols and Phenols 26
2.6.2 Properties and Uses of Phenols 26
Take-Away 27

CHAPTER THREE
ALKANOIC ACIDS
3.1 Introduction 30
3.1.1 Dicarboxylic Acids 31
3.1.2 Aromatic Acids 31
3.2 General Preparation of Alkanoic Acids & their
Properties 31
3.3 Differences between Neutralization and Esterification 31
3.4 Alkanoates 33
3.5 Fats and Oils 34
3.6 Detergents 35
3.7 Polymers 37
3.7.1 Addition Polymerization 37
3.7.2 Condensation Polymerization 38
3.8 Natural and Synthetic Polymers 39
3.9 Rubber 39
3.9.1 Natural Rubber 39
3.9.2 Synthetic Rubber 40
3.10 Polymeric Amides 40
3.11 Carbohydrates 41
Take Away 43

CHAPTER FOUR
IUPAC NOMENCLATURE OF ORGANIC COMPOUNDS

4.1 Functional Groups 46

4.2 Naming of Alkanes 48
4.3 Naming of Alkenes 51
4.4 Naming of Alkynes 52
4.5 Naming of Alkanols 53
4.6 Naming of Alkanoic Acids 54
4.7 Naming of Alkanoates 55
4.8 Naming of Alkanals (Aldehyde) 55
4.9 Naming of Alkanones 56
4.10 Naming of Amides 56
4.11 Naming of Amines 59
4.12 Naming of Nitriles 57
4.13 Naming of Ethers 58
4.14 Naming of Cycloalkanes 58
General Practices Questions 60
 DEDICATION

To the individuals that has positively inspired me, helping to bring out
the best in me over the years,
and
To you wanting to improve your understanding of organic chemistry,
because
This book will help you do just so the easiest way possible.

i
 ACKNOWLEDGMENTS

My sincere gratitude goes to the Almighty God for his

undeserved kindness, mercy and timely blessings during the course of
this work and my life in general.
Special thanks to the following teachers and administrators for
their sound, constructive advice and encouragements that has
construbuted to the completion of this book: Mr Omosule (Vice
principal of Ofedepe Secondary Schools, Okitipupa, Ondo state),Mrs
A. Adesugba (proprietor of Laurel Schools, Okitipupa, Ondo state), Mr
Matthew, the vice-principal (Academics) and Mr Adetolure of Stella
Maris College, Okitipupa, Ondo State.
I also wish to extend my appreciation to the Mr. E. Akinbohun
the proprietor, and Mr Ojajuni, principal of Emmanuel Royal College,
Okitpupa, Ondo state, for their kind human disposition and
understanding. Thanks to you my good friend Omerhiowa Onoriode
for your display of kindness and sense of maturity during the course
of this work.
The list would not be complete without the name of Dr. Opele
J.K. (National Centre for Technology Management (NACETEM),
OAU, Ile-Ife), Dr. Adeleke A.G., & Dr. Afolabi A.O. of Obafemi
Awolowo University, Ile-Ife, and Mr. Ajibola A.J, for their mentorship
which greatly contributes to whatever good I grow to achieve in life.
Thank you for helping me learn from your wealth of experience!
If I have seen any further, it is by standing on the
shoulders of giants, and that is why I say thanks to all of you who, in
one way or the other contributed to my experience in life; helping me to
grow. Even if your name is not here as a result of space, just know you
are always on my mind!

ii
 THE SECRETS OF ACADEMIC SUCCESS
To be successful in your study of organic chemistry and other
subjects, you must start to make the following a habit with all
earnestness:
Confidence: This involves facing whatever topic you are faced with,
fearlessly. Nothing is too difficult to understand. If you set your
heart to learn, you will know!
Understanding of Facts: You must take the pain to study and listen
with insight to the principles and rules connected to the topic
concerned.
Practice: Chemistry as a branch of science could prove to be volatile
(escapes easily just as methylated spirit exposed to air). But
constant practice can help to impress the knowledge for a long
time. Failing to practice will have you forget almost everything you
know.

NOTE THIS!
Others can help you, guide you, direct you, channel you, point
you in the right direction and even give you opportunities but in the
final analysis, no one can make for you the critical decisions that will
determine your future and fortune.
Personal success is a result of two factors – knowing what you
want and paying the price to achieve it. Whatever you become in the
future is a function of what you choose to do now. Winners are not
made on the ring, they are only recognized there. Preparation is the
KEY!

iii
 INTRODUCTION
ORGANIC CHEMISTRY AT A GLANCE

Definition
Organic chemistry can be defined as the study of carbon
compounds. This definition goes wider in scope than the previous
limited definition that organic chemistry applies only to the study of
substances of plant and animal origin. This is because; most of the
substances from living organisms can also be synthesized from
inorganic materials in the laboratory.
The presence of many organic compounds is due to the
ability of carbon to
i catenate, i.e., combine with one another to form straight
chains, branched-chains or ring compounds containing many carbon
atoms.
ii. combine with hydrogen (H), oxygen (O), nitrogen (N) and the
halogens.
iii. form single, double or triple covalent bonds.

Characteristics of Organic Compounds

1. Flammability: Most organic compounds such as wood,
coal, oil, petrol and natural gas are used as fuels because of their
ability to burn exothermically in an excess supply of air to yield
carbon(IV)oxide (CO2) and water (H2O) as the major compounds
formed.

2. Low Melting and Boiling Point: As a result of the weak

intermolecular forces of attraction between the atoms of organic
compounds, they tend to have low melting and boiling

3. Covalency: Carbon atoms of organic compounds form stable

covalent bonds with one another. As such, they do not ionize in
solution and are non-conductors of electricity.

iv
4. Thermal Instability: Some organic compounds decompose
into simpler fractions when heated to temperature of about
o
500 C and above. Hence, they are unstable in the presence of
high temperature.
5. Reactivity: Reactions involving organic compounds tend to
be slower compared to the inorganic compounds.

v
 CHAPTER ONE
HYDROCARBONS
1.1 INTRODUCTION
Hydrocarbon is coined from two words – HYDRO and
CARBON. Thus, hydrocarbons are compounds containing hydrogen
and carbon. Hydrocarbons are the major component of the thick, dark
viscous liquid - CRUDE OIL. This complex mixture of hydrocarbons
contains gaseous, liquid and solid alkanes (forming 90% of
petroleum), alkenes, cycloalkanes and aromatic hydrocarbon (such as
benzene, ethyl benzene & naphthalene). Other components of crude oil
includes oxygen, nitrogen and sulphur. Nigerian crude oil is termed
“sweet crude” because little or complete absence of sulphur, and
therefore causes less pollution.
All hydrocarbons can be represented by the molecular formula
CxHy, where x and y represents the number of carbon (C) and hydrogen
(H) respectively present.

1.2 CLASSIFICATION OF HYDROCARBONS

Figure 1.2 represents the detailed classification of hydrocarbons
with specific example

1
 Hydrocarbon
Aliphatic Aromatic e.g. benzene
Acyclic Cyclic
Alkan Alkene Alkyne Cyclooalkanes e.g Cyclopentane
e.g methane e.g ethene e.g ethyne
Figure 1.2 Classifications of Hydrocarbons

Hydrocarbons could broadly be referred to as either saturated

or unsaturated. SATURATED HYDROCARBONS are
hydrocarbons in which the tetravalency of the carbon atoms is fully
satisfied by single bonds Examples of these are the alkanes. While
UNSATURATED HYDROCARBONS are the ones that contain
one or more double (-C=C-) or triple bonds hence they can undergo
ADDITION REACTION. Examples of these hydrocarbons are the
alkenes as alkynes.

1.2.1 ALKANES
These are saturated hydrocarbons containing only carbon-
carbon (-C-C-) and carbon-hydrogen (-C-H-) single bond. They are
represented by the general formula CnH2n+2, where n is an integer or
whole number. Alkanes are also called paraffins Examples of the
first-four (4) members of the group are as follows:

2
 Table 1.1: First-Four (4) Members of Alkane

Name Molecular formula (CnH2n+2)

Methane or Marsh gas N=1, CH4
Ethane N=2, C2H6
Propane N=3, C3H8
Butane N=4, C4H10
From the table, it could be seen that the difference between the
different members of the group is –CH2. This difference among series
of organic compounds with the same functional group is called the
HOMOLOGOUS SERIES.

1.2.2 ALKENES
Alkenes otherwise called olefins are unsaturated hydrocarbons
consisting of at least one double bond between the carbon atoms in the
molecule having the general formula of CnH2n. Members of this class of
hydrocarbon includes the following.
Table 1.2: List of the First-Four Members of Alkenes
Name Molecular Formula (CnH2n)
Methene N=1, CH2
Ethene N=2, C2H4
Propene N=3, C3H6
Butene N=4, C4H8
… … …

The first member of the series (methene, CH2) does not exist. The
difference between the members of the series could also be noticed
here to be –CH2. Alkenes have the functional group of –C=C-. It is
formed by replacing the –ane of the alkane with –ene.

1.2.3 ALKYNES
These are unsaturated hydrocarbons containing at least one
triple bond between the carbon atoms in the molecule. This is given by
the general formula of CnH2n-2. The functional group of alkyne is -C≡C-
. It is formed by replacing the –ane of alkene with –yne.

3
 Table 1.3: List of the First-Twenty Members of Alkynes
Name Molecular formula (CnH2n-2)
Ethyne C2H2
Propyne C3H4
Butyne C4H6
Pentyne C5H8

1.2.4 Comparison Between Alkanes, Alkenes and Alkynes

Comparison in terms of
§ Properties
Alkane Alkene Alkyne
General Formula CnH2n+2 CnH2n CnH2n-2
Nature Saturated Unsaturated Unsaturated
Reactions Involvedin § Substitution § Addition § Addition
§ - § Polymerization § Polymerization

§ Formation
Alkenes and ALKYNES are formed by replacing the –ane of
ALKANE with –ene and –yne respectively.

§ Removal and/or Addition of Hydrogen

Two atoms of hydrogen are removed from alkane to form
alkene, and consequently two are also removed from the alkene
formed to form alkyne. Examples include
ALKANE ALKENE ALKYNE
C 2H 6 C 2H 4 C 2H 2
C 3H 8 C 3H 6 C 3H 4
C 4H 10 C 4H 8 C 4H 6
C 5H 12 C 5H 10 C 5H 8
C 6H 14 C 6H 12 C 6H 10
… … …

1.2.5 CYCLIC HYDROCARBONS

This has the end carbon atoms of an acyclic carbon chain
joined together by single covalent bond to form a ring or loop.
Examples of these are the cycloalkanes as shown by table 1.4.

4
 H H

H C C H

H C C H

H C H
H H
Cyclopentane

1.2.6 AROMATIC HYDROCARBONS

These are cyclic compounds which contain one or more
benzene (C6H6) rings. The two industrial sources of aromatic
hydrocarbons are from the destructive distillation of coal and
reforming of petroleum. Other aromatic hydrocarbons include phenol,
toluene and xylene.

OH CH3 CH3
CH3
Phenol Toluene Xylene

Benzene Structure
Benzene was discovered in 1825, but its structure was obscured
until 1865 that August Kekule proposed its structure. He showed that
the structure of benzene is a resonance hybrid canonical forms which
are both of equal energy content.

5
 H H
C C
H C C H H C C H
H C C H H C C H
C C
H H

These two structures above could be represented by

which is the intermediate of and

1.2.7 Haloalkanes
They are chemical compounds formed when one or more of the
hydrogen in an alkane have been replaced by halogen atoms (such as
Bromine (Br), Chlorine (Cl), Fluorine (F) etc). The general formula of
haloalkanes is CnH2n+1X, where X represents a halogen atom. Examples
include Bromoethane (C2H5Br), Chloropropane (C3H4Cl), Iodobutane
(C4H9I), Fluoromethane (CH3F).

1.3 TERMS ASSOCIATED WITH HYDROCARBONS

Homologous Series
This is a series of organic compounds with the same functional group
ascending in steps by –CH2 or molecular mass of 14.

6
 Characteristics
1. They can be represented by the same general formula e.g.
CnH2n for alkenes.
2. Each member of the series by a –CH2 group.
3. The members show regular gradation of physical properties
4. They express similar chemical properties, e.g. alkanes are
fairly unreactive.
5. Each member of the series can be prepared by the same general
method.

§ Functional Groups
A functional group is an atom or radicals (group of atoms) that are
common to a homologous series which determines the chemical
properties of the series e.g. –OH, -COOH, -C=C-, NH2 etc.

§ Cracking and Reformation of Gasoline

ü Cracking
This is the breaking down of the large molecules in fuel oil into
smaller molecules of greater volatility. This process involves
splitting heavy molecules into smaller molecules in the presence
of high temperature and pressure. Cracking could be either
catalytic or thermal.
If the breaking down of the larger molecules of hydrocarbon is
done in the presence of heat and pressure only, it is termed
THERMAL CRACKING, but if it iso in theo presence of catalyst
such as silica/alumina catalyst at 450 C-550 C and at ordinary
pressure to produce high octane petrol, then it is termed
CATALYTIC CRACKING.
C12 H26 C6H 14 + C4H8 + C2H4
Dodecane Hexane Butene Ethene

ü Reforming
This involves the alteration of the molecular structure of the
hydrocarbons. This is the conversion of straight chain
hydrocarbons to branched-chain hydrocarbons in the C6 to C10
range to improve the octane rating of the motor fuel, e.g.,

7
 CH3 – CH2 – CH2 – CH3 CH3 – CH - CH3
Butane CH3
2-Methypropane
§ Octane Rating
This is the measure of the performance of the fuel in fuel engine. The
octane rating of fuel is raised by the presence of branched-chain
hydrocarbons e.g. 2,2,4-trimethylpentane (iso-octane)
CH3C (CH3)2 CH2 CH (CH3) CH3
2,2,4-Trimethylpentane
Octane number ranges from 0 to 100. Thus, heptane C7H16 that
produces much knocking is given the value of 0 and iso-octane which
produces little knocking is given value of 100.
§ Knocking
This is the tapping sound in the cylinder of an ignition engine as a result
of abnormal combustion in the engine which makes the engine to lose
power. This could be prevented by the addition of branched-chain
alkanes (2,2,4-trimethylpentane or iso-octane) or lead tetraethyl.

1.4 REACTIONS INVOLVING HYDROCARBONS

1.4.1 Substitution Reaction

This reaction is the most common reaction alkanes undergo. It involves
the direct replacement of hydrogen in the alkane molecule by another
atom or group. An example is in methane with sunlight acting as a
catalyst.
CH4 + Cl2 u.v CH3 Cl + HCl
Chloromethane

CH3Cl + Cl2 u.v CH2Cl2 + Hcl

Dichloromethane

CH2Cl2 + Cl2 u.v CHCl3 + HCl

Trichloromethane

CHCl3 + Cl2 u.v CCl4 + HCl

Tetrachloromethane

8
 1.4.2 Combustion
This is a reaction involving burning of hydrocarbon in excess oxygen
to produce carbon(IV)oxide and water. It can be represented by the
general equation.

CxHy + (x + Y/4) O2 x CO2 + y/2 H2O

where CxHy represents any of the class of hydrocarbon e.g. C2H4
(ethene).

1.4.3 Addition Reaction

This is a type of reaction in which there is direct addition of an
attacking atom or radical (group of atoms) across the double or triple
bond of an unsaturated compound to yield a saturated product or at
least one with a high degree of saturation. Examples include
Ø Addition of hydrogen

CH2 = CH2 + H2 Ni Catalyst CH3 – CH3

0
150 C
ethene ethane
ØAddition of halogens or halogen acids

CH2 = CH2 + HBr 250C CH3 – CH2Br

ethene 1-bromoethane
0
CH2 = CH2 + Br2 Ni25 C
Catalyst
CH2Br – CH2Br
1,2-dibromoethane

CH CH + Br2 CHBr = CHBr Br2 CHBr2 – CHBr2

Ethyne 1,2-dibromoethene 1,1,2,2- tetrabromoethane

Chlorine gives similar reaction.

1.4.4 Polymerization
This is the process of linking together many units of simple
molecules called monomers of the same substance to form more
complex molecules called polymers e.g.
Ø With an alkene (e.g. ethane) at 60° C, pressure and catalyst.
Ethene polymerizes to give polyethene.
9
 0
2n [CH2 = CH2] 60 C (--- CH2 – CH2 – CH2 – CH2 ---)n
Pressure
Catalyst
ethene Polythene
With an alkyne (e.g. ethyne)
Ethyne polymerizes when passed through a red-hot tube to
form benzene.
red – hot

1.5 ISOMERISM
“ISO” means same and “MER” means part, so ISOMERS are different
compounds having the same molecular formula. The existence of these
compounds (called Isomers) with the same molecular formula but
having some physical and/or chemical properties is termed
ISOMERISM.
§ Structural Isomerism
In this case, the compounds have the same molecular formula but
different structural formula. These compounds are called structural
isomers e.g.
1. Butane
C4H10 : CH3 – CH2 – CH2 – CH3 CH3 – CH – CH3
(2 Isomers) Butane CH3
2 – methylpropane

2. Pentane
C5H12: CH3 – CH2 – CH2 – CH3: CH3 – CH – CH2 – CH3
(3 Isomers) n – Pentane CH3
2-methylbutane

Ch3
CH3 – C – CH3
CH3
2,2 – Dimethylpropane

10
 Geometrical Isomerism
This is a form of isomerism which exists between compounds with the
same structural formula, arising because of their relative inability to
rotate about a double bond or a ring structure, e.g.
1. H Cl H H
C = C C = C
Cl H Cl Cl
Trans – 1,2 – Dichloroethene Cis – 1,2 – Dichloroethene

2.
H3C H H3C CH3
C=C C=C
H CH3 H H
Trans But-2-ene Cis But-2-ene

Optical Isomerism
This is a form of isomerism in which the compounds with the same
molecular formula assumes different configurations when
encountered by light, and are able to rotate plane polarized light either
towards the right – dextrorotatory or to the left – laevorotatory. e.g.
Lactic acid.

H H
CH3 C COOH HOOC CH3 CH3
OH OH
mirror
latic acid

11
 Calculation of Isomers
No mathematical formula exists in which the number of
isomers of a carbon compound can be calculated. Table 1.7 shows the
number of structural isomers the first twenty (20) carbon atoms of
alkane family can assume.

Table 1.5 Number of isomers for the first twenty (20) member of
alkane family.
Form ula N am e N um ber of Form ula N am e N um ber
Isom ers of
Isom ers
CH 4 M ethane 1 C 11 H 24 n-undacane 159
C 2H 6 Ethane 1 C 2 H 26 n-dodecane 355
C 3H 8 Propane 1 C 13 H 28 n-tridecane 802
C 4 H 10 n-butane 2 C 14 H 30 n-tetradecane 1858
C 5 H 12 n-pentane 3 C 15 H 32 n-pentadecane 4347
C 6 H 14 n-hexane 5 C 16 H 34 n-hexadecane 10359
C 7 H 16 n-heptane 9 C 17 H 36 n-heptadecane 24894
C 8 H 18 n-octane 18 C 18 H 38 n-octadecane 60523
C 9 H 20 n-nonane 35 C 19 H 40 n-nonadecane 148284
C 10 H 22 n-decane 75 C 20 H 42 n-Icosane 366319

Test for the Classes of Hydrocarbon

1. Test for Unsaturation
§ Unsaturated hydrocarbons (Alkenes & alkynes) decolorize
bromine or bromine water on mixing on mixing together.
But the alkanes have no effect.
§ Unsaturated hydrocarbons (Alkenes & alkynes) also
decolorize the purple colour of acidified potassium
tetraoxomanganate(VII) solution. Alkane does not show
any visible change.
2. Distinguishing Test between Ethene and Ethyne.
When each is passed through an aqueous ammoniacal
solution of copper(I)chloride or silver(I)chloride at room
temperature, ethyne produces a reddish brown precipitate
of copper(I)acetylide or silver(I)acetylide while ethane
shows no reaction.
12
1.6 FORMATION OF CRUDE OIL
Petroleum is formed in deep sedimentary beds from animal
and vegetable debris as a result of their bacterial decomposition
under pressure. The petroleum, being less dense than the surrounding
water, then gets expelled from the source beds and migrate upward
through porous rock (such as sandstone and some limestone) until it
is finally blocked by nonporous rock (such as shale or dense
limestone). In this way, petroleum deposits become trapped by
geologic features caused by the folding, faulting, and erosion of the
Earth's crust.

Refining of Petroleum
Refining simply refers to the separation of useful products
(such as petrol, kerosene etc.) from crude oil. This is done in a
petroleum refinery by a technique called fractional distillation which
involves taking advantage of the boiling point ranges of the different
fractions using a fractionating column. Table 1.6 shows the different
fractions obtained from crude oil and the ranges of their boiling
point.

Table 1.6: Fractions from crude and their boiling point ranges.
Fraction Composition of Boiling Point Uses
Carbon Chains Ranges(oC)
Natural Gas C 1-C 4 <20 Industial & Domestic
Fuel
Petroleum ether C 5-C 6 30-60 Organic Solvent
Naphtha C 7-C 8 60-90 Organic Solvent
Gasoline C 6-C 12 75-200 Fuels for vehicles
and solvent for
paints & grease
Kerosene C 12-C 18 200-300 For lighting and
heating, fuels for jet
engines etc.
Gas oils and Diesel C 12-C 25 300-400 Raw material for
oil cracking process, fuel
for diesel engines.
Lubricating oils C 25- C 35 >500 Road construction

13
 If you don't accept complete responsibility for your life, no one will do it for you!
TAKE- AWAY

1) A. What is the structure of the straight-chain compound that

is isomeric with 2,2,4- trimethylpentane
B. How would you identify ethane and ethyne if left in
anunlabeled bottles respectively.
C. The equation
nCH2=CH2→ (-CH2-CH2-CH2-CH2-)n

represents a chemical process

I. Name the process,
II. Name the product formed,
III. Would ethane undergo the same process? Give a reason
for answer.
2) A. Explain the term 'polymerization'.
B. List three conditions under which ethene will undergo
polymerization. What is the product formed.
C. Two hydrocarbons A and B were each shaken with bromine
water. A decolorized the solution while B did not.
I. To what classes of hydrocarbons do A and B belong?
II. Which of A or B can polymerize? Give reasons.

3) A. List three characteristics of a homologous series.

B. Give an example of
I. Alkene
II. Alkyne
C. Two hydrocarbons X and Y were treated separately with
acidified potassium tetraoxomanganate(VII) solution. X decolorized
the solution and Y did not. Which of X and Y will undergo
I. Substitution reaction only.
II. Both addition and substitution.
III. Polymerization.

14
4) Briefly identify the important distinctions between a
saturated hydrocarbon and unsaturated hydrocarbon.
5) Draw the structure of each of the following compound.
a. 2-methyl-2-pentene
b. 2,3-dimethyl-1-butene
c. Cyclohexene
d. 5-methylhex-1-ene
e. 3-ethylpent-2-ene
f. 4-methylhex-2-ene.

15
Play now and pay later or pay now and play later; whichever way, you just have
to pay!
WORKSHEET

16
Play now and pay later or pay now and play later; whichever way, you just have to
pay!
WORKSHEET

17
 CHAPTER TWO
ALKANOLS

2.1 INTRODUCTION
Alkanols are organic compounds formed when a hydroxyl
group (-OH) get linked to the alkyl groups. All alkanols contain at least
one hydroxyl group (-OH) as a functional group. They have the general
formula represented by CnH2n+1OH. Table 2.1 illustrates the connection
between alkanol formations from the alkyl group.

Table 2.1: Alkanol formation from the alkyl groups

Alkane Alkyl (Alkane-H) Alkanols (Alkyl+OH)
Name Molecular Name Molecular Name Molecular
Formula Formular formula
CnH2n+2 CnH2n+1 CnH2n+1OH
Methane CH4 Methyl CH3 Methanol CH3OH
Ethane C2H6 Ethyl C2H5 Ethanol C2H5OH
Propane C3H8 Propyl C3H7 Propanol C3H7OH
Butane C4H10 Butyl C4H9 Butanol C4H9OH
Pentane C5H12 Pentyl C5H11 Pentanol C5H11OH

From table 2.1, it can be seen that the alkanols are formed by simply
attaching the hydroxyl group (-OH) to the alkyl group. While the alkyl
groups are formed by removing an atom of hydrogen from each of the
alkane members. This process of removing hydrogen from the alkane
members to form alkyl is called DEHYDROGENATION.

2.2 CLASSIFICATION OF ALKANOLS

The classification of alkanols is shown by figure 2.2.

Alkanols
Monohydric Polyhydric
Primary Secondary Tertiary Dihydric Trihydric
e.g. ethan-1,2-diol e.g Propan-1,2,3-triol
e.g. ethanol e.g propan-1-ol e.g. 2-methylpropan-2-ol

Figure 2.2: Classification of Alkanols

18
2.2.1 Monohydric Alkanols
These are alkanols with only one hydroxyl group (-OH) in their
molecule. The first three members of the family are:
§ Methanol: CH3OH (Commonly known as wood spirit).
§ Ethanol: CH3CH2OH or C2H5OH
§ Propanol: CH3CH2CH2OH or C3H7OH
Methanol (wood spirit) is obtained by the destructive distillation of
wood.

Classes of Monohydric Alkanols

Monohydric alkanols are classified into primary, secondary and
tertiary.

Table 2.2: Classes of Monohydric Alkanols

Alkanols General Examples Functional Group

Formula

I. Primary alkanol H CH3CH2OH - CH2OH

R C OH ethanol
H
1
ii. Secondary alkanol R (CH3)2CHOH - CHOH
R C OH Propan -2-01
H
I
iii. Tertiary alkanol R (CH3)3COH - COH
R C OH 2-methylpropan-2-01
RII

2.2.2 Polyhydric Alkanols

This class of alkanols contains more than one hydroxyl
groups per molecule. Table 2.3 shows the different forms of
polyhydric alkanols with an example each.

19
 Table 2.3: Classes of Polyhdric Alkanols
Alkanol Example Structure
I.Dihydric alkanol Ethane-1,2-diol H H
(ethylene glycol) H C C H
OH OH
ii.Trihydric alkanol Propan-1,2,3-triol H H H
(glycerol) H C C C H
OH OH OH
2.3 PROPERTIES OF ALKANOLS
2.3.1 Physical Properties
I. Physical State: The lower members are colourless with
distinctive odour and a burning taste.
II. Solubility: The lower members are highly water-soluble due to
the presence of the hydroxyl group (-OH), but solubility
decreases as the homologous series ascends due to increase in
molecular weight.
III. Melting Point: The simpler alkanols have low melting points.
IV. Boiling Point: Their boiling points are considerably higher
than those of the alkanes because of the presence of hydrogen
bonding between the hydroxyl group (-OH).
2.3.2 Chemical Properties
I. Reaction with Metals
The hydrogen atom of the hydroxyl group of alkanols are
liberated by strong electropositive metals (K, Na, Mg, Zn) to
form alkoxides
ROH + Na RONa + ½ H2(g)
Sodium alkoxide
Examples
I.CH3 OH + Na CH3ONa + ½ H2(g)
Sodium methoxide

II.C2H5OH + Na C2H5ONa + H2(g)

Sodium ethoxide

20
I. Dehydration of ethanol with concentrated H2SO4
a) When concentrated H2SO4 is in excess, ethene is
formed.
0
C2H5OH 180 C C2H4 + H2O
Ethanol Conc. H2S04 ethene
(Excess)
b) When the ethanol is in excess, ether is formed.
0
2C2H5OH 145 C CH3CH2OCH2CH3 +H2O
(excess) Conc.H2S04 ethoxyethane
(ether)
II. Reaction with acids (ESTERIFICATION)
Alkanols react with alkanoic acids in the presence of
concentrated H2SO4 acting as a catalyst to form alkanoates
(esters)
ROH + RI COOH RI COOR +H2O
Alkanol Alkanoic Ether
Examples
CH3OH + CH3COOH CH3COOCH3 + H 2O
Ethanol Ethanoic acid Methylethanoate

C2H5OH + CH3COOH CH3COOC2H5 + H2O

Ethanol Ethanoic acid Ethylethanoate

III. Oxidation of Alkanols

a. Oxidation to Alkanals and Alkanoic Acids
Primary alkanols are oxidized to alkanols on heating with
acidified potassium heptaoxochromate (VI) (K2Cr2O7) or
acidified potassium tetraoxomanganate (VII), KMnO4.
O
ROH + [O] R C + H 2O
Alkanal H
Example O
CH3CH2OH + [O] CH3 C + H 2O
Ethanol Ethanol H

21
 If the oxidizing agent (KMnO4 or K2Cr2O7) is in excess, there is
complete oxidation to ethanoic acid.

CH3CH2OH + 2[O] CH3 COOH + H2O

Likewise O
CH3CH2OH + 2 [O] CH3 CH2 C + H2 O
Propanal Propanal H

2CH3CH2CH2OH + 2 [O] 2 CH3 CH2 CH2 COOH + H2O

butanol butanoic acid

b. Oxidation to Alkanones: Oxidizing secondary alkanols give

alkanones

H O
R C OH + [O] R C + H2O
RI R I

Examples
H O
H3C C OH + [O] H3C C + H2O
CH3 CH3
Propan-2-ol Propanone

c. Oxidation to Dicarboxylic Acids: Oxidizing a dihydric

alkanol (e.g. ethan-1,2-diol) with HNO3 yields an ethanedioic acid.

CH2 OH
+ 4 [O] COOH + 2H2O
CH2OH COOH
Ethanedioic acid

22
I. Iodoform Reaction

This is a reaction whereby a mixture of ethanol, a few crystals of iodine

o
and washing soda is heated at 70 C to give a pale yellow crystals tri

-iodomethane (iodoform) on standing. Methanol does not give similar

reaction, hence a test for distinguishing between ethanol and methanol

methanol.
I2 Na2C03
C2H5 OH I2 CH3 CHO CH3 CHO CHI3
Iodoform
2.4 PRODUCTION OF ETHANOL
Fermentation
This is the breaking down of a sugar (glucose) into ethanol
carbon (IV) oxide by the action of organic catalyst called enzyme.
C6 H12 O6 Zymase 2 C2 H5 OH + 2 CO2
Fermentation is the last reaction stage of ethanol formation as the
following method of production shows.

1. Fermentation of Starch (from potatoes or cereals)

Diastase (from malt)
2n (C6 H10O5) (s) + n H2O(l) n C12 H22 O11 (aq)
Starch maltose
Invertase (maltose)
C12H22O11 (aq) +H2O (l) 2C6H12O6 (aq)
Maltose Glucose
Zymase
C6 H12 O6 (aq) 2 C2 H5 OH (aq) + 2 CO2 (g)
Glucose ethanol

23
The ethanol formed is then subjected to fractional distillation to obtain
a solution containing 95.6% ethanol which could further be dehydrated
with calcium oxide to obtain absolut ethanol with 99.5% ethanol.

From Cane Sugar

C12 H22 O11 (aq) + H2 O(l) Invertase C6 H12 O6 (aq) + C6 H12 O6

300C
Sucrose glucose fructose

C6 H12 O6 (aq) Zymase 2 C2 H5 OH (aq) + 2 CO2 (g)

Glucose ethanol
The solution obtained is subjected to fractional distillation to obtain a
fraction containing about 95.6% of ethanol. This could further be
dehydrated to obtain absolute ethanol with 99.5% ethanol with use of
calcium oxide.
PRODUCTION OF METHANOL
Methanol is produced byo
heating
o
a mixture of hydrogen and carbon
(II) oxide to about 300 C-400 C in the presence of chromium (III)
oxide/zinc oxide catalyst under 200atm.

Catalyst
CO (g) + 2H2 (g) 300 C-400 C
0 0 CH3 OH
200atm Methanol
Uses of Alkanols
Methanol
üUsed as a solvent.
üProduction of organic chemicals.
üFuel in aircraft engine.
üMaking methylated spirit.
Ethanol
üUsed as an organic chemical.
üFor production of other organic compounds e.g. ethanoic
acid, ether etc.
üServes as a constituent of drinks such as beer and wine.
üUsed as an anit-freezing agent.
24
üFor preservation of specimens and food substances.
Glycerol
§ Making dynamite, shoe polish and creams.
2.5 PHYSICAL PHENOMENON ASSOCIATED WITH
ALKANOLS
1) The white appearance of fresh palm wine is a result of the
suspension of yeast.
2) Fresh palm wine should not be kept or transported in sealed
container because of the tendency of the container to explode due
to the large volume of carbon (IV) oxide released during its
fermentation.
3) Fresh palm wine has a sweet taste because of the high content of
unfermented sugar.
4) When fresh milk is left standing for a long time, hydrolysis occurs
in the presence of bacteria called bacilla acidi pacti to form lactic
acid which is responsible for the sour taste of the milk.
5) Fresh palm wine goes sour when left for a long time due to the
production of ethanoic acid by bacterial oxidation of ethanol
present in fermented palm wine.

2.6 PHENOLS
These compounds sometimes called phenolics, are compounds
consisting of a hydroxyl group (-OH) bonded directly to an aromatic
hydrocarbon group. The simplest of this class is phenol (C6H5OH)
which is also called hydroxybenzene and in water, carbolic acid.
OH

Phenol
The acidity of phenol is very weak but are more acidic then alkanols
due to their stable phenoxide (or phenolate) ions formed from the loss
of positive hydrogen ion (H+) from the hydroxyl group of phenol
OH O

+ H+
Phenoxide ion

25
2.6.1 Differences between Phenols and Alkanols
§The hydroxyl group of phenol is not bonded to a saturated
carbon atom unlike the alkanols.
§They have higher acidities due to the strong attachment
between the aromatic ring and the oxygen, and a relatively
loose bond between the oxygen and hydrogen.

2.6.2 Properties of Phenol

§It is soluble in organic solvents such as ether and ethanol. It's
also soluble in water due the presence of hydrogen bonding
between the hydrogen and oxygen atoms.
§Corrosive and poisonous.

Uses
§Making nylon, insecticides, dyes, explosives and disinfectants.
§It could be used as organic solvent.

26
 The CHOICES you make in Life eventually MAKE YOU, and DETERMINES where you eventually END UP.

TAKE-AWAY
1) A. When crushed cassava was warmed with dilute
hydrogen chloride acid, a sweet-tasting compound, D was
obtained. When compound D was treated with the enzyme, zymase
and the mixture distilled, a clear and colourless liquid, E, was
obtained. When liquid E was warmed with ethanoic acid in the
presence of a few drops of concentrated tetraoxosulphate (IV) acid,
a compound, F, with fruity smell was obtained.
i. To what class of compounds does D belong?
ii. Name E and F.
iii. Write the functional group in F.
iv. Write the equation for the reaction between E and
ethanoic acid.
v. Name the type of reaction that takes place
between E and ethanoic acid.
B. Write chemical equations to illustrate the oxidation of
i. a secondary alkanol.
ii. a dihydric alkanol.
2) A. What is fermentation?
B. How would you prepare absolute ethanol, starting from
cane sugar?
C. Account for the solubility of methanol and ethanol in
water.
D. Draw the structure of the straight-chain compound
isomeric with 2,2,4-trimethyl pentane.
E. Account for the fact that phenol is a stronger acid than
ethanol.
F. List three uses of methanol and glycerol each.

27
You can't depend on your EYES when your IMAGINATION is out of FOCUS!
WORKSHEET

28
You can't depend on your EYES when your IMAGINATION is out of FOCUS!
WORKSHEET

29
 CHAPTER THREE
ALKANOIC ACIDS
3.1 INTRODUCTION
These are groups of organic compounds with a carbonyl group (-
CO-) and a hydroxyl group (-OH). They have the general O
representation of R C
OH

where R represents an hydrogen atom O or an alkyl group. They

have a functional group of C or –COOH or –CO2H. The first
four members of the group OH

are as shown by table 3.1.

Table 3.1 Examples of alkanoic acids
IUPAC Name Formula Structure
O
Methanoic acid HCOOH H C
OH
O
Ethanoic acid CH3COOH CH3 C
OH
O
Propanoic acid C2H5COOH CH3- CH2 C
OH
O
Butanoic acid C3H7COOH Ch3- CH2 – CH2 C
OH
From the table, it can be seen that the name of the series are given
by replacing the –ane ending in the corresponding alkanes by –oic
acids. Further, the examples above can be classified as
monocarboxylic acids because of the presence of only one
O
carboxylic end (-COOH or C ) in each case.
OH
3.1.1 Dicarboxylic Acids
These are alkanoic acids with two carboxylic groups. Examples
include

30
 COOH COOH
and
COOH CH2
Ethanedioic acid COOH
Propanedioic acid
3.1.2 Aromatic Acids
These are alkanoic acids with benzene ring attached. An
example is

COOH
Phenyl methanoic acid

3.2 General Laboratory Preparation of Alkanoic Acids

Alkanoic acids can be prepared by the complete oxidation of a
primary alkanol using potassium heptaoxochromate (VI) or potassium
tetraoxomanganate (VII) with dilute tetraoxosulphate (VI) acids.
CH3 CH2 OH+2[O] CH3COOH+H2O
ethanol ethanol acid
Physical Properties
1) The first three members of the series are liquids which are
completely soluble in water, due to the presence of
hydrogen bonding. Members from C4-C9 are also
liquid and are partially soluble in water while the higher
members are solids and irtually insoluble.
2) There is an increase in the boiling point of the acids with an
increase in the molecular mass. But this property is
affected by branching which tends to lower it a s i n o t h e r
compounds.
3) The first three members have pungent odours while
butanoic acid has a rancid odour.

31
 Chemical Properties
1) Monocarboxylic acids act as weak monobasic acid e.g.
CH3COOH (aq) CH3 COO- (ag) +H+ (ag)
2) They liberate carbon (IV) oxide from metallic trioxocarbonate
(IV)
2CH3COOH(ag) + CaCO3 CH3(COO)2 Ca(aq) + H2(l) +CO2(g)

3) Monocarboxylic acid also reacts with bases to form salt and water
only.
- +
CH3COOH(aq)+NaOH(aq) CH3COO Na (aq) + H2O(l)
Acid base salt
4) Ester formation: A reversible reaction called ESTERIFICATION
occurs when an alkanoic acid is heated with an alkanol to form
ester (alkanoate) e.g.
Esterification
CH3COOH(aq)+C2H5OH(aq) CH3 COOC2H5 (l) + H2O(l)
Ethanoic acid ethanol Hydrolysis Ethyl ethanoate
(Ester)
5) Reduction to Alkanols: Alkanoic acids are reduced by
lithium tetrahydridoaluminate (III) to alkanols, e.g.

CH3 COOH + 4[H] CH3 CH2OH + H2O

Ethanoic acid Ethanol
3.3 Differences between Neutralization Reaction and
Esterification
Table 3.3 Differences between Neutralization Reaction and
Esterification
Esterification Neutralization
1. Reaction is covalent in nature. Reaction is ionic.
2. The reaction is slow The reaction is relatively fast
3. Reaction is reversible Reaction is irreversible.
4. An ester and water are formed Salt and water are formed
5. Catalyst is necessary for the reaction to Catalyst is unnecessary for the reaction.
occur.

32
Uses of Alkanoic Acids
1. Methanoic acid is used in dyeing, tanning and coagulating
rubber.
2. Ethanoic acid is used in coagulating rubber latex.
3. Ethanoic acid is used as a weak acid.
4. Higher carboxylic acids are used in soaps and detergents
production.

3.4 Alkanoates (or Esters)

These are sweet smelling compounds formed from the reaction
between an acid and an alkanol.
Alkanol +Alkanoic acid Alkanoate + water
(ester)
This type of reaction is called ESTERIFICATION. The
alkanoates have the general formula of
O
R- C
1
O R
The functional group of alkanoate is

O
-C
O - R1

Physical Properties of Alkanoate

1. They have a fruity sweet odour.
2. They are soluble in organic solvents but insoluble in water.
3. They are colourless neutral liquids.

Chemical Properties of Alkanoate

A. Ethyl ethanoate is insoluble in sodium hydrogen
trioxocarbonate (VI).
B. They do not decolourize bromine water.
C. Hydrolysis of alkanoate with dilute mineral acids (H2SO4 or
HCl) on boiling yields ethanol and ethanoic acid.
33
D. Alkaline hydrolysis of ethyl ethanoate yields sodium or
potassium ethanoate (soap) and ethanol. This process is
called SAPONIFICATION.
1 1
R COOR + Na OH RCOONa + R OH
Soap
e.g
CH3COO CH3 + Na OH CH3 COONa + CH3 OH

CH3 COO CH3 + Na OH CH3 COO Na + CH3 OH

Uses of Alkanoates
§ Flavouring of foods, glues, oils, resins, paints etc.

3.5 FATS AND OILS

Fats are solid at room temperature, and of animal origin while
oils are liquids and of plant origin. They are naturally occurring esters
(alkanoates) and are grouped as glycerides. Fats are saturated
glycerides at room temperature while oils are unsaturated, and can be
made saturated by exposure to oxygen or by hydrogenation.
They contain fatty acids such as octadecanoic acid (stearic
acid), hexadecanoic acid (palmitic acid), octadec-9-enoic acid (oleic
acid) and glycerol (propan-1,2,3-triol). These can be classified as
SATURATED (having no double bonds in their hydrocarbon chain)
and UNSATURATED (having one or more double bond in their
hydrocarbon chain).

CHEMICAL PROPERTIES OF FATS & OILS

I. HYDROGENATION
Liquid unsaturated oils are hardened and become saturated by the
addition (bubbling) of hydrogen across the double bonds in the
unsaturated carbon chains of the oils under the influence of finely
o
divided iron catalyst at 180 C. This is used in the production of
margarine.
34
II. ATMOSPHERIC OXIDATION
This involves exposing the unsaturated fatty acid and their esters to
atmospheric oxygen in the presence of light to give saturated
derivatives.
III. SAPONIFICATION
This is the process of hydrolyzing fats and oils with caustic alkali to
yield propan-1,2,3-triol (glycerol and soap) i.e.
fat and oil + caustic alkali soaps + propan-1,2,3-triol
(glycerol)

Uses of Fats and Oils

1. Manufacture of soap by saponification.
2. For making glycerol.
3. For the production of margarine.
4. Used in the manufacture of paints, candles etc.
3.6 DETERGENTS
Detergents can be classified as SOAPY DETERGENTS and
SOAPLESS
DETERGENTS.
Soapy Detergent (or simply soap)
This is sodium or potassium salt of an organic acid. The sodium soaps
of organic acids are hard soap while the potassium salts of the organic
acids are soft soaps e.g.
ü Sodium salt of octadecanoic acid (stearic acid), C17H35COONa
(hard soap).
ü Potassium salt of hexadecanoic acid (palmitic acid),
C15H31COOK (soft soap).
Production of Local Soap
Local soap is prepared by burning palm fronds, wood or plantain husks
to obtain the alkali. The ash obtained is then dissolved in water and
filtered. Finally, the filtrate is boiled with palm oil.
35
It should be noted that the soap is usually soft because the wood ash
contains mainly potassium ions, while the black colour of the soap is
because of the ash used.
Soapless Detergents
These are sodium or potassium of sulphonated long chain
hydrocarbons.
Principles of Manufacture
Detergent is manufactured from long chain alkene, CnH2n where n
ranges from 12 to 20. The general formula of detergent is RSO3-Na+.
Steps
1. Sulphonation of alkene with concentrated tetraoxosulphate
(VI) acid, H2SO4.
C 15H 30 + H 2 SO 4 C 1 5 H 3 1 SO 4 H
A lken e Su lp h o n ated alken e
2. Treating the sulphonated alkene with sodium hydroxide
solution to obtain the sodium salt of the sulphonated alkene.

C15 H31 SO4 + Na OH C15 H31 SO4 Na + H2O

Detergent
Note: The carbon chain and ionic groups can be varied, e.g. alkyl
benzene sulphonate detergent.
Every detergent has a tail (hydrocarbon end), C15H31 and ionic
water soluble head SO4Na

C15 H31SO4 Na(s) C15 H31 SO4 (aq) + Na+ (aq)

The Cleansing Action of Soap
The nature of soap having one electrovalent (polar) end which
is a carboxylate salt end and one covalent (non-polar) end which is a
hydrocarbon chain end makes it act as a cleansing agent.
O
C17 H35 C
O- Na+
Non-polar end Polar end
(hydrophobic end) (Hydrophilic end)

36
The hydrophilic end (polar end) attracts water hence are water soluble
while the hydrophobic end (non-polar end) attracts oils hence oil
soluble. This makes soap molecule create a kind of attraction between
the water and oils to form stable emulsions which can be washed away.
Comparison between Soapy and Soapless Detergent
I. Scum Formation
Soapless detergents contains water soluble ions (such as
Ca,2+ Mg2+ or Fe3+) as such do not form scum unlike soapy
detergent.
II. Surface Area
Soapless detergents have larger surface area hence can
enable water to spread and penetrate more fully over and through
an article being washed. The surface area of soap is v e r y m u c h
reduced.
III. Solubility
Soapless detergents are more soluble in water than soapy
detergent.
IV. Acidic and Alkaline Condition
Soapless detergents can be used in both alkaline and acidic
conditions unlike soaps.
3.7 POLYMERS
Polymers are large organic molecules made up from regularly
repeating small chemical molecular units called monomers which are
linked together. This process of linking two or more monomers
together to form a high molecular mass of compound called polymer is
called POLYMERIZATION.
Types of Polymerization
§ Addition Polymerization
§ Condensation Polymerization
3.7.1 Addition Polymerization
This is a type of polymerization in which the unsaturated units called
monomers break their double bonds to form links such that the
empirical formulas of both are the same e.g.
ü Formation of polyethene as polymer from ethane (monomer).

37
 2n[CH2= CH2] n (... CH2- CH2- CH2 …)
Ethene polyethene
üFormation of poly(chloroethene) or polyvinyl chloride (PVC)
as polymer from chloroethene (vinyl chloride) monomer in the
presence of hydrogen peroxide as catalyst.
n CH2 = CHCl ... CH2- CHCl [ CH2 CHCl]nCH2CHCl
chloroethene or vinylchloride poly(chloroethene) or polyvinyl chloride (monomer)

üFormation of poly(phenylethene) commonly called

polystyrene from monomer phenylethene (or styrene) using
benzoyl peroxide as catalyst.
n CH2 = CH CH2- CH [ CH2- CH]n CH2- CH-

üPoly(propenonitrile) from propenonitrile as a monomer under

an organic peroxide catalyst.
n CH = CHCN … CH2 [CHCN- CH2]n CH CN…
Propenonitrile poly (propenonitrile)
3.7.2 Condensation Polymerization
This form of polymerization occurs when the monomers are
linked by a reaction in which small molecules of water or ammonia
are eliminated. Examples include
§ Nylon 6.6 from hexane-1,6-diamine, H2N-(CH2)6-NH and
hexanedioc acid (adipic acid), COOH-(CH2)4-COOH by the
elimination of water.

..
O O.
HOOC-(CH2)4-CO OH + H - (CH2)6 - NH2-H2O ...N-(CH2)6-N .. C-(CH2)4-C ...
Hexanedioic acid Hexane-1,6-diamime H H
§ Terylene formed by the condensation of benzene-1,4-
dicarboxylic acid (terephthalic acid) and ethan-1,2-diol using an
acid catalyst.
38
3.8 NATURAL AND SYNTHETIC (ARTIFICIAL)
POLYMERS

§ Natural Polymers
These are polymers formed in plants and animals. They include
carbohydrates such as starch and cellulose, proteins and rubbers.

§ Synthetic (Artificial) Polymers

These are plastics with the ability to be softened by heat and pressure,
and then be moulded to any desirable shape. Examples include
polyethene, polypropene, polystyrene, terylene, Perspex, bakelite and
urea-methanal. The first five examples are referred to as
thermoplastics since they can be remoulded under applied heat
without breaking, while the other two (2) are referred to as thermosets
– they cannot be remoulded once formed.

3.9 RUBBER

3.9.1 Natural Rubber

This is a polymer of 2-methylbuta-1,3-diene monomer formerly called
ISOPRENE.
CH3 CH3
nCh2 =C-CH=CH2 -(CH2C=CH CH2)n-
2-mathybuta-1,3-diene natural rubber
Rubber occurs as a sticky material and can be improved by a process
called VULCANIZATION which involves the addition of controlled
amount of sulphur to rubber. The sulphur cross-links the rubber
molecules together at the double bonds giving rise to a superior
product. This results in the elasticity of the rubber and improves its
strength and toughness.
CH3 CH3
2(…. CH2- C=CH-CH2...) 2S ...CH2-C- CH-CH2-
S S
-CH2 - C -CH-CH2-
- CH3
Vulcanized rubber
39
3.9.2 Synthetic Rubber
Examples of these include
ü Poly(2-chlorobuta-1,3-diene) or neoprene.
ü Styrenebutadiene rubber (SRR)
ü Thiokol
ü Poly(buta-1,3-diene)
ü Poly(2-methylpropene)

3.10 POLYMERIC AMIDES

These are otherwise known as polyamides. They are polymers
characterized by peptide linkage between the units.
O
C N
H
Examples are nylon and proteins

§ PROTEINS
They are organic compounds whose basic structural units are amino
acids represent with the general formula
H
R- C-COOH
Nh2
From the structure, it could be seen that amino acids contain the amino
group (-NH2) and carboxyl group (-COOH). The peptide linkage can
be noticed in the structure as shown by
O...
.
C N
H
This is formed from the elimination of water between the –COOH
group of one acid and the NH2 group of an adjacent one, i.e.

O H O
-C + N -H2O -C - N -
O-H H H
Peptide link
40
3.11 CARBOHYDRATES
These are compounds containing carbon, hydrogen and oxygen with
the hydrogen and oxygen occurring in the artio of 2:!. They have the
general representation of Cx(H2O)y.

Classification of Carbohydrates
Carbohydrates are classified into either simple or complex sugar.

SIMPLE SUGAR
They are crystalline solids with a sweet taste. They further divided into
ü Monosaccharides e.g. glucose & fructose.
ü Disaccharide, e.g. maltose and sucrose.

Glucose (C6H12O6)
They are either ringed or straight chain.

CHO CH2OH
H - C - OH H - C O OH
HO-C - H C OH H C
H- C -OH HO - C C H
H- C - OH H OH
CH2 OH
Aldehyde form â-glucose
Straight chain structure Ring structure
The presence of aldehyde group (-CHO) in glucose is responsible for
the reducing property of glucose, hence it is referred to as a
REDUCING SUGAR. They are also called ALDOSE because of the
aldehyde group (-CHO) present.
Preparation of Glucose
i. Acid hydrolysis of starch at 70oC

(C6 H10 O5) + nH2O n (C6H12O6)

Starch Glucose

41
ii. Photosynthesis in plants

Sunlight
6CO2(g)+ 6H2O(l) Chlorophyll C6H12O6(aq)+ 6O2(g)
Glucose

Fructose
This is an isomer of glucose. They are referred to as ketose
because of the presence of the ketone (-CO-) group present.

CH2OH
C= O
HO - C - H
H - C - OH
H - C - OH
CH2OH
Fructose

C12 H22 O11 + H2O dilute H2SO4 C6H12 O6 + C6H12 O6

glucose fructose
(C6H10 O5)n

COMPLEX SUGAR (C6H10O5)n

They are called polysaccharides, and are condensation
polymers of glucose. Examples include starch, cellulose, dextrin and
glycogen.

42
 Keep fighting to learn more, grow more and become more
TAKE-AWAY
1A. Describe in details the process of soap production, indicating
all necessary equations.
B. Explain the differences between detergents and ordinary
soaps in laundry activities.
C. Explain briefly how oils are used to obtain
i. Margarine
ii. Soap
iii. Glycerol
2A. What are fats and oils, stating the differences between the two.
B. When liquid E was warmed with ethanoic acid in the
presence of a few drops of concentrated tetraoxosulphate (VI)
acid, a compound, F, with fruity smell was obtained.
i. Name E and F.
ii. Write the functional group in F.
iii. Write the equation for the reaction between E and
ethanoic acid in the presence of concentrated
etraoxosulphate (VI) acid.
iv. Name the type of reaction that taking place between
E and ethanoic acid.
C. Give at least four differences between neutralization and
sterification.
D. Describe how you obtain a sample of ethanol from cassava.
E. Explain the sour taste found in (i) grape fruits (ii) sour
milk (iii) vinegar (iv) rancid butter
43
WORKSHEET

44
WORKSHEET

45
 CHAPTER FOUR
IUPAC NOMENCLATURE OF ORGANIC COMPOUNDS

4.1 FUNCTIONAL GROUPS

They are atoms, radicals (group of atoms) or a bond common to a
homologous series of organic compound, and determine the chemical
properties of such series. Table 4.1 shows some functional groups
peculiar to some series of organic compounds, while table 4.2 shows
the placement of functional groups and, how they affect naming.

Homologous General Functional

Series Formula Group
Alkanes R- H -
Haloalkanes R - X -X
Alkanols R - OH - OH
Ethers R - ORI - ORI
Alkanals H O
C=O -C
RI H
Alkanones R
C= O C= O
I
R
O O
Carboxylic acids R-C -C
OH OH
O O
Ethers R -C -C
I I
OR OR

Primary Amines R - NH2 - NH2

O O
Amides R - C -C
NH2 NH2
Nitriles R-C N - C N

46
Note: X represents halogen atoms such as F, Cl, Br or I. Also R and R'
represents alky group.

Table 4.2: placement of functional groups

Functional Name as Name as prefix
Group Suffix
O
-C - Oic acid -
OH

-COOR alkyl…- carboxylate alkoxy carbonyl

- COOH - Carboxylic acid Carboxy-

O-
-C alkyl…oate
OR

O
-C amide -
NH2
C O - One Oxo -

C O - al Oxo -
H

- CN -Carbonitrile Cyano -

-OH - Ol Hydroxy -

-NH2 - Amine Amino -

- Cl - Chloro -

- Br - Bromo-

-I - Iodo -

47
4.2 NAMING OF ALKANES

Rules
1. All alkanes ends with –ane.
2. For branched-chain structures, the longest chain of carbon
atoms should be identified and numbered e.g.
1 2 3 4
CH3 - CH- CH2 - CH3
CH3
3. The compound's name is derived from the alkane which has the
same number of carbon atoms as the longest chain. The parent
compound of this example has four (4) carbon, hence the
naming ends with butane.
1 2 3 4
CH3 - CH- CH2 - CH3
CH3
2-methylpentane
4. Number the carbon atoms in the longest chain, starting from
the end nearest to the substituent.
4
CH3- 3CH- 2CH2- 1CH3 Incorrect
CH3
3-methyl butane
1
CH3- 2CH- 3CH2- 4CH3 Correct
CH3
2-methyl butane
5. The compound is named by listing the position of the
substituent, the name of the substituent and the name of the
alkane.
1
CH3- 2CH- 3CH2- 4CH3
CH3
2-Methyl Butane
48
6. If there are more than one substituent, their positions and
names must all be included e.g.

CH3
1 2 3 4 5
CH3- CH- CH2- CH2- CH3
CH3
2,2- Dimethyl pentane

CH3
1
CH3- 2CH- 3C- 4CH3 - 5CH3
CH3 CH3
2, 3, 3-trimethyl pentane

Demonstrable Examples on Alkane

1. CH3CH(CH3)CH(CH3)CH2CH3

H H H
CH3- C - C - C - CH3
CH3 CH3 H
Or
H H H H H
1 2 3 4 5
H- C - C - C - C - C -H
H H-C-HH - C- H H H
H H
2,3- Dimethylpentane

49
2. C(CH3)4

CH3
3 1 2
CH3- C - CH3
CH3
2,2-Dimethyl Propane

3. H
1 3 2 4 1 2 3 4
CH3- C- CH2- CH3 or CH3 CH3 (CH3) CH2 CH3
CH3
2-methyl butane

4. CH3 CH2C (CH3)2 CH2

H CH3 CH3
4 3 2 1
4
CH3- C-2 CH- CH23
or CH3-CH2- C-CH2
H CH3 CH3
2,2-dimethyl butane

5. Cl
1 2 3 4
CH3 - C- CH2-CH3 or 1CH3 2CCH3 (Cl) 3CH2 4CH3
CH3
2-chloro-2-methyl butane
6.
1 2 3 4
CH3- CH- CH- CH3 Or CH3 CH (Cl) CH (Cl) CH3
Cl Cl 2,3-dichlorobutane

50
7.
Cl Cl
H -C - C -H
Cl Cl
1,1,2,2-tetrachloroethane
4.3 NAMING OF ALKENES
Rules
1. The parent compound is gotten by locating the longest
branched-chain, this gives the root name, followed by the
suffix –ene.
2. The position of the double bond is indicated by the smaller of
the numbers given to the carbon atoms between which the
double bond lies, e.g.
4 3 2 1 1 2 3
CH
3
- CH2 - CH=CH2 and CH 3- CH= CH - CH 3
But - 1-ene but - 2- ene

3. When there is chain branching, the carbon atoms carrying

the double bonds bear the smallest number possible

5
CH3 - 4CH2 - 3CH2 - 2CH =1CH2 1
CH3 - 2CH = 3C - 4CH - 5CH3
CH3 CH3 CH3
2- Methylpent-1-ene 3,4-dimethylpent-2-ene

Demonstrable Examples of Alkenes

CH3
1 2 3 4 1 2 3 4
1. CH3 - C(CH3) = C(CH3) - CH3 Or CH3- C = C - CH3
CH3
Trans-2,3-dimethylbut-2-ene
1 2 3 4 1 2 3 4
2. CH3 - C(CH3) = C(CH3) - CH3 Or CH3 - C = C - CH3
Cis -2,3-dimethylbut-2-ene Ch3 Ch3

51
3. 5CH3 - 4CH2- 3C= 2C-1CH Or 5CH3 - 4CH2-3C(CH3)=2C(CH3)1CH3
CH3CH3
2,3-dimethylbut-2-ene
CH3
4 3 2 1 4 3 2 1
4. CH3 CH(CH3)2 CH = CH2 Or CH3 - C - CH = CH2
3,3-Dimethylbut-1-ene CH3

CH3
5. 5CH3 4C(CH3)2 3CH= 2CH - 1CH3 Or 5CH3 - 4 C -3CH = 2CH-CH3
4,4-dimethylpent-2-ene CH3

CH3
6. 1CH2 = 2C - 3CH2Cl
3-chloro-2-methylprop-1-ene

4.4 NAMING OF ALKYNES

This system of naming is the same as that of the alkenes,
except that the suffix –yne is added to the to the root name.
5 4 3 2 1 5 4 3 2 1
1. CH3 - CH2 - CH2 - CH CH 2. CH3 - CH2 - C C - CH3
pent-1-yne pent-2-yne
CH3
3. CH3 - C - C - 4. H3C - C-
4 3 2
-1CH - CH3
Ch3 propyne
3,3-dimethylbut-1-yne

52
4.5 ALKANOLS
This system of naming involves replacing the –ane ending with
–ol

ALKANOLS
3 2 1
1. CH3 - CH - CH3
OH
propan-2-ol

CH3 H
2. H3 C - C - 1C - OH
3 2
Or CH3CH (CH3)CH2OH
H H
2-methylpropan-1-ol
3
CH3
1 2
3. H C - C - OH
3 Or CH3 C (CH3)2OH
CH3
Butan-2-ol
1
CH3
2
4. H3C - C - OH
3
CH3
2 -methylpropan-2-ol
1
H H CH2 OH
2 1 2
5. H - C - C-H Or CH2 OH
OH OH
Ethan-1,2-diol
1
6. CH2 OH H H H
2 32 1
CH OH Or H -C -C - C - H
3
CH2 OH OH OH OH
Propan -1,2,3-triol

53
4.6 ALKANOIC ACIDS
This is formed by replacing the final –e of the name of the alkane
having the same number of carbon atom
ALKANOIC
O
1. 3CH3 - 2CH - 1C
H
Propanoic acid
O
2. 4CH3 - 3CH2 - 2CH2 - 1C
OH
Butanoic acid
1
3. COOH
Ethanedioic acid
2
COOH
2 1
4. H - C - COOH
H - 3C - 4COOH
Cis-butenedioic acid HCOOH Methanoic acid
5. H CH3COOH Ethanoic acid
HO - 2C - 1COOH
3 4
HO - C - COOH CH3 CH2 COOH Propanoic acid
H
2,3 - dihydroxylbutanedioic acid
CH3 CH2 CH2 COOH Butanoic acid
e.t.c
6. H
H - 1C - COOH
HO -2C - COOH
H - 3C - COOH
H
2-hydroxypropan - 1,2,3-tricarboxylic acid

7. COOH
OH
2 - hydroxylbenzoic acid

8. COOH

Benzoic acid

H O
3
9. CH3CH(CH3) COOH Or CH3 2C - 1C
Ch3 OH
2 - methylpropanoic acid

54
4.7 ALKANOATES
In naming these, the alky group is named first followed by the
name of an alkanoic acid with a –oate ending as the suffix.

1. HCOOCH3 Methyl methanoate

2. H COOC 2H5 Ethyl methanoate
3. CH3COOCH3 Methyl ethanoate
4. CH3COOC2 H5 Ethyl ethanoate
5. CH3 COOCH 2CH2CH3 Propyl ethanoate
6. CH3 CH2 COO CH3 Methyl propanote

4.8 ALKANAL (Aldehyde)

The members of the series are named by replacing the –ane
ending of alkane with –al.
1. H H H
H -1C = O Or C=O Or H- C
methanal H O

2. H Or H H
2
CH3 -1C = O
1 2 1
C=O Or CH3 - C
2
Ethanal CH3 O

H H
3. 4CH3 3CH2 2CH2 - 1C = O Or 1
C=O
2
C H
Butanal 4
CH
3
3
CH 2

H H H
1
4. C=O Or C=O Or C
Phenylmethanal O

H H
5. 3CH3 2CH2 1C = O Or C=O
2
H2
propanal 3
CH 3 C

H
6. 5CH3 4CH2 3CH2 2CH2 1C = O
Pentanal
Or
H
5
CH3 4CH2 3CH2 2CH2 1C
O
55
4.9 ALKANONE (Ketone)
The members of this are named by replacing alkanes by the suffix –on

O O
1. 5CH3 - 4CH2 - 3CH2 - 2C - 1CH3 Or 5CH3 - 4CH2 - 3CH2 - 2C
Pentan-2-one CH3
O O
1 2 3 4 5 1 2 3
2. CH3 - CH2 - C - CH2 - CH3 Or CH3 - CH2 - C
4
Pentan-3-one CH2 5CH3
O
3. 1CH3 - 2C - 3CH2 - 4CH3 Or 1
CH3 - 2C
O CH3
Butan-2-one
O O
3 2 1 3 2
4. CH3 - C - CH3 Or CH3 - C
1
Propan-2-one CH3

4.10 AMIDES
They are determined by the presence of the functional
carboxamide group.
O O
1. H - C 4. 4
CH3 3CH2 2CH2 - 1C
NH2
NH2
Methanamide
Butanamide
O
2 1
2. CH3 - C O
NH2 5. 5CH3 4CH2 3CH2 2CH2 1
C
Ethanamide NH2
Pentanamide
O O
3. CH3 CH2 - C 6 5 4 3 2 1
6. CH3 CH2 CH2 CH2 CH2 C
NH2
Hexanamide NH2
Propanamide

56
4.11 AMINES
They are characterized by the presence of the functional amino group, -
NH2. There are three classification of amines – primary, secondary and
tertiary according to the number of substituted by hydrogen atoms.
AMINES
H R R
R - N Or R1- N - H R1- N - R11
H
Primary Amine Secondary Amine Tertiary Amine

EXAMPLE
H H
1
1. CH3 N 4. 3CH3 2CH2 1
CH2 N
H H
Methylamine Propylamine

H H
2
2. CH3 1CH2 N 5. 5CH3 4CH2 3CH 2CH2 1CH2N
Ethylamine H Pentylamine H

3. NH2 H H
Or N 6. CH3 CH2 CH2 CH2 CH2 CH2 N
H H
Phenylamine Or Aniline Hexylamine

4.12 NITRILES

2 1 3. 4CH33CH22CH21C N
1. CH3 - C N Butanitrile
Ethanenitriles
4. 5CH3 4CH2 3CH2 2CH2 1C N
Pentanitrile
2. 3CH32CH21C N
6 5 4 3 2 1
Propanenitrile 5. CH3 CH2 CH2 CH2 CH2 C N
Hexanenitrile
57
4.13 ETHERS
They are organic compounds whose structure has the
general form.
R1 – O – R2
Where “R1” and “R2” represents organic radicals, usually carbon
chains.
R1 = R2 (Symmetrical ether)
R1 ≠R2 (Unsymmetrical ether)

1. CH3 - O - 1CH3 6. 2CH31CH2 - O - 3CH22CH21CH3

Methoxymethane Ethoxypropane

2. CH3 - O - CH2CH3 2 1 4
7. CH3 CH - O - CH2 CH2 CH2 CH3
3 2 1

Methoxyethane
Ethoxybutane

3. CH3 - O -3CH22CH21CH3
Methoxypropane 8.3CH32CH21CH2- O-3CH2 2CH2 1CH3
Propoxypropane
4. CH3 - O - 5CH24CH23CH22CH21CH3 3 2 1 4
9. CH3 CH2 CH2 - O - CH2 CH2 CH2 CH3
3 2 1

Methoxypentane
Propoxy butane
3 2 1 5 4 3 2 1
5. 2CH31CH2-O-2CH2 1CH3 10. CH3 CH2 CH2-O- CH2 CH2 CH2 CH2 CH3
ethoxyethane Propoxypentane

4.14 CYCLOALKANES
CH2 CH2
or
H2C CH2 H2C CH2
Cyclopropane H2C
H2C CH2 CH2
Or Cyclohexane
H2 C CH2

H 2C CH2 Cyclohex2 ane

Cyclobutane CH
Cyclobutane H2C CH2
CH2 H2C CH2
H2C CH2 H2C CH2
H2C CH2
Cyclopentane
Cycloheptane

58
 MORE EXAMPLES OF ALKANONES AND
ALKANOIC ACIDS

ALKANONE
O O
6 5 4 3 2 1 6 5 4 3 2
CH3 CH2 CH2 CH2 - C - CH3 Or CH3 CH2 CH2 CH2 - C
1
Hexan - 2- one Ch3
O O
7
CH3 6CH25CH24CH2 3CH2 -2C- 1CH3 Or 7
CH3 6CH2 5CH2 4CH2 3CH2 2C
1
Heptan-2-one CH3
O O
5 4 3 2 1 5 4 3
CH3 CH2- C- CH2 CH3 Or CH3 CH2 - C
2 1
Pentan - 3- one CH2 CH3
O O
6 5 4 3 2 1 6 5 4 3
CH3 CH2 CH2 - C - CH2 CH3 Or CH3 CH2 CH2 - C
2 1
Hexan - 3 - one CH2 CH3
O O
7
CH3 6CH2 5CH2 4CH2 - 3C- 2CH2 1CH3 OR 7
CH3 6CH2 5CH2 4CH2 - 3C
2 1
Heptan - 3 - one CH2 CH3

ALKANOIC ACIDS
O O
5
3
CH32CH12C CH34CH23CH22CH21C
Propanoic acid OH Pentanoic acid OH

O O
6
4
CH3 3CH2 2CH2 1C CH35CH24CH23CH22CH21C
Butanoic acid OH Hexanoic acid OH
O
4
CH3 3CH2 2CH2 1C
Butanoic acid OH

59
Success comes when opportunities meet PREPAREDNESS. When opportunities come, it
becomes too late to prepare.
General Practice Questions (with Answers in Bold Letters)
1 The reaction between ethanoic acid and sodium hydroxide is
an example of A. esterification B. neutralization C.
hydroxylation D. hydrolysis
2 The label on a reagent bottle containing a clear organic
liquid dropped off. The liquid was neutral to litmus and
gave a colourless gas with metallic sodium. The liquid must
be an. A. alkanoate B. alkene C. alkanol D. alkane
3 When excess ethanol is heated to 145oC in the presence of
concentrated H2SO4 the product is A. ethyne B. diethyl
sulphate C. diethyl ether D. acetone
4 Organic Chemistry is the branch of Chemistry that deals
with ------- and -------A. Hydrogen & oxygen B. Carbon
& Carbon C. Carbon & Sulphur D. Carbon & Hydrogen
5 The principal constituents of natural gas is A. methane B.
ethane C. propane D. butane
6 Cotton is almost pure A. starch B. protein C. animal
fibre D. cellulose
7 Organic molecules that have the suffix-ene are unsaturated
hydrocarbons that have A. a single bond B. double
bond C. a triple bond D. an ionic bond
8 Which of the following is not a member of the homologous
series of the paraffins?A. C3H8 B. C5H12 C. C15H32
D. C24H48
9 Palm wine turns sour with time because A. the sugar
content is converted into alcohol B. the CO2 formed
during the fermentation process has a sour taste C. it
is commonly adulterated by the tappers and sellers
60
 D. microbiological activity results in the production of organic
acids within it.
10 Alkanals can be differentiated from alkanones by reaction
with A. 2, 4 – dinitrophenylhydrazine B. hydrogen cyanide
C. sodium hydrogen sulphite D. Tollen's reagent
11 Catalytic hydrogenation of benzene produces A. an
aromatic hydrogenation B. margarine C. cyclohexane
D. benzene
12 Esterification of propane-1, 2, 3-triol and unsaturated
higher carboxylic acids will produce. A. fats B.
soap C. alkanols D. ester
13 Which of the following types of reactions takes place
between C2H4 and the halogens? A. Substitution B.
Addition C. polymerization D. Oxidation
14 The IUPAC names for the compounds CH3COOH and
CH2 = CH2 are respectively; A. acetic acid and ethane
B. ethanoic acid and ethene C. methanoic acid and
ethylene D. acetic acid and ethane
15 The flume used by welders in cutting metal is A. butane
flames B.acetylene flame C. kerosene flame D. oxy
acetylene flame E. oxygen flame
16 Consecutive member is an alkane homologous series
differ by A. CH B. Ch2 C. CH3 D. CnH2 E. CnH3n
17 The cracking process is very important in the petroleum
industry because it A. Gives pure products B. yield more
lubricant C. yield more engine fluid D. yield more
asphalt E. yields more candle wax
18 Alkaline hydrolysis of naturally occurring fats and oil
yields A. fats and acid B. soap and glycerol C.

61
 19 Which of the following is used as 'anti-knock' in automobile
engines? A.tetra methyl amine B. lead tetra ethyl C.glycerol
D. n-heptanes
20 Which of the following compound is NOT formed by the
action of chlorine on methane A. CH3Cl B. C2H3Cl
C. CH2Cl2 D. CHCl3
21 Local black soap is made by boiling palm oil with liquid
extract of wood ash. The function of the ash is to provide the
A. acid B. ester C. alkali D. alkanol E. common salt
22 Which of the following is not a natural occurring polymer?
A. starch B. cellulose C. 2-methylbuta-1,3-diene D. wool
E. styrene
23 The alkanol obtained from the production of soap is A.
ethanol B. glycol C. methanol D. gycerol E.propanol
24 The following are miscible with water except A. ethyl
ethanoate B. methanol C. ethanoic acid D.methanoic
acid E. ethanol.
25 Hydrolysis of ethyl ethanoate with dilute mineral acids
yields A. methanol and water B. ethanol and ethanoic
acid acid C. methyl ethanoate and ethanol D. glycerol
and water E. water and salt only.
26 The reducing property of glucose is due to the presence of
A. OH B. COOH C. CHO D. CH2OH E. C=O

62

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