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SIMPLIFIED APPROACH

TO

ORGANIC CHEMISTRY
FOR

SENIOR SECONDARY SCHOOLS

ADEKANMI SOLAPE MUYIWA


NCE – Biology/Chemistry
B.Sc.Ed Chemistry
M.Sc in view Chemistry
08036642075, 08029057683

CROWNTURN PRESS
LAGOS, NIGERIA
ADEKANMI, S.M © 2019

All Right Reserved

ISBN:

CONTACT: 08036642075, 08029057683

CROWNTURN PRESS
LAGOS, NIGERIA
PREFACE

Chemistry Students have been observed to be having problem in organic


chemistry, although many do perform much better when it comes to inorganic
chemistry. The reason for this have been traced to lack of basic understanding of
organic chemistry.
ACKNOWLEDGEMENT

The timidity of omniscience is the commencement of sagacity. I give glory to God

who is the beginning and the end of all things. He is the giver of knowledge, who has

given me knowledge and wisdom with providence and guidance to wtite this book.

It is with burning desire to appreciate the effort of my parents for their effort

both directly and indirectly towards my success in life. I pray, Almighty God guide

them and continue to provide for them.

I then wish to express my sincere gratitude to my dearly wife, for her

perseverance, kindness and advice through it all. I pray almighty God continue to be

with her.

“Prosperity will surely bring friends but adversity will prove them” It is

with genuine intention to consolidate on the effort of all my friends, the spirit of

unionism continue to be with you.

ADEKANMI SOLAPE MUYIWA

JULY 2019.
DEDICATION
This book is honourably dedicated to my children.

Desire

Desola

Desayo

Also to the integral sample of my past, present and upcoming


students.
CONTENT
PAGE
CHAPTER ONE – INTRODUCTION
1.00 Introduction
1.01 Hybridization in carbon
1.02 Functional groups in organic compounds
1.03 Uniqueness of carbon
1.04 Hydrocarbons
1.05 Types of hydrocarbon
1.06 Class of hydrocarbon
1.07 Group of hydrocarbon
1.08 Cracking/Pyrolysis in petroleum
1.09 Reforming in petroleum
1.10 Homologous series
1.11 General Characteristics of homologous series
1.12 Isomerism
1.13 Types of isomerism
1.14 Structural isomerism
1.15 Stereo isomerism

CHAPTER – ALKANES
2.01 Saturated hydrocarbon – alkanes
2.02 Naming of alkanes
2.03 Molecular structures of alkanes
2.04 Alkyl group
2.05 Nomenclature of alkanes
2.06 Laboratory preparation of methane
2.07 physical properties of alkane
2.08 Chemical Properties alkane
2.09 Uses of Alkane

CHAPTER THREE – ALKENES


3.01 Unsaturated hydrocarbons – alkenes
3.02 Naming of alkenes
3.03 Molecular structure of alkenes
3.04 Nomenclature of alkenes
3.05 Laboratory preparation of ethene
3.06 Physical Properties of ethene
3.07 Chemical properties of ethene
3.08 Uses of ethene

CHAPTER FOUR – ALKYNES


4.01 Unsaturated hydrocarbon – alkynes
4.02 Naming of Alkynes
4.03 Molecular structures of alkynes
4.04 Nomenclature of alkynes
4.05 Laboratory preparation of ethyne
4.06 Physical properties of ethyne
4.07 Chemical properties of ethyne
4.08 Uses of ethyne
4.09 Chemical test to distinguished between alkanes, alkenes and alkynes
CHAPTER FIVE – AROMATIC HYDROCARBON (BENZENE)
5.01 Aromatic hydrocarbon – benzene
5.02 The structure of benzene
5.03 Nomenclature of aromatic compounds
5.04 Physical Properties of benzene
5.05 Chemical Properties of benzene
5.06 Uses of benzene

CHAPTER SIX - ALKANOLS


6.01 Alkanols
6.02 Naming of alkanols
6.03 Molecular structure of alkanols
6.04 Nomenclature of alkanols
6.05 Types of alkanols
6.06 Classes of alkanols
6.07 Laboratory preparation of ethanol
6.08 Preparation of ethanol from sweet potato
6.09 Physical properties of alkanols
6.10 Chemical properties of alkanols
6.11 Test of alkanolsl
6.12 Use of alkanols

CHAPTER SEVEN - EMPIRICAL AND MOLECULAR FORMULAE


7.01 Determination of empirical and molecular formulae structure of organic compounds

CHAPTER EIGHT - ALKANOIC ACIDS


8.01 Alkanoic acids
8.02 Naming of alkanoic acid
8.03 Molecular structure of alkanoic acids
8.04 Nomenclature of Alkanoic acid
8.05 Physical properties of alkanoic acids
8.06 Chemical properties of alkanoic acids
8.07 Laboratory Preparation of ethanoic acid
8.08 Uses of ethanoic acid
8.09 Test for alkanoic acids

CHAPTER NINE - ALKANOATES


9.01 Alkanoates
9.02 Naming of alkanoates
9.03 Molecular Structure of Alkanoates
9.04 Physical properties of ethyl ethanoate
9.05 Chemical properties of ethyl ethanoate
9.06 Laboratory preparation of ethyl ethanoate
9.07 Uses of ethyl ethanoate
9.08 Fats and oils
9.09 Properties of Fats
9.10 Properties of Oils
9.11 Difference between Fats and Oils
9.12 Importance of Fats and Oils
9.13 Test for Fats and Oils
9.14 Soaps - saponification
9.15 Detergents
9.16 Advantages of soap
9.17 Disadvantages of soap
9.18 Advantage of detergent
9.19 Disadvantages of detergent
9.20 Margarine
9.21 Advantages of margarine over butter

CHAPTER TEN – AMINO ACIDS


10.01 Amino acids
10.02 Nomencalture of amino acids
10.03 preparation of amino acids
10.04 Physical properties of amino acids
10.05 Chemical properties of amino acids
10.06 Protein and sources
10.07 Properties of protein
10.08 Test for protein
10.09 Importance of protein

CHAPTER ELEVEN – AMINES


11.01 Amine
11.02 Classification of Amine
11.03 Laboratory Preparation of Amine
11.04 Indutrial Preparation of Amine
11.05 Physical Properties of Amine
11.06 Chemical Properties of Amine
11.07 Uses of Amine
11.08 Amides
11.09 Preparation of Amides
11.10 Physical Properties of Amides
11.11 Chemical Properties of Amides

CHAPTER TWELVE – POLYMERIZATION


12.01 Polymerization
12.02 Polymer
12.03 Characteristics of Polymers
12.04 Natural occurring polymers
12.05 Synthetic polymer
12.06 Disadvantages of synthetic polymer
12.07 Classes of polymers
12.08 Addition polymers
12.09 Condensation polymers
12.10 Plastics

CHAPTER THIRTEEN CARBOHYDRATES


13.01 Carbohydrates
13.02 Classes of carbohydrates
13.03 General feature of carbohydrates
13.04 Glucose
13.05 Laboratory preparation of glucose
13.06 Industrial Preparation of glucose
13.07 Properties of glucose
13.08 Test for glucose
13.09 Uses of glucose
13.10 Fructose
13.11 Disaccharide
13.12 Sucrose
13.13 Preparation of sucrose
13.14 Physical properties of sucrose
13.15 Chemical properties of sucrose
13.16 Test for sucrose
13.17 Uses of sucrose
13.18 Maltose
13.19 Physical properties of maltose
13.20 Lactose
13.21 Properties of lactose
13.22 Polysaccharide
13.23 Preparation of srarch
13.24 Properties of starch
13.25 Test for starch
13.26 Uses of starch
13.27 Cellulose
13.28 Properties of cellulose
13.29 Uses of cellulose
13.30 Garri Production

Test for protein, starch, sugar, and fats and oils

Objectives questions
CHAPTER ONE
1.01 INTRODUCTION
Organic chemistry can be define as the composition, properties, uses and changes that carbon undergo
during a chemical reaction. Organic chemistry is one of the major branches of chemistry that deals with
the chemistry of carbon compound. Unlike inorganic compounds that were obtained from minerals
underneath the earth crust, organic compounds were those obtained from vegetable or animal sources,
that is from materials produced by living organisms. Compounds from organic sources have a common
feature which is that they all contained the element carbon.

Organic chemistry therefore, is a field of immense importance to technology, it is the chemistry of dyes
and drugs, paper and ink, paints and plastics, gasoline and rubber tyres, and above it all, it is the
chemistry of the food we eat and the clothing we wear.

It is therefore imminent that all organic compound contain carbon with also one or more other
elements such as hydrogen, oxygen, chlorine, bromine, nitrogen and many others.

1.01 HYBRIDIZATION IN CARBON


Carbon belongs to group four in the periodic table of elements. The atomic number of carbon is
six and its electronic configuration is written as:

1S2, 2S2, 2P2


2P2

2S2

1S2

In all organic compounds, carbon exercise a covalency of four. This is obtained by unpairing the paired
2S orbital electrons and promoting this to the empty 2Pz orbital to give the excited state configuration.
Thus, we can distinguish between the ground and excited state configurations:
Ground State configuration

2P2

2S2

1S2

Excited Sate Configuration:

2S 2P

1S2

It is the mixture of these four orbitals in the excited state (2S and three 2P) containing an electron each
that gives carbon its tetravalency in all organic compounds.
The mixing of atomic orbitals to form equivalent molecular orbital is called hybridization. The product of
hybridization are called hybrid or molecular orbitals which are of equivalent energies. Three modes of
hybridization have been identified in carbon.
These are Sp3, Sp2 and Sp.

Sp3 Hybridization
In this type, one 2S atomic orbital is mixed with three 2P orbitals to form four Sp 3 hybrid orbitals, in
which each orbital is pointing towards a corner of a regular tetrahedron shape. The bond angle is 109.5 0.
when these orbitals are used in bonding, they form very strong bonds called sigma bonds.

This type of hybridization is found in all saturated compounds, for example as in all Alkanes. Let take
ethane (C2H6) as an example (the four hybrid orbitals are displayed on each carbon atom as well as the
S-orbital of hydrogen atoms)

Sp2 Hybridization
In Sp2 hybridization, one 2S atomic orbital is mixed with two of the three 2P orbitals to form four Sp 2
hybrid orbitals, which is triangular in shape with a bond angle of 1200. when these orbitals are used in
bonding, they form very strong bonds called sigma bonds. However the unused 2Pz orbital can overlap
laterally to form another bond which is weaker than sigma bond. It is called a Pi bond. These two bonds
(Sigma and Pi) give compound containing 2P2 hybrized carbon atoms double bonds. This type of
hybridization is found in all Alkenes. Example ethene (C2H4).
Sp Hybridization
In Sp hybridization, one 2S atomic orbital is mixed with one of the three 2P orbitals to form four Sp
hybrid orbitals, which is linear in shape with a bond angle of 1800. when these orbitals are used in
bonding, they form very strong bonds called sigma bonds. However the unused 2Py and 2Pz orbital can
overlap laterally to form another bonds which is weaker than sigma bond. It is called a Pi bond. These
bonds (Sigma and two Pi) give compound containing 2P hybrized carbon atoms triple bonds. This type of
hybridization is found in all Alkynes. Example ethyne (C2H2).
1.02 FUNCTIONAL GROUPS IN ORGANIC COMPOUNDS
Functional group is an atom or group of atoms which determines the characteristics chemical
properties of a particular class of organic compound. The chemistry of organic compounds is simply the
chemistry of various functional groups in their structures. These functional groups are sites were most
chemical reaction take place during a chemical change. They confer the different characteristics on
organics compounds.
The table below shows the various functional groups and the compounds in which they occur.

Group of organic compound Functional group Suffix


Alkyl -C- (Carbon – carbon single bond) yl
Alkanes -C- (carbon – carbon single bond) -ane
Alkenes -ene
C=C (Carbon – carbon double bond)

Alkynes -C≡C- (Carbon – carbon triple bond) -yne


Alkanols R – OH -ol
Alkanals (Aldehydes) O -al
R–C
H
Alkanones (Ketones) O -one
R-C
R
Alkanoic Acid (Carboxylic) O -oic
R–C
OH
Alkanoates (esters) O -oate
R–C
OR
Ethers R – O – R’
Primary Amines R – NH2
Carbon – nitrile R–C≡N
Cyano group R – CH

NOTE: In the IUPAC nomenclature, the lowest possible numbers are assigned to these functional groups
in the compounds containing them.

1.03 UNIQUENESS OF CARBON


It is clearly known that all organic compounds contain carbon, this is because carbon shows the
following exceptional chemical behaviours in relation to other chemical elements:
(a) It has valency of four, hence each carbon atom has a maximum combining capacity of four and it
can form chemical bonds with four other atoms of carbon or hydrogen and of other elements in
its compounds. This then shows that carbon atoms can attach themselves to other elements to
an extent not possible for atoms of any other elements.
(b) Carbon can form both simple and complex chains thousands of atoms long, or rings of all sizes
which are attached to other atoms, chiefly hydrogen, but also fluorine, chlorine, bromine, iodine,
oxygen, nitrogen and many others. The ability to form chains of identical atoms is called
CATENATION.
(c) Carbon is chemically stable in that when it is covenlently bonded, it has neither vacant orbital
nor lone pair of electron
(d) Carbon forms three types of orbital hybridization which are Sp 3, Sp2 and Sp.

1.04 HYDROCARBONS
Generally, organic compounds that contain only two elements of carbon and hydrogen are known as
Hydrocarbons. In other words, hydrocarbon may be referred to as organic compound containing
elements of carbon and hydrogen only. This then shows that organic compounds containing elements
other than carbon and hydrogen are not hydrocarbons, but may fall into classes of organic compounds.
A hydrocarbon therefore has a general molecular formular of CXHy where x and y are whole numbers, i.e
1,2,3,4 e.t.c.

1.05 TYPES OR CATEGORIES OF HYDROCARBONS


Hydrocarbons fall into two main categories:
1. Aliphatic Hydrocarbon
2. Aromatic Hydrocarbon

ALIPHATIC HYDROCARBONS: These are hydrocarbons containing chains of carbon atoms i.e open chain
compounds e.g CH3CH2CH2CH2CH3.
TYPES OF ALIPHATIC HYDROCARBONS
I. ACYCLIC HYDROCARBON: These are carbon to carbon chain molecule e.g Alkanes, Alkenes and Alynes
II. CYCLIC HYDROCARBONS: These are made up of carbon atoms arrange in rings

OR C
Cyclopropane
C C

OR C C
Cyclobutane
C C

C
C C
OR Cyclopentane
C C

OR C C Cyclohexane

C C

2. AROMATIC HYDROCARBONS: These are special group of cyclic compounds. In most cases they
contain six carbon atoms arranged in rings with alternate single and double bonds.
An example of aromatic hydrocarbon is benzene (C6H6)

C C

OR C C OR C C

C C C C

C C
Resonance Structure of Benzene.

HYDROCARBON

Aliphatic Aromatic (e.g Benzene)

Acyclic Cyclic

Alkane Alkene Alkyne Cyclopropane Cyclopentane Cyclohexane


1.06 CLASSES OF HYDROCARBONS
Hydrocarbons fall into three main classes with general molecular formulae given below:

HYDROCARBON GENERAL
MOLECULAR
FORMULAR
ALKANES CnH2n+2
ALKENES CnH2n
ALKYNES CnH2n-2

1.07 GROUPS OF HYDROCARBONS


Hydrocarbons can be group into two which are
(i) Saturated Hydrocarbons
(ii) Unsaturated Hydrocarbons
SATURATED HYDROCARBONS
A saturated hydrocarbon is one in which is joined carbon to carbon or molecule to molecule by a single
covalent bond, hence there is no space for further attachment of other atoms. In saturated
hydrocarbons, ech carbon exercise its maximum combining capacity with four other atoms of carbon or
hydrogen. For example, all members of the Alkane family, that is CH4, C2H6, C3H8 and so on are all
saturated hydrocarbons.
UNSATURATED HYDROCARBONS
An unsaturated hydrocarbon is one in which is joined carbon to carbon or molecule to molecule by a
double or triple covalent bond, in these hydrocarbons, the maximum capacity of carbon is not fully
utilised in combining with carbon or hydrogen, hence there is space for further attachment of other
atoms. All members of the Alkenes (C2H4, C3H6, C4H8 etc) and all alkynes (C2H2, C3H4, C4H6 etc) families
are unsaturated hydrocarbons.
1.08 CRACKING/PYROLYSIS IN PETROLEUM
When a higher alkanes are heated to high temperatures, their molecules vibrate strongly enough to
break bonds and form smaller molecules, one of which is alkene. Cracking is referred to as pyrolysis.
Cracking therefore is the breaking down of higher alkanes into smaller alkanes and alkenes. For
example, Octane under pyrolysis to give hexane (alkane) and ethene (alkene).
C8H18 C6H14 + C2H4
Octane Hexane ethene
Another example is that of undecane which undergoes pyrolysis to give nonane and ethene
C11H24 C9H20 + C2H4
Undecane nonane ethene
Cracking could be thermal or catalyst. In thermal cracking, the petroleum is subjected to a high
temperature and high pressure while in catalytic cracking, a catalyst, at very low temperature and
atmospheric pressure are used. The catalyst used in this case is a mixture of silicon(iv)oxide (SiO 2) and
aluminium oxide (Al2O3).
ADVANTAGES OF CRACKING
1. It yield large amount of useful by-product such as benzene.
2. It increases the yield of petrol from petroleum.
IMPORTANT OF CRACKING
1. It provide extra gasoline (petrol)
2. as a source of alkanes.
1.09 REFORMING IN PETROLEUM
This is when two smaller molecules of alkanes join to form a heavy one.
1.10 HOMOLOGOUS SERIES
Homologous series are group of compounds in which each member differ from the next by an addition
of –CH2- . for example. In the successive series of alkanes, methane (CH4) differs from ethane (C2H6) by
an addition of CH2, the same also apply to ethene(C2H4) and propene (C3H6) in Alkene and so on.
NOTE: Homologous series occur in Alkanes, Alkenes, Alkynes, Alkanols, Alkanoic acid and
carbohydrates.
1.11 GENERAL CHARACTERISTICS OF HOMOLOGOUS SERIES
Homologous series have the following characteristics:
(i) All members of the series have a general molecular formular e.g for Alkanes –CnH2n+2,
Alkenes –CnH2n, Alkynes –CnH2n-2
(ii) Each member differ from the next by –CH2- in molecular formular e.g in alkanes –CH4, C2H6,
C3H8, C4H10 and so on.
(iii) All members show similar chemical reactions e.g hydrocarbons react with oxygen to form
carbon (IV) oxide and water e.g.
CH4 + 2O2 CO2 + 2H2O
C2H4 + 3O2 2CO2 + 2H2O
2C2H2 + 5O2 4CO2 + 2H2O
(iv) The physical properties of members change gradually in the same direction along the series
e.g in alkanes, methane is CH4 is gas, pentane –C5H12, is liquid and C20H42 is solid.
(v) There have the same general methods of preparation. E.g any member of the alkanes family
can be prepared by the hydrogenation of the corresponding alkenes in the presence of Nickel
or platinum as a catalyst
CH2=CH2 CH3CH3.

1.12 ISOMERISM IN ORGANIC COMPOUNDS


Isomerism is defined as the existence of two or more compounds having the same molecular formular
but different molecular structures. The different molecular structures also made them have different
physical and chemical properties.

1.13 TYPES OF ISOMERISM


(i) Structural isomerism
(ii) Stereo Isomerism
1.14 (I) STRUCTURAL ISOMERISM
The occurrence of two or more compounds with the same molecular formular but different molecular
structures is known as structural isomerism.
TYPES STRUCTURAL ISOMERISM
(a) Chain isomerism: in this case, the isomer differ in the way the carbon atoms are arranged in the
molecule
e.g CH3CH2CH2CH3 CH3CHCH3
n-butane CH3
2-methylpropane (isobutne)
(‘n’ stands for normal compound while ‘iso’ means an isomer of the normal compound).
Also, n-pentane, 2-methylbutane and 2,2-dimethylpropane all have the same molecular formular, C5H12,
but different molecular structures.
CH3
CH3CH2CH2CH2CH3 CH3CHCH2CH3 CH3-C-CH3
n-pentane CH3 CH3
2-methylbutane 2,2-dimethylpropane
NOTE: In alkanes, isomerism starts from butane, hence it cannot take place in methane, ethane and
propane.
(b) position isomerism: Position isomers are those that have a substituent in different position on the
same carbon skeleton
e.g. CH3CH2CH2OH CH3CHCH3
propan-1-ol OH
propan-2-ol
(c) Functional Group isomerism: These are isomers having the same molecular formular but different
functional groups. They belong to different homologous series.
e.g.
H
(i) CH3CH2C CH3-CHCH3
O O
Propanal propan-2-one
(ii) CH3CH2OH CH3-O-CH3
Ethanol Methoxymethane
(dimethylether)
1.15 (II) STEREO ISOMERISM
In this type of isomerism, compounds have the same molecular formular but differ only in the way their
atoms are arranged in space.
TYPES STEREO ISOMERISM
(a) Geometrical isomerism: This type of isomerism is found in compounds having either a double bond,
triple bond or a ring structure. These multiple bonds prevent the free rotation of one carbon atom
relative to the other. There are two forms of geometric isomers, the Cis and Trans isomer. For example,
but-2-ene has two geometric isomer which are trans-but-2-ene and cis-but-2-ene as shown below.
H CH3 H H
C=C C=C
CH3 H CH3 CH3
Trans-but-2-ene Cis-but-2-ene

H Br H H
C=C C=C
Br H Br Br
Trans-1,2-dibromoethene Cis-1,2-dibromoethene

H COOH COOH COOH


C=C C=C
COOH H H H
Trans-butenedioic acid Cis-butenedioic acid
(b) Optical isomerism: These isomers have the same molecular and structural formular but cannot be
superimposed on each other. In other words, an optical isomer is one which is not super-imposable on
its mirror image. The essential feature is that an optical isomer has at least one carbon atom to which
four different groups or atoms are attached. Such a carbon atom is called chiral carbon or chiral centre.
E.g. 2-hydroxylpropanoic acid (Lactic acid).

CH3
The asterisked carbon (*C) is the
*C—H chiral carbon because four different
Groups or atoms are attached to it.
HO COOH
In glucose, there are several chiral carbon atoms.
CHAPTER TWO
2.01 SATURATED HYDROCARBON – ALKANES
Alkanes are saturated hydrocarbons which are generally referred to as PARAFFINS with a single bond. It
has a functional group of –C-C- and belongs to homologous series with a general molecular of CnH2n+2,
where n= 1,2,3,4 ……. For successive members of the group. The first - four member of the group are
gas, fifth – eighteen are liquid, and nineteen upwards are solid at room temperature. Natural gas
obtained from petroleum well is a good source of alkanes and it consists mainly methane.
2.02 NAMING OF ALKANES
The names of Alkanes family are derived by applying the general molecular formulae CnH2n+2 for each
member in the series.
When General Molecular Name
n= Formulae CnH2n+2
1. C1H2x1+2 = CH4 Methane
2. C2H2x2+2 = C2H6 Ethane
3. C3H2x3+2 = C3H8 Propane
4. C4H2x4+2 = C4H10 Butane
5. C5H2x5+2 = C5H12 Pentane
6. C6H2x6+2 = C6H14 Hexane
7. C7H2x7+2 = C7H16 Heptane
8. C8H2x8+2 = C8H18 Octane
9. C9H2x9+2 = C9H20 Nonane
10. C10H2x10+2 = C10H22 Decane
11. C11H2x11+2 = C11H24 Undacane
12. C12H2x12+2 = C12H26 Dodecane
13. C13H2x13+2 = C13H28 Tridecane
14. C14H2x14+2 = C14H30 Tetradecane
15. C15H2x15+2 = C15H32 Pentadecane
16. C16H2x16+2 = C16H34 Hexadecane
17. C17H2x17+2 = C17H36 Heptadecane
18. C18H2x18+2 = C18H38 Octadecane
19. C19H2x19+2 = C19H40 Nonadecane
20. C20H2x20+2 = C20H42 Icosane/Eiocosane
21. C21H2x21+2 = C21H44 Heneicosane
22. C22H2x22+2 = C22H46 Docosane
23. C23H2x23+2 = C23H48 Tricosane
24. C24H2x24+2 = C24H50 Tetracosane
25. C25H2x25+2 = C25H52 Pentacosane
26. C26H2x26+2 = C26H54 Hexacosane
27. C27H2x27+2 = C27H56 Heptacosane
28. C28H2x28+2 = C28H58 Octacosane
29. C29H2x29+2 = C29H60 Nonacosane
30. C30H2x30+2 = C30H62 Triacontane
31. C31H2x31+2 = C31H64 Hentriacontane
32. C32H2x32+2 = C32H66 Dotriacontane
33. C33H2x33+2 = C33H68 Tritriacontane
34. C34H2x34+2 = C34H70 Tetratriacotane
35. C35H2x35+2 = C35H72 Pentatriacontane
36. C36H2x36+2 = C36H74 Hexatriacontane
37. C37H2x37+2 = C37H76 Heptatriacotane
38. C38H2x38+2 = C38H78 Octatriacontane
39. C39H2x39+2 = C39H80 Nonatriacontane
40. C40H2x40+2 = C40H82 Tetracontane
41. C41H2x41+2 = C41H84 Hentetracontane
42. C42H2x42+2 = C42H86 Dotetracontane
43. C43H2x43+2 = C43H88 Tritetracontane
44. C44H2x44+2 = C44H90 Tetratetracontane
45. C45H2x45+2 = C45H92 Pentatetracontane
46. C46H2x46+2 = C46H94 Hexatetracontane
47. C47H2x47+2 = C47H96 Heptatetracontane
48. C48H2x48+2 = C48H98 Octatetracontane
49. C49H2x49+2 = C49H100 Nonatetracontane
50. C50H2x50+2 = C50H102 Pentacontane
51. C51H2x51+2 = C51H104 Henpentacontane
52. C52H2x52+2 = C52H106 Dopentacontane
53. C53H2x53+2 = C53H108 Tripentacontane
54. C54H2x54+2 = C54H110 Tetrapentacontane
55 C55H2x55+2 = C55H112 Pentapentacontane
56. C56H2x56+2 = C56H114 Hexapentacontane
57. C57H2x57+2 = C57H116 Heptapentacontane
58. C58H2x58+2 = C58H118 Octapentacontane
59. C59H2x59+2 = C59H120 Nonapentacontane
60. C60H2x60+2 = C60H122 Hexacontane
61. C61H2x61+2 = C61H124 Henhexacontane
62 C62H2x62+2 = C62H126 Dohexacontane
63. C63H2x63+2 = C63H128 Trihexacontane
64. C64H2x64+2 = C64H130 Tetrahexacontane
65. C65H2x65+2 = C65H132 Pentahexacontane
66. C66H2x66+2 = C66H134 Hexahexacontane
67. C67H2x67+2 = C67H136 Heptahexacontane
68. C68H2x68+2 = C68H138 Octahexacontane
69. C69H2x69+2 = C69H140 Nonahexacontane
70. C70H2x70+2 = C70H142 Heptacontane
71. C71H2x71+2 = C71H144 Henheptacontane
72. C72H2x72+2 = C72H146 Doheptacontane
73. C73H2x73+2 = C73H148 Triheptacontane
74. C74H2x74+2 = C74H150 Tetraheptacontane
75. C75H2x75+2 = C75H152 Pentaheptacontane
76. C76H2x76+2 = C76H154 Hexaheptacontane
77. C77H2x77+2 = C77H156 Heptaheptacontane
78. C78H2x78+2 = C78H158 Octaheptacontane
79. C79H2x79+2 = C79H160 Nonaheptacontane
80. C80H2x80+2 = C80H162 Octacontane
81. C81H2x81+2 = C81H164 Henoctacontane
82. C82H2x82+2 = C82H166 Dooctacontane
83. C83H2x83+2 = C83H168 Trioctacontane
84. C84H2x84+2 = C84H170 Tetraoctacontane
85. C85H2x85+2 = C85H172 Pentaoctacontane
86. C86H2x86+2 = C86H174 Hexaoctacontane
87. C87H2x87+2 = C87H176 Heptaoctacontane
88. C88H2x88+2 = C88H178 Octaoctacontane
89. C89H2x89+2 = C89H180 Nonaoctacontane
90. C90H2x90+2 = C90H182 Nonacontane
91. C91H2x91+2 = C91H184 Hennonacontane
92. C92H2x92+2 = C92H186 Dononacontane
93. C93H2x93+2 = C93H188 Trinonacontane
94. C94H2x94+2 = C94H190 Tetranonacontane
95. C95H2x95+2 = C95H192 Pentanonacontane
96. C96H2x96+2 = C96H194 Hexanonacontane
97. C97H2x97+2 = C97H196 Heptanonacontane
98. C98H2x98+2 = C98H198 Octanonacontane
99. C99H2x99+2 = C99H200 Nonanonacontane
100. C100H2x100+2 = C100H202 Hectane
101. C101H2x101+2 = C101H204 Henihectane
102. C102H2x102+2 = C102H206 Dohectane
110. C110H2x110+2 = C110H222 Decahectane
111. C111H2x111+2 = C111H224 Undecahectane
120. C120H2x120+2 = C120H242 Eiocosahectane

2.03 MOLECULAR STRUCTURES OF ALKANES

N ALKANES STRUCTURAL FORMULAR MOLECULAR FORMULAR


1. H CH4
CH4 H-C -H
Methane H
2. HH CH3CH3
C2H6 H-C-C- H
Ethane HH
3. HHH CH3CH2CH3
C3H8 H-C-C-C-H
Propane HHH
4. HHHH CH3(CH2)2CH3
C4H10 H-C-C-C-C-H
Butane HHHH
5. HHHHH CH3(CH2)3CH3
C5H12 H-C-C-C-C-C-H
Pentane HHHHH
6. HHHHHH CH3(CH2)4CH3
C6H14 H-C-C-C-C-C-C-H
Hexane HHHHHH
7. HHHHHHH CH3(CH2)5CH3
C7H16 H-C-C-C-C-C-C-C-H
Heptane HHHHHHH
8. HHHHHHHH CH3(CH2)6CH3
C8H18 H-C-C-C-C-C-C-C-C-H
Octane HHHHHHHH
9. HHHHHHHHH CH3(CH2)7CH3
C9H20 H-C-C-C-C-C-C-C-C-C-H
Nonane HHHHHHHHH
10. HHHHHHHHHH CH3(CH2)8CH3
C10H22 H-C-C-C-C-C-C-C-C-C-C-H
Decane HHHHHHHHHH
11. HHHHHHHHHHH CH3(CH2)9CH3
C11H24 H-C-C-C-C-C-C-C-C-C-C-C-H
Undecane HHHHHHHHHHH
12. HHHHHHHHHHHH CH3(CH2)10CH3
C12H26 H-C-C-C-C-C-C-C-C-C-C-C-C-H
Dodecane HHHHHHHHHHHH
13. HHHHHHHHHHHHH CH3(CH2)11CH3
C13H28 H-C-C-C-C-C-C-C-C-C-C-C-C-C-H
Tridecane HHHHHHHHHHHHH
14. HHHHHHHHHHHHHH CH3(CH2)12CH3
C14H30 H-C-C-C-C-C-C-C-C-C-C-C-C-C-C-H
Tetradecane H H HH H H H H H H H H H H
15. HHHHHHHHHHHHHHH CH3(CH2)13CH3
C15H32 H-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-H
Pentadecane HHHHHHHHHHHHHHH
16. HHHHHHHHHHHHHHHH CH3(CH2)14CH3
C16H34 H-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-H
Hexadecane HHHHHHHHHHHHHHHH
17. HHHHHHHHHHHHHHHHH CH3(CH2)15CH3
C17H36 H-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-H
Heptadecane HHHHHHHHHHHHHHHHH
18. HHHHHHHHHHHHHHHHHH CH3(CH2)16CH3
C18H38 H-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-H
Octadecane HHHHHHHHHHHHHHHHHH
19. HHHHHHHHHHHHHHHHHHH CH3(CH2)17CH3
C19H40 H-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-H
Nonadecane HHHHHHHHHHHHHHHHHHH
20. HHHHHHHHHHHHHHHHHHHH CH3(CH2)18CH3
C20H42 H-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-H
Eiocosane HHHHHHHHHHHHHHHHHHHH

2.04 ALKYL GROUP


These are groups of alkanes in which one hydrogen atom has been removed from the parent alkanes.
They have a general molecular formulae of CnH2n+1 and are named by replacing the –ane in parent
alkanes with –yl. They are often represented by capital letter R e.g.
When General Molecular Molecular Formulae Name
n= Formulae
CnH2n+1
1. C1H2x1+1 = CH3 CH3 Methyl
2. C2H2x2+1 = C2H5 CH3CH2 Ethyl
3. C3H2x3+1 = C3H7 CH3CH2CH2 Propyl
4. C4H2x4+1 = C4H9 CH3CH2CH2 CH2 Butyl
5. C5H2x5+1 = C5H11 CH3CH2CH2 CH2CH2 Pentyl
6. C6H2x6+1 = C6H13 CH3CH2CH2 CH2CH2CH2 Hexyl
7. C7H2x7+1 = C7H15 CH3CH2CH2 CH2CH2CH2 CH2 Heptyl
8. C8H2x8+1 = C8H17 CH3CH2CH2 CH2CH2CH2 CH2CH2 Octyl
9. C9H2x9+1 = C9H19 CH3CH2CH2 CH2CH2CH2 CH2CH2CH2 Nonyl
10. C10H2x10+1 = C10H21 CH3CH2CH2 CH2CH2CH2 CH2CH2CH2 CH2 decyl
2.05 NOMENCLATURE OF ALKANES
This is a systematic method of naming organic compounds using IUPAC method. In naming organic
compounds the following rules are to be followed.
RULE 1: Select the longest continuous carbon chain in the molecule and use the parent hydrocarbon
name of this chain as the base.
RULE 2: Every branch of the main chain should be considered a substituent derived from another
hydrocarbon e.g CH3 – methyl, CH3CH2- ethyl, and so on.
RULE 3: Number the carbon atoms of the continuous chain so that the substituent occur at the lowest
number possible
RULE 4: Give each substituent a name and number
RULE 5: For identical substituents, use di, tri, tetra, penta, hexa, and so on as applied.
RULE 6: Name the substituents alphabetically
RULE 7: Give the lowest possible number to the functional group.
NOTE: Halogen when they occur in organic compounds are named thus, chlorine = chloro, fluorine =
fluoro, bromine = bromo, iodine = iodo.
When you are asked to write the structure of any organic compound, you should always write the
structure in such a way as to show how all the atoms are boned to each other. E.g write the structure of
2-methyl butane. This should be written as shown below:

HHHH

H-C-C-C-C-H

H HH

H-C-H

H
Following strictly the above rules, one can then name perfectly any organic compound with ease. For
example, in naming the compound below, following the rules
CH3

CH3CH2CH2C-CH2CH3

CH3
In the above structure, there are six carbon atoms in the longest continuous chain. Therefore the parent
hydrocarbon has a name Hexane (RULE 1). There are methyl substituents derived from another
hydrocarbons (RULE 2)

Counting the position of the substituents on the continuous base chain, they both stand on the 4th
carbon atom when counting from left to right, but when counting from right to left, they appear on the
3rd carbon atom, hence the lowest position of 3rd carbon atom is considered (RULE 3)

Since the two substituents are similar, they are named dimethyl (RULE 4), hence the two substituents
have a number and name as 3,3-dimethyl (RULE 5). When this is combined with the parent hydrocarbon
(RULE 1), we obtain the name of the compound as 3,3-dimethylhexane.
Other examples with their names are shown below following the stated rules.
CH3 CH3
(i) CH3-C-CH2-CH-CH3 (ii) CH3CH2CH-CHCH3
CH3 CH3 CH2
2,2,4-trimethylpentane CH3
3,4-dimethylhexane

CH2CH3 CH3
(iii) CH3CH2-C-CH2CH3 (iv) CH3-C-CH3
CH2CH3 CH3
3,3-diethylpentane 2,2-dimethylpropane

CH3 CH3
(v) CH3CH2CHCH3 (vi) CH3—C----C-CH
CH3 CH3 CH3
2-methylbutane 2,2,4-trimethylpentane

(vii) CH3CH2CH—CHCH3 (viii) CH3CH2CHCH3


CH3 CH3 CH3
2,3-dimethylpentane 2-methylbutane

CH3 CH3
(ix) CH3-C-------CH—CH2CH2CH2CH3 (x) CH3CH2CHCH2CHCH2CH2CH3
CH3 CH2CH3 CH2CH3
2,2-dimethyl, 3-ethylheptane 5-ethyl, 3-methyloctane

Cl
(xi) CH3CH2CHCH3 (xii) CH3-C-CH2CH3
Cl Cl
2-chlorobutane 2,2-dichlorobutane

(xiii) CH3CH2CHCH2CHCH3 (xiv) CH3CHCH2CHCH3


Cl Br Cl Cl
2-bromo, 4-chlorohexane 2,4-dichloropentane

Cl Br Cl
(xv) CH3CH2-C-CH2-C-CH3 (xvi) CH3CHCH2-C-CH3
Cl Br Cl Cl
2,2-dibromo, 4,4-dichlorohexane 2,2,4-trichloropentane

CH3 H H CH3 CH3 H H CH3


(xvii) CH3 – C – C – C – C – CH3 (xviii) CH3 – C – C – C – C – CH3
CH2 CH2 CH2 CH2 CH2 CH2 CH2 CH2
CH3 CH3 CH3 CH3 CH2 CH2 CH2 CH2
4,5-diethyl,3,3,6,6-tetramethyloctane CH3 CH3
5,6-diethyl,4,4,7,7-tetramethyldecane
(xix) CH3 – CH2 – CH – CH3

CH2Cl
1-chloro – 2-methylbutane
2.06 LABORATORY PREPARATION OF METHANE (ALKANES)
Methane can be prepared in the laboratory by mixing an equal amount of grounded Sodium ethanoate
(CH3COONa) with soda lime(NaOH) in a hard glass flask. The mixture is then heated for sometime, then a
gas (methane) is evolved and collected over water because it is much less dense than air.
NOTE: When heating is completed, the delivery tube must be removed from water at instant, otherwise,
water may be forced back into the hot flask and cause an explosion. Soda lime acts as a source of
sodium hydroxide.

EQUATION FOR THE REACTION


CH3COONa(s) + NaOH(s) Na2CO3(s) + CH4(g)
Methane

2.07 PHYSICAL PROPERTIES OF METHANE (ALKANES)


1. It is a colourless and odourless gas
2. It is less dense than air
3. It is neutral to litmus paper
4. It is insoluble in water

2.08 CHEMICAL PROPERTIES OF METHANE


All alkanes undergo substitution and combustion reaction.
Combustion reaction of alkanes
1. It burn in air (Oxygen) to produce carbon(IV) oxide and water
CH4(g) + 2O2(g) CO2(g) + 2H2O(g)
CnH2n+2 + n + n + 1/2 O2 nCO2 + n + 1H2O

Substitution reaction of alkanes: This is a type of reaction in which other atoms replace those already
present in the compound.
2. Methane reacts with chlorine in the presence of ultraviolet light as a catalyst to produce the following
substitution products.
(a) CH4 + Cl2 CH3Cl + HCl
Monochloromethane
(b) CH3Cl + Cl2 CH2Cl2 + HCl
Dichloromethane
(c) CH2Cl2 + Cl2 CHCl3 + HCl
Trichloromethane
(d) CHCl3 + Cl2 CCl4 + HCl
Tetrachloromethane
The above reaction is also a chain reaction which proceed via the following three stages:
(i) Chain initiation
(ii) Chain propagation
(iii) Chain termination
(i) Chlorine molecule split into two equal parts by light.
Cl2 2Cl Chain initiation
(ii) The reactive chlorine radical attacks methane molecule.
CH4 + Cl CH3 + HCl
CH3 + Cl2 CH3Cl + Cl Chain propagation
(iii) The reaction can be terminated by any of the following steps.
CH3 + Cl CH3Cl
CH3 + CH3 CH3CH3
Cl + Cl Cl2
3. Methane reacts with bromine at room temperature or between 2500C – 4000C as catalyst to produce
the following substitution products:
(a) CH4 + Br2 CH3Br + HBr
Monobromomethane
(b) CH3Br + Br2 CH2Br2 + HBr
Dibromomethane
(c) CH2Br2 + Br2 CHBr3 + HBr
Tribromomethane
(d) CHBr3 + Br2 CBr4 + HBr
Tetrabromomethane
2.09 USES OF METHANE
It is used as a fuel both a home and industries.
CHAPTER THREE
3.01 UNSATURATED HYDROCARBON (ALKENES)
Alkene are unsaturated hydrocarbons which are otherwise referred to as OLEFINES with double bond. It
has a functional group of C=C and belong to homologous series with general molecular formular of
CnH2n where n= 1,2,,3,4…………. for successive members of the group. The first- four members are gas.
They are name by replacing the –ane in the parent alkanes by –ene.

3.02 NAMING OF ALKENES


The names of Alkenes family are derived by applying the general molecular formulae C nH2n for each
member in the series.
NOTE: Since alkenes contain double bonds between carbon to carbon i.e C=C therefore n=1 is not
visible.

When General Molecular Name


n= Formulae CnH2
2. C2H2x2= C2H4 Ethene
3. C3H2x3 = C3H6 Propene
4. C4H2x4 = C4H8 Butene
5. C5H2x5 = C5H10 Pentene
6. C6H2x6 = C6H12 Hexene
7. C7H2x7 = C7H14 Heptene
8. C8H2x8 = C8H16 Octene
9. C9H2x9 = C9H18 Nonene
10. C10H2x10 = C10H20 Decene
11. C11H2x11 = C11H22 Undacene
12. C12H2x12 = C12H24 Dodecene
13. C13H2x13 = C13H26 Tridecene
14. C14H2x14 = C14H28 Tetradecene
15. C15H2x15 = C15H30 Pentadecene
16. C16H2x16 = C16H32 Hexadecene
17. C17H2x17 = C17H34 Heptadecene
18. C18H2x18 = C18H36 Octadecene
19. C19H2x19 = C19H38 Nonadecene
20. C20H2x20 = C20H40 Icosene/Eiocosene
21. C21H2x21 = C21H42 Heneicosene
22. C22H2x22 = C22H44 Docosene
23. C23H2x23 = C23H46 Tricosene
24. C24H2x24 = C24H48 Tetracosene
25. C25H2x25 = C25H50 Pentacosene
26. C26H2x26 = C26H52 Hexacosene
27. C27H2x27 = C27H54 Heptacosene
28. C28H2x28 = C28H56 Octacosene
29. C29H2x29 = C29H58 Nonacosene
30. C30H2x30 = C30H60 Triacontene

N:B more of alkene naming can be achieved using the process in alkane naming. (31 – 120).
2.03 MOLECULAR STRUCTURES OF ALKENES
n ALKENES STRUCTURAL FORMULAR MOLECULAR FORMULAR
2. H H H2C=CH2
C2H4 C=C
Ethene H H
3. H H CH3CH=CH2
C3H6 H-C-C=C
Propene HH H
4. HH H CH3CH2CH=CH2
C4H8 H-C-C-C=C
Butene HHH H
5. HHH H CH3(CH2)2CH=CH2
C5H10 H-C-C-C-C=C
Pentene HHHH H
6. HHHH H CH3(CH2)3CH=CH2
C6H12 H-C-C-C-C-C=C
Hexene HHHHH H
7. HHHHH H CH3(CH2)4CH=CH2
C7H14 H-C-C-C-C-C-C=C
Heptene HHHHHH H
8. HHHHHH H CH3(CH2)5CH=CH2
C8H16 H-C-C-C-C-C-C-C=C
Octene HHHHHHH H
9. HHHHHHH H CH3(CH2)6CH=CH2
C9H18 H-C-C-C-C-C-C-C-C=C
Nonene HHHHHHHH H
10. HHHHHHHH H CH3(CH2)7CH=CH2
C10H20 H-C-C-C-C-C-C-C-C-C=C
Decene HHHHHHHHH H
11. HHHHHHHHH H CH3(CH2)8CH=CH2
C11H22 H-C-C-C-C-C-C-C-C-C-C=C
Undecene HHHHHHHHHH H
12. HHHHHHHHHH H CH3(CH2)9CH=CH2
C12H24 H-C-C-C-C-C-C-C-C-C-C-C=C
Dodecene HHHHHHHHHHH H
13. HHHHHHHHHHH H CH3(CH2)10CH=CH2
C13H26 H-C-C-C-C-C-C-C-C-C-C-C-C=C
Tridecene HHHHHHHHHHHH H
14. HHHHHHHHHHHH H CH3(CH2)11CH=CH2
C14H28 H-C-C-C-C-C-C-C-C-C-C-C-C-C=C
Tetradecene HHHHHHHHHHHHH H
15. HHHHHHHHHHHHH H CH3(CH2)12CH=CH2
C15H30 H-C-C-C-C-C-C-C-C-C-C-C-C-C-C=C
Pentadecene H H HH H H H H H H H H H H H
16. HHHHHHHHHHHHHH H CH3(CH2)13CH=CH2
C16H32 H-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C=C
Hexadecene HHHHHHHHHHHHHHH H
17. HHHHHHHHHHHHHHH H CH3(CH2)14CH=CH2
C17H34 H-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C=C
Heptadecene HHHHHHHHHHHHHHHH H
18. HHHHHHHHHHHHHHHH H CH3(CH2)15CH=CH2
C18H36 H-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C=C
Octadecene HHHHHHHHHHHHHHHHH H
19. HHHHHHHHHHHHHHHHH H CH3(CH2)16CH=CH2
C19H38 H-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C=C
Nonadecene HHHHHHHHHHHHHHHHHH H
20. HHHHHHHHHHHHHHHHHH H CH3(CH2)17CH=CH2
C20H40 H-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C=C
Eiocosene HHHHHHHHHHHHHHHHHHH H

3.04 NOMENCLATURE OF ALKENES


When writing the names for alkenes, adequate care must be taken because unlike in alkanes where
there is only single bond, alkenes contain double and it is on these double bonds that the naming of the
substituents are based. Thus in the molecule of CH3CH=CHCH3 is named but-2-ene.
Although the double bond joins carbon atoms to 2 and 3, the number 2 is used because it is the lowest
that is, give the lowest number to the double bond.
Other example are:
(i) CH3-CH2-CH2-CH=CH2 (ii) CH3CH2CH=CHCH3
Pent-1-ene pent-2-ene

CH3
(iii) CH3C=CHCH3 (iv) CH3-C=C-CH3
CH3 CH3
3-methylbut-2-ene 2,3-dimethylbut-2-ene

CH3 CH3 CH3


(v) CH3CH2C=CCH2CH3 (vi) CH3C-CH=CH-C-CH3
CH3 CH3 CH3
3,4-dimethylhex-3-ene 2,2,5,5-tetramethylhex-3-ene

(vii) CH3CH2C =CCH3 (viii) CH3C=CHCH3


CH3 CH3 CH3
2,3-dimethylpent-2-ene 3-methylbut-2-ene

CH3 CH3
(ix) CH2=C CH—CH2CH2CH=CH2 (x) CH3CH2CHCH=CHCH=C=CH2
CH3 CH2CH3 CH2CH3
2,2-dimethyl, 3-ethylhept-1,6-diene 3-ethyl, 6-methyloct-1,2,4-triene

Cl
(xi) CH3CH=CHCH3 (xii) CH3-C-CH=CH2
Cl Cl
2-chlorobut-2-ene 3,3-dichlorobut-1-ene

(xiii) CH3CH2C=CH=CHCH3 (xiv) CH3C=CHC=CH3


Cl Br Cl Cl
2-bromo, 4-chlorohex-2,3-diene 2,4-dichloropent-1,3-diene

Cl Br Cl
(xv) CH2=CH=C-CH=C-CH3 (xvi) CH3CHCH=C-CH3
Cl Br Cl Cl
5,5-dibromo, 3,3-dichlorohex-1,2,4-triene 2,4,4-trichloropent-2-ene
HHH H CH2CH3
(xvii) H-C-C-C-C=C (xviii) CH3CH = C
HH H H CH2CH2Cl
H-C-H 5-chloro -3-ethylpent-2-ene
H
3-methylpent-1-ene

CH3
(xix) H2C = C =
But-1,2-diene

3.05 LABORATORY PREPARATION OF ETHENE


Ethene is generally prepared in the laboratory by dehydration, that is, removal of water molecules from
alkanols such as ethanol (C2H5OH) by concentrated H2SO4 to form ethylhydrogen sulphate and water as
products.
C2H5OH + H2SO4 C2H5HSO4 + H2O.
When ethylhydrogen sulphate is heated, it releases ethene which is collected over water.
NOTE: The wash bottle of sodium hydroxide serves to remove sulphur(iv)oxide.

3.06 PHYSICAL PROPERTIES OF ETHENE (ALKENES)


1. It is colourless and odourless gas
2. It is neutral litmus paper
3. It almost insoluble in water
4. It is less dense than air.
3.07 CHEMICAL PROPERTIES OF ETHENE
Alkenes such as ethene undergoes addition reaction – a reaction in which one molecule of a compound
is simply added on to the alkenes at the position of the carbon – carbon double bond (C=C) and this is
converted to carbon – carbon single bond (C-C) that is, the alkanes. Examples of addition reaction are:
1. Reaction of ethene with hydrogen in the presence of nickel as a catalyst
H2C=CH2 + H2 Ni CH3CH3
ethene ethane
This reaction is important in the conversion of oil into margarine by the process known as
HYDROGENATION.
2. Reaction of ethene with chlorine to produce 1,2-dichloroethane.
CH2=CH2 + Cl2 ClCH2-CH2Cl
3. Reaction of ethene with bromine to produce 1,2-dibromoethane
CH2=CH2 + Br2 CH2Br-CH2Br
4. Reaction of ethene with oxygen or combustion reaction of ethene (alkenes) to produce
carbon(iv)oxide and water
CH2=CH2 + 3O2 2CO2 + 2H2O
5. Reaction of ethene with hydrogen halide(Hydrogen chloride)(HCl) to produce ethylchloride.
CH2=CH2 + HCl CH3CH2Cl
6. Reaction of ethene with water in the presence of dilute H2SO4 to produce ethanol
CH2=CH2 + H2O CH3CH2OH
7. Reaction of ethene with neutral KMnO4 to produce 1,2-ethan-diol (glycol)
CH2=CH2 + KMnO4 CH2-CH2
OH OH
1,2-ethan-diol
In the above 7 reaction, there is decolourisation of ethene and this reaction distinguishes alkenes from
alkanes which do not decolourise on addition of KMnO4

3.08 USES OF ETHENE


1. in the production of polythene which is used for making nylon or polythene bags and wrappers
2. In the manufacturing of margarine by the process of hydrogenation.
CHAPTER FOUR
4.01 UNSATURATED HYDROCARBON (ALKYNES)
Alkyne are also unsaturated hydrocarbons containing triple bond. It has a functional group of –C≡C- and
belong to homologous series with general molecular formular of CnH2n-2 where n= 1,2,3,4 ……….. for
successive members of the group. The first member of the group in alkynes family is ethyne (acetylene).
Alkynes are named by replacing –ane from the parent alkane with –yne.

4.02 NAMING OF ALKYNES


The names of Alkynes family are derived by applying the general molecular formulae C nH2n-2 for each
member in the series.
NOTE: Since alkynes contain triple bonds between carbon to carbon i.e C=C therefore n=1 is not visible.

When General Molecular Name


n= Formulae CnH2n-2
2. C2H2x2-2 = C2H2 Ethyne
3. C3H2x3-2 = C3H4 Propyne
4. C4H2x4-2 = C4H6 Butyne
5. C5H2x5-2 = C5H8 Pentyne
6. C6H2x6-2 = C6H10 Hexyne
7. C7H2x7-2 = C7H12 Heptyne
8. C8H2x8-2 = C8H14 Octyne
9. C9H2x9-2 = C9H16 Nonyne
10. C10H2x10-2 = C10H18 Decyne
11. C11H2x11-2 = C11H20 Undacyne
12. C12H2x12-2 = C12H22 Dodecyne
13. C13H2x13-2 = C13H24 Tridecyne
14. C14H2x14-2 = C14H26 Tetradecyne
15. C15H2x15-2 = C15H28 Pentadecyne
16. C16H2x16-2 = C16H30 Hexadecyne
17. C17H2x17-2 = C17H32 Heptadecyne
18. C18H2x18-2 = C18H34 Octadecyne
19. C19H2x19-2 = C19H36 Nonadecyne
20. C20H2x20-2 = C20H38 Icosyne/Eiocosyne
21. C21H2x21-2 = C21H40 Heneicosyne
22. C22H2x22-2 = C22H42 Docosyne
23. C23H2x23-2 = C23H44 Tricosyne
24. C24H2x24-2 = C24H46 Tetracosyne
25. C25H2x25-2 = C25H48 Pentacosyne
26. C26H2x26-2 = C26H50 Hexacosyne
27. C27H2x27-2 = C27H52 Heptacosyne
28. C28H2x28-2 = C28H54 Octacosyne
29. C29H2x29-2 = C29H56 Nonacosyne
30. C30H2x30-2 = C30H58 Triacontyne

N:B more of alkyne naming can be achieved using the process in alkane naming. (31 – 120).
4.03 MOLECULAR STRUCTURES OF ALKYNES

N ALKYNES STRUCTURAL FORMULAR MOLECULAR FORMULAR


2. HC≡CH
C2H2 H-C≡C-H
Ethyne
3. H CH3C≡CH
C3H4 H-C-C≡C-H
Propyne H
4. HH CH3CH2C≡CH
C4H6 H-C-C-C≡C-H
Butyne HH
5. HHH CH3(CH2)2C≡CH
C5H8 H-C-C-C-C≡C-H
Pentyne HHH
6. HHHH CH3(CH2)3C≡CH
C6H10 H-C-C-C-C-C≡C-H
Hexyne HHHH
7. HHHHH CH3(CH2)4C≡CH
C7H12 H-C-C-C-C-C-C≡C-H
Heptyne HHHHH
8. HHHHHH CH3(CH2)5C≡CH
C8H14 H-C-C-C-C-C-C-C≡C-H
Octyne HHHHHH
9. HHHHHHH CH3(CH2)6C≡CH
C9H16 H-C-C-C-C-C-C-C-C≡C-H
Nonyne HHHHHHH
10. HHHHHHHH CH3(CH2)7C≡CH
C10H18 H-C-C-C-C-C-C-C-C-C≡C-H
Decyne HHHHHHHH
11. HHHHHHH HH CH3(CH2)8C≡CH
C11H20 H-C-C-C-C-C-C-C-C-C-C≡C-H
Undecyne HHHHHHHH H
12. H H H H H H H H HH CH3(CH2)9C≡CH
C12H22 H-C-C-C-C-C-C-C-C-C-C-C≡C-H
Dodecyne H H H H H H H H HH
13. HHHHHHHHHHH CH3(CH2)10C≡CH
C13H24 H-C-C-C-C-C-C-C-C-C-C-C-C≡C-H
Tridecyne HHHHHHHHHHH
14. HHHHHHHHHHHH CH3(CH2)11C≡CH
C14H26 H-C-C-C-C-C-C-C-C-C-C-C-C-C≡C-H
Tetradecyne HHHHHHHHHHHH
15. HHHHHHHHHHHHH CH3(CH2)12C≡CH
C15H28 H-C-C-C-C-C-C-C-C-C-C-C-C-C-C≡C-H
Pentadecyne H H HH H H H H H H H H H
16. HHHHHHHHHHHHHH CH3(CH2)13C≡CH
C16H30 H-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C≡C-H
Hexadecyne HHHHHHHHHHHHHH
17. HHHHHHHHHHHHHHH CH3(CH2)14C≡CH
C17H32 H-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C≡C-H
Heptadecyne HHHHHHHHHHHHHHH
18. HHHHHHHHHHHHHHHH CH3(CH2)15C≡CH
C18H34 H-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C≡C-H
Octadecyne HHHHHHHHHHHHHHHH
19. HHHHHHHHHHHHHHHHH CH3(CH2)16C≡CH
C19H36 H-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C≡C-H
Nonadecyne HHHHHHHHHHHHHHHHH
20. HHHHHHHHHHHHHHHHHH CH3(CH2)17C≡CH
C20H28 H-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C≡C-H
Eiocosyne HHHHHHHHHHHHHHHHHH

4.04 NOMENCLATURE OF ALKYNES


The nomenclature of alkynes is similar to that of alkenes in many respects as shown in the structures
below. The only difference lies on the type of bonds, in alkenes (double bond) and alkynes (triple bond).

(i) CH3-CH2-C≡CCH3 (ii) CH3CH2CH2C≡CCH3


Pent-2-yne hex-2-yne

CH3 CH3
(iii) CHC≡CCH3 (iv) CH2-C≡C-CH2
CH3 CH3
4-methylpent-2-yne hex-3-yne

CH3 CH3 CH3


(v) CH3CHC≡CCHCH3 (vi) CH3C-C≡C-C-CH3
CH3 CH3 CH3
2,5-dimethylhex-3-yne 2,2,5,5-tetramethylhex-3-yne
CH3
(vii) CH3CH-C ≡CC-CH2CH3 (viii) CH3C≡CCH2
CH3 CH3 CH3
2,5,5-trimethylhept-3-yne pent-2-yne

CH3 CH3
(ix) CH≡CC-C=C-------CH—CH2CH2C≡CH (x) CH3C-CHC≡CC≡CC≡CH
CH3 CH2CH3 CH2CH3
6-ethyl,3,3-dimethyldec-1,6-diyne 8-ethyl, 8-methynon-1,3,5-triyne

Cl
(xi) CH3C≡CCHCH3 (xii) CH3-C-C≡CH
Cl Cl
4-chloropent-2-yne 3,3-dichlorobut-1-yne

(xiii) CH3CHC≡CC≡CCHCH3 (xiv) CH3CHC≡CCHC≡CH


Cl Br Cl Cl
2-bromo, 7-chlorooct-3,5-diyne 3,6-dichlorohept-1,3-diyne
H
H-C-H
HHH
(xv) H-C-C-C-CC≡CH
HHH
H-C-H
H
3,3-dimethylhex-1-yne
4.05 LABORATORY PREPARATION OF ETHYNES (ALKYNES)
Ethyne is prepared in the laboratory by adding cold water into calcium dicarbide (CaC 2). Much heat is
evolved and sand is placed beneath the flask to protect the flask from breakage. Ethyne is collected over
water. The chief impurity, phosphine, PH3 is absorbed by the acidified CuSO4 solution.
EQUATION FOR THE REACTION
CaC2 + 2H2O Ca(OH)2 + C2H2.
Ethyne

4.06 PHYSICAL PROPERTIES OF ETHYNE


1. It is colourless gas
2. It has sweet smell when pure
3. Almost insoluble in water
4. It is neutral to litmus
5. It is strongly exothermic
4.07 CHEMICAL PROPERTIES OF ETHYNE
Alkynes such as ethyne also undergoes addition reaction – a reaction in which one molecule of a
compound is simply added on to the alkynes at the position of the carbon – carbon triple bond (C≡C)
and this is converted to carbon – carbon single bond (C-C) that is, the alkanes. Examples of addition
reaction are:
1. Reaction of ethyne with hydrogen in the presence of nickel as a catalyst
CH≡CH + 2H2 Ni CH3CH3
ethyne ethane
2. Reaction of ethyne with bromine to produce 1,1,2,2-tetrabromoethane. The reddish brown colour of
bromine is destroyed.
CH≡CH + 2Br2 CHBr2-CHBr2
3. Reaction of ethyne with chlorine to produce hydrogen chloride
CH≡CH + Cl2 2C + 2HCl
4. Reaction of ethyne with oxygen or combustion reaction of ethyne (alkynes) to produce
carbon(iv)oxide and water
2CH≡CH + 5O2 4CO2 + 2H2O
5. Polymerization reaction of ethyne to produce benzene.
3C2H2 C6H6
6. Reaction of ethyne with water in the presence of dilute H2SO4 and mercury as a catalyst to produce
ethanal
CH≡CH + H2O CH3CHO
7. Reaction of ethyne with KMnO4 to produce 1,2-ethan-diol (glycol)
CH≡CH + KMnO4 CH2-CH2
OH OH
1,2-ethan-diol
4.08 USE OF ETHYNE
1. In oxy-acetylene flame for welding and cutting of metals
2. In oxy-acetylene torch
3. In preparation of acetic acid
4. as a starting material for making polyvinylchloride (PVC) which is used in electrical insulation and
water proofing.

3.09 CHEMICAL TESTS TO DISTINGUISHED BETWEEN ALKANES, ALKENES AND ALKYNES.


The following test can be performed to distinguished clearly the different classes of hydrocarbons, that
is, the alkanes, alkenes and alkynes.
All alkanes are saturated compounds while both alkenes and alkynes are unsaturated.
TEST 1: To the suspected hydrocarbons, add an acidified solution of KMnO4 or K2Cr2O7 solution. Alkanes
have no effect in any of these solutions while both alkenes and alkynes decolorized. Acidified KMnO4
solution changes from purple to colourless, while K2Cr2O7 changes from orange to green.
TEST 2: To the suspected hydrocarbons, add the solution of Ammonical copper (i) chloride. Alkanes and
alkenes have no effect, but alkynes form a yellowish or reddish –brown precipitate.
2NH4OH + 2CuCl + C2H2 CuC2 + 2NH4Cl + 2H2O.
TEST: To the suspected hydrocarbon, add solution of Ammonical silver tronitrate (v). Alkanes and
alkenes have no effect, but alkynes form a yellowish precipitate.
2NH4OH + 2AgNO3 + C2H2 2AgC + 2NH4NO3 + 2H2O.
CHAPTER FIVE
5.01 AROMATIC HYDROCARBONS – BENZENE
Aromatic hydrocarbons are class of unsaturated compounds like alkenes and alkynes but which have
properties different from that of alkenes and alkynes. The simplest and most important aromatic
hydrocarbon is benzene with molecular formular of C6H6.

5.02 THE STRUCTURE OF BENZENE


Benzene has a molecular formular of C6H6. The structure of benzene was obtained by Augusta Kekule in
1865 during which he proposed a ring structure in which alternate carbon atoms were joined by double
bonds.
H

H C C H

H C C H OR

H
Because of the peculiar properties of benzene, Kekule proposed a resonance structure for benzene in
which case the true structure is in between the structure below.

H H

C C

H C C H H C C H

H C C H H C C H

C C

H H

The principle behind these two structures is RESONANCE. To conform with the electron delocalization in
benzene, the structural formular of benzene is nowadays written as.

H C C H Rather than

H C C H

H
5.03 NOMENCLATURE OF AROMATIC COMPOUNDS
Aromatic compounds are sometimes known as ARENES. The hydrogen atoms in a benzene ring can be
substituted by other atom and groups. E.g:
(i) CH3 (ii) OH (iii) Cl

Methylbenzene Phenol Chlorobenzene


(Toluene)

(iv) NH2 (v) NO2 (vi) COOH

Phenylamine Nitrobenzene Benzoic acid


(Aniline)
NOTE: benzene is not the only aromatics hydrocarbon, many others exist, either substituted forms of
benzene or compounds containing different ring systems. E.g methylbenzene (C 7H8), 1,3-
dimethylbenzene (C8H10), naphthalene (C10H8) and anthracene (C14H10).
5.04 PHYSICAL PROPERTIES OF BENZENE
1. It is liquid at room temperature
2. it is immiscible with water
3. it has melting point of 60C and boiling point of 800C.
5.05 CHEMICAL PROPERTIES OF BENZENE
Although benzene contains three double bonds in its structure, however, most of its reactions are
substitution reactions. This because the double bonds in benzene are different from those in alkenes. In
alkenes, the electrons making up the double bond are located only between two carbon atoms
containing it (localized) whereas in benzene, the electron making up the double bonds are spread
(delocalized) between all the six carbon atoms. This notwithstanding, benzene also udergo some
addition reactions. These reactions destroyed the aromatic character of benzene whereas substation
reaction preserved the aromatic character.
ADDITION REACTIONS OF BENZENE
1. Benzene undergo addition reaction with hydrogen in the presence of Nickel as a catalyst to form
cylohexane.

+ 3H2

Benzene Cyclohexane
2. Benzene undergo addition reaction with chlorine in the presence of ultraviolet light as a catalyst to
form 1,2,3,4,5,6-haxachlorocyclohexane.

+ 3Cl2

Cyclohexane 1,2,3,4,5,6-haxachlorocyclohexane
3. Benzene undergo combustion reaction to form sooty, smoky flame which is characteristic of all
hydrocarbons containing a high percentage of carbon.

SUBSTITUTION REACTIONS OF BENZENE


1. Benzene react with chlorine in the absence of sunlight/ultraviolet light, using aluminium chloride as a
catalyst to form chlorobenzene.
Cl

+ Cl2 + HCl

Benzene
Benzenechloride
2. Benzene react with monochloromethane using Aluminium chloride as a catalyst to form
methylbenzene.
CH3

+ CH3Cl + HCl

Benzene
Methylbenzene

5.06 USES OF BENZENE


1. preparation of detergent
2. manufacture of polystyrene
3. manufacture of nylon
4. To produce insecticides.
CHAPTER SIX
6.01 ALKANOL
Alkanols are compounds containing one or more hydroxyl groups linked with an alkyl or aryl radicals.
Alkanols have a functional group of –OH and belong to homologous series with general molecular
formular of CnH2n+1OH where n= 1,2,3,4 …….. for successive member of alkanols. The first – two
members of the series are both liquids. They are methanol (CH3OH) and ethanol (CH3CH2OH). Alkanols
are derived by replacing the –ane in the parent alkanes by –ol.

6.02 NAMING OF ALKANOLS


The formular of individual members of alkanol are obtained by applying the general molecular formular
(CnH2n+1OH)

When General Molecular Name


n= Formulae CnH2n+1OH
1 C1H2x1+1OH CH3OH Methanol
2. C2H2x2+1OH = C2H5OH Ethanol
3. C3H2x3+1OH = C3H7OH Propanol
4. C4H2x4+1OH = C4H9OH Butanol
5. C5H2x5+1OH = C5H11OH Pentanol
6. C6H2x6+1OH = C6H13OH Hexanol
7. C7H2x7+1OH = C7H15OH Heptanol
8. C8H2x8+1OH = C8H17OH Octanol
9. C9H2x9+1OH = C9H19OH Nonanol
10. C10H2x10+1OH = C10H21OH Decanol
11. C11H2x11+1OH = C11H23OH Undacanol
12. C12H2x12+1OH = C12H25OH Dodecanol
13. C13H2x13+1OH = C13H27OH Tridecanol
14. C14H2x14+1OH = C14H29OH Tetradecanol
15. C15H2x15+1OH = C15H31OH Pentadecanol
16. C16H2x16+1OH = C16H33OH Hexadecanol
17. C17H2x17+1OH = C17H35OH Heptadecanol
18. C18H2x18+1OH = C18H37OH Octadecanol
19. C19H2x19+1OH = C19H39OH Nonadecanol
20. C20H2x20+1OH = C20H41OH Icosanol/Eiocosanol
21. C21H2x21+1OH = C21H43OH Heneicosanol
22. C22H2x22+1OH = C22H45OH Docosanol
23. C23H2x23+1OH = C23H47OH Tricosanol
24. C24H2x24+1OH = C24H49OH Tetracosanol
25. C25H2x25+1OH = C25H51OH Pentacosanol
26. C26H2x26+1OH = C26H53OH Hexacosanol
27. C27H2x27+1OH = C27H55OH Heptacosanol
28. C28H2x28+1OH = C28H57OH Octacosanol
29. C29H2x29+1OH = C29H59OH Nonacosanol
30. C30H2x30+1OH = C30H61OH Triacontanol

N:B more of alkanols naming can be achieved using the process in alkane naming. (31 – 120).
6.03 MOLECULAR STRUCTURES OF ALKANOL

N ALKANOL STRUCTURAL FORMULAR MOLECULAR


FORMULAR
1. CH3OH H CH3OH
Methanol H-C -OH
H
2. HH CH3CH2OH
C2H5OH H-C-C-OH
Ethanol HH
3. HHH CH3(CH2)2OH
C3H7OH H-C-C-C-OH
Propanol HHH
4. HHHH CH3(CH2)3OH
C4H9OH H-C-C-C-C-OH
Butanol HHHH
5. HHHHH CH3(CH2)4OH
C5H11OH H-C-C-C-C-C-OH
Pentanol HHHHH
6. HHHHHH CH3(CH2)5OH
C6H13OH H-C-C-C-C-C-C-OH
Hexanol HHHHHH
7. HHHHHHH CH3(CH2)6OH
C7H15OH H-C-C-C-C-C-C-C-OH
Heptanol HHHHHHH
8. HHHHHHHH CH3(CH2)7OH
C8H17OH H-C-C-C-C-C-C-C-C-OH
Octanol HHHHHHHH
9. HHHHHHHHH CH3(CH2)8OH
C9H19OH H-C-C-C-C-C-C-C-C-C-OH
Nonanol HHHHHHHHH
10. HHHHHHHHHH CH3(CH2)9OH
C10H21OH H-C-C-C-C-C-C-C-C-C-C-OH
Decanol HHHHHHHHHH
11. HHHHHHHHHHH CH3(CH2)10OH
C11H23OH H-C-C-C-C-C-C-C-C-C-C-C-OH
Undecanol HHHHHHHHHHH
12. HHHHHHHHHHHH CH3(CH2)11OH
C12H25OH H-C-C-C-C-C-C-C-C-C-C-C-C-OH
Dodecanol HHHHHHHHHHHH
13. HHHHHHHHHHHHH CH3(CH2)12OH
C13H27OH H-C-C-C-C-C-C-C-C-C-C-C-C-C-OH
Tridecanol HHHHHHHHHHHHH
14. HHHHHHHHHHHHHH CH3(CH2)13OH
C14H29OH H-C-C-C-C-C-C-C-C-C-C-C-C-C-C-OH
Tetradecanol H H HH H H H H H H H H H H
15. HHHHHHHHHHHHHHH CH3(CH2)14OH
C15H31OH H-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-OH
Pentadecanol HHHHHHHHHHHHHHH
16. HHHHHHHHHHHHHHHH CH3(CH2)15OH
C16H33OH H-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-OH
Hexadecanol HHHHHHHHHHHHHHHH
17. HHHHHHHHHHHHHHHHH CH3(CH2)16OH
C17H35OH H-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-OH
Heptadecanol HHHHHHHHHHHHHHHHH
18. HHHHHHHHHHHHHHHHHH CH3(CH2)17OH
C18H37OH H-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-OH
Octadecanol HHHHHHHHHHHHHHHHHH
19. HHHHHHHHHHHHHHHHHHH CH3(CH2)18OH
C19H39OH H-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-OH
Nonadecanol HHHHHHHHHHHHHHHHHHH
20. HHHHHHHHHHHHHHHHHHHH CH3(CH2)19OH
C20H41OH H-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-OH
Eiocosanol HHHHHHHHHHHHHHHHHHHH

6.04 NOMENCLATURE OF ALKYANOLS


Alkanols are named using the IUPAC method by considering the functional group of alkanols (-OH) and
the position of attachment of other substituents on the carbon atoms. The lowest number is given
to –OH. For example:
H
(i) CH3-C-OH H
CH3 (ii) CH3CH2C- OH
Propan-2-ol CH3
Butan-2-ol

CH3 CH3
(iii) CH3-C-CH2OH (iv) CH3-C-CH2CH2CH3
CH3 OH
2,2-dimethylpropan-1-ol 2-methylpent-2-ol

CH3 OH
(v) CH3-C-CH2CHCH2CH3 (vi) OH-C-OH
CH3 OH OH
5,5-dimethylhex-3-ol methan-1,1,1,1-tetraol

CH3 OH OH
(vii) CH-CCH-C-------CH—CHCHCH3 (viii) CH3CHCH2CHCH2CHCH3
CH3 CH2CH3 OH OH OH
5,5-dimethyl, 4-ethyloctan-2,3-diol heptan-2,4,6-triol

OH OH Cl Br
(ix) CH3C---CCH3 (x) CH3-C----CH-CH-CH-CH3
Cl Cl OH OH OH
2,3-dichlorobutan-2,3-diol 4-bromo,2-chlorohexan-2,3,5-triol
H
H-C-H
HHH H H
(xi) H-C-C-C-CC-C-OH
HH H HH
H-C-H
H
3,3-dimethylhex-1-ol

6.05 TYPES OF ALKANOLS


Alkanols may be classified into three types depending on the attachment of the alkyl radical to the
functional group (-OH).
1. PRIMARY ALKANOLS: These are alkanols in which the hydroxyl group (OH) is directly attached to a
carbon atom. E.g

H H H H H H H
H—C—OH H—C – C – OH H – C – C – C – C – OH
H H H H H H H
Methanol ethanol propanol

2. SECONDARY ALKANOLS: These are alkanols in which the hydroxyl group (OH) is directly attached to a
carbon atom which attaches itself further to two other carbon atoms. E.g

H H H
CH3—C—OH CH3—C – CH2CH3 CH3 – C – CH2CH2CH3
CH3 OH OH
Propan-2-ol Butan-2-ol Pentan-2-ol

3. TERTIARY ALKANOLS: These are alkanols in which the hydroxyl group (OH) is directly attached to a
carbon atom which attaches itself further to three other carbon atoms. E.g

CH3 CH3 CH3 CH3


CH3—C—OH CH3—C – CH2CHCH3 CH3 – C – CH2 – CH2 – CH2 – CH2 – OH
CH3 OH CH3
2-methylpropan-1-ol 2,4-dimethylpentan-1-ol 5,5-dimethylhexan-1-ol

6.06 CLASSES OF ALKANOLS


There are three classes of alkanols base on the number of hydroxyl groups in the molecule.
1.MONOHYDRIC ALKANOLS: These are alkanols that contains only one hydroxyl group (OH), e.g
CH3OH CH3CH2OH CH3CHCH3 CH3CH2CHCH3
OH OH
Methanol ethanol propan-2-ol butan-2-ol

2.DIHYDRIC ALKANOLS: These are alkanols that contains two hydroxyl group (OH), e.g
CH2CH2 CH3CHCH2CH2
OH OH OH OH
Ethan-1,2-diol Butan-1,3-diol

3.TRIHYDRIC ALKANOLS: These are alkanols that contains three hydroxyl group (OH), e.g
CH2CHCH2 CH2-CH-CH2-CH2
OH OH OH OH OH OH
propan-1,2,3-triol Butan-1,2.4-triol
6.07 LABORATORY PREPARATION OF ETHANOL
Ethanol is prepared in the laboratory by the process of ALCOHOLIC FERMENTATION. This is a form of
anaerobic respiration during which simple sugar such as glucose (C6H12O6) is converted into ethyl alkanol
(C2H5OH) and carbon (iv) oxide (CO2) by an enzyme called zymase present in the yeast.
C6H12O6 2C2H5OH + CO2
Glucose ethanol

6.08 PREPARATION OF ETHANOL FROM SWEET POTATO


Sweet potato can be converted into ethanol by first crushing and pressure cooking it using a pressure
cooker for some time. The crushed potato releases starch granules and this starch granules are treated
with malt for an hour at temperature between 500C – 600C. malt is a partially germinated barley
containing an enzyme diastase. The starch contained in the potato is then converted by the enzyme
diastase into maltose by hydrolysis.
2(C6H10O5)n + nH2O nC12H22O11
Starch Maltose
At room temperature, yeast is added and an enzyme known as maltase or invertase which is presence
in yeast converts the maltose to glucose and fructose by catalytic hydrolysis process.
C12H22O11 + H2O C6H12O6 + C6H12O6
The resulting liquid mixture is subjected to fractional distillation to give aqueous ethaol.
NOTE: Other raw materials from which ethanol can be obtained through the process is alcoholic
fermentation are: palm wine, cassava, sugar cane and grains.

6.09 PHYSICAL PROPERTIES OF ETHANOL


1. It is liquid at room temperature and pressure.
2. it is volatile and colourless
3. it has a characteristics smell
6.10 CHEMICAL PROPERTIES OF ETHANOL
1. Ethanol react with metals to liberate hydrogen gas and form metallic ethoxide.
2C2H5OH + 2Na 2C2H5ONa + H2
Sodium ethoxide
2. ethanol react with concentrated tetraoxosulphate(vi) (H2SO4) in two stages to form ethene (C2H4)
STAGE 1:
C2H5OH + H2SO4 C2H5HSO4 + H2O
Ethylhydrogen tetraoxosulphate(iv)
STAGE:
C2H5HSO4 C2H4.

3.ethanol can be oxidized in two ways to form ethanoic acid.


(i) reaction with KMnO4 to yield ethanal, CH3CHO.
C2H5OH CH3CHO
Ethanol Ethanal
(ii) reaction with KMnO4 to yield ethanal, CH3CHO with acidified potassium heptaoxodichromate
(vi), K2Cr2O7 to yield ethanioc acid
CH3CHO CH3COOH
Ethanal Ethanoic acid
It should be noted, that oxidation of a primary alkanol like propan-1-ol will produce corresponding
alkanoic acid (propanoic acid) while the oxidation of a secondary alkanol like propan-2-ol will produce
an alkanoate (propanone)

4. Ethanol react with chloride of phosphorous to yield ethylchloride and liberate steamy fumes of
hydrogen chloride.
C2H5OH + PCl5 C2H5Cl + PCl3 + HCl
Ethylchloride
5. Ethanol react with ethanoic acid CH3COOH, in presence of acid catalyst to form an ester
(ethylethanoate) and water. This process is called ESTERIFICATION reaction.
C2H5OH + CH3COOH H+ CH3COOC2H5 + H2O
Ethanol ethanoic acid ethyl ethanoate

6.11 TEST FOR ALKANOLS


1. Dip in litmus paper, alkanols is neutral to litmus
2. Add a very small piece of sodium metal to suspected compound in a test tube. Rapid effervescence
with the giving a ‘pop’ sound with a lighted splint indicates the compound is an alkanol.

6.12 USES OF ALKANOLS


1. As a methylated spirit
2. As a fuel
3. As organic solvent
4. In brewing industries during fermentation of beer
5. In the preparation of organic acid such as ethanoic acid.
CHAPTER SEVEN
7.01 DETERMINATION OF EMPIRICAL/MOLECULAR FORMULAE AND MOLECULAR STRUCTURES OF
ORGANIC COMPOUNDS.
EMPIRICAL FORMULAR: is a formula that simply gives the relative number of atoms of each element
present in a molecule. It is the simplest formula.
MOLECULAR FORMULA: is a formula that state the actual number of each kind of atom found in a
molecule.
A substance whose empirical formula is CH2 have a molecular formula C2H4, C4H8 and so on. The
empirical formula of a compound can be found if the percentage composition and relative atomic
masses of each elements in the compound are known. Also, the empirical formula can be related to the
molar mass of a compound in order to obtain the molecular formular for the compound.
EXAMPLE1: An organic compound has the composition 55% of carbon, 9% hydrogen and 36% oxygen.
Calculate the empirical formular for the organic compound. (C= 12, H= 1, O= 16)
NOTE: Always check that the addition of the percentage composition of all elements present in a
compound equal to 100.
SOLUTION:
CARBON HYDROGEN OXYGEN
Relative composition: 55 9 36
Divide by atomic mass: 55 9 36
12 1 16
=4.58 = 9.00 = 2.25
Divide by the smallest: 4.58 9 2.25
2.25 2.25 2.25
=2 =4 =1
Hence the empirical formular = C2H4O.
EXAMPLE 2: What is the empirical formula of an organic compound whose percentage composition is
carbon, 52.2%, hydrogen, 13.1% and oxygen, 34.7% (C = 12, H = 1, O = 16).
SOLUTION:
CARBON HYDROGEN OXYGEN
Relative composition: 52.2 13.1 34.7
Divide by atomic mass: 52.2 13.1 34.7
12 1 16
=4.35 = 13.1 = 2.17
Divide by the smallest: 4.35 13.1 2.17
2.17 2.17 2.17
=2 =6 =1
Hence the empirical formular = C2H6O.
EXAMPLE 3: An organic compound contains carbon, 62.1%, hydrogen, 10.3% and oxygen, 27.6% by
mass.
(i) Find the empirical formula of the compound
(ii) If the molar mass of the compound is 58.0g, find its molecular formula. (C = 12, H = 1, O = 16).
SOLUTION:
CARBON HYDROGEN OXYGEN
Relative composition: 62.1 10.3 27.6
Divide by atomic mass: 62.1 10.3 27.6
12 1 16
=5.1 = 10.3 = 1.8
Divide by the smallest: 4.35 13.1 1.8
1.8 1.8 1.8
=3 =6 =1
Hence the empirical formular = C3H6O.
(ii) To calculate the molecular formula, relate the empirical formula to the molar mass.
(Empirical formula)n = Molar mass
(C3H6O)n = 58
(3x12 + 1x6 + 16x1)n = 58
(58)n = 58
n = 1
The molecular formula = (C3H6O)n = C3H6O.
EXAMPLE 4: A hydrocarbon contains 20.80% of hydrogen and has a relative molar mass of 30, what is
the
(i) empirical formula
(ii) molecular formula (C = 12, H = 1).
SOLUTION:
Hydrocarbon is known to contain carbon and hydrogen only. Since the percentage composition of all
elements in a compound must be equal to 100. Therefore, the percentage composition of carbon which
is the second element contained by a hydrocarbon equals 79.20%. i.e 100 – percentage composition of
hydrogen (20.80%).
CARBON HYDROGEN
Relative composition: 79.20 20.80
Divide by atomic mass: 79.20 20.80
12 1
=6.60 = 20.80
Divide by the smaller: 4.60 20.80
6.60 6.60
=1 =3
Hence the empirical formular = CH3.
(ii) To calculate the molecular formula, relate the empirical formula to the molar mass.
(Empirical formula)n = Molar mass
(CH3)n = 30
(12 + 1x3)n = 30
(15)n = 30
n = 2
The molecular formula = (CH3)n = C2H6.
EXAMPLE 5: A carbohydrate contains 40% and hydrogen 6.72%, Calculate its empirical formula and the
molecular formula, if the molar mass is 180 (C = 12, H = 1, O = 16).
SOLUTION:
Carbohydrate contains the elements carbon, hydrogen and oxygen, but from the question above oxygen
is missing, hence the percentage composition of oxygen equals 100 – (percentage composition of
carbon and hydrogen)
= 100 – (40 + 6.72)
= 100 – 46.72
= 53.30%
CARBON HYDROGEN OXYGEN
Relative composition: 40 6.72 53.3
Divide by atomic mass: 40 6.72 53.3
12 1 16
=3.33 = 6.72 = 3.33
Divide by the smallest: 3.33 6.72 3.33
3.33 3.33 3.33
= 1 =2 =1
Hence the empirical formular = CH2O.
(ii) To calculate the molecular formula, relate the empirical formula to the molar mass.
(Empirical formula)n = Molar mass
(CH2O)n = 180
(12 + 1x2 + 16)n = 180
(30)n = 180
n = 180/30
n = 6
The molecular formula = (CH2O)n = (CH2O6)
= C6H12O6.
The molecular formula = C6H12O6.
EXAMPLE 6: A hydrocarbon contains 92.40% of carbon. If the vapour density of the hydrocarbon is 39.
Find
(i) empirical formula
(ii) molecular formula (C = 12, H = 1).
SOLUTION:
Hydrocarbon is known to contain carbon and hydrogen only. Since the percentage composition of all
elements in a compound must be equal to 100. Therefore, the percentage composition of hydrogen
which is the second element contained by a hydrocarbon equals 7.60%. i.e 100 – percentage
composition of carbon (92.40%).
CARBON HYDROGEN
Relative composition: 92.40 7.60
Divide by atomic mass: 92.40 7.60
12 1
=7.70 = 7.60
Divide by the smaller: 7.70 7.60
7.60 7.60
=1 =1
Hence the empirical formular = CH.
(ii) To calculate the molecular formula, relate the empirical formula to the molar mass.
(Empirical formula)n = Molar mass
But molecular mass = 2 x vapour density
(CH)n = 2 x 39
(12 + 1)n = 78
(13)n = 78
n = 6
The molecular formula = (CH)n = C6H6.
EXAMPLE 7: Calculate the empirical formular of an organic compound containing 81.8% carbon and
18.2% hydrogen (C = 12, H = 1).
SOLUTION:
CARBON HYDROGEN
Relative composition: 81.8 18.2
Divide by atomic mass: 81.8 18.2
12 1
=6.82 = 18.2
Divide by the smaller : 6.82 18.2
6.82 6.82
=1 = 2.67
The carbon : hydrogen {C:H} ratio of 1:2.67 is too far from whole numbers and so the lowest multiple of
this which gives a whole number ratio is the empirical formular, i.e 1:2.67, 2:5.34, 3:8.01, 4:10.68 etc.
Hence the empirical formular = C3H8.
EXAMPLE 8: What is the empirical formular of an oxide of phosporius that contains 43.6% phosphorous
and 56.4% oxygen (P = 31, O = 16).
SOLUTION:
PHOSPHOROUS OXYGEN
Relative composition: 43.6 56.4
Divide by atomic mass: 43.6 56.4
31 16
=1.41 = 3.53
Divide by the smaller: 1.41 3.53
1.41 1.41
=1 = 2.5
The phosphorous : oxygen {P:O} ratio of 1:2.5 is not a whole number ratio and so the lowest multiple,
which gives a whole number ratio is the empirical formulae, i.e 1:2.5, 2:5.0, 3:7.5 etc.
Hence the empirical formular = P2O5.
CHAPTER EIGHT
8.01 ALKANOIC ACIDS
Alkanoic acids are compound containing a carbonyl group attached to the hydroxyl group (-OH).
Alkanoic acids have a functional group of O
– C – OH and belongs to homologous series with general
molecular formula of CnH2n+1COOH. Where 1,2,3,4 ………….. for successive member of n. One of the
members of the series is ethanoic acid with general formula CH3COOH. The names are derived by
replacing the – ane in the parent alkanes with – oic acid.

8.02 NAMING OF ALKANOIC ACIDS


The formular of individual members of alkanoic acids are obtained by applying the general molecular
formular (CnH2n+1COOH)

When General Molecular Formulae Name


n= CnH2n+1COOH
0. C0H2x0+1COOH = HCOOH Methanoic acid
1. C1H2x1+1COOH = CH3COOH Ethanoic acid
2. C2H2x2+1COOH = C2H5COOH Propanoic acid
3. C3H2x3+1COOH = C3H7COOH Butanoic acid
4. C4H2x4+1COOH = C4H9COOH Pentanoic acid
5. C5H2x5+1COOH = C5H11COOH Hexanoic acid
6. C6H2x6+1COOH = C6H13COOH Heptanoic acid
7. C7H2x7+1COOH = C7H15COOH Octanoic acid
8. C8H2x8+1COOH = C8H17COOH Nonanoic acid
9. C9H2x9+1COOH = C9H19COOH Decanoic acid
10. C10H2x10+1COOH = C10H21COOH Undacanoic acid
11. C11H2x11+1COOH = C11H23COOH Dodecanoic acid
12. C12H2x12+1COOH = C12H25COOH Tridecanoic acid
13. C13H2x13+1COOH = C13H27COOH Tetradecanoic acid
14. C14H2x14+1COOH = C14H29COOH Pentadecanoic acid
15. C15H2x15+1COOH = C15H31COOH Hexadecanoic acid
16. C16H2x16+1COOH = C16H33COOH Heptadecanoic acid
17. C17H2x17+1COOH = C17H35COOH Octadecanoic acid
18. C18H2x18+1COOH = C18H37COOH Nonadecanoic acid
19. C19H2x19+1COOH = C19H39COOH Icosanoic acid/
Eiocosanoic acid
20. C20H2x20+1COOH = C20H41COOH Heneicosanoic acid
21. C21H2x21+1COOH = C21H43COOH Docosanoic acid
22. C22H2x22+1COOH = C22H45COOH Tricosanoic acid
23. C23H2x23+1COOH = C23H47COOH Tetracosanoic acid
24. C24H2x24+1COOH = C24H49COOH Pentacosanoic acid
25. C25H2x25+1COOH = C25H51COOH Hexacosanoic acid
26. C26H2x26+1COOH = C26H53COOH Heptacosanoic acid
27. C27H2x27+1COOH = C27H55COOH Octacosanoic acid
28. C28H2x28+1COOH = C28H57COOH Nonacosanoic acid
29. C29H2x29+1COOH = C29H59COOH Triacontanoic acid
30. C30H2x30+1COOH = C30H61COOH Hentriacontanoic acid

N:B more of alkanoic acids naming can be achieved using the process in alkane naming. (31 – 120).
8.03 MOLECULAR STRUCTURES OF ALKANOIC ACIDS

n ALKANOIC STRUCTURAL FORMULAR MOLECULAR FORMULAR


ACIDS
0. O HCOOH
HCOOH H-C -OH
Methanoic acid
1. H O CH3COOH
CH3COOH H-C-C-O H
Ethanoic acid H
2. HH O CH3CH2COOH
C2H5COOH H-C-C-C-OH
Propanoic acid HH
3. HHH O CH3(CH2)2COOH
C3H7COOH H-C-C-C-C-OH
Butanoic acid HHH
4. HHHH O CH3(CH2)3COOH
C4H9COOH H-C-C-C-C-C-OH
Pentanoic acid HHHH
5. HHHHH O CH3(CH2)4COOH
C5H11COOH H-C-C-C-C-C-C-OH
Hexanoic acid HHHHH
6. HHHHHH O CH3(CH2)5COOH
C6H13COOH H-C-C-C-C-C-C-C-OH
Heptanoic acid HHHHHH
7. HHHHHHH O CH3(CH2)6COOH
C7H15COOH H-C-C-C-C-C-C-C-C-OH
Octanoic acid HHHHHHH
8. HHHHHHHH O CH3(CH2)7COOH
C8H17COOH H-C-C-C-C-C-C-C-C-C-OH
Nonanoic acid HHHHHHHH
9. HHHHHHHHH O CH3(CH2)8COOH
C9H19COOH H-C-C-C-C-C-C-C-C-C-C-OH
Decanoic acid HHHHHHHHH
10. HHHHHHHHHH O CH3(CH2)9COOH
C10H21COOH H-C-C-C-C-C-C-C-C-C-C-C-OH
Undecanoic HHHHHHHHHH
acid
11. HHHHHHHHHHH O CH3(CH2)10COOH
C11H23COOH H-C-C-C-C-C-C-C-C-C-C-C-C-OH
Dodecanoic HHHHHHHHHHH
acid
12. HHHHHHHHHHHH O CH3(CH2)11COOH
C12H25COOH H-C-C-C-C-C-C-C-C-C-C-C-C-C-OH
Tridecanoic HHHHHHHHHHHH
acid
13. C13H27COOH HHHHHHHHHHHHH O CH3(CH2)12COOH
Tetradecanoic H-C-C-C-C-C-C-C-C-C-C-C-C-C-C-OH
acid H H HH H H H H H H H H H
14. C14H29COOH HHHHHHHHHHHHHH O CH3(CH2)13COOH
Pentadecanoic H-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-OH
acid HHHHHHHHHHHHHH
15. C15H31COOH HHHHHHHHHHHHHHH O CH3(CH2)14COOH
Hexadecanoic H-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-OH
acid HHHHHHHHHHHHHHH
16. C16H33COOH HHHHHHHHHHHHHHHH O CH3(CH2)15COOH
Heptadecanoic H-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-OH
acid HHHHHHHHHHHHHHHH
17. C17H35COOH HHHHHHHHHHHHHHHHH O CH3(CH2)16COOH
Octadecanoic H-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-OH
acid HHHHHHHHHHHHHHHHH
18. C18H37COOH HHHHHHHHHHHHHHHHHH O CH3(CH2)17COOH
Nonadecanoic H-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-OH
acid HHHHHHHHHHHHHHHHHH
19. HHHHHHHHHHHHHHHHHHH O CH3(CH2)18COOH
C19H39COOH H-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-OH
Eiocosanoic HHHHHHHHHHHHHHHHHHH
acid
20. C20H41COOH HHHHHHHHHHHHHHHHHHHH O CH3(CH2)19COOH
Heneiocosanoic H-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-OH
acid HHHHHHHHHHHHHHHHHHHH

8.04 NOMENCLATURE OF ALKANOIC ACIDS


Alkanoic acids are named using the IUPAC method by considering the functional group of alkanoic acids
O
( - C - OH) and the position of attachment of other substituents on the carbon atoms. The lowest
number is given. For example:

(i) COOH (ii) COOH

COOH CH2
Ethanedioic acid
COOH
Propan-1,3-dioic acid

COOH

CH – CH3

CH3-C – CH3

COOH
2,2,3- trimethyl butan-1,3- dioic acid
8.05 PHYSICAL PROPERTIES OF ETHANOIC ACID (ALKANOIC ACIDS)
1. It is a colourless liquid
2. It has a pungent odour of vinegar
3. It has a boiling point of 1180C and melting point of 170C
4. It is soluble in water
5. It is weak electrolyte.
6. It turns blue litmus paper red
8.06 CHEMICAL PROPERTIES OF ETHANOIC ACID
Ethanoic acid is neutralized by alkalis and base to form salts called ethanoates (esters)
1. Ethanoic acid react with sodium hydroxide (NaOH) to form sodium ethanoate (CH 3COONa) and water
CH3COOH + NaOH CH3COONa + H2O
2. Ethanoic acid react with metals such as iron filling to liberate hydrogen gas.
2CH3COOH + Fe heat (CH3COO)2Fe + H2
3. Ethanoic acid is heated with soda lime (NaOH), to form methane gas (CH 4) and carbon (iv) oxide
CH3COOH + NaOH CH4 + CO2
4. Ethanoic acid react with ethanol to form ethyl ethanoate and water. Alkanoic acid react with Alkanol
to form Alkanoate (ester) and water only. This process is analogous to NEUTRALIZATION reaction in
inorganic compounds. Hence, the process where by an alkanoic acid react with alkanol to form
alkanoate (ester) and water is called ESTERIFICATION reaction.
CH3COOH + CH3CH2OH CH3COOCH2CH3 + H2O
Ethyl ethanoate

8.07 LABORATORY PREPARATION OF ETHANOIC ACID


Ethanoic acid can be prepared in the laboratory in two ways or stages by oxidation of ethanol with
potassium hexaoxodichromate (iv) (K2Cr2O7) acidified with tetraoxosulphate (vi) (H2SO4)

STAGE 1: C2H5OH K2Cr2O7 CH3CHO + H2O


Ethanol ethanal
STAGE 2: CH3CHO K2Cr2O7 CH3COOH
Ethanal ethanoic acid

8.08 USES OF ETHANOIC ACID


1. For making cellulose ethanoate
2. For making non-inflammable safety film
3. For making textile fibres such as rayon
4. For making vinylethanoate which is used in emulsion paints, adhesive for woods, paper, glass and
brick.
5. As a vinegar for preserving food
6. To coagulate rubber latex.

8.09 TEST FOR ALKANOIC ACIDS


1. They turns litmus paper red.
2. react the suspected compound with sodium hydrogentrioxocarbonate (iv) (NaHCO 3). Effervescence of
a gas, carbon (iv) oxide evolved confirms alkanoic acid.
CHAPTER NINE
9.01 ALKANOATES (ESTERS)
Alkanoates are the products of condensation reaction between alkanoic acids and akanols. They can
also be prepared by reacting alkanols with acid anhydrides. Alkanoate have a functional group of
O
R - C – O-R
and belong to homologous serie with general molecular formula of CnH2n+1COOCnH2n+1. The first member
is methylethanoate. Alkanoates are named by indicating the stem alkanol from which the alkanoate is
derived with the suffix – yl follow by a stem indicating the acid with the suffix – oate.

9.02 NAMING OF ALKANOATES


The formular of individual members of alkanoates are obtained by applying the general molecular
formular (CnH2n+1COOCnH2n+1)

When General Molecular Formulae Name


n= CnH2n+1COOCnH2n+1
1. C1H2x1+1COOC1H2x1+1 = CH3COOCH3 Methylethanoate
2. C2H2x2+1COOC2H2x2+1 = C2H5COOC2H5 Ethylpropanoate
3. C3H2x3+1COOC3H2x3+1 = C3H7COOC3H7 Propylbutanoate
4. C4H2x4+1COOC4H2x4+1 = C4H9COOC4H9 Butylpentanoate
5. C5H2x5+1COOC5H2x5+1 = C5H11COC5H11 Pentylhexanoate
6. C6H2x6+1COOC6H2x6+1 = C6H13COOC6H13 Hexylheptanoate
7. C7H2x7+1COOC7H2x7+1 = C7H15COOC7H15 Heptyloctanoate
8. C8H2x8+1COOC8H2x8+1 = C8H17COOC8H17 Octylnonanoate
9. C9H2x9+1COOC9H2x9+1 = C9H19COOC9H19 Nonyldecanoate
10. C10H2x10+1COOC10H2x10+1 = C10H21COOC10H21 Decylundecanoate
11. C11H2x11+1COOC11H2x11+1 = C11H23COOC11H23 Undecyldodecanoate
12. C12H2x12+1COOC12H2x12+1 = C12H25COOC12H25 Dodecyltridecanoate
13. C13H2x13+1COOC13H2x13+1 = C13H27COOC13H27 Tridecyltetradecanoate
14. C14H2x14+1COOC14H2x14+1 = C14H29COOC14H29 Tetradecylpentadecanoate
15. C15H2x15+1COOC15H2x15+1 = C15H31COOC15H31 Pentadecylhexadecanoate
16. C16H2x16+1COOC16H2x16+1 = C16H33COOC16H33 Hexadecylheptadecanoate
17. C17H2x17+1COOC17H2x17+1 = C17H35COOC17H35 Heptadecyloctadecanoate
18. C18H2x18+1COOC18H2x18+1 = C18H37COOC18H37 Octadecylnonadecanoate
19. C19H2x19+1COOC19H2x19+1 = C19H39COOC19H39 Nonadecyleicosanoate
20. C20H2x20+1COOC20H2x20+1 = C20H41COOC20H41 Eiocosylheneicisanoate
21. C21H2x21+1COOC21H2x21+1 = C21H43COOC21H43 Heneicosyldocosanoate
22. C22H2x22+1COOC22H2x22+1 = C22H45COOC22H45 Docosyltricosanoate
23. C23H2x23+1COOC23H2x23+1 = C23H47COOC23H47 Tricosyltetracosanoate
24. C24H2x24+1COOC24H2x24+1 = C24H49COOC24H49 Tetracosylpentacosanoate
25. C25H2x25+1COOC25H2x25+1 = C25H51COOC25H51 Pentacosylhexacosanoate
26. C26H2x26+1COOC26H2x26+1 = C26H53COOC26H53 Hexacosylheptacosanoate
27. C27H2x27+1COOC27H2x27+1 = C27H55COOC27H55 Heptacosyloctacosanoate
28. C28H2x28+1COOC28H2x28+1 = C28H57COOC28H57 Octacosylnonacosanoate
29. C29H2x29+1COOC29H2x29+1 = C29H59CO C29H59 Nonacosyltriacontanoate
30. C30H2x30+1COOC30H2x30+1 = C30H61COOC30H61 Triacontylhentriacontanoate

N:B more of alkanoates naming can be achieved using the process in alkane naming. (31 – 120).
9.03 MOLECULAR STRUCTURES OF ALKANOATES

N ALKANOATES STRUCTURAL FORMULAR MOLECULAR


FORMULAR
1. CH3COOCH3 H O H CH3COOCH3
Methylethanoate H-C –C- O – C-H
H H
2. C2H5COOC2H5 HH O HH CH3CH2COOCH2CH3
Ethylpropanoate H-C-C- C – O – C-C- H
HH HH
3. C3H7COOC3H7 HHH O HHH CH3(CH2)2COO(CH)2CH3
Propylbutanoate H-C-C-C-C- O – C-C-C-H
HHH HHH
4. C4H9COOC4H9 HHHH O HHHH CH3(CH2)3COO(CH)3CH3
Butylpentanoate H-C-C-C-C-C- O – C-C-C-C-H
HHHH HHHH
5. C5H11COOC5H11 HHHHH O HHHHH CH3(CH2)4COO(CH)4CH3
Pentylhexanoate H-C-C-C-C-C-C- O – C-C-C-C-C-H
HHHHH HHHHH
6. C6H13COOC6H13 HHHHHH O HHHHHH CH3(CH2)5COO(CH)5CH3
Hexylheptanoate H-C-C-C-C-C-C-C- O – C-C-C-C-C-C-H
HHHHHH HHHHHH
7. C7H15COOC7H15 HHHHHHH OHHHHHHH CH3(CH2)6COO(CH)6CH3
Heptyloctanoate H-C-C-C-C-C-C-C-C- O – C-C-C-C-C-C-C-H
HHHHHHH HHHHHHH
8. C8H17COOC8H17 HHHHHHHH O HHHHHHHH CH3(CH2)7COO(CH)7CH3
Octylnonanoate H-C-C-C-C-C-C-C-C- C-O – C-C-C-C-C-C-C-C-H
HHHHHHHH HHHHHHHH
9. C9H19COOC9H19 HHHHHHHHH O HHHHHHHHH CH3(CH2)8COO(CH)8CH3
Nonyldecanoate H-C-C-C-C-C-C-C-C-C- C-O – C-C-C-C-C-C-C-C-C-H
HHHHHHHHH HHHHHHHHH
10. C10H21COOC10H21 HHHHHHHHHH O HHHHHHHHHH CH3(CH2)9COO(CH)9CH3
Decylundecanoate H-C-C-C-C-C-C-C-C-C-C-C – O – C-C-C-C-C-C-C-C-C-C-
HHHHHHHHHH HHHHHHHHHH

9.04 PHYSICAL PROPERTIES OF ETHTL ETHANOATE


1. Colourless volatile liquid
2. It has a pleasant smell of fruit
3. Slightly soluble in water
4. Boils at 750C

9.05 CHEMICAL PROPERTIES OF ETHYL ETHANOATE


1. It undergo hydrolysis to form ethanol and ethanoic acid
CH3COOC2H5 + H2O CH3COOH + C2H5OH
Ethyl ethanoate ethanoic ethanol
2. It react with sodium hydroxide to form sodium ethanoate and ethanol
CH3COOC2H5 + NaOH CH3COONa + C2H5OH
Sodium ethanoate
3. it undergo reduction to form ethanol
CH3COOC2H5 + 2H2 2C2H5OH
9.06 LABORATORY PREPARATION OF ETHYL ETHANOATE
Ethyl ethanoate is prepared in the laboratory by reacting ethanol with ethanoic acid in the presence of a
strong acid as a catalyst such a tetraoxosulphate (vi) acid (H2SO4).
CH3CH2OH + CH3COOH H2SO4 CH3COOCH2CH3 + H2O
Ethyl ethanoate
The above reaction is an ESTERIFICATION reaction.

9.07 USES OF ETHYL ETHANOATE


1. Use chiefly in dissolving polystyrene cement
2. Use in perfumes and cosmetics
3. Use in artificial flavour for foods

9.08 FATS AND OILS


Fats and oils are naturally occurring alkanoates (esters) and they belong to group of compound known
as LIPIDS. They are used as energy storing compound in plants and animals and are derived from
propan-1,2,3-triol, CH2OH-CHOH-CH2OH which is commonly called GLYCEROL. Most fats are triesters
derived from propan-1,2,3-triol and a variety of long – chain alkanoic acids, sometimes called FATTY
ACIDS. A simple fat molecule can be obtained from a molecule of propan-1,2,3-triol and three molecules
of octadecanoic acid.

CH2OH CH2OOC(CH2)16CH3

CHOH + 3[HOOC(CH2)16CH3] CHOOC(CH2)16CH3


Octadecanoic acid
CH2OH CH2OOC(CH2)16CH3
Propan-1,2,3- propan-1,2,3-triyl
triol trioctadecanoate.
9.09 PROPERTIES OF FATS
1. Solid at room temperature
2. Found mainly in animals
3. High melting point
4. Contain saturated alkanoic acid e.g C15H31COOH (animal fat)
9.10 PROPERTIES OF OILS
1. Liquid at room temperature
2. Found mainly in plants
3. Low melting point
4. Contain unsaturated alkanoic acid e.g CH3(CH2)7CH=CH(CH2)7COOH.
9.11 DIFFERENCES BETWEEN FATS AND OILS.

S/N FATS OILS


1. Solid at room Liquid at room temperature
temperature
2. Found mainly in animals Found mainly in plants
3. High melting point Low melting point
4. Contain saturated Contain unsaturated
alkanoic acid e.g alkanoic acid e.g
C15H31COOH (animal fat) CH3(CH2)7CH=CH(CH2)7COOH.
9.12 IMPORTANCE OF FATS AND OIL
1. Fats and oil provide more energy to animals than carbohydrates.
2. Fats supply essential fatty acids to animals
3. Fats and oils also provide fat soluble vitamins
4. They help in the maintenance of body temperature.
9.13 TEST FOR FATS AND OILS
TEST OBVERSATION INFERENCE
(i) Transluscent Test The drop of oil becomes
(i) Drop oil on a spot on more transluscent, i.e, it The transluscency
a filter paper, allows more light to shows the presence of
(ii) Observe the spot pass through when held fats and oils
against a source of light in front of it.
(ii) Sudan (iii) Test Red colouration appears
(i) Add few drops of before boiling. A black Fats and Oils is present
sudan (iii) solution to oil precipitate is formed on
in a test tube, boiling
(ii) Boil the solution
9.14 SOAPS –SAPONIFICATION
Soap contains the sodium or potassium salts of long chain alkanoic acids. Such as sodium hexadecanoate
(sodium palmitate) and sodium octadecanoate (sodium stearate). Soap making involves hydrolysis of
esters by alkali. The process is known as SAPONIFICATION. This is the hydrolysis of fats and oil with
caustic alkali to yield propan-1,2,3-triol and the corresponding sodium or potassium salts of the
component fatty acids. These salts are the principal constituents of soap.
Soap is a sodium or potassium salts of an alkanoates and each contain two parts: (RCOONa+) for sodium
soap and (RCOOK+) for potassium soap.
(i) R – alkyl radical is a non – water soluble hydrocarbon
(ii) COONa+ and COOK+ is soluble in water
In the cleaning action of soap, the water soluble part COOK+ or COONa+ removes the dirt from clothes
while the non – water soluble hydrocarbon part removes the grease and both are rinsed from dress as
waste water.
NOTE: Sodium salts produce soft soap while potassium salts produce hard soap.
9.15 DETERGENTS
Detergents are sodium salts of sulphonated alkenes. They are prepared by reacting an alkene ( n=12 to
20) with concentrated tetraoxosulphate (vi) acid and then hydrolyse the product with sodium hydroxide
solution.
C15H30 + H2SO4 C15H31SO4H
C15H31SO4H + NaOH C15H31SO4Na + H2O
Detergent

9.16 ADVANTAGES OF SOAP


1. It makes water to wet materials more effectively by lowering its surface tension
2. It emulsify oil or grease
3. It is biodegradable, that is, they can be broken down by bacterial.

9.17 DISADVANTAGES OF SOAP


1. It form scum on clothes with hard water
2. Raw materials are expensive and could be used for human consumption
3. It wastes soap when washing with hard water

9.18 ADVANTAGES OF DETERGENT


1. They don’t form scum on clothes with hard water
2. Raw materials are cheap and easily available
3. They are more soluble in water than soap, therefore increase the cleaning properties.
9.19 DISAVANTAGES OF DETERGENT
1. They are non – biodegradable, that is, they cannot be broken down by bacterial.
2. They causes water pollution.
9.20 MARGARINE
Margarine is made from double bond containing compounds through the process of HYDROGENATION,
this is used to convert edible oils such as palm oil which consist of long chain alkanoic acids which
convert double bond into margarine. When oils are treated with hydrogen in the presence of Nickel as a
catalyst, carbon chains of double bonds becomes saturated thereby raising the melting point of the oil
so that it becomes solid, at room temperature.
9.21 ADVANTAGES OF MARGARINE OVER BUTTER
1. It contains less of fats such as cholesterol which are hazardous to health
2. It is cheaper than butter because it is made from vegetable rather than an animal sources which are
expensive to produce.
CHAPTER TEN

10.01 AMINO ACIDS


Amino acids are derivatives of carboxylic acids in which one hydrogen atom of alkyl group has been
replaced by an amino group, - NH2. Amino acids are the basic structural units of proteins with the
general molecular formular:
R
H – C - COOH
NH2
The carbon atom of the amino acid to which the functional group is attached is known as the α-carbon.
There are three forms of amino acids:
1. The acid condition H3+NCH2COOH
2. The neutral condition H3+NCH2COO
3. The basic condition H2NCH2COO
H3+NCH2COOH H3+NCH2COO H2NCH2COO
Acid condition neutral condition basic condition

10.02 NOMENCLATURE OF AMINO ACIDS


(i) H (ii) H (iii) H
H – C – COOH CH3- C – COOH H2N – C
NH2 NH3 CH3
Amino ethanoic acid 2 – amino propanoic SH
(glycine) acid (alanine) cysteine

O
(iv) H2N – CH2 – CH2 – CH2 – CH2 – C
OH
5 –aminopentanoic acid

NH2 O
(v) HO – CH2 – CH - C
OH
2 – amino, 3-hydroxypropanoic acid (serine)

O NH2 O
(vi) C- CH2-CH2-CH-C
HO OH
2 – amino -1,5-pentadiamine (glutamic acid)

NH2 O
(vii) CH3 – CH-CH-C
OH OH
2- amino – hydroxyl butanoic acid (threonine)

H Br Br O
(viii) N–C–C–C
H H Br OH
3-amino-2,2,3-tribromopropanoic acid
10.03 PREPARATION OF AMINO ACIDS
Amino acids are prepared by treating alkanal with cyanide ions, in the presence of ammonium ions.

10.04 PHYSICAL PROPERTIES OF AMINO ACIDS


1. They are salt – like and ionic because of formation of the zwitterions e.g N +H3 . CH2 . COO-
2. They are more soluble in water than in less polar solvents such as ether
3. They have low solubility in non-polar solvents
4. α- amino acids are crystalline solids with high melting and boiling point

10.05 CHEMICAL PROPERTIES OF AMINO ACIDS


1. Amino acids react with alkanols in the presence of an acid catalyst to give esters.
2. Amino acids on heating react with sodium trioxocarbonate(iV) solution to liberate carbon(iv) oxide
3. Amino acids react with acyl chlorides or acid anhydrides to give acylated products
4. Amino acids reacts with dioxonitrate (III) acid to give nitrogen and the corresponding hydroxyl
carboxylic acid

10.06 PROTEINS
Proteins may be regarded as the products of successive condensation between carbonyl group of one
amino acid and the amino group of another amino acid. proteins are complex combinations of amino
acids which are essential constituents of living cells, being responsible for growth and the mainteinance
of all tissues.

SOURCES OF PROTEIN: Milk, Egg, Fish, Cheese, Meat, Chicken. While plant sources are: Beans,
groundnut, soyabeans, cowpea e.t.c

10.07 PROPERTIES OF PROTEINS


1. Denaturation
2. Hydrolysis

10.08 TEST FOR PROTEINS


1. Biuret test: Add about 1cm3 of dilute causic soda solution into a test tube containing some dilute egg
white solution. Then add 1% copper(II) tetraoxosulphate(vi) solution drop by drop and shake
thoroughly. The formation of a violet colouration indicates the presence of proteins.
2. Million’s test: Add few drops of million’s reagent to some egg – white solution in a test tube. The
formation of a white precipitate which turns brick – red on heating indicates the presence of propteins
3. Trioxonitrate(V) acid Test: Add few drops of concentrated hydrogen trioxonitrate(v) acid to 2cm3 of
egg – white solution. The formation of an intense yellow colour indicates the presence of proteins.

10.09 IMPORTNCE OF PROTEIN


1. Proteins is used for the growth of young ones
2. It is used for the repair of worn – out tissues or cells
3. It aids reproduction
4. It is used for the production of enzymes
5. It is also used for production of hormones
6. It is used for tissue and cell formation.
CHAPTER ELEVEN

11.01 AMINES
Organic compounds that are obtained by replacing one or more of hydrogen atoms of ammonia (NH3)
by alkyl or aryl groups. Amines are drived from ammonia by replacing the hydrogen atoms, one at a time
with carbon – containing groups. The fundament groups are R-NH2, R2 – NH, R3 – N
Amine are classified into primary, secondary and tertiary according to the number of substituted
hydrogen.

11.02 CLASSIFICATION OF AMINES


PRIMARY AMINES: These are amines that have one alkyl or aryl group attached to the nitrogen of an
amine e.g H
R – NH2 R–N
H
(i) CH3NH2 (ii) C6H5NH2 (iii) C6H5CH3NH2 (iv) CH3(CH2)3CHNH2
Methylamine phenylamine phenylmethylamine CH3
(benzylamine) hexyl-2-amine or haxan-2-amine

(v) CH3CH2NH2 (vi)


Ethylamine CH2NH2

Benzylamine

SECONDARY AMINES: These are amine that have two alkyl or aryl groups attached to the nitrogen of
amine e.g
(i) CH3CH2 – N – CH2CH3 (ii) CH3 CH3
H N
diethylamine

N, N – dimethylamine
TERTIARY AMINES: These are amine that have three alkyl or aryl groups attached to the nitrogen of
amine e.g
(i) (C2H5)3N (ii) CH3 – N – CH3
triethylamine CH3
N,N,N –trimethylamine

11.03 LABORATORY PREPARATION OF AMINE


1. From alkyl halide: can be prepare from alkylhalides in the presence of excess ammonia
2. By the reduction of nitriles: Nitriles give primary amine on reduction with powerful reducing agents
in ether.

11.04 INDUSTRIAL PREPARATION OF AMINES


Trioxo-nitrate (v) acid readily converts alkanes to nitroalkanes using nickel as a catalyst

11.05 PHYSICAL PROPERTIES OF AMINES


1. first two members of amine –mthylamine and –ethylamine are gas, while others are liquid at room
temperature and pressure.
2. The smaller amines are soluble in water.
3. Amine have strong odour characteristic of dead fish.
11.06 CHEMICAL PROPERTIES OF AMINES
1. Reacion as organic base: primary, secondary and tertiary amine are all basic, like ammonia they have
a lone pair of electrons on the nitrogen atoms.
C6H5NH2 + HCl C6H5N+H3Cl+
Phenyl ammonium chloride
2. Like ammonia secondary and tertiary amines are alkylated to give _ - substituted derivatives.
H CH3
CH3 – N – CH3 + C2H5Br CH3 – N – CH3 + HBr

11.07 USES OF AMINES


Amines are used in the manufacture of polyamides or nylon.

AMIDES
11.08 AMIDES
An amide is a compound in which the – OH group of a carboxylic acid is replaced by – NH2. When the –
OH is replaced by – NHR, the product is called a nitrogen – substituted amide i.e N- substituted amide.
Amide are characterised by the presence of functional amino group.
O
-C
NH2
Amides are named as derivatives of carboxylic acids, by dropping the ending –oic of the parent
carboxylic acid and replace with the ending amide e.g.
O O
CH3 – C CH3 – C
OH NH2
Ethanioc ethanamide
Other examples of amides are:
(i) O (ii) O
H–C C2H5 – C
NH2 NH2
Methanamide propanamide

(iii) O (iv) CH3 O


CH3 – C CH3 – (CH2)7CHC
N – CH3 NH2
H 2- methyl decanamide
N - Methyl ethanamide
(v) NH2 (vi) CH3 CH3

CH3
P- toluidine N,N – dimethylamine

(vii) CH3
NH CH
CH3
N- isopropylcyclopentylamine
(viii) NH2 (ix) NH2 (x) NH2
OH

NO2 O - hydroxyaniline
M - nitroaniline OCH3
P - methoxyaniline

11.09 PREPARATION OF AMIDES:


1. from ester, acylhalides or acid anhydrides: when esters, acylhalides or acid anhydrides are treated
with concentrated ammonia solution or liquid ammonia, amides are obtained
O O
CH3C + NH3 CH3 – C + CH3OH
O – CH3 NH2
Methyl ethanoate ethanamide
2. by partial hydrolysis of nitriles: this is achieved by dissolving the nitrile in concentrated
tetraoxosulphate(vi) acid. the mixture is then poured into water

11.10 PHYSICAL PROPERTIES OF AMIDES


1. With the exception of methanamide, a liquid with a high boiling point, amides are crystalline solids at
room temperature.
2. The melting and boiling points of amide are much higher than expected.

11.11 CHEMICAL PROPERTIES OF AMIDES


1. Amides are very weak base and also very weak acids
2. Amide are readily hydrolysed when treated with dilute acid or alkali to give the carboxylic acid and
ammonia is liberated.
3. Primary amides are reduced to primary amines with sodium and ethanol or with lithium tetrahydrido
aluminate (III).
4. Reaction with dioxonitrate (III) acid to yield carboxylic acid with the evolution of nitrogen
CHAPTER TWELVE
12.01 POLYMERIZATION
The phenomenon whereby smaller molecules combine together to form very large or complex
molecules is known as POLYMERIZATION. Polymerization therefore is the process where smaller
molecule combine together to form one giant or complex molecule with no gain or loss of any materials.
The original material is called the monomer while the product form is called a polymer.
For example, if ethyne is heated in a red hot tube, it is polymerized into benzene.
3C2H2 C6H6
Polymerization as a chemical reaction is characteristic of unsaturated compounds. In the reaction, the
double bonds are broken to form a long chain of single bond units.

12.02 POLYMER
Polymers are substances with very large molecules which are themselves built up by the repetition of
smaller chemical units. The formation of a polymer from smaller chemical unit is thus termed
polymerization as in the equation below:
n(CH2=CH2) (-CH2-CH2-)n

12.03 CHARACTERISTICS OF POLYMER


1. Highly branded polymer tend to have lower tensile strength and melt easily
2. Polymer with much cross-linking tend to be rigid, hard and fairly brittle
3. Polymers tend to be strong and difficult to melt as the intermolecular forces between chain are high
4. The strength and melting point of a polymer increase with chain length

12.04 NATURAL OCCURING POLYMERS


1. Wood
2. Wool
3. Cotton
4. Rubber
5. Protein

12.05 SYNTHETIC POLYMERS


1. Nylon
2. Plastic
3. Textiles
4. Perspex
5. Polyvinylchloride

12.06 DISADVANTAGES OF SYNTHETIC POLYMER


1. They non-biodegradable i.e cannot be broken down by bacteria
2. they cannot be economically recycled.

12.07 CLASSES OF POLYMERS


1. Addition Polymer
2. Condensation Polymer

12.08 ADDITION POLYMERS: This is the built up of polymer from monomer without any elimination, so
that the empirical formular of both the monomer and polymer are the same. Examples of addition
polymers are:
(a) Polythene- used for making firms and sheeting for bags and wrappers.
(b) Polypropylene- used for making ropes.
(c) Polystyrene – used to produce electric insulators, toys, shoes soles and dishes
(d) Polybutylene – use for making car tyres
(e) Perspex – used for making glass
(f) Polyvinylchloride (PVC) – used for coating fabrics, for covering wires and cables and making
gramophone records.
(g) Acrilan – used for making textiles

12.09 CONDENSATION POLYMERS: This is the built up of polymer from monomer with elimination of
small molecule material such as water. Example of condensation polymer are:
(a) Polyesters – used as the bonding resin in glass, fibre, plastics as well as in wide application in the
textile industry.
(b) Terylene – used in textile industries.

12.10 Plastics: are polymer which are more easily deformed


TYPES OF PLASTICS
1. Thermosoftening: these are plastics that can be moulded by melting. E.g polythene
2. Thermosetting: these are plastics that cannot be remelted. E.g bakelite.
CHAPTER THIRTEEN
13.01 CARBOHYDRATES
Carbohydrates are compounds containing carbon, hydrogen and oxygen only. The hydrogen and oxygen
atoms are in ratio 2:1. The general molecular formula for this class of homologous series is C xH2yOy or
Cx(H2O)y . Example of carbohydrates are water soluble sugars such as sucrose and glucose and larger
insoluble sugars such as starch, glycogen and cellulose.
SOURCES OF CARBOHYDRATES: Rice, yam, maize, millet, guinea corn, potatoes, bread, Garri e.t.c
13.2 CLASSES OF CARBOHYDRATES.
1. SIMPLE SUGARS: these are crystalline and soluble in water and have sweet taste. E.g glucose, fructose
and sucrose
2. COMPLEX SUGARS: these are otherwise called polysaccharide. They are non – crystalline, insoluble in
water and tasteless e.g starch and cellulose. They have very high relative molecular masses.
Carbonhydrates are polyhydroxyl and aldehydes. Polyhydroxyl (ketones compound) which yeild one of
these compounds on hydrolysis.
CHO CH2OH
H-C-OH C=O
OH-C-H C-H
H-C-OH H-C-OH
H-C-OH H-C-OH
CH2OH CH2OH
Glucose Fructose
Monosaccharide: A carbohydrate that cannot be hydrolyzed to simpler compound, e.g Glucose,
Fructose and Galactose.
Disaccharide: A carbohydrate that can be hydrolyzed to two monosaccharide molecules. E.g Sucrose,
Lactose and Maltose
Polysaccharide: A carbohydrate that can be hydrolyzed to many monosaccharide molecules. E.g
Cellulose, Starch and Glycogen.
A monosaccharide with an aldehyde(Alkanal) group is knowns as ALDOSE and if it contains
keto(Alkanone) group is known as KETOSE.
Depending on the number of C atoms it contains, a monosaccharide is known as triose, tetrose,
pentose, hexose and so on.
Glucose is aldohexose while fructose is keto-hexose. Most naturally occurring monosaccharides are
pentose (5-C) and hexoses (6-C).
Carbohydrates that reduce fehling (or Benedict’s) or Tollen’s reagents are known as reducing sugars. All
disaccharides whether aldose or ketose are reducing sugar. Most disaccharides are reducing sugar.
Sucrose (table sugar) is a notable exception, for it is non-reducing sugar.
13.03 GENERAL FEATURES
TRIOSES
We regard C3H6O3 as the simplest molecule formula of a sugar. There are three isomeric triose. Two of
which are enantiomeric.
CHO CHO
H-C-OH HO-C-H
CH2OH CH2OH
D- Glyceraldehyde L-Glyceraldehyde
D- and L- glyceraldehydes may be regarded as the parents of two series of Aldose sugars.
Form glycerol
CH2OH
*CHOH
CH2OH
Carbon 2 I Chiral carbon atom because it is bounded to four different GROUPS not atoms
TETROSES (ET)
CHO CHO
H-C-OH HO-C-H
H-C-OH H-C-OH
CH2OH CH2OH
D- Erythrose D-Threose
All –OH point to right -OH on C -2

CHO CHO
HO-C-H H-C-OH
HO-C-H HO-C-H
CH2OH CH2OH
L- Erythrose L-Threose
All –OH point to left All –OH point to right

ALDOPENTOSES (D- SERIES) RAXL


CHO CHO CHO CHO
H-C-OH HO-C-H H-C-OH HO-C-H
H-C-OH H-C-OH HO-C-H HO-C-H
H-C-OH H-C-OH H-C-OH H-C-OH
CH2OH CH2OH CH2OH CH2OH
D- Ribose D-Arabinose D-Xylose D- Lyxose
All –OH point to right –OH on C- 2 -OH on C-3 -OH on C-2 & C-3

ALDOHEXOSES (D-SERIES) STRUCTURES.


CHO CHO CHO CHO
H-C-OH HO-C-H H-C-OH HO-C-H
H-C-OH H-C-OH HO-C-H HO-C-H
H-C-OH H-C-OH H-C-OH H-C-OH
H-C-OH H-C-OH H-C-OH H-C-OH
CH2OH CH2OH CH2OH CH2OH
D-Allose D-Altrose D-Glucose D- Mannose
All –OH point to right –OH on C- 2 -OH on C-3 -OH on C-2 & C-3
ALL ATRUIST GLADLY MAKE
CHO CHO CHO CHO
H-C-OH HO-C-H H-C-OH HO-C-H
H-C-OH H-C-OH HO-C-H HO-C-H
OH-C-H OH-C-H HO-C-H HO-C-H
H-C-OH H-C-OH H-C-OH H-C-OH
CH2OH CH2OH CH2OH CH2OH
D- Gulose D-Indose D-Galactose D- Talose
- OH on C-4 –OH on C- 2 & C-4 -OH on C-3 & C-4 -OH on C-2, C-3 & C-4
GUMS IN GALLON TANKS
RING STRUCTURE

FURAN PYRAN
In linear structure
H OH H OH
C C
CHOH CHOH
CHOH CHOH
CHOH CHOH
CH2OH CHOH
5-member furanose CH2OH
6-member pyranose

Carbohydrate

Simple sugar Complex sugar

Monosaccharide Disaccharide Polysaccharide

Glucose Fructose Galactose Sucrose Maltose Lactose Starch Glycogen Cellulose

13.04 GLUCOSE:
Glucose is the most important simple sugar found in fruits such as grapes, in honey and the cell sap of
plants. Glucose is the main source of energy for animal tissue and it is sythesized by plants during
photosynthesis and exist in two forms – an open chain and a cylic forms.
H
C=O CH2OH H
H-C-OH H C O
OH-C-H C H C
H-C-OH OH OH H OH
H-C-OH C C
CH2OH H OH
Open chain Glucose Cyclic form of glucose
13.05 LABORATORY PREPARATION OF GLOCOSE
By hydrolysis of sucrose with dilute acid in the presence of ethanol
C12H22O11 + H2O heat H2SO4 C6H12O6 + C6H12O6
13.06 INDUSTRIAL PREPARATION OF GLOCOSE
By hydrolysis of starch using dilute acid under pressure
(C5H10O5)n +nH2O nC H O
6 12 6
Starch glucose
13.07 PROPERTIES OF GLUCOSE
1. glucose is a strong reducing agent because of the presence of the –CHO group
2. when heated glucose with concentrated tetraoxosulphate(vi) acid, a black residue of carbon is formed
3. Glucose solution is readily fermented to ethanol and carbon(iv) oxide by the enzymes zymase.
13.08 TEST FOR GLUCOSE
Add a few drops of fehling’s solution to glucose solution in a test tube. A brick-red precipitate is
obtained on boiling
13.09 USES OF GLUCOSE
1. Glucose is use in the manufacturing of jam and sweets.
2. It is use as an immediate source of energy for sick people and sportmen.
13.10 FRUCTOSE (Fruit sugar or laevulose)
Fructose like glucose has the molecular formulae C6H12O6 and its structure is:

CH2OH O H
C=O HOCH2
OH-C-H C C
H-C-OH OH H OH CH2OH
H-C-OH C C
CH2OH OH H
Open chain Fructcose Cyclic form of fructose
Fructose is usually found together with glucose in sweet fruit and honey. It is also obtained from the
hydrolysis of sucrose. In many way fructose resembles glucose. The only difference is the behaviour of
the two sugar towards oxidation agents. E.g on oxidation with trioxonitrate(v) acid, fructose gives a
mixture of acid each containing less than six carbon atom.
13.11 DISACCHARIDES
Disaccharide are produced by the condensation of two molecules of monosaccharides and elimination
of one molecule of water. The two molecule component monosaccharides may be different or the
same. They have general formular of C12H22O11. All disaccharide are crystalline solid which are soluble in
water.

Component Disaccharide
Glucose + fructose Sucrose (Cane sugar)
Glucose + Galactose Lactose (milk sugar)
Glucose + Glucose Mlatose (malt sugar)

13.12 SUCROSE
Sucrose has the molecular formular C12H22O11. It is the common granulated sugar used to sweeten food.
It occurs naturally in many plants and fruits. The main source is sugar cane and sugar beef

H CH2OH H CH2OH O H
C O
C H C O C C
OH H H OH
OH C C C C CH2OH
H OH OH H

13.13 PREPARATION OF SUCROSE


Sucrose is prepared from juice of sugar cane or sugar beef. The juice from suagar cane or beef is first
extracted with water warmed to about 800C. the solution is then purified by treatment with slaked lime
and carbon(iv)oxide. The purified solution is concentrated by evaporation.

13.14 PHYSICAL PROPERTIES OF SUCROSE


1. Sucrose is colourless crystalline solid, with very sweet taste
2. It dissolves readily in water but not in akanol
13.15 CHEMICAL PREPERTIES OF SUCROSE
1. Sucrose chars on strong heating with concentrated H2SO4
2. When sucrose is heated to a temperature of about 2100C, which is above its melting point but below
its charring temperature, a yellow-brown substance known as caramel is obtained
3. Sucrose is readily hydrolysed by dilute acids or enzyme.

13.16 TEST FOR SUCROSE


Add few drops of freshly prepared seliwanoff reagent to 5cm3 of sucrose solution in a test tube, warm in
water bath. The mixture turns red after ten(10) minutes

13.17 USES OF SUCROSE


1. Sucrose is used for sweeten food
2. It is used for preserving food
3. It is also used to produce ethanol by fermentation
4. Caramel is used for flavouring and in confectionery

13.18 MALTOSE
Maltose is another disaccharide with molecular formular C12H22O11 and the structural formular is:

H CH2OH H H CH2OH H
C O C O
C H C O C H C
OH H OH H
OH C C C C OH
H OH H OH
Maltose is obtained by the action of malt on starch. Maltose contains the enzyme diastase

13.19 PHYSICAL PROPERTIES OF MALTOSE


1. It is a crystalline, white solid and soluble
2. It melts between 1600C – 1650C
3. Maltose is hydrolysed by dilute acids or by enzyme maltase
4. Maltose is a reducing sugar

13.20 LACTOSE
Lactose is also known as milk sugar and occurs in the milk of mammals. It is not found in plants. Its
molecular formular is C12H22O11. While its structural formular is:
OH CH2OH H H H OH H
C O C C
C H C O C OH H C
OH H H
H C C C O OH
H OH CH2OH

13.21 PROPERTIES OF LACTOSE


1. Lactose is crystalline, soluble, white solid
2. It melts at 2030C
3. It is hydrolysed by dilute acids or by the enzymes lactase to an equimolar mixture of glucose and
galactose.
13.22 POLYSACCHARIDES
Polysaccharides are high polymers of very long chain of monosaccharides linked together by
condensation with the molecular weights ranging from a few thousands to several millions. Important
polysaccharide are glycogen, cellulose, starch and insulin.

13.23 PREPARATION OF STARCH


The raw materials (e.g potato or cassava tubers) are first peeled and crushed to break the plant cells and
release the starch granules. The crushed pulp is then mixed with water to extract the starch. It forms
suspension which is allowed to stand for some time, leaving behind the white starch residue and the
water above is decanted.

13.24 PROPERTIES OF STARCH


1. Starch is a white, odourless and teasteless powder.
2. It is insoluble in cold water but soluble in hot water, forming a colloidal solution which sets into a jelly
on cooling.
3. Starch is hydrolysed by dilute acids to yield a mixture of maltose and glucose. Further hydrolysis give
glucose.
4. It is dcomposed on heating in the presence of the enzyme diastate to form maltose sugar
5. Starch does not contain any free carbonyl group, it does not reduce fehling’s solution. Hence it is not
a reducing sugar.

13.25 TEST FOR STARCH


Add a few drops iodine to some boiled starch. A dark – blue colouration, which disappears on heating
and reappears on cooling results.

13.26 USES OF STARCH


1. It is used mainly as food
2. It is used to produce ethanol and glucose
3. It is used as a stiffening agent.

13.27 CELLULOSE
Cellulose is the main structural component of plant cell walls and plant fibres. The main sources of
cellulose include cotton and wood. It is the most widely distributed organic compound.

13.28 PROPERTIES OF CELLULOSE


1. Cellulose is white solid which is not soluble in water and ordinary organic solvent.
2. It is not easily hydrolysed by dilute acids
3. The enzymes cellulase readily hydrolyse cellulose

13.29 USES OF CELLULOSE


1. It is used in the manufacturing of paper, cellophane, textile and ropes.
2. In the manufacturing of gum, cotton and explosives.

13.30 GARRI PRODUCTION


To make Garri, cassava tubers are peeled, washed and grated or crushed to produce a mash. The mash
could be mixed with palm oil (Oil Garri) before being placed in a porous bag. It is then placed in an
adjustable press machine or place heavy stone on the bag for 1 – 3 hours to remove excess starchy
water. When the cassava has become dry enough, it is ready for the next step. It is then sieved and fried
in a large clay or iron frying pot with or without palm oil. The resulting dry granular Garri can be stored
for long periods. It may be poured or ground to make a fine flour.
TEST FOR PROTEIN, STARCH, SUGAR, FATS AND OILS, WATER

S/N COMPOUNDS TEST OBVERSATION INFERENCE


1 TEST FOR (i) Biuret’s test
PROTEINS (i) take a small quantity of fresh
milk or egg white solution.
(ii) Add 1cm3 of protein and
sodium hydroxide and 1% Mixture will turn Protein is present.
copper(ii) solution in drops to purple or violet
(iii) Shake the mixture after each colour
drop
(iv) do not heat
(ii) Million’s Test
(i) Put 3cm3 of protein food, e.g
fresh egg white in test tube A red precipitate Protein is present
(ii) Add 3cm3 of million’s reagent would appear
(iii) warm the mixture in a water
bath for few minutes
(iii) Xanthoproteic Test A white precipitate
(i) Put 2cm3 of egg white or milk forms, which turns
solution in a test tube yellow on heating.
(ii) Add about 1cm3 of conc. On cooling the Protein is present
Trioxonitrate(v) acid and 3cm3 of content after
ammonium hydroxide solution adding excess
(iii) Heat the solution NH4OH, the
(iv) allow it to cool solution becomes
orange.
2. TEST FOR STARCH (i) Collect any starch material like The colour will Starch is present
bread or yam, change to blue-
(ii) Add few drops of dilute iodine black
solution
3 TEST FOR SIMPLE (i) Put a small quantity of glucose A brick-red or Glucose is present
SUGARS, e.g solution in a test tube orange precipitate
glucose and (ii) Add 2% Benedict solution is seen
fructose (iii) Boil the mixture for 4 – 6
minutes
4 TEST FOR (i) Put a small quantity of sucrose
REDUCING SUGAR, solution in a test tube
e.g sucrose, (ii) Add few drops of Benedict or A yellow Sucrose or non-
maltose or lactose Fehling’s solution precipitate is reducing sugar is
(iii) Add few drops of HCl obversed present
(iv) Boil the mixture for few
minutes
NOTE: Dilute HCl and boiling will
help to hydrolized the sucrose to
simple sugars, e.g glucose
5 TEST FOR FATS (i) Transluscent Test The drop of oil
AND OILS (i) Drop oil on a spot on a filter becomes more The transluscency
paper, transluscent, i.e, it shows the
(ii) Observe the spot against a allows more light presence of fats
source of light to pass through and oils
when held in front
of it.
(ii) Sudan (iii) Test Red colouration
(i) Add few drops of sudan (iii) appears before Fats and Oils is
solution to oil in a test tube, boiling. A black present
(ii) Boil the solution precipitate is
formed on boiling
6 TEST FOR WATER Dip a blue, dry cobalt chloride The colour of the
paper in a food item paper changes Water is present.
from blue to pink

OBJECTIVE QUESTIONS
1. Which of the following compounds determines the octane rating of petrol? A. 1, 2, 3
trimethylpentane B. 2, 3, 5 - trimethyloctane C. 2, 3, 5 trimethylpentane D. 2, 2, 4 - trirnethylpentane
2. Which of the following compounds would react with ethanoic acid to give a sweet smelling liquid?
A. Alkane B. Alkanol C. Alkanal D. Alkyne
3. The reaction between alkanoic acid and alkanols in the presence of a mineral acid is known as
A. saponification B. hydrolysis C. esterification D. dehydration
4. The following substances are examples of addition polymer except A. nylon. B. perspex
C. polyethane. D. polychloroethane.
5. When bromine is added to ethene at room temperature, the compound formed is
A. 1, 1 - dibromoethane B. 1, 1 - dibromoethene. C. 1, 2 - dibromoethane, D. 1, 2 - dibromoethene.
6. The compound that makes palm wine taste sour after exposure to the air for few days is
A. ethanol. B. ethanoic acid. C. methanol. D. methanoic acid.
7. The reagent that can be used to distinguish ethene from ethyne is A. ammoniacal silver trioxonitrate
(V) solution. B. Benedict solution. C. bromine water. D. Fehling’s solution.
8. Which of the following pairs of compounds belongs to the same homologous series?
A. C3H8 and C3H6 B. C2H6 and C4H10 C. C4H10 and C5H10 D. C2H4 and C4H10
9. The final products of the reaction of ethyne with excess hydrogen chloride is
A. CH3CHCl2 B. CH2ClCH2Cl C. CH2=CHCl D. CH3CCl3
10. The reaction between C2H2 and HBr is called
A. Addition B. Oxidation C. Polymerization D. Substitution
11. The gas given off when ethanol react with sodium is
A. Carbon(IV) oxide B. Hydrogen C. Methane D. Oxygen
12. CH3 CH3 CH3 H

C=C C=C
H H H CH3
The two compound represented by the structural formulae above are
A. Geometrical isomer B. Optical isomer C. Chain isomer D. Linkage isomer
13. Which of the following compound will not decolourized acidified KMnO 4 solution A. C2H5OH B. C6H10
C. C6H6 D. C6H14

14. An alkyne with six carbon atoms per molecule has relative molecular mass of A. 72 B. 82 C. 84 D. 86
15. A characteristic of the alkane family is …….. reaction
A. Addition B. Elimination C. Neutralization D. Substitution
16. The alkyl group is represented by the general formulae
A. CnH2n B. CnH2n+1 C. CnH2n+2 D. CnH2n-1
17. An isomer of C5H12 is A. 2-methyl butane B. 2-ethyl butane
C. 2-methyl pentane D. 2-methyl propane
18. Cyclohexane and benzene have an equal number of
A. carbon atom B. double bonds C. hydrogen atoms D. Single bonds
19. H CH3 H H H H
I I I I I I
H ----- C ------ C ------ C ----- C ------ C ----- C ------ H
I I I I I I
H CH3 H H H H
The IUPAC nomenclature of the compound above is A. 2-dimethyl hexane
B. 2-ethyl hexane C. 2,2-dimethyl hexane D. 5,5 dimethyl hexane
20. Ethene undergoes mainly addition reactions because it is
A. Hydrocarbon B. Unsaturated C. Easily polymerized D. covalent compound
21. Which of the following compounds is not a natural polymer
A. polyethene B. protein C. rubber D. starch.
22. The property which makes alcohol soluble in water is the
A. Boiling point B. hydrogen bond C. Ionic character D. covalent nature
23. When ethanol is heated with excess concentrated tetraoxosulphate(VI) acid, the organic product
formed is A. Ethanal B. Ethanoic acid C. Ethane D. Ethene
24. The organic compound with the following structure represents
CH3
I
CH3 ---- C ------ C2H5
I
OH
A. Primary alkanol B. Secondary Alkanol C. Tertiary Alkanol D. analkanol
25. What is the IUPAC name of the compound with the following structure
H
I A. 2-methyl butane B. 2-methyl prop-2-ene
H ------ C -----C = C ---H C. 2-methyl prop-1-ene D. but-2-ene
I I
H H
H--C—H
I
H
26. Protein in acid solution undergo A. polymerization B. hydrolysis C. fermentation D. substitution.
27. The intermedicate product formed when ethanol is progressively oxidised to ethanioc acid with
potassium heptaoxodichromate (VI) is A. butanal B. ethanal C. methanal D. propanal.
28. The formular CH2O for ethanoic acid is regarded as its A. molecular formular
B. general formular C. empirical formular D. structural formular.
29. An organic compound which gave effervescence with sodium hydrogen carbonate (IV) is likely to be
an A. alkanioc acid B. aromatic hydrocarbon C. alkanoate D. alkanone.
30. The chemicals used for testing for the presence of proteins include the following expect A. million’s
reagent B. fehling’s solution C. concentrated HNO3 D. NaOH(aq) and CuSO4(aq).
31. Plastics which lose their plasticity on being subjected to heat are said to be
A. thermosetting B. polymeric C. thermoplastic D. biodegradable.
32. Detergents are better than soaps for washing in hard water because A. hard water contains insoluble
calcium salts B. they contain bleaching powder C. they contain palmitic acid d. they do not form
insoluble calcium and magnesium salts
33. Fructose and glucose are A. allotropes of each other B. both disaccharides
C. isomer of each other D. isotopes of each other.
34. An example of a non-reducing sugar is A. fructose B. glucose C. lactose D. sucrose.
35. Which of the following is used widely in the manufacturing of flavours and perfumes A. Alkanoates
B. Alkanones C. Alkanes D. Aliphatic compounds.
36. The by-product of the fermentation of sugar to ethanol is A. propane-1,2,3-triol B. ethyl ethanoate
C. ethanedioic acid D. carbon(IV)oxide.
37. The ash, used for making black soap locally, provides A. glycerol B. potassium ion C. sodium chloride
D. stearic acid.
38. The hydrolysis of groundnut oil by potassium hydroxide is known as
A. hydrogenation B. saponification C. esterification D. neutralization.
39. The alkanoate CH3CH2COOC2H5 is the product of the reaction between
A. ethanoic acid and ethanol B. ethanoic acid and propanol C. propanoic acid and ethanol D. propanoic
acid and propanol.
40. The alkanol obtained from the production of soap is A. dihydric alkanol
B. monohydric alkanol C. trihydricalkanol D. tertiary alkanol.

41. CH3COOH(g) CH4(g) + CO2(g). The reaction above is


A. acidification B. carboxylation C. decarboxylation D. methylation.
42. Which of the following structures corresponds to the functional group of alkyl alkanoate?
O
A. C O H B. C O H

C. C O C D. C O C
O

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