Professional Documents
Culture Documents
TO
ORGANIC CHEMISTRY
FOR
CROWNTURN PRESS
LAGOS, NIGERIA
ADEKANMI, S.M © 2019
ISBN:
CROWNTURN PRESS
LAGOS, NIGERIA
PREFACE
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
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
JULY 2019.
DEDICATION
This book is honourably dedicated to my children.
Desire
Desola
Desayo
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
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.
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
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.
NOTE: In the IUPAC nomenclature, the lowest possible numbers are assigned to these functional groups
in the compounds containing them.
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.
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
Acyclic Cyclic
HYDROCARBON GENERAL
MOLECULAR
FORMULAR
ALKANES CnH2n+2
ALKENES CnH2n
ALKYNES CnH2n-2
H Br H H
C=C C=C
Br H Br Br
Trans-1,2-dibromoethene Cis-1,2-dibromoethene
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
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
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
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
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.
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.
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
CH3
(iii) CH3C=CHCH3 (iv) CH3-C=C-CH3
CH3 CH3
3-methylbut-2-ene 2,3-dimethylbut-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
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
N:B more of alkyne naming can be achieved using the process in alkane naming. (31 – 120).
4.03 MOLECULAR STRUCTURES OF ALKYNES
CH3 CH3
(iii) CHC≡CCH3 (iv) CH2-C≡C-CH2
CH3 CH3
4-methylpent-2-yne hex-3-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
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
+ 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.
+ Cl2 + HCl
Benzene
Benzenechloride
2. Benzene react with monochloromethane using Aluminium chloride as a catalyst to form
methylbenzene.
CH3
+ CH3Cl + HCl
Benzene
Methylbenzene
N:B more of alkanols naming can be achieved using the process in alkane naming. (31 – 120).
6.03 MOLECULAR STRUCTURES OF ALKANOL
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
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
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
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
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
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
N:B more of alkanoates naming can be achieved using the process in alkane naming. (31 – 120).
9.03 MOLECULAR STRUCTURES OF ALKANOATES
CH2OH CH2OOC(CH2)16CH3
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.
10.06 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
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.
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
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
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
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
12.08 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.
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
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
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
13.18 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
13.20 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
13.27 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.
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.
C. C O C D. C O C
O