CHEM 130 2023 Allocations & Course Outline

DEPARTMENT OF CHEMISTRY
CHEM 130: INTRODUCTION TO ORGANIC CHEMISTRY
TEACHING SHEDULE – CHEM 130 MARCH TO JUNE 2019

LECTURER GROUP(S) TIME & ROOM
Prof. Kinyanjui S11, S12, SP14, S15 Monday 6-7 p.m B2
163# Thursday 7-9 a.m B2

Dr. Mwangi E14, E12 Monday 6-7 p.m B4

Ms. Wawerũ E11 Monday 6-7 p.m B5
Reg. no. 01027 to 06250 Thursday 7-9 a.m B5
183#
*Mr. Wanjaũ E11-Reg. no 06251 to 01027 Monday 6-7 p.m B1

K18, K16, N12 Thursday 7-9 a.m B1
184#
Mr. Mzuga B11, B12, B13, B14, B15, V11 Monday 6-7 p.m NPL6A
177# Thursday 7-9 a.m FT1
Ms. Winnie H11, K11, K12, K15 Monday 6-7 p.m B3

* Coordinator
Course Assessment:
Main Exam: 70% Assignments - 5%
CAT 1 & CAT 2 - 15%
Practical marks: 10%
References:
1. Bruce P. Y.: Organic Chemistry.5th Ed.
2. Carey, F: Organic Chemistry. 7th Ed.
3. Wade J. R. Organic Chemistry. 4th Ed
4. Morrison and Boyd: Organic Chemistry. 6 th Ed.
5. Solomons: Organic Chemistry.4th Ed.
6. John Mc Murrey.: Fundamentals of Organic Chemistry. 7th Ed.
i
7. Vollhardt. P. and Schore Neil.: Organic Chemistry – Structure and Function. 6th Ed.
8. Hornback J. M.: Organic Chemistry. 2nd Ed.
9. Relevant E-learning materials.
Credit Factor: 3.0 (Lectures 30 HRS, Practical sessions 30 HRS)
Course Description: Introduction to the major families of organic compounds: Alkanes,

alkenes, alkynes, alkyl halides, aldehydes and ketones, carboxylic acids, aliphatic amines,
phenols and ethers (nomenclature, preparation, reactions and qualitative analysis).
Course Objectives:
1. Name organic compounds using the IUPAC nomenclature rules.
2. Describe common preparation methods and reactions for organic compounds.
3. Describe simple qualitative tests in the laboratory for identifying various functional groups of
organic compounds.
Learning Outcomes: At the end of the course, learners should be able to:
1. Write correct structures of organic molecules and apply IUPAC rules in naming them.
2. Identify hybridization schemes and functional groups in organic molecules.
3. Describe the common preparation methods for the various families of organic molecules.
4. Describe and explain the common reactions of the various families of organic molecules undergo.
5. Distinguish different families of organic molecules using simple qualitative analytical tests.
Lecturers:
*Mr. Wanjau, Dr. Mwangi, Prof. Kinyanjui, Ms. Waweru, Mr. Mzuga & Ms. Winnie
WEEK COURSE OUTLINE PRACTICALS
1-2 Introduction to Organic Chemistry: Electronic configuration of Registration for

carbon; Hydrocarbons - hybridization: sp3, sp2 and sp. Catenation; Practicals
Elemental analysis (qualitative): Empirical and molecular formula.
3-5 Alkanes: Sources, nomenclature, structural isomerism, physical Determination of

properties, preparations. Chemical reactions: combustion, mechanism melting point and
for free radical substitution.Cycloalkanes (Monoclic & bicyclic): boiling point.
nomenclature, geometric isomerism, uses.
6-7 Alkenes: Sources, preparation, nomenclature, structural isomers and Elemental analysis.
geometric isomers (E-Z), physical properties. Chemical reactions
(addition and oxidation). Identification and analysis. Polymerization & Qualitative analysis of
uses. (CAT 1) alkenes and alkynes.
8-9 Alkynes: sources; preparation; nomenclature; physical Qualitative analysis of

properties,chemical reactions: additions and oxidation. Qualitative alcohols and carboxylic
analysis. Uses. acids.
10-12 Functional groups: Alcohols (alkanols), alkylhalides, aldehydes

(alkanals) and ketones (alkanones), carboxylic acids, aliphatic amines,
phenols, ethers (nomenclature and qualitative analysis). CAT 2)
UNIVERSITY EXAMINATIONS
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CHEM 130: Organic Chemistry I
Course outline
1.0 Introduction to organic chemistry:
1.1 Electronic configuration of carbon;

1.2 Hybridization, sp3, sp2 and sp.
1.3 Elemental analysis (qualitative).
1.4 Hydrocarbons
2.0 Alkanes:
2.1. Sources
2.2 Nomenclature
2.3 Structural isomerism
2.4 Physical properties
2.5 Chemical reactions
2.6 Mechanism for free radical substitution
2.7 Cycloalkanes: nomenclature, geometric isomerism
2.8 Preparation of alkanes
3.0 Alkenes
3.1 Sources
3.2 Nomenclature
3.3 Structural isomers, geometric isomerism (Cis – Trans, E-Z,)
3.6 Preparation of alkenes
3.7 Qualitative analysis of alkenes
4.0 Alkynes
4.1 Sources
4.2 Nomenclature
4.5 Preparation of alkynes
4.6 Qualitative analysis of alkynes
5.0 Functional groups
5.1 Alcohols, carboxylic acids, ketones,aldehydes,alkylhalides, and aliphatic amines,

phenols, ethers.
5.2 Their nomenclature and qualitative analysis).
References books:
iii
Organic Chemistry by Wade L. G.
Organic Chemistry by Wellinger and Stermitz
Organic Chemistry by Morrison and Boyd
Fundamentals of Organic Chemistry by John McMurry
Organic Chemistry by Solomon.
Organic Chemistry by F. Carey.
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TABLE OF CONTENTS
1.0 INTRODUCTION TO ORGANIC CHEMISTRY ....................................................................................... 7
1.1 Electronic configuration of carbon ........................................................................................................... 7
1.2 Hybridization, sp3, sp2 and sp.................................................................................................................. 8
1.3 Elemental analysis (qualitative) .............................................................................................................. 20
1.4 Hydrocarbons ......................................................................................................................................... 22
2.0 ALKANES ................................................................................................................................................. 23
2.1 Sources of alkanes .................................................................................................................................. 25
2.2 Nomenclature of alkanes ........................................................................................................................ 25
2.3 Structural isomerism in alkanes .............................................................................................................. 31
2.4 Physical properties ................................................................................................................................. 31
2.5 Preparation of alkanes ............................................................................................................................ 40
2.6 Mechanism for free radical substitution ................................................................................................. 36
2.7 Cycloalkanes .......................................................................................................................................... 37
2.8 Chemical reactions of alkanes ................................................................................................................ 34
3.0 ALKENES ................................................................................................................................................. 45
3.1 Sources of alkenes .................................................................................................................................. 45
3.2 Nomenclature of alkenes ........................................................................................................................ 45
3.3 Structural isomerism in alkenes (Cis ,Trans, E, Z) ................................................................................. 47
3.4 Physical properties of alkenes ................................................................................................................ 50
3.5 Preparation of alkenes ............................................................................................................................ 50
3.6 Chemical reactions of alkenes ................................................................................................................ 52
3.7 Qualitative test for alkenes ..................................................................................................................... 59
4.0 ALKYNES ................................................................................................................................................. 61
4.1 Sources of alkynes .................................................................................................................................. 61
4.2 Nomenclature of alkynes ........................................................................................................................ 61
4.3 Isomerism in alkynes .............................................................................................................................. 63
4.4 Physical properties of alkynes ................................................................................................................ 64
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4.5 Preparation of alkynes ............................................................................................................................ 70
4.6 Chemical reactions of alkynes ................................................................................................................ 65
4.7 Qualitative test for alkynes ..................................................................................................................... 71
5.0 FUNCTIONAL GROUPS .......................................................................................................................... 73
5.1 ALCOHOLS (ALKANOLS) .................................................................................................................. 74
5.2 CARBOXYLIC ACIDS ......................................................................................................................... 76
5.3 KETONES ............................................................................................................................................. 77
5.4 ALDEHYDES ........................................................................................................................................ 78
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1.0 INTRODUCTION TO ORGANIC CHEMISTRY
Organic Chemistry, branch of chemistry in which carbon compounds and their reactions are
studied.
The compounds of carbon constitute the central chemicals of all living thing on this planet.
A wide variety of classes of substances—such as drugs, vitamins, plastics, natural and

synthetic fibers, as well as carbohydrates, proteins, and fats—consist of organic molecules.
Organic chemists determine the structures of organic molecules, study their various reactions,
and develop procedures for the synthesis of organic compounds.
Organic chemistry has had a profound effect on modern life: It has improved natural
materials and it has synthesized natural and artificial materials that have, in turn, improved
health, increased comfort, and added to the convenience of nearly every product
manufactured today.
Naturally occurring Synthetic
carbohydrates, proteins, fats and oils, vitamins plastics, many medicines and drugs,
detergents, insecticides, many dyes
Of all elements, carbon alone is able to form an immense diversity of compounds ranging
from simple methane molecule to complex molecules such as carbohydrates, fats, proteins,
vitamins e.t.c
Most organic molecules contain mainly C and H in their structures and in some cases O, S
and N.
All living things contain organic compounds. Furthermore, many of the modern products and
materials upon which we depend are organic.
The knowledge of organic chemistry enables chemist to develop and manufacture drugs,
agricultural chemicals, anesthetics and other chemicals whose effects on life processes are
important to humans.
Carbon atoms bond strongly to one another covalently forming long chains/skeletons and
rings, aunique phenomenon referred to as catenation.
1.1 Electronic configuration of carbon
Carbon has 6 electrons, 2 in the first shell and 4 in the second/outer shell.
Egerton University is ISO 9001:2008 Certified

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The four valence electrons of Carbon are shared to form four covalent bonds and so it
exercises a valency of four.
6C : (1s22s22p2) or (1s22s2 2px1 2py12pz0)
The first energy level has the 1s orbital. The ‘s’ orbital accommodates a maximum of two
electrons.
The 4 electrons in the the second energy level are organized into the 2s and 2p orbitals. The
one 2s has 2 electrons while the three 2p orbitals all accommodate 6 electrons in total in this
case.
The ‘s’ orbital is spherical in shape. The ‘p’ orbitals are dumbell shaped and are oriented in x,
y and z planes. All the three ‘p’ orbitals i.e. pxpypz are all degenerate meaning they are of
same energy (see figure 1)
y y y
Increasing
energy x x x
2p z z z
2px 2py 2pz
y
1s
x
2s z
2s
Figure 1: Energy profile and shapes of s and p orbitals

The 2s orbitals are lower in energy than the 2p orbitals.
The the 2px 2pyand 2pz are superimposed at 900 to one another.
Carbon atoms have no lone pairs or empty orbitals in their outer shells, so that they are
unable to form dative bonds. This properties is responsible for the kinetic stability of its
compounds.
1.2 Hybridization, sp3, sp2 and sp

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It is the four valence electrons that take part in bonding. Cabon can form single, double or
triple bonds depending on how orbitals of the valence shell (2s2 2px1 2py12pz0) mix or
combine.
The mixing or combining of atomic orbitals to form a new set of atomic orbitals that are
available for bonding is called Hybridization.
In orbital hybridization, thenewly constructed atomic orbitals are neither‘s’ or ‘p’ but are now
referred to as hybrid orbitals.
Bond angles in organic compounds are usually close to 1090, 1200 or 1800.
These bond angles are explained by the valence shell electron pair repulsion theory. An angle
of 109.50 is the largest possible separation for the 4 electron pairs, 1200 for 3 electron pairs
and 1800 for two electron pairs. These shapes cannot result from bonding between simple ‘s’
and ‘p’ orbitals.
Hybridization explains the actual bond angles and type bonding (single, double or triple) in
all organic compounds.
Carbon is also unique in its ability to hybridize. Its four bonding electrons can undergo hybridization
to form:
- Tetrahedral (sp3) hybrid orbitals as in alkanes

- Trigonal (sp2) hybrid orbitals as in alkenes
- Linear (sp) hybrid orbitals as in alkynes
1.2.1 sp3 hybridization (sp3 hybrid orbitals)
In sp3 hybridization, the (2s) and (2px , 2py & 2pz) are all hybridized resulting into four
equivalent orbitals arranged tetrahedrally i.e. pointing towards the four corners of the regular
tetrahedron.
(a) ground state (b) excited state (c) hybridized state
2p 2p
sp3
2s 2s
atomic orbitals of carbon one electron from the 2s the s and p orbitals are combined to
at ground state is promoted to a 2p orbital form 4 equivalent sp3 hybrid orbitals

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Figure 2: Illustration of sp3 hybridazation
The resulting 4 orbitals are called sp3 hybrid orbitals because they composed of one (2s) and
three (2p) orbitals (see figure 2). The four electrons in the sp3 orbitals are the ones that form
covalent bonds with other atoms.
Each of the four sp3 hybrid orbitals has 25% ‘s’ character and 75% ‘p’ character.
The energy of the four sp3 hybrid orbitals are a little less than that of the 2p orbitals but
somewhat greater than that of the 2s orbital.
The shape of sp3 hybrid orbitals resembles that of p orbitals except that the dumbell is lop-
sided and the electron is more likely to be found in the space that extends out a greater
distance in one direction from the nucleus (see figure 3).
2s 2px sp3
Figure 3: shape of an sp3 hybrid orbital
Each sp3 hybrid orbital has one node two lobes of unequal sizes which make the electron
density greater on one side of the nucleus. The larger lobe in each case overlaps with the
orbitals of another atom such as hydrogen during bond formation.
Hybrid orbitals form sigma() bonds when they overlap with other orbitals of the same or
different types (see figure 4).

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overlap
+
1s sp3 s-sp3 sigma bond e.g. C-H
overlap
+
sp3 sp3 sp3 - sp3 sigma bond e.g. C-C
H
s - sp3
sigma 1s
H
bond sp3
109.50
H C H 109.50
H C
sp3
H 1s sp3
sp 3 1s
H
0
109.5 1s 109.50
H
H H
C
H
H
Figure 4: sigma bond formation

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The four s-sp3 in methane (CH4) are localized molecular orbitals that define its tetrahedral
structure.
sp3 hybridization is extended to compounds that contain C-C single bonds such as saturated
alkanes e.g. ethane, propane, butane e.t.c.
The C-C single bonds allow free rotation in space that is analogous to ‘wheel and axle’ in
motion, the axle resembling the bond in this case.
1.2.2 sp2 hybridization (sp2 hybrid orbitals)
In sp2 hybridization, one of the electrons in the 2s orbital is promoted to a 2p orbital. The 2s
and two of 2p orbital are then hybridized resulting into three equivalent sp 2 hybrid
orbitalsthat are degenerate (see figure 5).

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2p 2p 2pz
sp2
2s 2s
one s and two of the 2p orbitals are combined to
atomic orbitals of carbon one electron from the 2s
form 3 equivalent sp2 hybrid orbitals leaving one
at ground state is promoted to a 2p orbital
of the 2p orbitals undisturbed
Figure 5: illustration of sp2 hybridization

The remaining orbital (one of 2p) is undisturbed.
The three sp2 orbitals all lie on the same plane and are directed to the corners of a equilateral
triangle, a trigonal plannar arrangement. The bond angle is 1200.
The remaining 2p orbital is perpendicular to the plane formed by the three sp 2 hybrid orbitals.
Each of the three sp2 hybrid orbitals has 33.3 % ‘s’ character and 66.6% ‘p’ character.
Each of the three sp2 hybrid orbitals contain a single electron such that the electronic
configuration is (1s)2 (2sp2)1 (2sp2) 1 (2sp2) 1 (2p) 1.
Carbon uses sp2 hybrid orbitals to form sigma bonds with other carbon atoms such as the case
of ethane (CH2CH2) molecule.
The undisturbed 2p orbitals of the two carbon atoms of ethene overlap in a side by side
manner resulting into the formation of pi (π) molecular bond (see figure 6).

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sp2
1200 1200
+ +
C
sp2
sp2
1s 2px 2py
1200
Trigonal planar
N/B The 2pz remained undisturbed in the example given.

1/2 bond
2pz 2pz
sp2 sp2 sp2 sp2
sp2 sp2  bond

C + C C C
sp2 - sp2 sp2
sp2 sp2 sp2
1/2 bond
ethene
H bond H
s-sp2 s-sp2
bond C C bond
H bond H
Figure 6: Geometry of sp2 hybridization

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The trigonal arrangement occur in compounds that contain a double bond which is regarded
as being made up of a strong sigma () bond between two sp2 hybrid orbitals and a weaker pi
(π) bond.
As opposed to the sp3 hybrid orbitals, there is restricted rotation about the double bond.
The C=C (double) bond is shorter than the C-C (single) bond because the electron pairs draw
the nuclei more closer together than a single electron pair does.
Electrons in the π bond are less tightly held and are more polarized and so chemical reactions
involving alkenes involve initial attack at the π electrons of the double bond.

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Structure and shape of the benzene C6H6 molecule:
Benzene C6H6 is a cyclic compound with six carbon atoms joined in a ring. Each carbon
atom is sp2 hybridised, and the ring is planar. Each carbon atom has one hydrogen atom
bonded to it and an unhybridised 2p orbital perpendicular to the plane of the  bonds of the
ring. Each of these six 2p orbitals can contribute one electron for  bonding. This type of p-
orbital system leads to complete delocalisation of all six  electrons giving rise to a highly
stable structure of the benzene molecule.
It is known that all carbon-carbon bond length in benzene is the same, 0.140 nm. All six
bonds are longer than C=C double bonds, but shorter than C-C single bonds. From the bond
lengths plus a body of other evidence, chemists have concluded that benzene is a
symmetrically molecule with six ring  bonds (C-C bonds) and six  bonds of C-H bonds.
Instead of alternating double and single bonds, the six  electrons are completely delocalised
in a cloud of electronic charge above and below the ring.
1.2.3 sp hybridization (sp hybrid orbitals)
A combination of the 2s with only one 2px orbital makes results into formation oftwo sp
hybrid orbitals. These orbitals extend in opposite directions from the carbon atoms (see figure
7).

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2p 2p 2py 2pz
sp2
2s 2s
one s and one of the 2p orbitals are combined to
atomic orbitals of carbon one electron from the 2s form 2 equivalent sp hybrid orbitals leaving two
at ground state is promoted to a 2p orbital of the 2p orbitals undisturbed
Figure 7: illustration of sp hybridization
The angle between the hybrid orbitals is 180oso as to minimize the repulsion between the
electrons placed in these two sp2 orbitals.
The remaining two valence electrons occupy the other two 2p orbitals (2p y and 2pz) that are
mutually perpendicular to the two sp hybrid orbitals.
sp hybridization results into a linear bonding arrangement.
Each sp hybrid bond has 50% ‘s’ character and 50% ‘p’ character. The two sp orbitals share a
common axis but their lobes are oriented in opposite directions.
The C – C triple bond in alkynes is viewed as multiple bonds of the +π + π type. The triple
bond is composed of one sigma bond formed by the overlap of sp hybrid orbitals from each
carbon plus two π bonds that arise from the 2p y& 2pz overlaps.

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1800
+ sp sp
C
1s 2px
N/B The 2py & 2pz remained undisturbed in the example given.
y y
z z
x C C x
 bond (sp - sp)

 bond from 2pz overlap
 bond (sp - s)
H C C H
 bond from 2py overlap
ethyne/acetylene
Figure 8: Geometry of sp hybrid orbital
Shorter bonds tend to be stronger bonds. As the ‘s’ character increases, the electron pairs are
more strongly leading to contraction of the inter nuclear distance held hence requiring more
energy to cleave/break.

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In summary:
Hybridization Geometry Approximate Number Number Number Number

Bond angles of of of sigma of
Hybrid remaining bonds pi bonds
orbitals orbitals
sp3 Tetrahedral 109.50 4 0 1 0
sp2 Trigonal 120 0
3 1 1 1
planar
sp linear 1800 2 2 1 2
As the hybridization of carbon becomes more ‘s’ like and less ‘p’ like, the bond length
decreases and the bond energy increases.
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Bond C-C C=C CC
Bond enthalpy kJmol-1 346 610 835
In the molecule given below, the arrows indicate selected atoms and bonds. Write the correct
type of hybridization in the case of selected atoms and the type of bonding (sigma, pi or both)
for the selected bonds.
H H H O
H C C C C C H
C H H
Determine the geometry of the following molecules and hence specify the hybridization state
of all the central carbon atoms.
- CH3CH=CH2
- (CH3)3CH
- CH3CN
The following two compounds have the same molecular formula C 5H8 but different structures :
H CH3
CH3 CH3 C CH CH C
C C C H H
H H
Give the hybridization states of all carbon atoms for both compounds.
1.3 Elemental analysis (qualitative)

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Common elements found in organic compounds include C, H, N, O, P, S, Br and certain
metals.
The molecular formula gives the exact number of atoms of each element in one molecule of
the compound.
The molecular formula of a given compound is determine by two step process:
- Determination of the empirical formula, which is the simplest whole number ratio
of atoms of different elements present in the compound.
- Determination of molecular weight of the compound using mass spectrometer
instrument.
Problem.
A compound was found to contain 42.9% C, 2.4% H, 16.7% N and 38.1% O by weight. Find
its molecular formula given that its molecular weight is 168 g/mol.
Solution:
C H N
O
Mass in 100g 42.9 2.4 19.7

38.1
Moles (42.9/12) (2.4/1) (16.7/14)

(38.1/16)
Moles 3.58 2.4 1.19

2.38
Ratio of atoms (3.58/1.19) (2.4/1.19) (1.19/1.19)

(2.38/1.19)
Ratio of atoms 3 2 1
2
The empirical formula is C3H2NO2
N/B The calculation may not give the actual integers at this stage. It may give ratios such
as 1.5: 1 or 1.33:1 or 1.67:1. These rendered in the lowest integral equivalents i.e. 3:2, 4:3,
5:3 respectively.
The molecular formula is integral multiple of the empirical formula. Given that the molecular
weight is 168. The molecular weight can be computed as follows:
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(C3H2NO2)n = 168
84 n = 168
n=2
The molecular formula is C6H4N2O4
1.4 Hydrocarbons
Hydrocarbons are compounds containing carbon and hydrogen only.
Hydrocarbons are divided into two main classes: Aliphatic and Aromatic, based on their
structures.
Aliphatic hydrocarbons are further sub-divided into families/groups: Alkane, Alkenes,

Alkynes and their cyclic analogues (see figure 9).
Hydrocarbons
Aliphatic Aromatic
Alkanes Alkenes Alkynes Cyclic aliphatic
Figure 9: Classification of hydrocarbons
The molecules of both saturated and unsaturated aliphatic compounds are open-chain
(acyclic) or simple rings (cyclic) structures.
The term aromatic refers to a major class of unsaturated cyclic organic compounds which
includes benzene and its derivatives. Benzene is an unsaturated, but highly stable, cyclic
molecule containing six carbon atoms.
Aromatic hydrocarbons are hydrocarbons which have benzene ring in their structures.
They are sometimes called arenes.
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Bond C-C C=C CC
Bond enthalpy 346 610 835

kJmol-1
2.0 ALKANES
Alkanes are saturated hydrocarbons with general formula CnH2n+2.
Cyclic alkanes have the general formula CnH2n.
Where n is an integer.
All the carbon atoms in alkanes are sp3 hybridized.
A series of compounds in which each member differ from the next member by a constant
amount is called a homologousseries.

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Homologous series of some straight chain alkanes include:
numbe name formul structure Line bond (or skeletal) structure

r of a
carbon
s
1 Methane CH4 CH4
2 Ethane C2H6 CH3CH3
3 Propane C3H8 CH3CH2CH3 H2
C
H3C CH3
4 Butane C4H10 CH3(CH2)2CH3 H2
C CH3
H3C C
H2
5 Pentane C5H12 CH3(CH2)3CH3

6 Hexane C6H14 CH3(CH2)4CH3
7 Heptane C7H16 CH3(CH2)5CH3
8 Octane C8H18 CH3(CH2)6CH3
9 Nonane C9H20 CH3(CH2)7CH3
10 Decane C10H22 CH3(CH2)8CH3
11 undecane C11H24 CH3(CH2)9CH3
12 dodecane C12H26 CH3(CH2)10CH3
13 tridecane C13H28 CH3(CH2)11CH3

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N/B Straight chain alkanes are named according to the number of carbon atoms they have.
2.1 Sources of alkanes
1. Petroleum:
- is the primary source of alkanes.
- its is a complex mixture of organic compounds most of which are alkanes and
aromatic hydrocarbons.
- there are also small amounts of oxygen, nitrogen and sulfur containing compounds.
2. Fossil:
- Anaerobic oxidation of plant materials is a chief source of methane, the first

member of the alkane family.Natural gas is mainly composed of methane.
2.2 Nomenclature of alkanes

There are two systems of naming:
i) Semi-systematic (common system)

ii) International Union of Pure and Applied Chemistry - IUPAC -(Current system)
Example:
CH3
neopentane (old system)
H3C C CH3
2,2-dimethylpropane (IUPAC system)
CH3

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RULE 1:
(a) Find the longest continuous chain of carbon atoms and use the name of this chain as
the base or parent of this compound.
Example:
Side chain or substituent
CH3 H H H
equivalent to
2 4 6
H3C C C C C CH3
1 3 5
H H H H
2-Methylhexane
CH3
6 4
5 3
2
1
3-Methylheptane
- The longest continuous chain has 6 carbons and not 3 or 4 carbons. And it is
considered the parent/base of the compound. Sometimes not obvious, you may
need to turn corners.
- The group attached to the main chain is considered as branch and is called a
substituent. And so methyl group is considered.
- If a hydrogen is removed from an alkane, the partial structure normally
represented as “R-“ that remains is called an alkyl group. They are named by
replacing the suffix “-ane” with ‘-yl’.
o For example: CH4 – methane becomes CH3 – methyl. R = -CH3
C2H6 –ethane becomes C2H5– ethyl. R = -C2H5
- When the ‘R’ group is attached to a halogen, it is referred to as an akyl halide.

- Br-CH3 = Bromomethane, Cl -CH3 = Chloromethane are examples of alkyl
halides.

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(b) If two chains of equal length are present, choose the one with the larger number on
branching points.
CH3 CH3
2 4 6 4 6
1 3 5 H3C 3 5
2
1
Hexane with two substituents Hexane with one substituent
(correct) (Incorrect)
3-Ethyl,2-methylhexane

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RULE 2:
Number the carbon atoms in the parent/main chain beginning at the end nearer to the first
branching point. The first substituent encountered along the main chain receives the lowest
possible number.
CH3 CH3
2 4 6 8 7 5 3 1
1 3 5 8 6 4 2
7
CH3 CH3
(correct) (Incorrect)
2,3-dimethylhexane 6,7- are higher numbers compared to 2,3-
RULE 3:
Identify the number of substituents and locate each by the number assigned on the main chain
according to its point of attachment.
- Use hyphens to separate various prefixes and commas to separate numbers.

- If there are two substituents on the same carbon, assign them both the same
number.
7 5 3 1
6 4 2
3-ethyl-4,4,7-trimethylnonane
RULE 4:
The parent alkane is the last part of the name and is preceded by names of the substituent
groups and their numerical locations. Write the name as a single word.
- If two or more substituents are present, name them in alphabetical order.

- Use prefixes di-, tri-, tetra- if identical substituents are present on the main chain.

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- The prefixes are ignored in determining the alphabetical order.
Br NO2
4-bromo-3-ethyl,4,4,7-trimethylnonane 4-fluoro-2-methyl-3-nitroheptane
NH2
F
4-ethyl-5-fluoroo-3-methylnonane
3-Amino-2,4,5-trimethyloctane
Me
3 1
6 4 2
Et Me
6-ethyl-3,4-dimethyloctane 3-ethyl-2,4-methylheptane
3,3-Dimethyl-5-(2-methylpropyl)-4-propylnonane 3-Ethyl-5-(1-ethyl-2-methylpropylnonane
3-Ethyl-2,5,6-trimethyl octane
5-(1,1-dimethylpropyl)-5-(2-methylpropyl) nonane

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One further word in naming alkyl groups; certain prefixes can be used e.g. sec – (secondary),
tert – (tertiary). There are four possibilities:
10 20
H H
R C H R C H
H R
30 40
R
H
R C R R C R
R
R
10 Primary 20 Secondary 30 Tertiaryand 40 Quartenary
sec-butyl group
tert-butyl group
Isopentyl
isopropyl group (1-methylethyl)

isobutyl group

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Problems:
Identify the carbon atoms that are primary, secondary and tertiary in the structures drawn
under rule 3 above.
Draw alkane that meets the following descriptions.
1) An alkane with two tertiary carbon atoms

2) An alkane with one secondary carbon atom.
3) An alkane with three primary carbon atoms.
2.3 Structural isomerism in alkanes
- Isomers are different compounds with similar molecular formula.

- Structural isomers (constitutional isomers) are compounds that have the same
molecular formula but differ in the way atoms are arranged.
Example;
Butane (C4H10) has two isomers.

CH3
H2
C CH3 CH
H3 C C H 3C
H2 CH3
n-Butane 2-Methylpropane
Problem:
Draw all the possible isomers of pentane and hexane.
The normal alkanes from C1 to C4 are gasses at room temperature e.g. methane.
C5 to C17 are liquids e.g. kerosene.
C18 onwards are solids e.g. wax.
- All organic compounds including hydrocarbons are less dense than water.

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Solubility
- Alkanes are generally non polar and dissolve only in non-polar solvents such as
benzene, ether and chloroform.
- Alkane are insoluble in water and other highly polar solvents. The non-polar
nature of alkanes is due to the fact that atoms on alkane molecules are held
together by covalent bonds.
Melting point
- Alkanes with even number of carbon atoms generally pack better into solid
structure and therefore higher temperatures are required to melt them compared to
those with odd number of carbon atoms. This is because alkanes with even
number of carbon atoms pack so as to permit greater intermolecular attraction
between the atoms.
- Highly symmetrical compounds often melt at abnormally high temperatures

because molecule are also known to pack well in their crystal lattice.
- The highly branched alkanes melt at higher temperatures than the straight chain
alkanes with the same number of carbon atoms. This is because branching gives it
a more compact structure.
Problem:
Of the two isomers of butane, which one would be expected to melt at a higher temperature.
Boiling point
- Larger molecules have large surface areas resulting into increased intermolecular
Van-der-waals forces of attraction. This is true in the case of straight chain alkane
where the boiling points increase with increasing number of carbon. Decane
(C10H22) has higher boiling point than pentane (C5H12)
- In general, highly branched alkanes have lower boiling points than normal
(straight chain) alkanes.
With branching, the shape of a molecule tends to approach that of a sphere. As
this happens, the surface area is decreased resulting into weaker intermolecular
forces that would require lower temperatures to overcome.

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Consider the three isomers of pentane C5H12.
n-Pentane 2,2-Dimethylpropane 2-Methylbutane
n-pentane 2,2-Dimethylpropane 2-Methylbutane

0
Bpt.( C) 36 10 28
Mpt. (0C) -130 -20 -160
- n-Pentane and 2-Methylbutane are larger isomers. They have larger surface areas
and increased van-der-waals forces than 2,2-Dimethylpropane.
- 2,2-Dimethylpropane which is highly symmetrical has abnormally high melting

point.

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2.5 Chemical reactions of alkanes
The bonds in alkanes are single covalent and non-polar and hence they rarely react.
1. Combustion
Alkanes burn in air to give carbondioxide and water.
CH4 + 2 O2 CO2 + 2H2O + Energy
2CH4 + 3O2 2CO + 4 H2O + Energy
(incomplete combustion)
2. Nitration
CH3CH2CH2NO2
HNO3
CH3CH2CH3
4000C CH3CH(NO2)CH3
3. Oxidizing agent
- Alkane can be oxidized by potassium permanganate (KMnO4).

- Only when the alkane is tertiary.

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CH3 CH3
KMnO4
H 3C CH H3 C C OH
O CH3
CH3
tertiary alcohal
4. Halogenation
- Under proper conditions, alkanes react with halogens, X2 i.e. (Cl2, Br2,I2 & F2) to
form alkyl halides.
H H
light
H C H + Cl-Cl H C Cl + HCl
4000C
H H
monohalogenated product
- If excess halogen is present, the reaction can proceed to polyhalogenated products.

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5. Pyrolysis (cracking)
400-600oC
Alkane Smaller alkanes + H2
- The decomposition of a larger compound by means of heat alone in known as
pyrolysis. The pyrolysis of alkanes particularly when petroleum is concerned is
known as cracking.
- Cracking is mostly done in the industrial production of fuels.
H2, Heat
C12H26 C5H12 + C7H16 (catalytic hydrocracking)
Catalyst
shorter alkanes
C12H26 Heat C5H10 + C7H16 (catalytic cracking)

Catalyst
shorter alkanes
and alkenes
2.6 Mechanism for free radical substitution
A reaction mechanism is a step by step by step description of the bond breaking and bond
forming process that occurs when reagents react to form products.
Halogenations of alkanes occur via free radical (atom with one or more unpaired electron that
is represented by a dot) chain reaction. It is a three step process.
1. The initiation step:
light
Cl Cl Heat
Cl + Cl
2. Propagation step
H H
H C H Cl H C + HCl
H H
H H
H C Cl Cl H C Cl + Cl
H H

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Termination step
Cl Cl Cl Cl
H H H H
H C C H H C C H
H H H H
H H
H C Cl H C Cl
H H
2.7 Cycloalkanes
- Are alkanes in which the carbon atoms form a ring and the general molecular
formula is CnH2n.
- Examples:
cyclopropane cyclobutane cyclopentane cyclohexane
Geometric isomerism
- Are compounds with the same molecular formula but differ in orientation in
space.
- examples:

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H3 C CH3
H
CH3
H H
CH3
H
Trans-1,3-dimethylcyclobutane Cis-1,3-dimethylcyclobutane
(methyl groups pointing in opposite sides of the plane) (methyl groups all pointing on the same side of the plane)
H3 C
H3 C
CH3
Trans-1,2-dimethylcyclobutane
Cis-1,2-dimethylcyclobutane
H3C
- In addition to the monocyclic compounds, there are more complicated compounds

with bridges linked across the rings. They are referred to as polycyclic.
Nomenclature of cycloalkanes:
- Cycloalkanes are named by adding the prefix ‘cyclo’ to the name on the
corresponding open chain alkane with same number of carbon atoms in the ring
- The ring is numbered in the direction that gives the lowest possible numbers to the
substituent groups at the first point of difference between the two directions. The
alphabetical order of listing the groups still applies.
- Examples:
CH2CH3
3 4 2
1 3 1
2 2
4
1 3
1-Isopropyldecane 1,1,2-Dimethylhexane 1,2,4-Trimethylhexane

4-Ethyl-1,2-dimethyloctane
- When the ring contains fewer carbon atoms than the alkyl group attached, the
compound is named as an alkane otherwise, it is named as a cycloalkane.

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2-Cyclopropylheptane 1-ethyl-2-methylcyclopentane
- According to the IUPAC system of cycloalkanes consisting of two rings only and
having two or more atoms in common take the prefix ‘bicyclo’ followed by the
name of the corresponding alkane.
- The number of carbon atoms in each of these bridges connecting the two carbon
atoms is indicated in brackets in descending order.
- Numbering begins with one of the bridgeheads and proceeds by the longest
possible path to the other bridgehead.
- Numbering then proceeds from this atom by the longer unnumbered path back to
the first bridgehead and is completed by the shortest path.
Examples:
One carbon bridge
Bridge head
Two caron bridge

Two caron bridge
Bridge head

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1 2
Cl
1 3
I 8
2 9
7 4
6 5
2-Iodobicyclo[2.2.2]octane
Bicyclo[3.3.0]octane 3-Chlorobicyclo[4.2.0]nonane
3 1 1 3
2
6
Br
4
5 7
3-Methylbicyclo[4.2.2]decane 7-Bromo-5-ethyl-2,3-dimethylbicyclo[2.2.1]heptane
Cl
F
Br 1
2
6
7
3
5
4
C(CH3)3
6-Bromo-3-tertbutyl-2-methylbicyclo[2.2.1]heptane
Cl
2-Chloro-4-fluorobicyclo[3.2.0]heptane 2-Chloro-1-ethyl-5-methylbicyclo[2.2.1]heptane
2.8 Preparation of alkanes

1. Hydrogenation of alkenes
Pt or Pd or Ni
In general; CnH2n + H2 CnH2n+2
(alkene) (alkane)
Ni
CH2=CH2 + H2 CH3CH3
Ethene Ethane
Pt
+ H2
1-Butene Butane

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2. Reduction of alkyl halides by metal and acid
Zn/H+ R-H + ZnX2

(a) RX
Alkyl halide Alkane
e.g.
H2 H2
C CH3 + C CH3
Zn/H
(i) H3C CH H3C C
H2
Br
Zn/H+
(ii)
Cl
(b) Primary (10 ) and secondary (20) alkyl halides are readily reduced by
LiAlH4 (Lithium Aluminium Hydride)
LiAlH4 R-H + LiAlX4
RX
10 alkyl halide alkane
e.g.
H3 C CH3 H3 C CH3
(i) LiAlH4
CH C
H2
Br
Cl LiAlH4
(ii)

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3. Use of Grignard reagent
Alkyl halides in ether (solvent) reacts with magnesium to form an alkyl magnesium
halide (Grignard reagent) which on treatment with water or dilute acids are decomposed
to an alkane.
ether H+ or H2O
RX + Mg R-Mg-X R-H
alkyl halide grignard reagent Alkane
e.g.
H2
H2 H3C CH3
H3 C CH3 Mg C
(i) C
C
C CH
CH ether H2
H2
Mg-Br
Br
H+ or H2O
H2
H3C C CH3
C C
H2 H2
H2
Br Mg C Mg-Br
(ii)
ether H3C C
H2 Propylmagnesiumbromide
H+ or H2O
H2
C
H3 C CH3

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4. Coupling of alkyl halides with organometallic
Li CuX
RX R-Li R2CuLi
10,20 or 30 alkyl lithium Lithiumdialkyl
alkyl halide
R'X
(must be 1o)
R'-R
(alkane)
e.g.
H2 H2 CuI
Li
(i) C C (CH3CH2)2CuLi
H3C Cl H3 C Li
CH3Cl
CH3CH2CH3
N/B. The above procedure is useful of lengthening the carbon chain.
5. Wurtz reaction
2 Na
R'X + R-X dry ether R'-R + X2
e.g.
2 Na
(i) CH3CH2Br + CH3CH2CH2Br dry ether
CH3CH2-CH2CH2CH3

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6. Decarbonylation
- By heating the sodium salt of a carboxylic acid in soda lime.
C NaOH
R-H + Na2CO3
R ONa CaO
alkane
e.g.
NaOH
(i) CH3CH2COONa CH3CH3
CaO

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3.0 ALKENES
- Are unsaturated hydrocarbons with general formula CnH2n.
- A study of the reactions of alkenes is really the study of c=c double bond that
consists of one
sigma and one pi bond.
- Due to the presence of the pi bond, that causes unsaturation, alkenes are more reactive
than
alkanes.
- There is no free rotation about the c=c double bond. The double bond is rigid.
- older name of this family of compounds that is still often used is ‘olefins’
3.1 Sources of alkenes
- Catalytic cracking of petroleum

- Dehydration of ethanol that is produced by fermentation of carbohydrates.
3.2 Nomenclature of alkenes
- Names are derived by replacing the ending –ane of the corresponding alkane with
–ene e.g
CH2=CH2 Ethene CH3CH=CH2 Propene
- The longest carbon chain with the double bond is considered to be the parent alkene.
- The chain is numbered in the direction that gives the double bonded carbon atoms
the lowest possible numbers.
- The rules for naming alkanes are pretty much the same as those for alkanes
exceptthat the double bond is given preference in numbering the chain. This
because the double bond is regarded as the functional group in the molecule.
- In substituted alkenes the numbers and names of substituents are mentioned first,
followed by the position of the double bond and lastly by the name of the parent
alkene.
- Examples

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2
1 3
CH3CH=CHCH2CH3
2-Pentene or Pent-2-ene
5
4 8
7
4 2
3
3 1
6
2
5
6-Methyl-3-octene or 6-Methyloct-3-ene
1
3-Ethyl-2-methyl-1-pentene or 3-Ethyl-2-methylpent-1-ene
CH3
2
CH3
1 2 3 4 5 1
CH3C CHCHCH3
CH3
CH3 CH3
5,5-Dimethyl-1- hexene or 5,5-Dimethylhex-1-ene
4-Methylpent-2-ene or 4-Methyl-2-pentene
- :
- When two or more double bonds are present, the terminal –ane of the
corresponding alkane is replaced by –adiene, atriene e.t.c to obtain the name of the
compound e.g
CH2=CHCH=CH2 1, 3-Butadiene
- The longest chain containing both double bonds is taken to be the parent chain.
H2C CHCHCH2CH2CH3
3-Propyl-1,4-pentadiene
HC CH2
- If more than one substituent is present, the substituents are named in alphabetical
order e.g.
Cl C2H5
CH3CH2C CCHCH2CH3 3-Chloro-5-ethyl-4-methyl-3-heptene
CH3
- Cyclic alkenes are named by prefixing the word ‘cyclo-‘ or ‘bicyclo’ (whichever is
applicable) to the name of the corresponding open chain alkene. The carbon
atoms of the double bond are considered to be atposition 1. e.g.

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CH3
H3C
Cyclopentene 1,2-Dimethylcyclopentene 5-Methyl-1,3-cyclohexadiene
2.3 Structural isomerism in alkenes(Cis ,Trans, E, Z)
- Rigidity and lack of rotation of theC=C double bonds in alkenes give rise to ‘Cis’ and
‘Trans’ geometric isomerism depending on how the groups attached to the double bond
are oriented in space.
- The different spatial arrangement of the groups around the double bond give rise to
difference in chemical properties.
- Geometric isomerism cannot exist if either of the doubly bonded carbon atoms carry
identical groups. e.g.
4 3
H3C-H2C H
2 1
Identical groups Geometric isomerism not possible
C C
H H
1-Butene
4 4 1
H3 C H H3C CH3
3 2 3 2
C C 1
C C
H CH3 H H
Trans-2-butene Cis-2-butene Geometric isomerism

occur with different groups
3 attached to either carbon.
Cl H Cl CH3
1 2 1 2
C C C C
3
H CH3 H H
Trans-1-chloro-1-propene Cis-1-chloro-1-propene
- However, the ‘Cis – Trans’ nomenclature system can only be applied to a small number
of alkenes.
- For instance the ‘Cis – Trans’ system cannot distinguish between the two isomers of 2-
Bromo-1-chloro-1-flouroethene.

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1 Cl Br
1
Br has a higher prority
1 2
Cl>F Br>H than H.
C C
2 F H 2
(Z) - 2-Bromo-1-chloro-1-fluoroethene
1
Cl H
2
1 2
Cl>F C C Br>H
2 F Br 1
(E) - 2-Bromo-1-chloro-1-fluoroethene
- In the modern ‘E-Z’ system of the Cahn Ingold Prelog convention, priorities are assigned
to each of the two groups attached to each of the two carbons based on their atomic
numbers.
- We simply consider the two groups attached to the same carbon atom of the double bond
and decide which has a higher priority.
- The higher the atomic number, the higher the priority.
- When higher priority groups at each carbon atom are on the same side, the isomer is
designated letter (Z) (zusamen meaning together).
- It two groups of higher priority are on opposite sides of the double bond, it is designated
letter (E) (entegen meaning opposite).
- Examples:

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Br H3C H Cl
H H
C C C C C C
H3CH2C CH2CH2CH3 H CH3 Br CH2CH3
Trans-2-butene
(E)-3-Bromo-3-heptene or (Z)-1-Bromo-1-chloro-1-butene
(E)-2-Butene
Cl CH3 I Br
C C C C
F CH2CH3 Cl CH3
(E)-1-Chloro-1-fluoro-2-methylbut-1-ene (Z)-2-Bromo-1-chloro-1-iodoprop-1-ene
Cl
F
H3C CH2CH3
C C
H CH(CH3)2
(E)-3-Chlorohex-2-ene (Z)- 2-Fluoro-2-heptene
(E)-3-Ethyl-4-methyl-2-pentene
(2E,5Z)-3-Ethylhept-2,5-diene
(E)-6-secbutyl-3-methyl-7-cyclopropyl-2-decene
- Trans-alkenes are usually higher melting than their cis isomers because of higher symmetry,
but their boiling points differ very little.
- The cis-isomer has lower m.p., lower density and higher solubility than that of the trans-
isomer. These properties can be explained by the existence of intramolecular hydrogen
bonding in the cis-isomer, which reduces the chance of intermolecular hydrogen bonding, and
thus weaken interactions between molecules of the cis-isomer.

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3.4 Physical properties of alkenes
- The first three members of alkenes are gases at room temperature (C 2-C4), C5-C15
are liquids at room temperature and >C15 are solids at room temperature.
- They burn with a luminous flame.
- They’re insoluble in water, but more soluble than alkanes in some polar solvents
like alcohols.
- They’re less volatile than alkanes and their boiling points and melting points
increase with increase in molecular mass.
- They are less dense than water.
- Boiling points increase with increasing number of carbons.
3.5 Preparation of alkenes

1. Dehydrohalogenation of alkyl halides
alcohol
C C + KOH C C
X H
alkylhalide alkene
e.g.
alcohol
(i) CH3CH2CH2Br + KOH CH3CH=CH + KBr + H2O
Cl alcohol
+ KOH
(ii)
alcohol CH3CH=CHCH3 + CH3CH2CH=CH2

(iii) CH3CH2CHCH3 + KOH
major product minor product
Br 80% 20%
N/B. The most highly substituted is formed preferentially according to Zaitzeff's rule

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2. Dehydration of alcohols
- Alcohals are converted to alkenes elimination of a water molecule (dehydration).
- This occurs in the presence of an acid and some heat.
C C heat
+ H2SO4 C C + H2O
H OH
alcohal alkene
e.g.
heat
(i) CH3CH2CH2OH + H2SO4 CH3CH=CH2
OH heat
+ H2SO4
(ii)
CH3
H3 C
heat
(iii) CH3-C-OH + H2SO4 C CH2
H3C
CH3
3. Dehalogenation of vicinal dihalides
- The method is purely 1,2-elimination of the vicinal halides.
CH3COOH
C C + Zn C C + ZnX2
X X
alcohal alkene
e.g.
CH3COOH
(i) CH3CHCHCH3 + Zn CH3CH=CHCH3
Cl Cl
CH3COOH
(ii) Cl + Zn
Cl

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4. Reduction of alkynes
R R
Lindlar catayst
C C Cis 'anti'
H2/Pd
H H
R-C C-R
R H
Na/NH3 (liquid) Trans 'syn'
C C
H R
e.g.
H3 C CH3
Lindlar catayst
C C Cis
H2/Pd
H H
CH3-C C-CH3
H3 C H
Na/NH3 Trans
C C
liquid
H CH3
- The hydrogenation here is partial.
- The ‘cis’ alkene product is almost 98%.
3.6 Chemical reactions of alkenes
- Most reactions occur at the double bond because it is the functional group.
- The double bond is an electron rich centre. These electrons attack nuclei of other atoms
that are relatively electron deficient.
- The pi electrons of alkenes are therefore nucleophilic and react readily with electrophiles.

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1. Addition of hydrogen (Reduction)
R R
R R
H2, Pd, Ni
C C H C C H
H H
H H
e.g.
H2, Pd, Ni
(i) CH3CH2CH2CH=CH2 CH3CH2CH2CH2CH3
H2, Pd, Ni
(ii)
(iii) 3 H2
Catalyst
Heat
2. Halohydrin formation
R R
R R
H2 O
C C + X2 H C C H
H H
OH X
Halohydrin
e.g.
OH
H2O
(i) CH3CH2CH2CH=CH2 + Br2 CH3CH2CH2CHCH2
Br

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3. Addition of sulphuric acid
C C + H2SO4 C C
H OSO3H
e.g.
H H
Conc. H2SO4
H3C C CH3 H 2O H3C C CH3
(i) CH3CH=CH2
OSO3H Heat OH
Isoproylhydrogensulphate Propan-2-ol
CH3 CH3 CH3

(ii) Conc. H2SO4 H 2O
H3C C CH2 H3C C CH3 H3C C CH3
Heat
OSO3H OH
tert-butylalcohol
N/B: Hydrogen adds the carbon atom with the larger number of hydrogen atoms
4. Addition of hydrogen halide (Markovnikovs rule)
- Addition of hydrogen halide to alkenes is governed by Markovnikovs rule.
- The rules states that when an acidic molecule adds to an asymmetric alkene, the major
product is the one in which the hydrogen atom attaches itself to the carbon atom already
carrying the larger number of hydrogen atoms.
- The reverse rule is referred to as ‘Antimarkovnikov’ when hydrogen peroxide (or any
other peroxide) is used.
- Alkenes form addition products with halogen acids in the following order of reactivity:
HI > HBr > HCl > HF . HI being the most reactive while HF being the least reactive.

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CH3 CH3 CH3
H3C
C C + HBr H C C H
H H H Br
Symmetric alkene
H CH2CH3
HCl H C C H
Markovnikov's
product
H Cl
H CH2CH3
C C
H H
H CH2CH3
Asymetric alkene HCl Antimarkovnikov's
H C C H
product
H 2 O2
Cl H
CH3 CH2CH3
HCl H C C CH3
Markovnikov's
product
H Cl
H3C CH2CH3
C C
H CH3
CH3 CH2CH3
Asymetric alkene HCl Antimarkovnikov's
H C C CH3
product
H2 O 2
Cl H
N/B: The halide adds to the more highly substituted carbon according to markovnikov's rule unless a peroxide is used.
HBr Markovnikov's
product
Br
Antimarkovnikov's
HBr product
ROOR
Br
5. Hydration of alkenes
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- Addition of H2O across the double bond in the presence of dilute acid to form an alcohol.
dil. H2SO4
C C + H2O C C
OH
e.g.
H H
H+
(i) CH3CH=CH2 + H2O H3C C C H
OH H
Propan-2-ol
H+
(ii) + H 2O
OH
3-Methyl-3-hexanol
N/B: Hydrogen attaches to the carbon with higher number of hydrogen atoms
6. Ozonolysis
- This reaction is used to determine the location of the double bond in alkenes
because it involves cleavage of the double bond to give carbonyl compounds.
- Ozone is considered a mild oxidant.
O
R R R
R
C C + O3 C C
R R
R R O O
Ozone
Ozonide
Intermediate
Zn H2O
R R
O + O C
R R
Carbonyl compounds

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H3 C CH2CH3 H3C CH2CH3
Zn / H2O
(i) C C + O3 C O + O C
H H H
H
2-Pentene Ethanal Propanal
O
O3
(ii) + O
Zn / H2O
Propanal
4-Methyl-3-hexene Butan-2-one
(iii) O3
Zn / H2O
O
7. Oxidation of alkenes
a. Moderately strong oxidizing agents
e.g. HIO4 or (CH3COO-) 4Pb

O
HIO4
(CH3)2C=CH2 CH3CCH3 + HCHO
b. Strong oxidizing agents

They include acidified K2Cr2O7 or acidified KMnO4.
O
K2Cr2O7
(CH3)2C=CH2 CH3CCH3 + HCOOH
H+ or hot

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8. Hydroboration of alkenes
- Alkenes undergo hydroboration with diborane (BH 3)2 to yield a trialkylborane (R3B), which
upon oxidation gives an alcohol.
H H R-CH2CH2 CH2CH2R
B
+ B
3 R-CH=CH2 2
H
Borane R-CH2CH2
NaOH / H2O2
3 R-CH2CH2-OH
- The hydroboration – oxidation process gives products that correspond to anti-

markovnikovs addition of water across the double bond.
e.g.
CH3 CH3
(i) (BH3)2 NaOH / H2O2
H3C C CH2 H3C C CH2
H OH
(ii) OH
(BH3)2 NaOH / H2O2 Anti-markovnikovs
product
(BH3)2 NaOH / H2O2

(iii)
OH
9. Polymerization
- A process that involves the joining together of many small molecules to form very
large molecules.
- The small molecules that form polymers are called monomers.
- When ethene it heated under high pressure with oxygen, a compound of high
molecular weight (approx. 20,000) is obtained which is essentially an alkane.

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e.g.
H H
O2, Heat
(i) n CH2=CH2 C C
Pressure
H H n
Ethylene
Polyethylene
H H H H
(ii) O2, Heat

n C C C C
Pressure
H Cl H Cl n
Vinylchloride Polyvinylchloride
- A compound made of many ethene (or ethylene) units is called polyethene (or
polyethylene).
- Polymerization of substituted ethylenes is also possible. e.g. polyvinylchloride
that used to make plastic pipes.
3.7 Qualitative test for alkenes
- Qualitative tests involve the detection of the presence of alkenes or basically test
for unsaturation.
- Important general laboratory observations in testing mostly include:
o Colour changes or disappearances
o Effervesence or bubbles of a gas produced
o Peculiar smell
o Formation of precipitate
o Flame produced during burning i.e. luminous or non-luminous, sooty or
not
o Water droplets on the surface of test tube during heating.
(a) Bromine test:

- Addition of Br2 in CCl4is used for the detection of the C=C double bond.

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R R
R R
CCl4
C C + X2 H C C H
H H
X X
e.g.
(i) CH3CH2CH2CH=CH2 + Br2/CCl4 CH3CH2CH2CHBrCH2Br
Red Colourless
Br
CCl4
+ Br2
(ii)
Br
- Alkenes decolorize Bromine water (Orange) or Bromine in CCl4 (Red).
(b) Baeyer’s test:

- Cold dilute KMnO4 solution (Baeyer’s reagent) is also decolorized by alkenes.
cold
C C + KMnO4 C C
OH-
OH OH
Purple colourless diol

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4.0 ALKYNES
- Another class of unsaturated hydrocarbons with a general formula CnH2n-2 n=2,3,4…..

- They contain carbon carbon tripple bonds as their functional group.
- The triple bond is made of one sigma bond and two pi bonds.
4.1 Sources of alkynes

- The simplest member of this group is acetylene (or ethyne) C 2H2 and is of chief
industrial importance. It is obtained by:
(a) Reaction of water and Calcium carbide.
(b) High temperature oxidation of methane.
4.2 Nomenclature of alkynes
- Alkynes are named in the same way as alkanes. The terminal –ane in the corresponding
alkane is replaced by –yne. The location of the triple bond is indicated by a number in
such a way that the carbon preceding the triple bond is given the lowest possible
number.
- The hydrogen atom attached to the carbon of the triple bond is called acetylenic
hydrogen which is weakly acidic and can be removed by a strong base.
Acetylenic hydrogen
R C C H Ethyne
- The locations of the substituent groups attached to the branched alkynes are also
indicated by numbers.

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e.g.
HC CH Ethyne
CH3C CH Propyne terminal tripple bond
CH3CHC CH 3-Methyl-1-butyne
CH3
H3 C C C CH2CH2 5-Chloro-2-pentyne
Cl
CH3
6-Methylhept-2-yne or 6-Methyl-2-heptyne
Internal
tripple bond
3-Octyne
CH3
CH3
CH3
2,2,5-Trimethyl-3-hexyne
C
CH3
- When the molecule contains more than one triple bond the suffix –ane of the
corresponding alkane is replaced by a –di yne (2 triple bonds), -atriyne (3 triple bonds)
etc.
HC CC CH 1,3-Butadiyne
HC CCH2CH2C CH 1,5-Hexadiyne
- When both a double bond and a triple bond are present in the same molecule, then the
hydrocarbon is called an alkenyne. The multiple bonds are given numbers as low as
possible.
-
CH3CH CHC CH 3-Penten-1-yne
HC CCH2CH CH2 1-Penten-4-yne

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- Double bond takes preference over the triple bond when there is a choice in numbering
that is given the lowest number possible.
H H H H H
H3 C C C C C C C C
H H H H
Oct-1-ene-6-yne
- Ketones also takes preference over the triple bond when there is a choice in numbering
that is given the lowest number possible.
H H O
HC C C C C CH3
H H
Hex-5-yne-2-one
- When a triple bond and an alcoholic group (-OH) are present, the –OH comes last and
the numbering is done from the end bearing the –OH group e.g.
HC CCH2CH2OH 3-Butyn-1-ol
H3 C
C
C CH3
C C
H H
Z-2-Hex-4-yne
Isomerism in alkynes
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EGERTON UNIVERSITY
The first two alkynes do not show any isomerism.
(a) Position isomerism
Due to the various structures obtained by varying the position of the triple bond
e.g.
CH3CH2C CH 1-Butyne
CH3C CCH3 2-Butyne
(b) Structural isomerism

Caused by differences in the type of carbon chain e.g.
CH3CH2CH2C CH 1-Pentyne
CH3CHC CH 3-Methyl-1-butyne
CH3
(c) Functional isomerism
Alkynes can be visualized as isomers of dienes (or alkenes) e.g.
CH3CH2C CH H2C CHCH CH2
1-Butyne 1,3-Butadiene
N/B Unlike alkenes, alkynes do not show geometric isomerism.
4.3 Physical properties of alkynes
- They are less generally volatile than either alkanes or alkenes.

- C2-C4 are gases, C5-C13 are liquids and >C13 are solids.
- They are colorless and odorless compounds, except ethyne which has a garlic odor.
- The boiling points, melting points, densities and heat of combustion increase with
increase in molecular mass.
- They’re sparingly soluble in water but readily soluble in organic solvents.

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4.5 Chemical reactions of alkynes
- Alkynes undergo reactions typical to those of alkenes. The triple bond is the functional
group.
1. Hydrogenation (Addition reaction)

It occurs in 2 stages.
H H H H
Pt/H2 Pt/H2
H C C H C C H C C H
H H H H
- Reduction of an alkyne at the double bond stage can unless the triple bond is a
terminal one, yield either Cis - alkene or Trans - alkene. Whichever of the two
predominates depend kind of the reducing agent.
H C2H5
Na, NH3(Liq)
C C Trans
H3 C H
H3 C C C C 2 H5
H3 C C2 H5
H2 / Pd C C Cis
Lindlar catalyst H H

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2. Reaction with haloacids (HCl, HBr)

Br H
(i)
HBr H3 C C C H HBr H3 C C C H
H3C C C H
Br H Br H
Markovnikovs product
H Br
(ii)
HBr H3 C C C H HBr H3 C C C H
H3 C C C H
Peroxide Peroxide
H Br H Br
Anti-markovnikovs product
3. Reaction with halogens (Br2, Cl2)
X X
X2 X2
R C C H C C C C H
X X X X
e.g.
Br Br
Br2 Br2 H3C C C H

H3 C C C H H3 C C C H
CCl4 CCl4
Br Br Br Br
4. Hydration (addition of H2O)
- Like alkenes, alkynes can also be hydrated in the presence of an acid (and HgSO 4 for
simple) and water.

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- The process leads to keto-enol tautomerism. Compounds whose structures differ
markedly in arrangement of atoms but which exist in easy and rapid equilibrium are
called tautomers.
- The keto tautomer is mostly favored.
Tautomers H
H2SO4 R C C H
R C C H + H2O R C C H
HgSO4
OH H O OH
enol keto
e.g.
H2SO4
(i) H3 C C C H + H2O H3C C CH3
HgSO4
O
H2SO4
(ii) H C C H + H2O H3C C H
HgSO4
O

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5. Reaction with Alkylmagnesium halide or alkyllithium
- Only works with terminal alkynes
e.g.
(i) H3C C C H + C2H5-MgBr C2H6 + H3C C C MgBr
(ii) H3C C C H + C4H9-Li C4H10 + H3C C C Li
6. Ozonolysis
e.g.
1. O3
(i) H3C C C H H3C C O + O C H
2. Zn / H3O H H
1. O3
(ii) H3C C C C2H5 H3C C O + O C C2H5
2. Zn / H3O H H
7. Reaction of metal acetylides and alkynyl/Grignard reagent with carbonyl

(Aldehyde and Ketones)
R C C Na + C O R C C C O Na
Metal acetylide
H+
R C C C OH

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R C C MgX + C O R C C C O MgX
alkynyl grignard
reagent
H+
R C C C OH
e.g.
CH3
H3C
(i) H C C Li + C O H C C C O Li
H3C
CH3
H+
CH3
H C C C OH
CH3
2-Methylbut-3-yne-2-ol
CH3
H3C
(ii)
H+
H3 C C C MgBr + C O H3 C C C C OH
H
H
Pent-3-yne-2-ol

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4.6 Preparation of alkynes
1. Calcium carbide
- Used for laboratory as well as industrial preparation of ethyne.
CaC2 + 2H2O C2H2 + Ca(OH)2
2. Dehydrohalogenation of alkyl dihalides

- This involves double dehydrohalogenation of dihaloalkanes. The dihalide may be a
vicinal or geminal.
KOH NaNH2
C C C C C C
alcoholic
Alkyne
X X X
e.g.
H H H
KOH NaNH2
(i) H3C C C H H3 C C C H H3C C C H
alcoholic
Br Br Br Alkyne
Vicinal dihalide
(ii) Br H H
H3 C C C CH2CH3 KOH NaNH2

H3C C C CH2CH3 H3 C C C CH2CH3
alcoholic
Br H Br Alkyne
Geminal dihalide
3. Reaction of sodium acetyledes with primary alkyl halides

- Used in the conversion of smaller alkynes to a larger ones.
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- Sodamide (NaNH2) in liquid ammonia is a strong base capable of abstracting the
acetylenic hydrogen from the terminal alkyne.
- The smaller alkyne must be terminal and the alkyl halide must be primary.
NaNH2 R-X
C C H C C Na C C R
0
terminal alkyne must be 1
e.g.
NaNH2
(i) H3C C C H H3 C C C Na + NH3
CH3(CH2)4CH2-I
H3 C C C CH2(CH2)4CH3 + NaI
2-Nonyne
4.7 Qualitative test for alkynes
(a) Bromine test

- They also decolorize Br2 in CCl4.
e.g.
Br Br
Br2 Br2 H3 C C C H
H3 C C C H H3C C C H
CCl4 CCl4
Br Br Br Br
(b) Baeyer’s test

- Cold dilute KMnO4 solution (Baeyer’s reagent) is also decolorized by alkenes.
- Alkynes are oxidized to carboxylic acid.
OO KMnO
KMnO4 4
CH3COOH + HCOOH
CH3C CH CH3CCH -
OH- OH
(c) Ammoniacal silver nitrate or Ammoniacal copper nitrate

- Terminal alkynesgive a white precipitate when treated with ammoniacal silver
nitrate.

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- This distinguishes between terminal and non-terminal alkynes.
- Terminal alkynesgive a brick red precipitate when treated with ammoniacal copper
nitrate.
e.g.
AgNO3 / NH3
(i) CH3CH2C CH CH3CH2C C Ag
Etthanol
White colored ppt.
CuNO3 / NH3
(ii) CH3CH2C CH CH3CH2C C Cu
Etthanol
Brick red ppt.
AgNO3 / NH3
(iii) CH3CH2C CCH3 No reaction
or CuNO3 / NH3
internal alkyne

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5.0 FUNCTIONAL GROUPS
- A functional group is an atom, a group of atoms, or a bonding arrangement, which is responsible

for thecharacteristic reactivity and physical properties of an organic compound or class of
compounds.
- The structure of a typical carbon compound can be considered as two parts : a saturated carbon-
hydrogen ‘skeleton’, which is comparatively unreactive, and a reactive part consisting of one or
more functional groups. Two examples are shown below :
Functional groups
H H H H H H
H C C C O-H N C C C C H
H H H H H H
- In the event that there are more than one functional group in a molecule, the following
order of preference is given in the choice of the principal functional group which is to be
given the lowest number.
(i) Carboxylic acids

(ii) Aldehydes
(iii) Ketones
(iv) Alcohals
(v) Double bond
(vi) Tripple bond
(vii) Atoms and alkyl groups.
(viii) Alkanes

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5.1 ALCOHOLS (ALKANOLS)
- These are organic compounds of the general formula R-OH, where the hydroxyl group (-
OH) is attached to an alkyl group(R) or cycloalkyl group.
- The OH group is the functional group of the alcohol and determines their reactivity and
characteristics. They from a homologous series of the general formula C nH2n+1OH, where
n is the number of carbon atoms. E.g CH3CH2OH.
Nomenclature (IUPAC rules)
1) Name the longest carbon chain to which the hydroxyl group is attached. The chain name
is obtained by dropping the final e from alkane name and adding the suffix –ol.
2) Number the chain starting at the end nearest the hydroxyl group and use the appropriate
number to indicate the position of the –OH group. NB; in numbering the longest carbon
chain, the hydroxyl group has priority over double and triple bond as well as over alkyl,
cycloalkyl and halogens substituents.
3) Name and locate any other substituent present.
4) In the alcohol where the –OH group is attached to a carbon atom in a ring, the hydroxyl
group is assumed to be on carbon 1.
Examples
CH3 CH3
(a) CH3CH2CCH2CH2CH3 3-Methyl-3-hexanol (f)
1,2-Dimethylcyclopentanol
OH OH
CH3
(b) CH3CH2CHCH2CH3 2-Ethyl-1-butanol
OH
CH2OH
OH
(g) 3,4-Dimethylcyclohexanol
CH3
(c) CH3CHCHCH2CHCH3 2,5-Dimethyl-3-hexanol CH3
CH3 CH3
(h) Cyclohexanol
(d) CH3CH2CHCH3 3-Methyl-1-pentanol
CH2CH2OH OH
(e) CH2=CHCH2OH 2-Propen-1-ol

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Physical properties of alcohols
1) Boiling points of alcohols are higher than those of the hydrocarbons of approximately
the same molecular weight. This is due to hydrogen bonding between alcohol
molecules.
R O H
H O R
hydrogen bond
2) Alkanols are soluble in water. Their solubility however decreases gradually as the
hydrocarbon part of the molecule increase.
Classification of alcohols
They are classified as primary (10), secondary (20) or tertiary(30) depending on the number of
carbon bearing groups attached to carbon bearing hydroxyl (-OH).
Primary alcohol is an alcohol in which the hydroxyl bearing carbon is attached to only one
other carbon, a secondary alcohol is an alcohol in which the hydroxyl bearing carbon is
attached to two other carbon atoms while a tertiary alcohol is an alcohol in which the
hydroxyl bearing carbon atom is attached to three other carbon atoms.
Examples
CH3
CH3CH2OH CH3CHOH CH3COH
CH3 CH3
0
1 alcohol 20 alcohol 30 alcohol
Qualitative test for alcohols
Lucas test:
- 10, 20 and 30alcohols are distinguished based on their reactivity towards hydrogen
halides (Lucas test). Lucas reagent, a mixture of conc.HCl/ZnCl 2. The reaction proceeds
and the alcohol is converted to alkyl halide.
ZnCl2
C OH HCl C Cl
Clear solution Cloudy suspension due to

formation of 3o or 2o alkyl
halide

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EGERTON UNIVERSITY
- Formation of alkyl chloride is indicated by cloudiness that appear when the chloride
separates from the solution; hence the time required for cloudiness to appear is a
measure of reactivity of the alcohol.
30 alcohol – forms cloudiness immediately

20 alcohol - forms within 5 minutes
10 alcohol – do not form appreciably at room temperature.
5.2 CARBOXYLIC ACIDS
- They have the general formula R-COOH.

- They are named by replacing the –ane of the corresponding alkane with –oic acid.
- The functional group (-COOH) is always terminal.
- The carbonyl carbon (C=O) is assigned position 1 in numbering the longest chain.
Examples:
H O
H C C O-H
Ethanoic acid
H
H H O
H C C C O-H Propanoic acid
H H
O
C
OH 2,5-Dimethylhexanoic acid
Qualitative test for carboxylic acids
Sodium hydrogen carbonate
- Carboxylic acids react with sodium hydrogen carbonate to give a precipitate.
O O
NaHCO3
H3C C O-H H3C C O-Na + H2O + CO2
Ethanoic acid Sodiumethanoate (ppt)

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5.3 KETONES
- They have the general formula RCOR.

- They are named by replacing –e in the corresponding alkane with –one.
- The carbonyl carbon (C=O) takes priority in numbering the longest chain.
Examples
H H O
O
CH3(CH2)3CH2 C CH2CH2CH3 H C C C CH3
H H
4-Nonanone 2-Butanone
O
O
H3C C CH3
2-Propanone
6-Methylhept-5-ene-3-one or
Acetone
Qualitative test for ketones
Iodoform/Haloform test.
- Used to distinguish methyl ketones

- Aqueous solutions of iodine and potassium iodide are added to basic solutions of 2-
pentanone and 3-pentanone. The iodoform reaction is a classical test for methyl
ketones.
-
- A light yellow precipitate of iodoform forms immediately with the methyl ketone 2-
pentanone.
O O
NaOH
CH3(CH2)3CH2 C CH3 + I2 CH3(CH2)3CH2 C O- Na+ + CH3I

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5.4 ALDEHYDES
- They have the general formula R-CHO.

- They are named by replacing –e in the corresponding alkane with –al.
- The carbonyl carbon (C=O) is always terminal.
Examples:
H3C C H Ethanal
H H O
H C C C H Propanal
H H
OH O
C 2,-Methyl-5-hydroxyhexanal
H
Qualitative test for aldehydes
Fehling’s test:
- This test is very specific for aldehydes; only aldehydes will give a positive result. Any
alcohol or ketone will give a negative result.
- It is basedupon the ability of the aldehyde group to reduce the Cu+2 ion of Cu(OH)2
(which
is blue) to the Cu+1 ion of Cu2O (which is dark red) in the presence of a base.
O O
NaOH
H3C C H 2 Cu(H2O) H3 C C O-Na + Cu2O + H2O
Blue Dark red

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EGERTON UNIVERSITY
Silver mirror test/ Tollens’ reagent.
- Most Aldehydes reduce Ammoniacal Silver Nitrate solution to give a precipitate of
Silver metal (pronounced coating on test tube wall).
O O
R C H Ag(NH3)2+ OH- R C OH + 2 Ag + NH4OH
Tollens' reagent Silver (precipitated)

79

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DEPARTMENT OF CHEMISTRY

CHEM 130: INTRODUCTION TO ORGANIC CHEMISTRY

TEACHING SHEDULE – CHEM 130 MARCH TO JUNE 2019

163# Thursday 7-9 a.m B2

165# Thursday 7-9 a.m B4

*Mr. Wanjaũ E11-Reg. no 06251 to 01027 Monday 6-7 p.m B1

188# Thursday 7-9 a.m B3

Course Description: Introduction to the major families of organic compounds: Alkanes,

1-2 Introduction to Organic Chemistry: Electronic configuration of Registration for

3-5 Alkanes: Sources, nomenclature, structural isomerism, physical Determination of

8-9 Alkynes: sources; preparation; nomenclature; physical Qualitative analysis of

10-12 Functional groups: Alcohols (alkanols), alkylhalides, aldehydes

1.0 Introduction to organic chemistry:

1.1 Electronic configuration of carbon;

5.0 Functional groups

5.1 Alcohols, carboxylic acids, ketones,aldehydes,alkylhalides, and aliphatic amines,

1.0 INTRODUCTION TO ORGANIC CHEMISTRY ....................................................................................... 7

1.1 Electronic configuration of carbon ........................................................................................................... 7

1.2 Hybridization, sp3, sp2 and sp.................................................................................................................. 8

1.3 Elemental analysis (qualitative) .............................................................................................................. 20

1.4 Hydrocarbons ......................................................................................................................................... 22

2.0 ALKANES ................................................................................................................................................. 23

2.1 Sources of alkanes .................................................................................................................................. 25

2.2 Nomenclature of alkanes ........................................................................................................................ 25

2.3 Structural isomerism in alkanes .............................................................................................................. 31

2.4 Physical properties ................................................................................................................................. 31

2.5 Preparation of alkanes ............................................................................................................................ 40

2.6 Mechanism for free radical substitution ................................................................................................. 36

2.7 Cycloalkanes .......................................................................................................................................... 37

2.8 Chemical reactions of alkanes ................................................................................................................ 34

3.0 ALKENES ................................................................................................................................................. 45

3.1 Sources of alkenes .................................................................................................................................. 45

3.2 Nomenclature of alkenes ........................................................................................................................ 45

3.3 Structural isomerism in alkenes (Cis ,Trans, E, Z) ................................................................................. 47

3.4 Physical properties of alkenes ................................................................................................................ 50

3.5 Preparation of alkenes ............................................................................................................................ 50

3.6 Chemical reactions of alkenes ................................................................................................................ 52

3.7 Qualitative test for alkenes ..................................................................................................................... 59

4.0 ALKYNES ................................................................................................................................................. 61

4.1 Sources of alkynes .................................................................................................................................. 61

4.2 Nomenclature of alkynes ........................................................................................................................ 61

4.3 Isomerism in alkynes .............................................................................................................................. 63

4.4 Physical properties of alkynes ................................................................................................................ 64

4.6 Chemical reactions of alkynes ................................................................................................................ 65

4.7 Qualitative test for alkynes ..................................................................................................................... 71

5.0 FUNCTIONAL GROUPS .......................................................................................................................... 73

5.1 ALCOHOLS (ALKANOLS) .................................................................................................................. 74

5.2 CARBOXYLIC ACIDS ......................................................................................................................... 76

5.3 KETONES ............................................................................................................................................. 77

5.4 ALDEHYDES ........................................................................................................................................ 78

1.0 INTRODUCTION TO ORGANIC CHEMISTRY

A wide variety of classes of substances—such as drugs, vitamins, plastics, natural and

Naturally occurring Synthetic

detergents, insecticides, many dyes

1.1 Electronic configuration of carbon

Egerton University is ISO 9001:2008 Certified

6C : (1s22s22p2) or (1s22s2 2px1 2py12pz0)

Figure 1: Energy profile and shapes of s and p orbitals

1.2 Hybridization, sp3, sp2 and sp

Egerton University is ISO 9001:2008 Certified

- Tetrahedral (sp3) hybrid orbitals as in alkanes

1.2.1 sp3 hybridization (sp3 hybrid orbitals)

(a) ground state (b) excited state (c) hybridized state

Egerton University is ISO 9001:2008 Certified

CHEM 130 2023 Allocations & Course Outline

CHEM 130 2023 Allocations & Course Outline