Introduction To

Organic Chemistry

Chapter 7
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7.1
Functional Groups and
Nomenclature
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Properties of Carbon

• covalence of 4
• can bond with each other to form straight chain,
branched chain and rings
• can form single, double and triple bonds

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Classification of Carbon

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Types of Formula

• Molecular formula – C6H14

• Structural formula -
H H H H H H

H C C C C C C H

H H H H H H

• Condensed formula – CH3CH2CH2CH2CH2CH3

• Line formula -
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Types of Compound
Hydrocarbon

Aliphatic Aromatic
(do not contain (contain one or
benzene ring ) more benzene rings)

alkane cyclo alkene

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i ) Alkanes (single covalent bonds / saturated

hydrocarbons )
general formula CnH2n + 2 n=1,2....
ex: n = 1 C1H4 name : methane
n=2 C2H6 name : ethane
n=3 C3H8 name : propane

ii ) Cycloalkanes
CnH2n n=3,4....

ex: cyclohexane ; C6H12

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iii ) Alkenes (double covalent bonds / unsaturated

hydrocarbons ) H H
CnH2n n = 2 , 3 . . . . C C
H H
ex: C2H4 name : ethene

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7.2 Mechanism
 Mechanisms

Sequence of steps which occurs during a chemical reaction

Free radical reaction

Nucleophilic substitution, addition reaction
Electrophilic substitution, addition reaction
Elimination reaction

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Nucleophiles
• Nucleophiles are ions or molecules that are rich in
electrons.

• They are either negatively charged ions or have an atom

with lone pair of electrons.

• Examples are OH-, H2O, NH3, RCOO-, Cl-, Br-, I-, F-,
carbanion and most reducing agents.

• Nucleophiles react by way of donating their lone pair of

electrons. Thus they are Lewis bases and are
represented by the symbol Nu-.

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• Nucleophiles attack carbon atoms which have low

electron density (having a partial positive charge) by using
its lone pair of electrons to form a coordinate bond with
the electron deficient carbon atom in organic molecules.

• Ex: the reaction between aqueous sodium hydroxide

(where the nucleophile is the OH- ion) and chloromethane.

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Electrophiles
• Electrophiles are ions or molecules that are electron
deficient.

• They are either positively charged ions or have an atom

which carries a partial positive charge or have an atom
which does not have an octet electron.

• Examples of electrophiles are H+, ,CH3+, Br2, AlCl3,

FeBr3, ZnCl2, SO3 and most oxidizing agents.

• Electrophiles attack carbon atom which are electron-rich

by accepting a lone pair of electron from the electron-rich
carbon to form a coordinate bond. Hence, they are Lewis
acids.
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• Ex: the reaction between ethene and hydrogen chloride.

The HCl molecule is polarized as shown below:

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Free Radicals
• In chemistry, a radical is an atom molecule or ion that
has an unpaired valence electron. With some exceptions,
these unpaired electrons make radicals highly chemically
reactive.

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Homolytic and heterolytic cleavage of bonds

• Bond cleavage, or bond fission, is the splitting of chemical

bonds. This can be generally referred to as dissociation
when a molecule is cleaved into two or more fragments.

• In general, there are two classifications for bond

cleavage: homolytic and heterolytic, depending on the
nature of the process.

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• In homolytic cleavage, or homolysis, the two electrons in

a cleaved covalent bond are divided equally between the
products. This process is also known as homolytic
fission or radical fission.

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• In heterolytic cleavage, or heterolysis, the bond breaks in

such a fashion that the originally-shared
pair of electrons remain with one of the fragments. Thus, a
fragment gains an electron, having both bonding
electrons, while the other fragment loses an electron. This
process is also known as ionic fission.

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7.3 Isomerism
 Isomers

Different compounds that have the same molecular formula

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Structural Isomerism
Structural isomerism occurs when two or more organic
compounds have the same molecular formulae, but
different structures.

These differences tend to give the molecules different

chemical and physical properties. There are three types of
structural isomerism :

• chain isomerism
• positional isomerism

• functional isomerism

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Chain Isomerism
Chain isomerism occurs when the way carbon atoms are
linked together is different from compound to compound.

There are three chain isomers of C5H12 shown below. Note

that these isomers have the same empirical formula as
pentane, but different conformations.

Examples:
pentane 2-methylbutane 2,2-dimethylpropane

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Positional Isomerism
Positional isomerism, occurs when functional groups are in
different positions on the same carbon chain.

Examples:
1-butanol 2-butanol

1-butene 2-butene

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Functional Isomerism
Functional isomerism occurs when substances have the
same molecular formula but different functional groups.

This means that functional isomers belong to different

homologous series.

Example:
• Alkene and cycloalkane

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Stereo-isomerism
Stereo-isomerism occurs when the atoms in a molecule can
have different arrangements in space. There are two types
of stereo-isomerism:
• geometrical isomerism
• optical isomerism

Geometrical isomers can have very different physical

properties, such as different melting points, but they tend to
have the same chemical properties.

Optical isomers have the same chemical and physical

properties, except that one structure rotates the plane of
polarized light to the right and the other rotates it to the left.

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Geometric Isomerism
Geometric isomerism occurs when substances have the
same molecular formula, but a different arrangement of
their atoms in space.

It is also called cis-trans-isomerism. The focus in

geometric isomerism is on how the molecule extends out
from the two carbon atoms that are double-bonded.

There are two characteristics of cis-trans isomerism:

• there must be a C=C bond in the molecule;
• each C=C must be bonded to two different groups of
atoms

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3 3 3

3
cis-2-butane trans-2-butene

• Both of these compounds are 2-butene.

• In cis-2-butene, both of the extensions of the carbon
chain are on the same side of the double bond. They are
right next to each other.
• In trans-2-butene, the extensions of the carbon chain are
on opposite sides. They are diagonal from one another.
• Geometric isomerism and the cis-trans designation can
also be applied to compounds with halogen atoms and
other side groups attached to the two double-bonded
carbon atoms.
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Optical Isomerism
• Occurs when substances have the same molecular and
structural formulae, but cannot be superimposed on the
other.
• They are mirror images to each other. Molecules like this
are called chiral (ky-ral). (other name are called as
enantiomers)
• A molecule or object that cannot be superimposed on
its mirror image is said to be chiral.
• An object that is superimposable on its mirror image
and has a plane of symmetry is achiral.

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chiral - describe an object that is NOT superimpose on its

mirror image
mirror Image

Br F F Br
C C
Cl H H Cl

achiral - describe an object that CAN superimpose on its

mirror image
H Cl H H Cl H

H C C C H H C C C H

H Cl H H Cl H
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How to identify an optical isomer?

• It must have a chiral carbon/centre.

• A chiral carbon/centre is a carbon atom that is bonded to

four different groups of atoms. (asymmetric carbon
atoms)
Ex: 2-hydroxypropanoic acid chiral centre is
shown by a star

The two enantiomers are:

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Which of the following have cis-trans isomers, which
have optical (mirror image) isomer and which have
none. Circle the answer.

H2C=CH2 cis-trans optical neither are

isomers present isomers present
present
CH3CHClF cis-trans optical neither are
isomers present isomers present
present
ClHC=CHF cis-trans optical neither are
isomers present isomers present
present

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