4.

1 INTRODUCTION
TO ORGANIC
COMPOUNDS
 Learning outcomes
 Describe the term aromatic compound,
Kekulé structure and resonance structure of
benzene
 AROMATIC COMPOUNDS

In earlier time, compounds are called

aromatic because of their pleasant odours.

Benzene has strong

pleasant odour.

Today, we use the word aromatic to refer to

benzene and its structural relatives.
 AROMATIC COMPOUNDS

Aromatic compound is a cyclic

conjugated molecule or ion that is
stabilized by  electron
delocalisation.

It is characterised by substitution
reactions.
 KEKULÉ’S STRUCTURE

 Kekule was the first to formulate a

reasonable representation of benzene
H

H C H
C
or
C C
H C H
H

The Kekule structure suggests alternating double

and single carbon-carbon bonds
The Kekule Structure for benzene

H H

or
H H

H
 Kekule structure
In 1865, August Kekule, proposed the first
definite structure for benzene.
 The carbon atoms of benzene ring are in the
ring, that they are bonded to each other by
alternating single and double bonds.
 One hydrogen is attached to each carbon
atoms.
 This structure satisfied the requirements
of the structural theory that carbon
atoms form four bonds and that all the
hydrogen atoms of benzene are
equivalent.

 However, Kekule structure can’t explain

why benzene molecules are not
undergoes addition reaction.
 Resonance Structure
In 1930s , Linus Pauling introduced the concept
of hybrid orbital and resonance.

 The bond angles of the carbon atoms in the

benzene ring are 120.

 The carbon atoms are sp2 hybridized and the

six overlapping p orbitals form a set of three
delocalised  bonds.
 As a result, the resonance structure of benzene
is a hybrid resonance from two Kekulé
structure as shown below:

hybrid resonance
structure
 RESONANCE STRUCTURE

Benzene is actually a resonance hybrid of the

two Kekulé structures.

equivalent to

resonance hybrid

All C–C bond length equal = 139 pm

Shorter than typical C–C (148 pm)

Longer than typical C=C (134 pm)

The six  electrons completely delocalized around the ring
 The circle represents the six 
electrons, distributed over the
six atoms of the ring!

All six C atoms and six p orbitals are equivalent

 THE CRITERIA FOR AROMATICITY

4 structural criteria must be satisfied for

compound to be aromatic