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THE STRUCTURE
OF BENZENE

© www.chemsheets.co.uk A2 1023 17-Nov-2023

 STRUCTURE OF BENZENE

Benzene = C6H6
Its structure was a mystery for many years - until Kekule’s
dream.
 STRUCTURE OF BENZENE

Problems with Kekule’s structure:

1) C-C bonds are all the same length (between C-C and C=C
length).

2) Benzene does not undergo addition reactions readily (e.g.

with bromine water).

3) H hydrogenation about 152 kJ mol-1 less than expected.

© www.chemsheets.co.uk A2 1023 17-Nov-2023

 STRUCTURE OF BENZENE

H H
C C
H H
C C

C H
C H
H C

H C H
C C
H

C C
H H
STRUCTURE OF BENZENE

http://www.isis.stfc.ac.uk/
 HYDROGENATION OF BENZENE

Energy
(kJ/mol)

152

-360

-240
-208
-120

© www.chemsheets.co.uk A2 1023 17-Nov-2023

 NAMING AROMATIC COMPOUNDS

CH3 Cl NO2 COOH

methylbenzene chlorobenzene nitrobenzene benzenecarboxylic acid

(toluene) (benzoic acid)

© www.chemsheets.co.uk A2 1023 17-Nov-2023

 NAMING AROMATIC COMPOUNDS
CH3 CH3

1,3-dimethylbenzene
(m-xylene)

CH3 1-chloro-4-methylbenzene
Cl

COOH COOH
OH

O2N NO2
2-hydroxybenzenecarboxylic
3,5-dinitrobenzenecarboxylic
acid
acid

© www.chemsheets.co.uk A2 1023 17-Nov-2023

 NAMING AROMATIC COMPOUNDS
NH2

phenylamine
(aniline)

2-phenylbutane

O CH3
CH CH2 C

phenylethene phenylethanone

© www.chemsheets.co.uk A2 1023 17-Nov-2023

 NAMING AROMATIC COMPOUNDS
O

C O O
O CH3 C CH3

phenylethanoate methyl benzenecarboxylate

(methyl benzoate)

NH C CH3

N-phenylethanamide

© www.chemsheets.co.uk A2 1023 17-Nov-2023