Benzene PPQ

1. This question is about the chemistry of benzene and substituted benzene

compounds.

In 1865, the Kekulé model was suggested for the structure of benzene.
Experimental evidence has led to the development of an updated model.
Both models are shown below.

 Explain the experimental evidence that led to the development of

the updated model from the Kekulé model of benzene.
 Describe the bonding in the updated model of benzene.

[4]

2. Which of the following support(s) the delocalised model for benzene

rather than the Kekulé model?
1: Benzene is less reactive than cyclohexene
2: A benzene molecule has a planar, hexagonal structure
The enthalpy change of hydrogenation of benzene is more
3:
exothermic than predicted from the Kekulé structure
A. 1, 2 and 3
B. Only 1 and 2
C. Only 2 and 3
D. Only 1

Your answer
[1]

3. Which statement(s) support(s) the delocalised model for the structure of

benzene?

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 1 All carbon–carbon bonds have the same length.
The enthalpy change of hydrogenation of benzene is less
2
exothermic than expected.
3 Bromine reacts with benzene less readily than with cyclohexene.

A 1, 2 and 3
B Only 1 and 2
C Only 2 and 3
D Only 1

Your answer [1]

4. Chemists often use two different structures to represent a molecule of

benzene, as shown below.

i. Describe, with the aid of suitable diagrams showing orbital overlap,

the difference in bonding between structure A and structure B.

In your answer, you should use appropriate technical terms,

spelled correctly.

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 [4]

ii. The table below shows the enthalpy changes for the reactions of
cyclohexene, C6H10, and benzene, C6H6, with hydrogen.

reaction enthalpy change / kJ mol−1

C6H10 + H2 → C6H12 −119
C6H6 + 3H2 → C6H12 −208
iii.

Using this information, suggest and explain whether structure A or

structure B is a better representation of benzene.

[2]

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Naming Aromatic Compounds – Worksheet 1
1. Use IUPAC rules to name the following aromatic compounds

a)

b)

c)

d)

e)
f)

g)

h) i)

TIP: When naming multiple groups always prioritise in alphabetical order. i.e. the chloro comes before the
methyl.

2. Draw the following aromatic compounds

a) 1,3-dimethyl-benzene
b) 1-bromo-3-nitro-benzene
c) 1-chloro-3-iodo-benzene
d) 3-hydroxy-benzoic acid

3. Draw the 3 isomers of C6H4Br2

END OF QUESTION paper

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