25 Aromatic chemistry

OCR Chemistry A Exam-style questions

1 Benzene can be represented by the structural formula shown below.

This structural formula is often preferred to other representations of benzene as it is

more consistent with the accepted model of the bonding in the benzene molecule.
a Describe the bonding in a benzene molecule.

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co
(4 marks)

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o.
b An earlier model of the bonding in benzene is known as the Kekulé model.
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i State how the Kekulé model differs from the accepted model of the
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bonding in benzene.

(1 mark)
o
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ii Describe three pieces of evidence that led scientists to reject the Kekulé
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model of the structure of benzene.

1
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2
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3 (3 marks)
2 Give the systematic name of the following molecules:
sh is

Structural formula Name

Th

C6H5OH a ……………………………………............ (1 mark)

b ……………………………………............ (1 mark)

c ……………………………………............ (1 mark)

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 25 Aromatic chemistry
OCR Chemistry A Exam-style questions
3 The molecule shown below is known by the non-systematic name 4-tertbutylaniline.

Some students attempt to devise a series of reactions to form 4-tertbutylaniline starting from
benzene.

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a i Name the substances present in the mixture, A, used in step 1.

o.
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ii Give the structural formula of the organic reagent B used in step 3.

(1 mark)
o

iii State and explain the conditions required for step 1.

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v i y re

(2 marks)
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iv The type of reaction that occurs in step 3 is named after the two chemists
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who first carried it out. Give the name of the reaction.

(1 mark)
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v Step 3 requires the use of a halogen carrier. Name a suitable halogen carrier.
Th

(1 mark)

b Step 3 can produce other products apart from 4-tertbutylaniline

i Draw the structure of an isomer of 4-terbutylaniline that is also likely to
form in step 3.

(1 mark)

© Oxford University Press 2016 http://www.oxfordsecondary.co.uk/acknowledgements

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This resource sheet may have been changed from the original 2
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 25 Aromatic chemistry
OCR Chemistry A Exam-style questions
ii Another group of students proposes a slightly different order for the
reactions to form 4-tertbutylaniline:

Comment on whether this reaction scheme is likely to produce the correct

isomer of 4-tertbutylaniline.

m
(2 marks)

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4 A group of students are given some samples of ethanol, dilute ethanoic acid, and

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a dilute solution of phenol in unlabelled bottles.

o.
The students are also provided with:
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 a solution of sodium hydroxide to which a few drops of universal indicator
have been added
 a solution of sodium carbonate.
o

Describe and explain how the students would use these solutions to identify the
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samples in the bottles. Give equations for any reactions that will occur during the
v i y re

procedure.
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(6 marks)

5 Benzene and cyclohexene both take part in reactions with bromine.

a Complete the table below to show:
 the product or products of the reaction
 the name of the mechanism of the reaction in each case.

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 25 Aromatic chemistry
OCR Chemistry A Exam-style questions

Reactants Product or products of Name of the mechanism

the reaction

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(4 marks)

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b Both reactions occur via the formation of a positively charged organic

o.
intermediate (carbocation).
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However, the second step of the reaction, involving this carbocation
intermediate is different for these two reactions.
i Draw the organic intermediate formed in each of the two reactions:
o

benzene  bromine:
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v i y re

cyclohexene  bromine:
ed d
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sh is

(4 marks)
Th

ii Describe and explain the differences between the second steps of these two
reactions. You should draw appropriate diagrams to illustrate your answer.

(4 marks)

© Oxford University Press 2016 http://www.oxfordsecondary.co.uk/acknowledgements

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