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Arenes / Benzene Chemistry

Question Paper

Level A Level
Subject Chemistry
Exam Board Edexcel
Topic Organic Chemistry III
Sub Topic Arenes / Benzene Chemistry
Booklet Question Paper
Paper Type Open-Response 2

Time Allowed: 45 minutes

Score: /37

Percentage: /100

Grade Boundaries:

A* A B C D E U

>85% 77.5% 70% 62.5% 57.5% 45% <45%

 Vintuchemtutor-66687094-place for all chem solutions

1 Some reactions of benzene are shown below.

CH3

reaction 1
reagent A with
AlCl3 catalyst
benzene methylbenzene
reaction 2

reaction 3 CH3COCl with AlCl3 catalyst

reagent B heat under reflux

compound X

SO3H

(a) (i) Suggest the formula of reagent A in reaction 1.

(1)

................................................................................................................................................................................................................................................

(ii) Write the equation to show how the catalyst, AlCl3, reacts with reagent A to
form the species which attacks the benzene ring.
(1)

(iii) Draw the structure of the intermediate ion formed when the species in (ii)
attacks the benzene ring.
(1)
 Vintuchemtutor-66687094-place for all chem solutions

(b) The methylbenzene formed in reaction 1 generally reacts in a similar way to

benzene but faster, as the ring is said to be activated.

(i) Explain how the presence of a methyl group activates the benzene ring.
(1)

..... ............ ............ ............ ........... ............ ............ ............ ............ ........... ............ .. .......... ............ ............ ........... ............ ............ ............ ............ ........... ...........

..... ............ ............ ............ ........... ............ ............ ............ ............ ........... ............ .. .......... ............ ............ ........... ............ ............ ............ ............ ........... ...........

(ii) Use your answer to (i) to explain why methylbenzene reacts faster.
(1)

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(c) (i) Draw the structural formula of compound X, formed in reaction 2.

(1)

(ii) The organic product of reaction 2 is also formed when the same reactants, but
with an aluminium catalyst, are heated using microwave radiation. Suggest two
reasons why this technique may be considered ‘greener’.
(2)

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(d) Name reagent B needed for reaction 3.

(1)

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(Total for Question = 9 marks)

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2 Paracetamol is possibly the most widely used analgesic (painkiller) in the world. It can
be made from phenol as shown below.

OH OH OH

Step 1 Step 2

NO2 NH2

Step 3

OH

NHCOCH3
Paracetamol

(a The nitration of phenol in step 1 uses dilute nitric acid at room temperature, whereas
the nitration of benzene requires a mixture of concentrated nitric and sulfuric acids at
about 55 C.

(i) Give the mechanism for the nitration of benzene, including the equation for the
reaction that produces the electrophile.
(4)
 Vintuchemtutor-66687094-place for all chem solutions

*(ii) Explain why phenol can be nitrated under much milder conditions than those
required to nitrate benzene.
(2)

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(iii) Suggest reagents that could be used step 2.

(2)

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(iv) Suggest the name or formula of a reagent that could be used step 3.
(1)

................................................................................................................................................................................................................................................

*(b) In the nitration of phenol, step 1, two compounds are produced.

OH OH
NO2

NO2
2-nitrophenol ophenol

These compounds can be separated by steam distillation, since 2-nitrophenol is

volatile in steam but 4-nitrophenol is not.

Describe briefly the technique of steam distillation and give ONE advantage of steam
distillation over normal distillation.
(3)
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 Vintuchemtutor-66687094-place for all chem solutions

(c) The nmr spectrum of paracetamol is given below. The peaks at 6.7 and 7.4 ppm are
due to the protons on the benzene ring and are both doublets.

Explain why these two peaks are doublets but all the other peaks are singlets.

[There is no need to refer to your data booklet]

(2)

OH

NHCOCH3
Paracetamol

11 10 9 8
δ / ppm

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(Total for Question = 14 marks)

 Vintuchemtutor-66687094-place for all chem solutions

3 Benzenecarboxylic acid (benzoic acid) and phenylmethanol (benzyl alcohol) are

compounds which occur naturally and have a wide range of uses. For example,
benzenecarboxylic acid is used as a food preservative and phenylmethanol is used as
a solvent.

A laboratory sequence for the preparation of these two compounds is shown below.

H O HO O

Step 1 Step 2
benzenecarboxylic acid

Step 3

OH

phenylmethanol

(a) In the first step of the synthesis, benzene reacts with hydrogen chloride and
carbon monoxide in the presence of aluminium chloride in an electrophilic
substitution called the Gattermann-Koch reaction. The hydrogen chloride and
carbon monoxide together behave as if they form the unstable species methanoyl
chloride (HCOCl).

(i) Explain why benzene undergoes substitution rather than addition reactions.
A detailed description of the bonding in benzene is not required.
(2)

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 Vintuchemtutor-66687094-place for all chem solutions

(ii) Give the mechanism for step 1, including the formation of the electrophile.
(4)

(iii) Identify the reagents and essential conditions used in the remaining steps of
the sequence. You may assume that the correct reaction temperatures are
being used.
(4)

Step 2 ... .. .. . .. .. . .. .. . .. .. . .. .. . .. .. . .. .. .. . .. .. . .. .. . .. .. .. . .. .. . .. .. . .. .. . .. .. .. . .. .. . .. .. . .. .. . .. .. . .. .. . .. .. . .. .. . .. . .. .. . .. . . .. .. . .. .. . .. .. . .. .. .. . .. .. . .. .. . .. .. . .. .. . .. .. . .. .. . .. . .. .. . .. .. . .. .. . .. .. . .. .. .. . .. .. . .. .. . .. .. . .. .. . .. .. . .. .. . .. .. . .. . .. .. . .. ....

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Step 3 ... .. .. . .. .. . .. .. . .. .. . .. .. . .. .. . .. .. .. . .. .. . .. .. . .. .. .. . .. .. . .. .. . .. .. . .. .. .. . .. .. . .. .. . .. .. . .. .. . .. .. . .. .. . .. .. . .. . .. .. . .. . . .. .. . .. .. . .. .. . .. .. .. . .. .. . .. .. . .. .. . .. .. . .. .. . .. .. . .. . .. .. . .. .. . .. .. . .. .. . .. .. .. . .. .. . .. .. . .. .. . .. .. . .. .. . .. .. . .. .. . .. . .. . . . .. .....

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*(b) Phenol reacts faster than phenylmethanol in electrophilic substitution reactions.

Suggest why this is so.
(4)

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(Total for Question =14 marks)