TOPIC 18: ORGANIC CHEMISTRY: ARENES

1 Benzene can be represented by the two forms, shown below.

(a) Describe a simple test-tube experiment that would suggest the form containing the three
double bonds is unlikely to be correct (2)

Test:

Result:

(b) The nitration of benzene with a mixture of concentrated nitric acid and sulfuric acid is an
example of an electrophilic substituion reaction.

(i) Give the formula of the electrophile in this reaction. (1)

(ii) Write an equation for the formation of this electrophile. (1)

(Total for Question 1 = 4 marks)

2 Benzene and ethene both react with bromine, but under different condtions.

(a) State the conditions needed for bromine to react with each compound. (2)

Conditions for benzene:

Conditions for ethene:

(b) State the type of reaction occurring in each case. (3)

Type of reaction with benzene:

Type of reaction with ethene:

(Total for Question 2 = 5 marks)

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document may have been altered from the original.
3 A hydrocarbon is known to contain a benzene ring. It has a molar mass of 106 g mol‒1 and has
the following composition by mass: C, 90.56%; H, 9.44%.

(a) Use the data to show that the empirical formula is C4H5. (2)

(b) Determine the molecular formula of the hydrocarbon. (1)

(c) Draw a structural formula for each of the four possible isomers of this hydrocarbon that
contain a benzene ring. (4)

(Total for Question 3 = 7 marks)

4 (a) State the observations made when bromine water is added to an aqueous solution of
phenol. (2)

(b) Explain why phenol reacts more readily than benzene with bromine. (2)

(Total for Question 4 = 4 marks)

TOTAL FOR ASSESSMENT = 20 MARKS

© Pearson Education Ltd 2019. Copying permitted for purchasing institution only. This material is not copyright free. This
document may have been altered from the original.