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13.

6 Aromatic Assessed Homework

Name : ..

Date Due : ..

Year 13
A2 Chemistry
2007 - 2008

13.6
Questions on
Aromatic Chemistry

80%

70%

60%

50%

40%

Below

57

13.6 Aromatic Assessed Homework

1.

(a)

The hydrocarbon M has the structure shown below.

C H 3C H

C
CH

(i)

C H

Name hydrocarbon M.
........................................................................................................................

(ii)

Draw the repeating unit of the polymer which can be formed from M. State
the type of polymerisation occurring in this reaction.
Repeating unit

(iii) The reaction between M and benzene in the presence of HCl and AlCl3 is
similar to the reaction between ethene and benzene under the same
conditions. Name the type of mechanism involved and draw the structure of
the major product formed in the reaction between M and benzene.
Name of mechanism
.......................................................................................
Major product

(iv)

Draw a structural isomer of M which shows geometrical isomerism.

Total 5 marks

13.6 Aromatic Assessed Homework


2.

(a)
An equation for the formation of phenylethanone is shown below. In
this reaction a reactive intermediate is formed from ethanoyl chloride. This
intermediate then reacts with benzene.
+
(i)

C H 3C O C l

A lC l 3

CO C H

+ H C l

Give the formula of the reactive intermediate.


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

(ii)

Outline a mechanism for the reaction of this intermediate with benzene to


form phenylethanone.

(4)
(Total 4 marks)
3.

(a)

Identify two substances other than benzene and ethene required in the
preparation of ethylbenzene.
Substance 1 ..
Substance 2 .

(a)

(2)

Write an equation for the reaction of these two substances with ethene to
form the reactive intermediate involved in the formation of ethylbenzene.
. (1)

(b)

Name and outline the mechanism for the reaction between this reactive
intermediate and benzene
Name of mechanism ...
Mechanism :

(4)
2

13.6 Aromatic Assessed Homework


(c)

Draw the structure of the product formed in a similar reaction between


benzene and cyclohexene

(1)
(d)

Ethylbenzene is used to make phenylethene which can be polymerised to


form poly(phenylethene). Name this type of polymerisation and draw the
structure of the repeating unit in the polymer
Type of polymerisation
Repeating unit:

(2)
TOTAL 10 marks

4.

Both cyclohexene and benzene react with hydrogen in the presence of a suitable catalyst to
form cyclohexane. For cyclohexene the enthalpy of hydrogenation is 120 kJmol -1 and for
benzene it is 208 KJmol-1

(a)

(i)

Write an equation for the reaction of benzene with hydrogen and identify
a suitable catalyst for this reaction.
Equation:.....
Catalyst:.......

13.6 Aromatic Assessed Homework


(ii)

Discuss the shape of, and the bonding in, the benzene molecule. Use the
data above in your answer.

(9)
(b)

Cyclohexene reacts with bromine in an appropriate solvent but benzene doesnt.


(i)

Name and outline the mechanism for the reaction of cyclohexene with
bromine and name the product of the reaction.
Name of mechanism:
Mechanism:

Name of product:

13.6 Aromatic Assessed Homework


(ii)

Explain why benzene does not undergo reactions with the same mechanism
as in (b)(i).

(iii)

Name the mechanism for the reaction which benzene undergoes but
cyclohexene does not.

(8)
TOTAL 17 marks

5.

(a)

Use the following data to show the stability of benzene relative to the hypothetical
cyclohexa-1,3,5-triene.

Give a reason for this difference in stability.

= 1 2 0 k J m o l1

3H

= 2 0 8 k J m o l1
(4)

(b)

Consider the following reaction sequence which starts from phenylamine.

N H

N H C O CH

S te p 1

N H CO C H

S te p 2

N H

N O

S te p 3

C H 3CO C l
N O

13.6 Aromatic Assessed Homework

(i)

State and explain the difference in base strength between phenylamine and
ammonia.

(ii)

Name and outline a mechanism for the reaction in Step 1 and name the
organic product of Step 1.

(iii)

The mechanism of Step 2 involves attack by an electrophile. Give the


reagents used in this step and write an equation showing the formation of
the electrophile.
Outline a mechanism for the reaction of this electrophile with benzene.

(iv)

Name the type of linkage which is broken in Step 3 and suggest a suitable
reagent for this reaction.

(17)
(Total 21 marks)
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