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Winter 1997 CH4

1.

(a)

Benzene and methylbenzene may be separated by fractional distillation. Sketch the


general form of the boiling point/composition diagram for such a mixture and use it to
explain the basis on which fractional distillation rests.
b.p. of methylbenzene

temperature
/C

b.p. of benzene
0

mole fraction of methylbenzene

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(6)

(b)

(i)

All lighter (more volatile) fractions from petroleum distillation are useful as fuels.
Suggest two reasons why the liquid fractions with 8 to 12 carbon atoms per
molecule are used as motor fuels, rather than the gaseous ones containing from one
to four carbon atoms.
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(2)

(ii)

Benzene is added to unleaded petrol to compensate for the absence of tetraethyl


lead. Both compounds are hazardous; which hazard is associated with benzene,
other than its flammability?
..........................................................................................................................
(1)

(iii)

Suggest two reasons why unleaded fuel has been promoted by government and the
petroleum industry.
..........................................................................................................................
..........................................................................................................................
(2)
(Total 11 marks)

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Winter 1997 CH4

2.

Benzene and methylbenzene may be separated by fractional distillation. Sketch the general form
of the boiling point/composition diagram for such a mixture and use it to explain the basis on
which fractional distillation rests.
b.p. of methylbenzene

temperature
/C

b.p. of benzene
0

mole fraction of methylbenzene

........................................................................................................................
........................................................................................................................
........................................................................................................................
........................................................................................................................
(6)

3.

(a)

All lighter (more volatile) fractions from petroleum distillation are useful as fuels.
Suggest two reasons why the liquid fractions with 8 to 12 carbon atoms per molecule
are used as motor fuels, rather than the gaseous ones containing from one to four
carbon atoms.
........................................................................................................................
........................................................................................................................
(2)

(b)

Benzene is added to unleaded petrol to compensate for the absence of tetraethyl lead.
Both compounds are hazardous; which hazard is associated with benzene, other than
its flammability?
........................................................................................................................
(1)

(c)

Tetraethyl lead or benzene are added to petrol to prevent pre-ignition.


What is pre-ignition, and why is it a problem?
........................................................................................................................
........................................................................................................................
(2)

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(d)

Suggest two reasons why unleaded fuel has been promoted by government and the
petroleum industry.
........................................................................................................................
........................................................................................................................
(2)
(Total 7 marks)

4.

(a)

Give the structural formula to show clearly the organic product formed from each of the
following mixtures. If you consider no reaction occurs, you should state no reaction.
(i)

1-bromobutane with KOH in water

(ii)

1-bromobutane with KOH in alcohol

(iii)

proponal with hydrogen cyanide

(iv)

1-bromopropane with
potassium cyanide

(v)

propan-1-ol with ammoniacal


silver nitrate

(vi)

propanone with ammoniacal


silver nitrate

(vii) propan-1-ol with acidified potassium


dichromate(VI), heated under reflux

(vii) propan-2-ol with acidified potassium


dichromate(VI), heated under reflux

(8)

(b)

For each of the four reactions (a)(i)(iv), state what type of reaction is occurring.
Reaction (a)(i) .....................................................................................................
Reaction (a)(ii) .......................................................................................................
Reaction (a)(iii) ......................................................................................................
Reaction (a)(iv) ......................................................................................................
(4)

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(c)

(i)

Give the mechanism for the reaction of hydrogen cyanide with propanal.

(3)

(ii)

If the pH of this reaction mixture is too low or too high, the reaction is very slow.
Explain why in both cases.
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(2)
(Total 17 marks)

5.

Consider the compound A


H

CH 3

NH2

OH H

which is related to the hormone adrenaline.


(a)

Draw the structures of the organic product(s) which you expect from the reaction
of A with.
(i)

phosphorus pentachloride

(1)

(ii)

dilute hydrochloric acid

(1)

(iii)

ethanoyl chloride

(2)

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(iv)

hot alkaline potassium manganate(VII)

(1)

(v)

hot concentrated sulphuric acid

(1)

(b)

Suppose that you have to purify a sample of A by recrystallisation from trichloromethane.


This solvent is toxic by inhalation and skin absorption but is not flammable.
(i)

What safety precautions would you take using this solvent?


..........................................................................................................................
..........................................................................................................................
(2)

(ii)

Describe in detail how you would recrystallise a sample of about 5 g of A.


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(5)

(iii)

What simple test would you use to determine the purity of your
recrystallised material?
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(2)
(Total 15 marks)

6.

(a)

Polymers may be naturally occurring or synthetic. Name


(i)

a synthetic polyalkene ............................................................................


(1)

(ii)

a synthetic polyamide .............................................................................


(1)

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(iii)

a natural polyamide ............................................................................


(1)

(iv)

a synthetic polymer containing no hydrogen ..............................................


(1)

(b)

Terylene is a polymer made from ethane 1,2-diol and benzene- 1,4-dicarboxylic acid. It is
a condensation polymer.
(i)

Draw the structural formulae of the two compounds which are used to
make Terylene.

(2)

(ii)

Give a structural formula for the polymer.

(2)

(iii)

Explain the meaning of the term condensation in this context.


..........................................................................................................................
(1)

(iv)

Suggest why polyesters are not suitable for use under strongly alkaline conditions.
..........................................................................................................................
..........................................................................................................................
(1)

(c)

Suggest why polymers such as Terylene soften over a range of temperatures rather than
having a sharp melting point.
....................................................................................................................................
....................................................................................................................................
(1)
(Total 11 marks)

7.

Polymers may be naturally occurring or synthetic. Name


(a)

a synthetic polyalkene ..........................................................................


(1)

(b)

a synthetic polyamide ...........................................................................

(c)

a natural polyamide ..........................................................................

(1)

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Winter 1997 CH4

(1)

(d)

a synthetic polymer containing no hydrogen ............................................


(1)
(Total 4 marks)

8.

Terylene is a polymer made from ethane 1,2-diol and benzene- 1,4-dicarboxylic acid. It is a
condensation polymer.
(a)

Draw the structural formulae of the two compounds which are used to make Terylene.

(2)

(b)

Give a structural formula for the polymer.

(2)

(c)

Explain the meaning of the term condensation in this context.


........................................................................................................................
(1)

(d)

Suggest why polyesters are not suitable for use under strongly alkaline conditions.
........................................................................................................................
........................................................................................................................
(1)
(Total 6 marks)

9.

Suggest why polymers such as Terylene soften over a range of temperatures rather than having a
sharp melting point.
......................................................................................................................
..................................................................................................................................
(1)

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