12.

3 EXTRA QUESTIONS
1.

(a)

How do the physical properties of the alkene homologous series change as the chain
length increases?
.....................................................................................................................................
.....................................................................................................................................
.....................................................................................................................................
(2)

(b)

For the reaction shown in the equation:

nC 2H

give the name of this process:

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

(c)

Most ethanol used in the chemical industry is manufactured by reacting together water
and ethene.
(i)

Write a balanced equation for this reaction.

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

(ii)

Outline the reaction conditions for this reaction.

...........................................................................................................................
...........................................................................................................................
(3)

(iii)

Classify this reaction, indicating the type of initial attack on the ethene.
...........................................................................................................................
(2)
(Total 10 marks)

2.

(a)

But-1-ene can be polymerised. Draw the repeating unit of the polymer of this
molecule.

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(1)

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(b)

(i)

(ii)

Draw the structure of buta-1,3-diene and give an approximate value for the
bond angle between three adjacent carbon atoms in the molecule.

Draw the structure of, and give the name of, the addition product formed when
buta-1,3-diene reacts with an excess of bromine. Name the type of mechanism
involved.
Structure of product

Name of product................................................................................................
Type of mechanism............................................................................................
(6)
(Total 7 marks)

3.

(a)

Write an equation for the formation of epoxyethane from ethene and explain why the
product is highly reactive.
Equation

Explanation. ...............................................................................................................
.....................................................................................................................................
(4)

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(b)

(i)

Show by an equation how one mole of epoxyethane reacts with one mole of water
and give a use for the product formed.
Equation

Use ....................................................................................................................
(ii)

Epoxyethane also reacts with ammonia. Suggest a structure for the compound
obtained when one mole of epoxyethane reacts with one mole of ammonia.

(3)
(Total 7 marks)

4.

Give one important commercial use of propene.

............................................................................................................................
(1)
(Total 1 mark)

5.

(i) Write an overall equation for the reaction of cyclohexene with hydrogen.

............................................................................................................................
(ii)

By stating a reagent and an observation, give a chemical test which would show
that this hydrogenation reaction has gone to completion.
Reagent(s) .........................................................................................................
Observation(s) ..................................................................................................
(3)
(Total 3 marks)

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6.

This question concerns the chemistry of ethene and compounds derived from it. Consider the
following statements and then answer the questions below.

Ethene may be polymerised to form poly(ethene).

Treatment of ethene with bromine gives a compound C.

(a)

(i)

Explain what is meant by the term polymerisation.

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

(ii)

Write an equation to represent the polymerisation of ethene.

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

(b)

Give the name of compound C.

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

(c)

Give the name of the mechanism of the reaction between ethene and bromine. Draw the
mechanism for this reaction.
Name of the mechanism.
.....................................................................................................................................
Mechanism

(4)
(Total 8 marks)

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7.

(a)

Give the reagent and the catalyst used for the conversion of ethene into epoxyethane.
Reagent........................................................................................................................
Catalyst.......................................................................................................................
(2)

(b)

Draw the structure of epoxyethane and explain why this compound is highly reactive.
Structure

Explanation.................................................................................................................
.....................................................................................................................................
.....................................................................................................................................
(3)

(c)

The polymerisation of propene to form poly(propene) is an important industrial process.

Name the type of polymerisation involved.
...............................................................................................................................
(1)

(d)

The structure of A is shown below. Circle those carbon atoms which must lie in the same
plane.

H
H

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C H

C H

CH

(1)
(Total 7 marks)

8.

(a)

(i)

Write an equation for the formation of epoxyethane from ethene, showing the
structure of the product.

(ii)

Explain why the epoxyethane molecule is highly reactive.

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

(iii)

Give the structure of the product formed by the reaction of one molecule of
epoxyethane with one molecule of water. Give one use for this product.
Structure

Use ..............................................................................................................
(5)

(b)

But-2-ene can exist in two isomeric forms. Give the structures of these two isomers and
name the type of isomerism.
Structure 1

Structure 2

Type of isomerism ................................................................................................

(3)
(Total 8 marks)

Mill Hill High School

9.

Propene reacts with hydrogen bromide by an electrophilic addition mechanism forming

2-bromopropane as the major product.
The equation for this reaction is shown below.
H 3C
H

H
C

+
H

H Br

H 3C

Br

(i)

Outline the mechanism for this reaction, showing the structure of the intermediate
carbocation formed.

(ii)

Give the structure of the alternative carbocation which could be formed in the
reaction between propene and hydrogen bromide.

(5)
(Total 5 marks)

Mill Hill High School

10.

Butenedioic acid has the formula HOOCCH=CHCOOH.

(a)

Describe a simple test in each case to show that butenedioic acid is unsaturated.
Test. ................................................................................................................
Result. .............................................................................................................
(2)

(b)

Draw the structure of the cis-isomer of butenedioic acid and give two reasons which
together explain why butenedioic acid shows geometrical isomerism.
Structure

Reason 1. .........................................................................................................
Reason 2. .........................................................................................................
(3)

(d)

Outline a mechanism for the reaction of butenedioic acid with hydrogen bromide.

(4)
(Total 9 marks)

11.

When 2-methylpent-2-ene reacts with hydrogen bromide two products are formed, one major
and one minor, each with molecular formula C6H13Br. Name these two products and account
for their formation by reference to the mechanism of the reaction.
(Total 13 marks)

12.

There are several non-cyclic structural isomers with the molecular formula C 6H12.
Identify one linear alkene of formula C6H12 which can exist as a pair of stereoisomers.
State the type of stereoisomerism shown, name the alkene and draw the structures of the
two isomers.
(Total 4 marks)

13.

(a)

Explain the meaning of the term stereoisomerism and explain how it arises.
(5)

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(b)

Outline a mechanism for the reaction of but-2-ene with hydrogen bromide. Discuss the
stereoisomerism shown by but-2-ene and also that shown by the product of this reaction.
(8)
(Total 13 marks)

14.

Epoxyethane is produced commercially by the oxidation of ethene.

State the reagent and the catalyst required for this process and identify two different types of
hazard associated with the production of epoxyethane. Write an equation for the reaction of
epoxyethane with water in a 1 : 1 mole ratio and give a use for the product obtained.
(Total 7 marks)

15.

(a)

Outline, together with an equation, how epoxyethane is manufactured from ethene.

(4)

(b)

Show, by means of equations, how one mole of epoxyethane reacts with one mole of
water.
(1)
(Total 5 marks)

16.

(b)

Cyclohexene reacts with bromine in an appropriate solvent.

(i)

Name and outline a mechanism for the reaction of cyclohexene with bromine and
name the product of the reaction.
(6)

(c)

Phenylethene, C6H5CH=CH2, is used to produce the polymer poly(phenylethene), known

as polystyrene. Draw the repeating unit of polystyrene.
(1)
(Total 7 marks)

17.

(b)

Outline, together with an equation, how epoxyethane is manufactured from ethene and
discuss the hazards of the process.
(Total 7 marks)

18.

At 40 C, hydrogen bromide reacts with buta-1,3-diene to produce both

1-bromobut-2-ene and 3-bromobut-1-ene.
(i)

Outline a mechanism to show how the two products are formed.

(ii)

Predict the major product of the reaction of one mole of hydrogen bromide with 2methylbuta-1,3-diene. Justify your choice.
(9)
(Total 9 marks)

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