1. (a) But-2-ene, CH3CH=CHCH3, exists as geometric isomers.

(i) Draw the geometric isomers of but-2-ene.

(2)

(ii) Explain how geometric isomerism arises.

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

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

(b) (i) Draw the structural formula of a compound which is an isomer of but-2-ene but
which does not show geometric isomerism.

(1)

(ii) Explain why the isomer drawn in (i) does not show geometric isomerism.

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

......................................................................................................................
(1)
(Total 5 marks)

2. (a) A sample of 2-bromobutane was heated with potassium hydroxide in ethanolic solution.
A reaction occurred producing a mixture of but-1-ene and but-2-ene.

(i) Write an equation for the above reaction to show the production of either but-1-
ene or but-2-ene.

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

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

(ii) State the type of reaction taking place.

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

(b) Some bromine solution was shaken with a sample of but-2-ene, and a reaction occurred.

(i) State what would be seen during this reaction.

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

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

1
 (ii) Draw the structural formula of the product of this reaction, and name this product.

Diagram:

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

(c) But-2-ene can exist as two stereoisomers.

(i) Draw the structural formula of the two stereoisomers of but-2-ene.

(2)

(ii) Explain why but-2-ene exists as two stereoisomers, and name this type of
isomerism.

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

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

..........................................................................................................................
(2)
(Total 9 marks)

3. (a) Ethene and propene are in the same homologous series. Explain the term homologous
series.

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

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

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

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

2
 (b) (i) Draw a representative length of the polymer chain of poly(propene).

(2)

(ii) State, with a reason, the empirical formula of poly(propene).

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

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

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

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

(c) Poly(propene) does not have a sharp melting temperature, but softens over a range of
temperature. Suggest why this is so.

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

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

(d) (i) Tetrafluoroethene, C2F4, also forms a polymer. Suggest why this polymer is very
inert.

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

(ii) Give one use for poly(tetrafluoroethene).

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

(e) Ethane and ethene both react with bromine. Ethane does not react at room temperature in
the dark, whereas ethene does so extremely quickly. Explain in terms of the bonding in
each molecule why this is so.

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

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

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

....................................................................................................................................
(3)
(Total 14 marks)

4. Cracking is an important process in the petrochemical industry. Cracking the fraction of crude
oil with a boiling range of 200–300 °C produces a number of useful alkanes and alkenes.

(a) Why does the original fraction of crude oil have a boiling range rather than a single
boiling point?

3
 .....................................................................................................................................

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

(b) The following equation represents one possible reaction which might occur during
cracking.

(i) Give the name of Product 1.

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

(ii) Give the molecular formula of Product 1.

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

(iii) Product 1 of this reaction is used as a component of petrol. Suggest ONE reason
why it is more suitable for this use than the original undecane.

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

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

(iv) State TWO necessary conditions used when cracking petroleum fractions.

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

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

(v) Draw a labelled diagram showing suitable apparatus and materials for ‘cracking’
a liquid such as ‘light paraffin’ in the laboratory. You should indicate how a
gaseous product of the reaction could be collected.

(4)

(c) There are several isomers of Product 2. One of them, an alkene, can be made from
2-bromo-2-methylpropane, which has the following formula:

4
 (i) Draw the structural formula of the alkene produced.

(1)

(ii) Name the type of reaction involved in the conversion of 2-bromo-2-methylpropane

to Product 2.

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

(iii) What reagent and conditions would be used to bring about this conversion?

Reagent ..............................................................................................................

Conditions ..........................................................................................................
(2)
(Total 14 marks)

5. (a) Bromine reacts with both ethane and ethene.

(i) Write the equations for the reactions below.

Ethane + bromine

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

Ethene + bromine

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

(ii) Classify the two reactions in terms of the type of reaction occurring.

Ethane + bromine

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

Ethene + bromine

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

5
 (b) Chloroethene (vinyl chloride), H2C==CHCl, can be polymerised in a similar type of
reaction to the polymerisation of ethene.

(i) Draw the full structural formula of the polymer poly(chloroethene), sufficient to
make the structure of the polymer clear.

(1)

(ii) State one use of poly(chloroethene).

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

(iii) State and explain one environmental problem arising from the disposal of
poly(chloroethene).

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

......................................................................................................................
(2)
(Total 10 marks)

6. (a) Halogenoalkanes react with many nucleophiles.

Define the term nucleophile.

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

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

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

(b) (i) Identify the reagent and conditions necessary for the conversion of iodoethane to
ethylamine, C2H5NH2.

Reagent:.........................................................................................................

Conditions:.....................................................................................................

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

(ii) State why the rate of reaction would be slower if bromobutane were used in place
of iodoethane, with all other conditions remaining the same.

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

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

6
 (d) Ethanol was heated under reflux with an excess of a mixture of potassium dichromate(VI)
and dilute sulphuric acid. Draw the full structural formnula of the organic product.

(1)
(Total 10 marks)

7. One of the most important industrial uses of chlorine is in the production of poly(chloroethene),
usually called PVC. A sequence of reactions used to make PVC is set out below.

(a) (i) Name compound A.

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

(ii) Give the structural formula of chloroethene.

(1)

(iii) It is important that hydrogen chloride gas is not allowed to escape into the
atmosphere.

Suggest a way in which its escape could be prevented.

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

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

7
 (b) (i) Chloroethene is polymerised by a reaction involving free radicals. Explain what is
meant by a free radical.

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

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

(ii) Give a necessary condition for the production of free radicals.

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

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

(c) (i) Ethane-1,2-diol, CH2OHCH2OH, is a useful compound which could be made from
compound A using a nucleophilic substitution reaction.

Suggest a suitable nucleophile for this reaction.

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

(ii) The diagram below shows part of the formula of compound A. Use the diagram to
show how your suggested nucleophile attacks A.

C Cl

(2)

(iii) What is the leaving group in this reaction?

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

(iv) Suggest a suitable chemical test you could use to confirm the identity of this
leaving group.

You should state the reagent you would use and give the observation expected.

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

..........................................................................................................................
(2)
(Total 11 marks)

8. The reaction between chlorine and methane, in the presence of ultraviolet light, involves the
formation of free radicals and includes the following steps:

• ο –1
A Cl2  2Cl ΔΗ = +242 kJ mol

8
 • • ο –1
B CH4 + Cl  HCl + CH3 ΔΗ = +4 kJ mol

• • ο –1
C Cl2 + CH3  CH3Cl + Cl ΔΗ = –97 kJ mol

• •
D Cl + Cl  Cl2

• •
E CH3 + CH3  CH3CH3

• • ο –1
F Cl + CH3  CH3Cl ΔΗ = –339 kJ mol

(a) (i) What is meant by a free radical? ....................................................................

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

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

(ii) Draw a ‘dot-and-cross’ diagram, showing outer shell electrons only, for a chlorine
free radical.

(1)

(iii) What type of bond breaking occurs in step A?

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

(b) Which of the steps, A to F, are chain propagation steps?

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

(c) (i) Write the equation for the overall reaction between one mole of chlorine and one
mole of methane molecules.

(1)

(e) The overall reaction was repeated using bromine gas instead of chlorine gas.

Would you expect step A for bromine to be more or less endothermic than step A for
chlorine? Justify your answer.

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

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

....................................................................................................................................
(2)
(Total 11 marks)

9
9. (a) Chlorine reacts with methane, CH4, to produce chloromethane.

(i) Write an equation for this reaction.

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

(ii) State a necessary condition for this reaction.

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

(b) Chlorine can react with but-2-ene to form an addition product.

(i) Draw the structural formulae of the two geometric isomers of but-2-ene.

Isomer I Isomer 2

(2)

(ii) Explain why but-2-ene exists as two geometric isomers.

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

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

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

(iii) Name the addition product when chlorine reacts with but-2-ene.

.....................................................................................................................................
(1)
(Total 7 marks)

10. The industrial processes involved in the production of poly(chloroethene) are summarised in the
flow chart:

ethane  ethene  1,2-dichloroethane  chloroethene  poly(chloroethene)

(a) (i) Ethane is converted to ethene by dehydrogenation.

Write a balanced equation, including state symbols, for this equilibrium reaction.

(1)

(ii) Explain why conditions of high pressure are less favourable for ethene production.

10
 ............................................................................................................................

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

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

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

(b) Draw a labelled diagram of an ethene molecule, showing the electron density distribution
in the  and  bonds between the carbon atoms.

(2)

(c) Give a chemical test which would distinguish between ethane and ethene.

State the result of your test with ethene.

Test ..............................................................................................................................

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

(d) 1,2-dichloroethane is formed from ethene by reaction with chlorine.

State the type and mechanism of this reaction.

Type ...................................................................................................................................

Mechanism .........................................................................................................................
(2)
(Total 9 marks)

11. But-1-ene undergoes the following reactions:

(a) State the reagent and conditions needed for Reaction 1.

Reagent ........................................................................................................................

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

11
 (b) (i) The reagent in Reaction 2 is gaseous hydrogen bromide.

Draw the full structural formula of compound A.

(1)

(ii) What type of reagent is hydrogen bromide in this reaction?

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

(c) Identify the reagent needed for Reaction 3.

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

(d) But-1-ene can be used to make an addition polymer.

Draw the repeating unit of the polymer.

(2)
(Total 8 marks)

12. Bromine reacts with both ethane, C2H6, and ethene, C2H4.

(a) The reaction of bromine with ethane occurs in ultraviolet light.

(i) By what type of mechanism does this substitution reaction occur?

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

(ii) Write the equation for a reaction of ethane with bromine.

(1)

(b) Bromine reacts rapidly with ethene without the need for light.

(i) Give the equation for this reaction using structural formulae.

12
 (2)

(ii) Name the product. ...........................................................................................

(1)

(c) Explain, in terms of the bonding in the two hydrocarbons, why the reaction of bromine
with ethene occurs so much more readily than that with ethane.

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

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

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

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

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

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

.....................................................................................................................................
(3)
(Total 8 marks)

13. (a) (i) Draw the structural formulae of the two geometric isomers of but-2-ene, C 4H8.

(2)

(ii) Explain, in terms of structure and bonding, why but-2-ene exists as two geometric
isomers whereas but-1-ene does not.

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

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

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

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

(iii) Draw the structural formula of another isomer with formula C 4H8.

(1)

(b) Alkenes can be used to make polymers.

(i) Draw enough of the chain of poly(propene) to make its structure clear.

13
 (2)

(ii) Explain why poly(alkenes) cause problems when they are disposed of in a
landfill site.

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

...........................................................................................................................
(2)
(Total 10 marks)

14. (a) Name the homologous series to which the organic compound CH2=CHCH3 belongs.

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

(b) Write the structural formula of a member of the series named in (a) which contains four
carbon atoms.

.....................................................................................................................................
(1)
(Total 2 marks)

14
17. Two reactions of a chloroalkane, X, are shown below.

Reaction1 Reaction2
Propanol-2-ol     Chloroalkane X     CH =CHCH
2 3
propene

(a) The chloroalkane X can be used to make propan-2-ol in Reaction 1.

(i) Name and draw the displayed formula of the chloroalkane X.

Name ...........................................................................................................

Displayed formula

(2)

(ii) Reaction 1 is an example of nucleophilic substitution. The nucleophile is the

hydroxide ion. Use the diagram below to show how it is able to attack the
chloroalkane X.

C C l

(2)

(b) (i) What type of reaction is Reaction 2?

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

(ii) Give the reagent and conditions needed for this reaction.

Reagent .............................................................................................................

Conditions .........................................................................................................

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

(c) Propan-2-ol has a higher boiling point than both the chloroalkane X and propene.

(i) Name the strongest intermolecular force between propan-2-ol molecules.

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

15
 (ii) Draw a diagram to show this force between two propan-2-ol molecules. Clearly
mark and label the bond angle between the molecules.

(2)

(d) Propene, CH2=CHCH3, can be polymerised forming poly(propene).

(i) Draw a section of the poly(propene) polymer chain formed from two monomer
units.

(2)

(ii) Explain, in terms of intermolecular forces, why poly(propene) is a solid at room

temperature.

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

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

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

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

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

...........................................................................................................................
(2)
(Total 14 marks)

18. (a) The molecule isoprene has the displayed formula

H C H
H H
C C C C
H H H

(i) Give the systematic name of isoprene.

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

16
 (ii) What colour change occurs when aqueous bromine solution is added to isoprene?

From ..................................................... to .......................................................

(1)

(iii) State the type and mechanism of this reaction.

Type ................................................ Mechanism .............................................

(2)

(iv) Suggest the displayed formula of the product formed when excess bromine reacts
with isoprene in the dark.

(1)

(b) Compound Q, an isomer of isoprene, has the structural formula

CH2 =CHCH2CH=CH2.

(i) Give the name of the intermolecular force present in both isomers.

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

(ii) Which isomer would you expect to have the higher boiling point? Justify your
answer.

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

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

...........................................................................................................................
(2)
(Total 9 marks)

19. (a) Draw the full structural formulae, showing all bonds, of:

(i) 2,4-dimethylpentane

(1)

(ii) 2-bromopropan-2-ol

(1)

17
 (b) Pent-2-ene shows geometric isomerism.

Draw the structures of the two geometric isomers.

Isomer 1 Isomer 2

(2)
(Total 4 marks)

24. (a) Compound A, CH3CHBrCH2CH3, can be converted into butan-2-ol by reaction with
potassium hydroxide solution.

(i) Name compound A.

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

(ii) Write an equation for the conversion of compound A into butan-2-ol.

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

(iii) Identify the solvent required for this reaction.

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

(iv) Classify this reaction.

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

(b) Compound A can also be converted into a mixture of the structural isomers but-1-ene and
but-2-ene by reaction with potassium hydroxide under different conditions.

(i) Write the ionic equation for the conversion of compound A into either but-1-ene
or but-2-ene.

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

(ii) What is the solvent required for this reaction?

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

18
 (iii) Classify this reaction.

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

(c) But-2-ene exists as two geometric isomers.

(i) Draw the structural formulae of these TWO geometric isomers.

(1)

(ii) Explain why but-2-ene exists as two geometric isomers.

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

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

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

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

...........................................................................................................................
(2)
31. Propene can be used to make other important chemical products. The processes involved can be
summarised in the diagram:

C om poundA C H 2(O H )C H (O H )C H 3

+H B r
R e a c tio n 1 R e a c tio n 2

C H 2 C H C H 3
P ro p e n e

R e a c tio n 3
R e a c tio n 4
+ H 2/N i

p o ly (p ro p e n e )

P ro p a n e
C H 3C H 2C H 2C l C H 3C H 2C H 3
R e a c tio n 5

(a) (i) Give the mechanism for Reaction 1.

19
 (3)

(ii) Explain why compound A and not its structural isomer is the major product in
Reaction 1.

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

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

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

(iii) Name compound A formed in Reaction 1.

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

(b) What is added in Reaction 2 to make the product CH2(OH)CH(OH)CH3?

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

20