OCR

A-Level
CHEMISTRY
Core Organic Chemistry
Haloalkanes 2

Time allowed
61 minutes

QUESTION PAPER

Score Percentage

/51 %
4.1 | CELL BIOLOGY | QUESTION PAPER 1 1
1 A student carries out an investigation on some halogenoalkanes.
(a) She decided to hydrolyse 1-bromopentane and 1-chloropentane using aqueous sodium
hydroxide.

State and explain the difference in the rates of hydrolysis of 1-bromopentane and
1-chloropentane.

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(b) A student wants to determine the structure of an unknown iodoalkane B.

She knows that the molecular formula of B is C4H9I.

The student heats B with aqueous sodium hydroxide. A reaction mixture forms containing the
organic compound C and I –(aq).

(i) Draw all of the possible structural isomers for B.

[4]

(ii) What is the molecular formula for compound C?

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(iii) The student purifies compound C and splits it into two portions.

■ She heats one portion of C with concentrated sulfuric acid. The product of this
reaction is methylpropene.

■ To the other portion of C, she adds acidified potassium dichromate(VI) and heats
the mixture under reflux. The product of this reaction is compound D.

■ The infrared spectrum for compound D is shown at the top of page 19.

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 100

transmittance
(%) 50

0
4000 3000 2000 1500 1000 500
wavenumber / cm–1

Use this evidence to suggest structures for B, C and D.

In your answer you should make clear how your explanations are linked to the evidence.

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2 A student carried out an investigation to compare the rates of hydrolysis of 1-iodopropane and
1-bromopropane. The student heated hot aqueous sodium hydroxide with each halogenoalkane
and found that 1-iodopropane was hydrolysed faster.

The equation for the reaction with 1-iodopropane is shown below.

CH3CH2CH2I + OH– CH3CH2CH2OH + I –

(a) (i) Outline the mechanism for this hydrolysis of 1-iodopropane.

Show curly arrows and relevant dipoles.

[3]

(ii) State the name of this type of mechanism.

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(b) Explain why 1-iodopropane is hydrolysed faster than 1-bromopropane.

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(c) Chlorofluoroalkanes, CFCs, were developed from fluoroalkanes and were used in aerosols
and as refrigerants. Under the Montreal Protocol, CFCs are now largely banned because of
their ozone-depleting properties. CFCs have now been replaced in many applications.

Suggest two reasons why there is still concern about ozone depletion.

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 (d) Fluoroalkenes are used to make polymers. For example, PVF, (CH2CHF)n, is used to make
non-flammable interiors of aircraft.

(i) Draw two repeat units of the polymer PVF showing all bonds.

[1]

(ii) Draw the structure of the monomer of PVF.

[1]

(e) Once polymers have been used, they become waste.

Outline two ways that waste polymers are processed usefully, rather than just dumped in
landfill sites.

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[Total: 12]

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3 Chlorofluorocarbons, CFCs, were once used as propellants in aerosols. CFCs contribute to ozone
depletion in the upper atmosphere.

(a) A CFC has the formula CF2Cl2.

State the three-dimensional shape of a CF2Cl2 molecule and the F–C–Cl bond angle.

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(b) Two reasons that CF2Cl2 was used as an aerosol propellant are that it has low reactivity and
will not hydrolyse in water.

(i) State one other reason why CF2Cl2 was developed for use as an aerosol.

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(ii) Suggest why CF2Cl2 does not hydrolyse in water.

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(c) Explain, with the aid of equations, how the presence of CFCs in the upper atmosphere leads
to ozone depletion.

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(d) Why are scientists concerned about ozone depletion?

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 (e) International agreements have reduced the use of CFCs. However the concentration of
atmospheric CFCs has hardly changed.

Suggest two reasons why.

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[Total: 10]

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4 This question is about halogenated hydrocarbons.

(a) Halogenoalkanes undergo nucleophilic substitution reactions with ammonia to form amines.
Amines contain the –NH2 functional group.

For example, 1-bromopropane reacts with ammonia to form propylamine, CH3CH2CH2NH2.

CH3CH2CH2Br + 2NH3 CH3CH2CH2NH2 + NH4Br

(i) Iodoethane is reacted with ammonia.

Write an equation for this reaction.

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(ii) The first step in the mechanism of the reaction between CH3CH2CH2Br and NH3 is
shown below. It is incomplete.

H H

+
CH3CH2 C Br CH3CH2 C NH3 + .............

H H

Complete the mechanism.

Include relevant dipoles, lone pairs, curly arrows and the missing product. [3]

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 (b) A student investigates the rate of hydrolysis of six halogenoalkanes.

The student mixes 5 cm3 of ethanol with five drops of halogenoalkane. This mixture is warmed
to 50 °C in a water bath. The student adds 5 cm3 of aqueous silver nitrate, also heated to
50 °C, to the halogenoalkane. The time taken for a precipitate to form is recorded in a results
table.

The student repeats the whole experiment at 60 °C instead of 50 °C.

time taken for a precipitate to form / s

halogenoalkane
at 50 °C at 60 °C
CH3CH2CH2CH2Cl 243 121
CH3CH2CH2CH2Br 121 63
CH3CH2CH2CH2I 40 19
CH3CH2CHBrCH3 89 42
(CH3)2CHCH2Br 110 55
(CH3)3CBr 44 21

Describe and explain the factors that affect the rate of hydrolysis of halogenoalkanes.

Include ideas about

• the halogen in the halogenoalkanes
• the groups attached to the carbon of the carbon–halogen bond (the type of
halogenoalkane)
• the temperature of the hydrolysis.

In your answer you should link the evidence with your explanation.

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(c) Poly(tetrafluoroethene), PTFE, and poly(chloroethene), PVC, are halogenated plastics.

(i) Write an equation, using displayed formulae, for the reaction to form PTFE from its
monomer.

[3]

(ii) The combustion of waste polymers can be used for energy production.
What problem is caused by disposing of PTFE and PVC in this way?

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[Total: 16]

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