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Class

Reg Number

Candidate Name .......................................................................

Chemistry H2 9746
Tutor Tutee
Revision Exercise 8: Alkanes and Alkenes
1

Geraniol, C9H15CH2OH, is a naturally occurring compound that contributes to the smell of

roses. The skeletal formula of geraniol is shown below.

(a)

Name the two different functional groups in geraniol.

................................................... and ...................................................

(b)

Geraniol has stereoisomers due to one of the double bonds in the molecule.

(i)

What is meant the term stereoisomer?

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(ii)

Name the type of stereoisomerism shown by geraniol.

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(iii)

State how this type of stereoisomerism arises in organic molecules.

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(iv)

Explain why one of the double bonds in geraniol does not give rise to stereoisomerism.
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OCR Jan 05 2814

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2

Cis-hex-3-en-1-ol is a colourless liquid also known as leaf alcohol. It has a powerful smell
of newly cut grass and it occurs naturally in a variety of plants, such as geranium, thyme
and tea. The structural formula of leaf alcohol is shown below.

(a)

Draw the organic product(s) formed when leaf alcohol reacts with

(i)

hydrogen in the presence of a suitable catalyst,

(ii)

excess hydrogen bromide.

(b)

Leaf alcohol reacts with bromine as shown in the equation below.

(i)

State what you would see when bromine reacts with leaf alcohol.
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(ii)

Complete, with the aid of curly arrows, the mechanism involved in the reaction between
leaf alcohol and bromine. Show any relevant dipoles, charges and lone pairs of electrons.

3(a)

OCR 2812 Jan 05

Part of the label from a Body Spray deodorant is shown below.

The alkanes act as the propellant and are nowadays commonly used as alternatives to
CFCs. The alkanes are highly flammable.
(i)

What is the molecular formula of 2-methylpropane?

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(ii)

Write a balanced equation for the complete combustion of butane.

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(iii)

Methyl-1-ethyl myristate is an ester and can be made by reaction of an alcohol with a

carboxylic acid. The structure of methyl-1-ethyl myristate is shown below.

Identify the alcohol used.

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(b)

Trifluorochloromethane, CF3Cl, is an example of a chlorofluorocarbon, CFC, that was

commonly used as a propellant in aerosols. Nowadays, CFCs have limited use because of
the damage caused to the ozone layer.

(i)

Draw a diagram to show the shape of a molecule of CF3Cl.

(ii)

Predict an approximate value for the bond angles in a molecule of CF3Cl.

bond angle ....................

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(iii)

Suggest a property that made CF3Cl suitable as a propellant in an aerosol.

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(iv)

When CFCs are exposed to strong ultraviolet radiation in the upper atmosphere, homolytic
fission takes place to produce free radicals.
Explain what is meant by the term homolytic fission.
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(v)

Suggest which bond is most likely to be broken when CF3Cl is exposed to ultraviolet
radiation. Explain your answer.
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(vi)

Identify the two free radicals most likely to be formed when CF 3Cl is exposed to ultraviolet
radiation.
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OCR 2812 Jan 05

Butane, C4H10, is used as a propellant in cans of hairspray. It often contains small amounts
of methylpropane.

(a)

Methylpropane is a structural isomer of butane.

(i)

Draw and label the full structural formulae for methylpropane and butane in the space
below.

(ii)

Explain the meaning of the term structural isomer.

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(b)(i)

The typical mass of butane in a small can of hairspray is 36 g.

Calculate the number of moles of butane in the can.
Give your answer to two significant figures.
Ar:C,12; H,1.0

(ii)

What volume would this amount of gas occupy at room temperature and pressure?
One mole of molecules of a gas at room temperature and pressure occupies
24dm3.

(c)

Butane is a very flammable gas. On rare occasions, cans of hairspray have caused injury
when thrown onto a garden bonfire.

(i)

Explain what happens to butane in the can and why this can lead to injury.
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(ii)

Write down the equation for the complete combustion of butane gas to give carbon dioxide
and water vapour.
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(iii)

Use your equation and the following bond enthalpies to calculate a value for the enthalpy
change of combustion for butane.

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(iv)

Would you expect the enthalpy change of combustion of methylpropane to be higher, lower
or about the same as that of butane?
Explain your answer.
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(a)(i)

OCR 2850 Jan 05

Crude oil is a complex mixture of hydrocarbons. Initial separation is achieved by fractional
distillation. The separate fractions are then further refined to produce hydrocarbons such as
decane.
State what is meant by the term hydrocarbon.
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(ii)

A molecule of decane contains ten carbon atoms. State the molecular formula of decane.
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(iii)

Deduce the empirical formula of decane.

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(b)

Dodecane, C12H26, is a straight chain alkane that reacts with chlorine to produce a
compound with molecular formula C12H25Cl.
C12H26 + Cl2 C12H25Cl + HCl
The reaction is initiated by the formation of chlorine free radicals from chlorine.

(i)

What is meant by the term free radical?

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(ii)

State the conditions necessary to bring about the formation of the chlorine free radicals
from Cl2.
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(iii)

State the type of bond fission involved in the formation of the chlorine free radicals.
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(iv)

The chlorine free radicals react with dodecane to produce C12H25Cl. Write equations for the
two propagation steps involved.
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(v)

How many different structural isomers can be formed when chlorine reacts with dodecane
to form C12H25Cl?
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(c)

Dodecane, C12H26, can be cracked into ethene and a straight chain alkane such that the
molar ratio ethene : straight chain alkane is 2:1.

(i)

Write a balanced equation for this reaction.

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(ii)

Name the straight chain alkane formed.

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OCR 2812 Jan 06

The graph below shows the boiling points of some alkanes.

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(a)

Draw a smooth curve through the points on the graph and estimate the boiling points of
octane C8H18, .............................. hexadecane, C16H34 ..............................

(b)

Isomerisation of hexane, C6H14, produces a mixture of structural isomers, three of which are
shown in the boxes below.

(i)

Draw, using skeletal formulae, two other structural isomers of hexane.

(ii)

Name isomer B.
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(iii)

Isomers A, B and C have different boiling points. In the boxes below, list the isomers A, B
and C in order of their boiling points.

(iv)

Explain the order given in (b) (iii).

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(d)

Oxygen-containing compounds can be added to improve the efficiency and performance of

fuels.
In Formula One racing cars, it is common practice to add oxygen-containing compounds,
such as 2-methylpropan-2-ol, (CH3)3COH. The amount of oxygen-containing compounds
added is strictly controlled by the Federation Internationale de lAutomobile, FIA.

(i)

Calculate the percentage by mass of oxygen in (CH3)3COH. Give your answer to three
significant figures.

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(ii)

Write a balanced equation for the complete combustion of (CH3)3COH.

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OCR June 06 2812
End of Paper