Q1.

The table below shows the structures of three isomers with the molecular formula
C5H10O

Isomer 1

(E)-pent-3-en-2-ol

Isomer 2

pentanal

Isomer 3

(a) Complete the table by naming Isomer 3.

(b) State the type of structural isomerism shown by these three isomers.

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(1)

(c) The compound (Z)-pent-3-en-2-ol is a stereoisomer of (E)-pent-3-en-2-ol.

(i) Draw the structure of (Z)-pent-3-en-2-ol.

(1)

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 (ii) Identify the feature of the double bond in (E)-pent-3-en-2-ol and that in
(Z)-pent-3-en-2-ol that causes these two compounds to be stereoisomers.

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(1)

(d) A chemical test can be used to distinguish between separate samples of Isomer 2
and Isomer 3.
Identify a suitable reagent for the test.
State what you would observe with Isomer 2 and with Isomer 3.

Test reagent ...............................................................................................

Observation with Isomer 2...........................................................................

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

Observation with Isomer 3............................................................................

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(3)

(e) The following is the infrared spectrum of one of the isomers 1, 2 or 3.

(i) Deduce which of the isomers (1, 2 or 3) would give this infrared spectrum.
You may find it helpful to refer to Table 1 on the Data Sheet.

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(1)

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 (ii) Identify two features of the infrared spectrum that support your deduction.
In each case, identify the functional group responsible.

Feature 1 and functional group ...........................................................

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

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Feature 2 and functional group ...........................................................

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(2)
(Total 10 marks)

Q2. The fractions obtained from petroleum contain saturated hydrocarbons that belong to
the homologous series of alkanes.

(a) Any homologous series can be represented by a general formula.

(i) State two other characteristics of homologous series.

Characteristic 1 ...................................................................................

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

Characteristic 2 ...................................................................................

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

(ii) Name the process which is used to obtain the fractions from petroleum.

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 (iii) State what is meant by the term saturated, as applied to hydrocarbons.

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

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(4)

(b) Decane has the molecular formula C10H22

(i) State what is meant by the term molecular formula.

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

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(ii) Give the molecular formula of the alkane which contains 14 carbon atoms.

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(iii) Write an equation for the incomplete combustion of decane, C10H22, to produce
carbon and water only.

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(3)

(c) When petrol is burned in an internal combustion engine, some nitrogen monoxide,
NO, is formed. This pollutant is removed from the exhaust gases by means of a
reaction in a catalytic converter.

(i) Write an equation for the reaction between nitrogen and oxygen to form
nitrogen monoxide.

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

(ii) Identify a catalyst used in a catalytic converter.

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 (iii) Write an equation to show how nitrogen monoxide is removed from the
exhaust gases as they pass through a catalytic converter.

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(3)
(Total 10 marks)

Q3. Octane is the eighth member of the alkane homologous series.

(a) State two characteristics of a homologous series.

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

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

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

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(2)

(b) Name a process used to separate octane from a mixture containing several
different alkanes.

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

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(1)

(c) The structure shown below is one of several structural isomers of octane.

Give the meaning of the term structural isomerism.

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

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

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

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(4)

(d) Suggest why the branched chain isomer shown above has a lower boiling point
than octane.

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

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

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

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(2)
(Total 9 marks)

Q4. Pent-1-ene is a member of the alkene homologous series.

(a) Pent-1-ene can be separated from other alkenes.

State the physical property of alkenes that allows them to be separated from a
mixture by fractional distillation.

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

(b) (i) State the meaning of the term structural isomerism.

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

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

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

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 (ii) Name the branched chain isomer of pent-1-ene shown below.

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(1)

(iii) Draw the structure of a functional group isomer of pent-1-ene.

(1)

(c) The cracking of one molecule of compound X produces pent-1-ene, ethene and
butane in a 1:2:1 mol ratio.
Deduce the molecular formula of X and state a use for the ethene formed.

Molecular formula of X .................................................................................

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

Use of ethene ...............................................................................................

Q5. Hexane is a member of the homologous series of alkanes.

(a) State two characteristics of a homologous series.

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 Characteristic 1 ............................................................................................

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

Characteristic 2 …….....................................................................................

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(2)

(b) (i) Hexane can be converted into 2,2-dichlorohexane.

Draw the displayed formula of 2,2-dichlorohexane and deduce its empirical

Displayed formula

Empirical formula ................................................................................

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

(ii) Explain why 2,2-dichloro-3-methylpentane is a structural isomer of

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

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(2)

(c) A reaction of hexane with chlorine is shown by the equation below.

C6H14 + 2Cl2 → C6H12Cl2 + 2HCl

Calculate the percentage atom economy for the formation of C6H12Cl2 in this reaction.

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

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

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(2)

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 (d) The boiling points of some straight-chain alkanes are shown below.

Alkane C4H10 C5H12 C6H14

Boiling point / °C – 0.5 36.3 68.7

(i) Explain the trend in these boiling points.

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

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

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

(ii) Name a process which can be used to separate C5H12 from C6H14

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(1)
(Total 11 marks)

Q6. Alkanes are saturated hydrocarbons which can be obtained from crude oil.
Pentane is an example of an alkane. A molecule of pentane contains five carbon atoms.

(a) (i) State the meaning of the term saturated and of the term hydrocarbon as
applied to alkanes.

Saturated ............................................................................................

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

Hydrocarbon .......................................................................................

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(2)

(ii) Give the general formula for the alkanes.

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 (1)

(b) Pentane burns completely in oxygen.

(i) Write an equation for this reaction.

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(1)

(ii) State how the products of this reaction may affect the environment.

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

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(1)

(c) Give the name of a solid pollutant which may form when pentane burns
incompletely in air.

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(1)

(d) One molecule of C9H20 can be cracked to form one molecule of pentane and one
other product.

(i) Write an equation for this cracking reaction.

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

(ii) Suggest a type of compound that can be manufactured from the other product
of this cracking reaction.

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

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

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 (iii) State why a high temperature is needed for cracking reactions to occur.

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

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(1)

(e) Pentane can react to form the following haloalkane Q.

(i) Name Q.

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

(ii) State the type of structural isomerism shown by Q and the haloalkane shown
below.

.............................................................................................................
(1)
(Total 11 marks)

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