Alkanes and Halogenoalkanes

Alkanes and
Halogenoalkanes
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4 There are several oxides of nitrogen.
4 (a) An oxide of nitrogen contains 25.9% by mass of nitrogen. Determine the empirical
formula of this oxide.
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4 (b) Give one reason why the oxide NO is a pollutant gas.
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(1 mark)
4 (c) The oxide NO reacts with oxygen to form nitrogen dioxide. Write an equation for this
reaction.
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(1 mark)
4 (d) Explain how NO is produced in the engine of a motor vehicle.
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(2 marks)
4 (e) Write an equation to show how NO is removed from the exhaust gases in motor
vehicles using a catalytic converter.
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(1 mark)
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7 Chlorine is a useful industrial chemical.
7 (a) Chlorine gas is used in the manufacture of chlorine-containing organic compounds.
7 (a) (i) Write equations for the following steps in the mechanism for the reaction of chlorine
with ethane to form chloroethane (CH3CH2Cl).
Initiation step
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First propagation step
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Second propagation step
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A termination step producing butane.
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(4 marks)
7 (a) (ii) Give one essential condition and name the type of mechanism in this reaction of
chlorine with ethane.
Essential condition .............................................................................................................
Type of mechanism ...........................................................................................................

(2 marks)
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4 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.
4 (a) (i) State the meaning of the term saturated and of the term hydrocarbon as applied
to alkanes.
Saturated ...................................................................................................................
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Hydrocarbon .............................................................................................................
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(2 marks)
4 (a) (ii) Give the general formula for the alkanes.
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(1 mark)
4 (b) Pentane burns completely in oxygen.
4 (b) (i) Write an equation for this reaction.
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(1 mark)
4 (b) (ii) State how the products of this reaction may affect the environment.
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(1 mark)
4 (c) Give the name of a solid pollutant which may form when pentane burns incompletely
in air.
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(1 mark)
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4 (d) One molecule of C9H20 can be cracked to form one molecule of pentane and one other
product.
4 (d) (i) Write an equation for this cracking reaction.
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(1 mark)
4 (d) (ii) Suggest a type of compound that can be manufactured from the other product of
this cracking reaction.
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(1 mark)
4 (d) (iii) State why a high temperature is needed for cracking reactions to occur.
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(1 mark)
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4 (e) Pentane can react to form the following haloalkane Q.
H Br H H Br
H C C C C C H
H H H H Cl
4 (e) (i) Name Q.
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(1 mark)
4 (e) (ii) State the type of structural isomerism shown by Q and the haloalkane shown
below.
Br
H C H
H3C C CH3
H C Cl
Br
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(1 mark)
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7 (a) Consider the following reaction.
H H
CH3 C CH3 + KOH CH3 C CH3 + KBr
Br OH
7 (a) (i) Name and outline a mechanism for this reaction.
Name of mechanism .................................................................................................
Mechanism
(3 marks)
7 (a) (ii) Name the haloalkane in this reaction.
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(1 mark)
7 (a) (iii) Identify the characteristic of the haloalkane molecule that enables it to undergo
this type of reaction.
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(1 mark)
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7 (b) An alternative reaction can occur between this haloalkane and potassium hydroxide as
shown by the following equation.
H H
CH3 C CH3 + KOH CH3 C CH2 + KBr + H2O
Br
Name and outline a mechanism for this reaction.
Name of mechanism ..........................................................................................................
Mechanism
(4 marks)
7 (c) Give one condition needed to favour the reaction shown in part (b) rather than that
shown in part (a).
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(1 mark)
7 (d) Alkenes can be polymerised to produce poly(alkenes).
7 (d) (i) State the type of polymerisation that alkenes undergo.
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(1 mark)
7 (d) (ii) Name the alkene that gives a polymer with the repeating unit shown below.
H CH3
C C
CH3 H
Name of alkene .........................................................................................................

(1 mark)
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10 (d) The reaction of chlorine with ethene is similar to that of bromine with ethene.
Name and outline a mechanism for the reaction of chlorine with ethene to form
1,2-dichloroethane, as shown by the following equation.
H2C CH2 + Cl2 ClCH2CH2Cl
(5 marks)
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Section B
Answer all questions in the spaces provided.
6 (a) There is a risk of gas explosions in coal mines. This risk is mainly due to the presence
of methane. If the percentage of coal-mine methane (CMM) in the air in the mine is
greater than 15%, the explosion risk is much lower. CMM slowly escapes from the
mine into the atmosphere.
Write an equation to show the complete combustion of methane.
Suggest one reason why there is a much lower risk of an explosion if the percentage
of CMM is greater than 15%.
State why it is beneficial to the environment to collect the CMM rather than allowing it
to escape into the atmosphere.
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6 (b) Methane can be obtained from crude oil. Some of this crude oil contains an impurity
called methanethiol (CH3SH). This impurity causes environmental problems when
burned.
Write an equation to show the complete combustion of methanethiol.
State why calcium oxide can be used to remove the sulfur-containing product of this
combustion reaction.
State one pollution problem that is caused by the release of this sulfur-containing
product into the atmosphere.
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7 Pentane is a member of the alkane homologous series.
7 (a) Give the general formula for the homologous series of alkanes.
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(1 mark)
7 (b) One of the structural isomers of pentane is 2,2-dimethylpropane.
Draw the displayed formula of 2,2-dimethylpropane.
State the type of structural isomerism shown.
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(2 marks)
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7 (c) A molecule of hydrocarbon Y can be thermally cracked to form one molecule of

pentane and two molecules of ethene only.
Deduce the molecular formula of Y.
State why high temperatures are necessary for cracking reactions to occur.
Give one reason why thermal cracking reactions are carried out in industry.
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7 (d) Write an equation for the incomplete combustion of pentane to form a solid pollutant.
Suggest why this solid pollutant is an environmental problem.
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7 (e) Pentane can react with chlorine as shown in the following equation.
C5H12 + Cl2 C5H11Cl + HCl
Calculate the percentage atom economy for the formation of C5H11Cl
Deduce how many straight-chain isomers of C5H11Cl could be formed.
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7 (f) Consider the following compound.

H Cl Cl H
H C C C C H
H H H
H C H
H C H
Name this compound.
Deduce the empirical formula of this compound.
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(2 marks)
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END OF QUESTIONS
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7 Halogens are used to make halogenated organic compounds.
7 (a) The refrigerant used in air conditioners is a mixture of fluorinated alkanes.

These compounds are made by fluorination reactions.
The mechanism for the reaction of fluorine with an alkane or with a fluoroalkane is a
free-radical substitution similar to the reaction of chlorine with methane.
7 (a) (i) Write the overall equation for the reaction of fluorine with methane to form
trifluoromethane (CHF3).
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(1 mark)
7 (a) (ii) Write equations for the following steps in the mechanism for the reaction of fluorine
with trifluoromethane (CHF3) to form tetrafluoromethane (CF4).
Initiation step
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A termination step leading to the formation of hexafluoroethane.
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(4 marks)
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7 (b) Chlorofluorocarbons (CFCs) were used as refrigerants.

In the upper atmosphere, ultra-violet radiation breaks bonds in the CFCs to produce a
reactive intermediate that catalyses the decomposition of ozone.
7 (b) (i) An example of a CFC is 1,1,1-trichloro-2,2-difluoroethane.

Draw the displayed formula of this CFC.
(1 mark)
7 (b) (ii) Identify a bond in a CFC that is broken by ultra-violet radiation to produce a reactive
intermediate.
Give the name of this reactive intermediate that catalyses the decomposition of ozone.
Write an overall equation for this decomposition of ozone.
Bond broken .......................................................................................................................
Name of the reactive intermediate .....................................................................................
Overall equation
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(3 marks)
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9 Organic reaction mechanisms help chemists to understand how the reactions of

organic compounds occur.
The following conversions illustrate a number of different types of reaction mechanism.
9 (a) When 2-bromopentane reacts with ethanolic KOH, two structurally isomeric alkenes are
formed.
9 (a) (i) Name and outline a mechanism for the conversion of 2-bromopentane into pent-2-ene
as shown below.
ethanolic KOH
CH3CH2CH2CHBrCH3 CH3CH2CH CHCH3
(4 marks)
9 (a) (ii) Draw the structure of the other structurally isomeric alkene produced when
2-bromopentane reacts with ethanolic KOH.
(1 mark)
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9 (b) Name and outline a mechanism for the following conversion.
CH3 CH3
Br2
CH3 C CH2 CH3 C CH2Br
Br
(5 marks)
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9 (c) Name and outline a mechanism for the following conversion.
NH3
CH3CH2CH2Br CH3CH2CH2NH2
(5 marks)
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4 Cetane (C16H34) is a major component of diesel fuel.
4 (a) Write an equation to show the complete combustion of cetane.
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(1 mark)
4 (b) Cetane has a melting point of 18 oC and a boiling point of 287 oC.
In polar regions vehicles that use diesel fuel may have ignition problems.
Suggest one possible cause of this problem with the diesel fuel.
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(1 mark)
4 (c) The pollutant gases NO and NO2 are sometimes present in the exhaust gases of
vehicles that use petrol fuel.
4 (c) (i) Write an equation to show how NO is formed and give a condition needed for its
formation.
Equation .............................................................................................................................
Condition ...........................................................................................................................
(2 marks)
4 (c) (ii) Write an equation to show how NO is removed from the exhaust gases in a catalytic
converter. Identify a catalyst used in the converter.
Equation .............................................................................................................................
Catalyst ..............................................................................................................................
(2 marks)
4 (c) (iii) Deduce an equation to show how NO2 reacts with water and oxygen to form
nitric acid (HNO3).
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(1 mark)
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4 (d) Cetane (C16H34) can be cracked to produce hexane, butene and ethene.
4 (d) (i) State one condition that is used in this cracking reaction.
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(1 mark)
4 (d) (ii) Write an equation to show how one molecule of cetane can be cracked to form
hexane, butene and ethene.
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(1 mark)
4 (d) (iii) State one type of useful solid material that could be formed from alkenes.
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(1 mark)
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Section A
1 Oxygen and ozone (O3) both occur as gases in the upper atmosphere.
Chlorine atoms catalyse the decomposition of ozone and contribute to the formation
of a hole in the ozone layer.
These chlorine atoms are formed from chlorofluorocarbons (CFCs) such as CF3Cl
1 (a) (i) Give the IUPAC name of CF3Cl
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(1 mark)
1 (a) (ii) Complete the following equation that shows the formation of a chlorine atom from a
molecule of CF3Cl
F C Cl → + Cl•
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F
(1 mark)
1 (a) (iii) State what the • represents in Cl•
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(1 mark)
1 (b) Write two equations that show how chlorine atoms catalyse the decomposition of
ozone into oxygen.
Equation 1 .........................................................................................................................
Equation 2 .........................................................................................................................
(2 marks)
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7 (a) The reaction of bromine with propane is similar to that of chlorine with methane.
Three steps in the mechanism for the bromination of propane to form 1-bromopropane
are shown below.
Step 1 Br2 → 2Br•
Step 2 Br• + CH3CH2CH3 → CH3CH2CH2• + HBr
Step 3 CH3CH2CH2• + Br2 → CH3CH2CH2Br + Br•
7 (a) (i) Name the type of mechanism in this reaction.
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(1 mark)
7 (a) (ii) Give an essential condition for Step 1 to occur.
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(1 mark)
7 (a) (iii) Name the type of step illustrated by Steps 2 and 3.
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(1 mark)
7 (a) (iv) In this mechanism, a different type of step occurs in which free radicals combine.
Name this type of step.
Write an equation to show how hexane could be formed from two free radicals in the
mechanism of this reaction.
Type of step ......................................................................................................................
Equation .............................................................................................................................
(2 marks)
7 (a) (v) Write an overall equation for the reaction between bromine and propane by the same
mechanism to produce octabromopropane (C3Br8).
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(1 mark)
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7 (b) Bromine reacts with alkenes, even though bromine is a non-polar molecule.
7 (b) (i) Explain why bromine molecules react with the double bonds in alkenes.
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(2 marks)
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7 (b) (ii) Name the type of mechanism involved in this reaction.
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(1 mark)
7 (b) (iii) Draw the structure of the compound with Mr = 387.6 formed when
penta-1,4-diene (H2C=CHCH2CH=CH2) reacts with an excess of bromine.
(1 mark)
7 (c) Two products are formed when propene reacts with hydrogen bromide.
Draw the structure of the intermediate that leads to the formation of the major product
in the reaction of propene with hydrogen bromide.
Give the name of this type of intermediate.
Structure of intermediate
Type of intermediate ..........................................................................................................

(2 marks) 12
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8 A student read the following passage on the Internet.
Haloalkanes contain a polar covalent bond. The carbon atom of the polar
covalent bond can be attacked by nucleophiles. Nucleophilic attack enables
haloalkanes to undergo substitution reactions.
A nucleophilic substitution reaction occurs when a haloalkane undergoes
hydrolysis; the rate of hydrolysis of the haloalkane is influenced by the
carbon–halogen bond enthalpy.
8 (a) Explain the meaning of each of the following terms in the information given above.
8 (a) (i) nucleophile
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(1 mark)
8 (a) (ii) substitution, as applied to nucleophilic substitution in a haloalkane
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8 (a) (iii) hydrolysis
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(1 mark)
8 (a) (iv) bond enthalpy, as applied to a carbon–halogen bond.
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(1 mark)
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8 (b) Outline a mechanism for the nucleophilic substitution reaction in which

2-bromopropane (CH3CHBrCH3) reacts with potassium hydroxide to form propan-2-ol.
(2 marks)
8 (c) Haloalkanes also undergo elimination reactions to produce alkenes.
8 (c) (i) Outline a mechanism for the elimination reaction in which 2-bromopropane reacts with
potassium hydroxide to form propene.
(3 marks)
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8 (c) (ii) A student obtained the following infrared spectrum for the product from this
elimination reaction.
100
Transmittance / % 50
0
4000 3000 2000 1000
Wavenumber / cm–1
Use information from the infrared spectrum to state and explain how the student
deduced that the product was an alkene.
You may find it helpful to refer to Table 1 on the Data Sheet.
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2 Compound X is shown below. It is a member of a homologous series of

hydrocarbons.
H H H
H C C C C H
H H H
2 (a) (i) Deduce the general formula of the homologous series that contains X.
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(1 mark)
2 (a) (ii) Name a process used to obtain a sample of X from a mixture containing other
members of the same homologous series.
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(1 mark)
2 (b) There are several isomers of X.
2 (b) (i) Give the IUPAC name of the position isomer of X.
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(1 mark)
2 (b) (ii) Draw the structure of a functional group isomer of X.
(1 mark)
2 (c) At high temperatures, one molecule of C15H32 can be converted into two molecules of
X and one molecule of another compound.
2 (c) (i) Write an equation for this reaction.
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(1 mark)
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2 (c) (ii) State the name of the process used to obtain a high yield of X from C15H32
Give one reason why this process is used in industry.
Name ..................................................................................................................................
Reason ...............................................................................................................................
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(2 marks)
2 (c) (iii) State why high temperatures are needed for this process.
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(1 mark)
2 (d) Compound X can be converted into compound Y.

Compound Y is shown below.
H H H H
H C C C C H
H H H H
2 (d) (i) Suggest the formula of a reagent that could be added to X in order to convert it into Y.
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(1 mark)
2 (d) (ii) Give one use of Y.
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(1 mark)
2 (d) (iii) Write an equation to show the reaction of Y in a limited supply of air to produce a solid
and water only.
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(1 mark)
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2 (d) (iv) When a sample of Y, contaminated with CH3SH, is burned completely in air, a toxic gas
is formed.
Identify this toxic gas and suggest a compound that could be used to remove the toxic
gas from the products of combustion.
Toxic gas ............................................................................................................................
Compound used to remove toxic gas ................................................................................
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(2 marks)
2 (d) (v) Suggest the name of the process that occurs when the toxic gas in part (d) (iv) is
removed.
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(1 mark)
2 (e) Explain why the boiling points of X and Y are similar.
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(2 marks)
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2 (d) The methanol produced by this synthesis has been described as a carbon-neutral fuel.
2 (d) (i) State the meaning of the term carbon-neutral.
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(1 mark)
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2 (d) (ii) Write an equation for the complete combustion of methanol.
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(1 mark)
2 (d) (iii) The equation for the synthesis of methanol is shown below.
CO2(g) + 3H2(g) CH3OH(g) + H2O(g)
Use this equation and your answer to part (d) (ii) to deduce an equation to represent
the overall chemical change that occurs when methanol behaves as a carbon-neutral
fuel.
Equation .............................................................................................................................
(1 mark)
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6 Chloromethanes, such as dichloromethane and trichloromethane, are produced in

industry as they have many uses.
Trichloromethane has been used in the manufacture of the refrigerant
chlorodifluoromethane.
6 (a) Chlorine can react with dichloromethane (CH2Cl2) to form trichloromethane (CHCl3).
6 (a) (i) Write an equation for each of the following steps in the mechanism for this reaction.
Initiation step
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(3 marks)
6 (a) (ii) Give one essential condition for this reaction and name the type of mechanism.
Essential condition .............................................................................................................
Type of mechanism ...........................................................................................................

(2 marks)
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6 (c) Explain, with the aid of equations and the intermediates that form in the ozone layer,
why the European Union has banned the use of chlorodifluoromethane (CHClF2) as a
refrigerant.
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6 (d) The compound 2,3,3,3-tetrafluoropropene is the refrigerant used in all new car air
conditioners.
6 (d) (i) Draw the displayed formula for 2,3,3,3-tetrafluoropropene.
(1 mark)
6 (d) (ii) Give one reason why 2,3,3,3-tetrafluoropropene is a more environmentally acceptable
refrigerant than chlorodifluoromethane.
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8 (b) (i) Name and outline a mechanism for the following reaction that occurs in Process 1.
BrCH2CH2CH2CH2Br + NaOH BrCH2CH2CH2CH2OH + NaBr
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(3 marks)
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3 Hexane (C6H14) is a member of the homologous series of alkanes.
3 (a) (i) Name the raw material from which hexane is obtained.
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(1 mark)
3 (a) (ii) Name the process used to obtain hexane from this raw material.
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(1 mark)
3 (b) C6H14 has structural isomers.
3 (b) (i) Deduce the number of structural isomers with molecular formula C6H14
Write the number in this box.
(1 mark)
(Space for working)
3 (b) (ii) State one type of structural isomerism shown by the isomers of C6H14
............................................................................................................................................
(1 mark)
3 (c) One molecule of an alkane X can be cracked to form one molecule of hexane and
two molecules of propene.
3 (c) (i) Deduce the molecular formula of X.
............................................................................................................................................
............................................................................................................................................
(1 mark)
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3 (c) (ii) State the type of cracking that produces a high percentage of alkenes. State the
conditions needed for this type of cracking.
Type of cracking ................................................................................................................
Conditions ..........................................................................................................................
............................................................................................................................................
(2 marks)
3 (c) (iii) Explain the main economic reason why alkanes are cracked.
............................................................................................................................................
............................................................................................................................................
(1 mark)
3 (d) Hexane can react with chlorine under certain conditions as shown in the following
equation.
C6H14 + Cl2 → C6H13Cl + HCl
3 (d) (i) Both the products are hazardous. The organic product would be labelled ‘flammable’.
Suggest the most suitable hazard warning for the other product.
............................................................................................................................................
(1 mark)
3 (d) (ii) Calculate the percentage atom economy for the formation of C6H13Cl (Mr = 120.5) in
this reaction.
............................................................................................................................................
............................................................................................................................................
(1 mark)
3 (e) A different chlorinated compound is shown below. Name this compound and state its
empirical formula.
H CH3 Cl
CH3 C C C Cl
H H CH3
Name .................................................................................................................................
Empirical formula ...............................................................................................................

(2 marks)
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4 Alkanes are used as fuels. A student burned some octane (C8H18) in air and found
that the combustion was incomplete.
4 (a) (i) Write an equation for the incomplete combustion of octane to produce carbon
monoxide as the only carbon-containing product.
............................................................................................................................................
(1 mark)
4 (a) (ii) Suggest one reason why the combustion was incomplete.
............................................................................................................................................
............................................................................................................................................
(1 mark)
4 (b) Catalytic converters are used to remove the toxic gases NO and CO that are produced
when alkane fuels are burned in petrol engines.
4 (b) (i) Write an equation for a reaction between these two toxic gases that occurs in a
catalytic converter when these gases are removed.
............................................................................................................................................
(1 mark)
4 (b) (ii) Identify a metal used as a catalyst in a catalytic converter.
Suggest one reason, other than cost, why the catalyst is coated on a ceramic
honeycomb.
Metal ..................................................................................................................................
Reason ..............................................................................................................................
............................................................................................................................................
(2 marks)
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4 (c) If a sample of fuel for a power station is contaminated with an organic sulfur
compound, a toxic gas is formed by complete combustion of this sulfur compound.
4 (c) (i) State one environmental problem that can be caused by the release of this gas.
...........................................................................................................................................
...........................................................................................................................................
(1 mark)
4 (c) (ii) Identify one substance that could be used to remove this gas.
Suggest one reason, other than cost, why this substance is used.
Substance ..........................................................................................................................
Reason why used ..............................................................................................................
............................................................................................................................................
(2 marks)
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2 (b) But-1-ene burns in a limited supply of air to produce a solid and water only.
2 (b) (i) Write an equation for this reaction.
............................................................................................................................................
(1 mark)
2 (b) (ii) State one hazard associated with the solid product in part (b) (i).
............................................................................................................................................
(1 mark)
2 (c) One mole of compound Y is cracked to produce two moles of ethene, one mole of
but-1-ene and one mole of octane (C8H18) only.
2 (c) (i) Deduce the molecular formula of Y.
............................................................................................................................................
(1 mark)
2 (c) (ii) Other than cracking, give one common use of Y.
............................................................................................................................................
(1 mark)
2 (d) In cars fitted with catalytic converters, unburned octane reacts with nitrogen monoxide
to form carbon dioxide, water and nitrogen only.
2 (d) (i) Write an equation for this reaction.
............................................................................................................................................
(1 mark)
2 (d) (ii) Identify a catalyst used in a catalytic converter.
............................................................................................................................................
(1 mark)
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5 Haloalkanes are used in the synthesis of other organic compounds.
5 (a) Hot concentrated ethanolic potassium hydroxide reacts with 2-bromo-3-methylbutane to

form two alkenes that are structural isomers of each other. The major product is
2-methylbut-2-ene.
5 (a) (i) Name and outline a mechanism for the conversion of 2-bromo-3-methylbutane into
2-methylbut-2-ene according to the equation.
(CH3)2CHCHBrCH3 + KOH (CH3)2C CHCH3 + KBr + H2O
Name of mechanism .........................................................................................................
Mechanism
(4 marks)
5 (a) (ii) Draw the displayed formula for the other isomer that is formed.
(1 mark)
5 (a) (iii) State the type of structural isomerism shown by these two alkenes.
............................................................................................................................................
(1 mark)
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5 (b) A small amount of another organic compound, X, can be detected in the reaction
mixture formed when hot concentrated ethanolic potassium hydroxide reacts with
2-bromo-3-methylbutane.
Compound X has the molecular formula C5H12O and is a secondary alcohol.
5 (b) (i) Draw the displayed formula for X.
(1 mark)
5 (b) (ii) Suggest one change to the reaction conditions that would increase the yield of X.
............................................................................................................................................
............................................................................................................................................
(1 mark)
5 (b) (iii) State the type of mechanism for the conversion of 2-bromo-3-methylbutane into X.
............................................................................................................................................
(1 mark)
5 (b) (iv) Identify one feature of this infrared spectrum of a pure sample of X that may be used
to confirm that X is an alcohol.
You may find it helpful to refer to Table 1 on the Data Sheet.
100
Transmittance / % 50
0
4000 3000 2000 1500 1000 500
Wavenumber / cm–1
Feature ...............................................................................................................................
............................................................................................................................................
(1 mark)
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7 Chlorine can be used to make chlorinated alkanes such as dichloromethane.
7 (a) Write an equation for each of the following steps in the mechanism for the reaction of
chloromethane (CH3Cl) with chlorine to form dichloromethane (CH2Cl2).
Initiation step
............................................................................................................................................
............................................................................................................................................
............................................................................................................................................
The termination step that forms a compound with empirical formula CH2Cl
............................................................................................................................................
(4 marks)
7 (b) When chlorinated alkanes enter the upper atmosphere, carbon–chlorine bonds are
broken. This process produces a reactive intermediate that catalyses the
decomposition of ozone. The overall equation for this decomposition is
2O3 3O2
7 (b) (i) Name the type of reactive intermediate that acts as a catalyst in this reaction.
............................................................................................................................................
(1 mark)
7 (b) (ii) Write two equations to show how this intermediate is involved as a catalyst in the
decomposition of ozone.
Equation 1...........................................................................................................................
Equation 2...........................................................................................................................
(2 marks)
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8 In each of the following questions, you should draw the structure of the compound in
the space provided.
8 (a) Draw the structure of the alkene that would form 1,2-dibromo-3-methylbutane when
reacted with bromine.
(1 mark)
8 (b) Draw the structure of the alcohol with molecular formula C4H10O that is resistant to
oxidation by acidified potassium dichromate(VI).
(1 mark)
8 (c) Draw the structure of the alkene that has a peak, due to its molecular ion, at m/z = 42
in its mass spectrum.
(1 mark)
8 (d) Draw the structure of the organic product with Mr = 73, made from the reaction
between 2-bromobutane and ammonia.
(1 mark)
4
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4 The following table shows the boiling points of some straight-chain alkanes.
CH4 C2H6 C3H8 C4H10 C5H12
Boiling point / ºC –162 – 88 – 42 –1 36
4 (a) State a process used to separate an alkane from a mixture of these alkanes.
............................................................................................................................................
(1 mark)
4 (b) Both C3H8 and C4H10 can be liquefied and used as fuels for camping stoves.
Suggest, with a reason, which of these two fuels is liquefied more easily.
............................................................................................................................................
............................................................................................................................................
............................................................................................................................................
(1 mark)
4 (c) Write an equation for the complete combustion of C4H10
............................................................................................................................................
(1 mark)
4 (d) Explain why the complete combustion of C4H10 may contribute to environmental
problems.
............................................................................................................................................
............................................................................................................................................
............................................................................................................................................
(1 mark)
4 (e) Balance the following equation that shows how butane is used to make the compound
called maleic anhydride.
..........CH3CH2CH2CH3 + .......... O2 → ..........C2H2(CO)2O + .......... H2O
(1 mark)
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4 (f) Ethanethiol (C2H5SH), a compound with an unpleasant smell, is added to gas to enable
leaks from gas pipes to be more easily detected.
4 (f) (i) Write an equation for the combustion of ethanethiol to form carbon dioxide, water and
sulfur dioxide.
...........................................................................................................................................
(1 mark)
4 (f) (ii) Identify a compound that is used to react with the sulfur dioxide in the products of
combustion before they enter the atmosphere.
Give one reason why this compound reacts with sulfur dioxide.
Substance ..........................................................................................................................
Reason ..............................................................................................................................
............................................................................................................................................
(2 marks)
4 (f) (iii) Ethanethiol and ethanol molecules have similar shapes.
Explain why ethanol has the higher boiling point.
............................................................................................................................................
............................................................................................................................................
............................................................................................................................................
............................................................................................................................................
(2 marks)
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4 (g) The following compound X is an isomer of one of the alkanes in the table on page 8.
H
H H
H C H
H C C C H
H C H
H H
H
4 (g) (i) Give the IUPAC name of X.
...........................................................................................................................................
(1 mark)
4 (g) (ii) X has a boiling point of 9.5 ºC.
Explain why the boiling point of X is lower than that of its straight-chain isomer.
............................................................................................................................................
............................................................................................................................................
............................................................................................................................................
............................................................................................................................................
(2 marks)
4 (g) (iii) The following compound Y is produced when X reacts with chlorine.
Cl
H Cl
H C H
H C C C H
H C H
H H
H
Deduce how many other position isomers of Y can be formed.

Write the number of other position isomers in this box.
(1 mark)
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4 (h) Cracking of one molecule of an alkane Z produces one molecule of ethane, one
molecule of propene and two molecules of ethene.
4 (h) (i) Deduce the molecular formula of Z.
............................................................................................................................................
(1 mark)
4 (h) (ii) State the type of cracking that produces a high proportion of ethene and propene.
Give the two conditions for this cracking process.
Type of cracking ................................................................................................................
Conditions ..........................................................................................................................
............................................................................................................................................
(2 marks)
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7 The refrigerant R410A, used in air conditioners, is a mixture of two fluoroalkanes,

pentafluoroethane and difluoromethane.
7 (a) (i) The mechanism for the reaction of fluorine with either an alkane or a fluoroalkane is
similar to that for the reaction of chlorine with methane.
Name the type of mechanism for the reaction of chlorine with methane.
............................................................................................................................................
(1 mark)
7 (a) (ii) Write equations for the following steps in the mechanism for the reaction of fluorine
with fluoromethane (CH3F) to form difluoromethane (CH2F2).
Initiation step
............................................................................................................................................
............................................................................................................................................
............................................................................................................................................
A termination step leading to the formation of 1,2-difluoroethane.
............................................................................................................................................
(4 marks)
7 (a) (iii) Write an overall equation for the reaction of fluorine with ethane to form
pentafluoroethane (CF3CHF2) by this mechanism.
............................................................................................................................................
(1 mark)
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7 (b) The refrigerant R112A (CCl3CF2Cl) has been banned because of concerns about
ozone depletion.
Give the IUPAC name for CCl3CF2Cl
...............................................................................................................................................
(1 mark)
7 (c) Nitrogen monoxide (NO) catalyses the decomposition of ozone into oxygen.
7 (c) (i) Write the overall equation for this decomposition.
...............................................................................................................................................
(1 mark)
7 (c) (ii) Use the overall equation to deduce Step 3 in the following mechanism that shows how
nitrogen monoxide catalyses this decomposition.
Step 1 O3 NO + O2
Step 2 NO + O3 NO2 + O2
Step 3 ...................................................................................................................................
(1 mark)
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5 Some oil-fired heaters use paraffin as a fuel.

One of the compounds in paraffin is the straight-chain alkane, dodecane (C12H26).
5 (a) Give the name of the substance from which paraffin is obtained.
State the name of the process used to obtain paraffin from this substance.
[2 marks]
Substance ..........................................................................................................................
Process ..............................................................................................................................
5 (b) The combustion of dodecane produces several products.
Write an equation for the incomplete combustion of dodecane to produce gaseous

products only.
[1 mark]
............................................................................................................................................
5 (c) Oxides of nitrogen are also produced during the combustion of paraffin in air.
5 (c) (i) Explain how these oxides of nitrogen are formed.

[2 marks]
............................................................................................................................................
............................................................................................................................................
............................................................................................................................................
............................................................................................................................................
5 (c) (ii) Write an equation to show how nitrogen monoxide in the air is converted into
nitrogen dioxide.
[1 mark]
............................................................................................................................................
5 (c) (iii) Nitric acid (HNO3) contributes to acidity in rainwater.
Deduce an equation to show how nitrogen dioxide reacts with oxygen and water to
form nitric acid.
[1 mark]
............................................................................................................................................
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5 (d) Dodecane (C12H26) can be cracked to form other compounds.
5 (d) (i) Give the general formula for the homologous series that contains dodecane.
[1 mark]
............................................................................................................................................
5 (d) (ii) Write an equation for the cracking of one molecule of dodecane into equal amounts of
two different molecules each containing the same number of carbon atoms.
State the empirical formula of the straight-chain alkane that is formed.
Name the catalyst used in this reaction.
[3 marks]
Equation ..............................................................................................................................
Empirical formula of alkane ................................................................................................
Catalyst ...............................................................................................................................
5 (d) (iii) Explain why the melting point of dodecane is higher than the melting point of the
straight-chain alkane produced by cracking dodecane.
[2 marks]
............................................................................................................................................
............................................................................................................................................
............................................................................................................................................
............................................................................................................................................
............................................................................................................................................
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5 (e) Give the IUPAC name for the following compound and state the type of structural
isomerism shown by this compound and dodecane.
[2 marks]
H CH3 CH3 CH3
H3C C C C C CH3
H CH3 CH3 CH3
IUPAC name ......................................................................................................................
Type of structural isomerism ..............................................................................................
5 (f) Dodecane can be converted into halododecanes.
Deduce the formula of a substance that could be reacted with dodecane to produce
1-chlorododecane and hydrogen chloride only.
[1 mark]
............................................................................................................................................
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5 Trifluoromethane (CHF3) can be used to make the refrigerant chlorotrifluoromethane

(CClF3).
5 (a) Chlorotrifluoromethane is formed when trifluoromethane reacts with chlorine.
CHF3 + Cl2 CClF3 + HCl
The reaction is a free-radical substitution reaction similar to the reaction of methane

with chlorine.
5 (a) (i) Write an equation for each of the following steps in the mechanism for the reaction of
CHF3 with Cl2
[4 marks]
Initiation step
............................................................................................................................................
............................................................................................................................................
............................................................................................................................................
Termination step to form hexafluoroethane
............................................................................................................................................
5 (a) (ii) Give one essential condition for this reaction.

[1 mark]
............................................................................................................................................
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5 (b) In some refrigeration systems, CHF3 has replaced CClF3 because of concerns about
ozone depletion.
5 (b) (i) Identify the species formed from CClF3 that is responsible for the catalytic
decomposition of ozone in the upper atmosphere.
[1 mark]
............................................................................................................................................
5 (b) (ii) Write an overall equation to represent the decomposition of ozone into oxygen.
[1 mark]
............................................................................................................................................
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Section B
8 The carboxylic acid 3-methylbutanoic acid is used to make esters for perfumes.
The following scheme shows some of the reactions in the manufacture of this
carboxylic acid.
Reaction 1
(CH3)2CHCH2OH (CH3)2CHCH2Br
Reaction 2
Reaction 3
(CH3)2CHCH2COOH (CH3)2CHCH2CN
3-methylbutanoic acid
8 (a) One of the steps in the mechanism for Reaction 1 involves the replacement of the
functional group by bromine.
8 (a) (i) Use your knowledge of organic reaction mechanisms to complete the mechanism for
this step by drawing two curly arrows on the following equation.
[2 marks]
Br-
+
H3C CH CH2 OH2 H3C CH CH2 Br + H2O
CH3 CH3
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8 (a) (ii) Deduce the name of the mechanism in Question 8 (a) (i).
Give the IUPAC name of (CH3)2CHCH2Br

[2 marks]
............................................................................................................................................
............................................................................................................................................
............................................................................................................................................
8 (b) Reaction 3 is an acid-catalysed reaction in which water is used to break chemical

bonds when the CN functional group is converted into the COOH functional group.
Infrared spectroscopy can be used to distinguish between the compounds in this
reaction.
Deduce the name of the type of reaction that occurs in Reaction 3.
Identify one bond in (CH3)2CHCH2CN and a different bond in (CH3)2CHCH2COOH

that can be used with infrared spectroscopy to distinguish between each compound.
For each of these bonds, give the range of wavenumbers at which the bond absorbs.
Use Table A on the Data Sheet when answering this question.
[3 marks]
............................................................................................................................................
............................................................................................................................................
............................................................................................................................................
............................................................................................................................................
............................................................................................................................................
............................................................................................................................................
............................................................................................................................................
............................................................................................................................................
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6 Central heating fuel, obtained by the fractional distillation of crude oil, contains saturated
hydrocarbons with the molecular formula C16H34
6 (a) Give the meaning of the terms saturated and hydrocarbon as applied to saturated
hydrocarbons.
[2 marks]
Saturated .............................................................................................................................
.............................................................................................................................................
Hydrocarbon ........................................................................................................................
.............................................................................................................................................
6 (b) If the boiler for a central heating system is faulty, a poisonous gas may be produced
during the combustion of C16H34
Write an equation for the reaction that forms this poisonous gas and one other product
only.
[1 mark]
.............................................................................................................................................
6 (c) Explain why the sulfur compounds found in crude oil should be removed from the
fractions before they are used for central heating fuel.
[2 marks]
.............................................................................................................................................
.............................................................................................................................................
.............................................................................................................................................
.............................................................................................................................................
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6 (d) A hydrocarbon C16H34 can be cracked to form C8H18, ethene and propene.
6 (d) (i) Write an equation to show this cracking reaction.

[1 mark]
.............................................................................................................................................
6 (d) (ii) Suggest one important substance manufactured on a large scale from propene.
[1 mark]
.............................................................................................................................................
6 (d) (iii) Draw the displayed formula of the functional group isomer of propene.
[1 mark]
6 (e) There are many structural isomers with the molecular formula C8H18
Draw the structure of 2,3,3-trimethylpentane.

[1 mark]
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6 (f) A compound C8H18 reacts with chlorine to give several haloalkanes.
Give the IUPAC name of the following haloalkane.

[1 mark]
CH3 H Cl
H3C C C C CH3
Cl H CH2
CH3
.............................................................................................................................................
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5 There are many uses of halogenated organic compounds despite environmental

concerns.
5 (a) Bromotrifluoromethane is used in fire extinguishers in aircraft.

Bromotrifluoromethane is formed when trifluoromethane reacts with bromine.
CHF3 + Br2 CBrF3 + HBr
The reaction is a free-radical substitution reaction similar to the reaction of methane with
chlorine.
5 (a) (i) Write an equation for each of the following steps in the mechanism for the reaction of
CHF3 with Br2
[4 marks]
Initiation step
.............................................................................................................................................
.............................................................................................................................................
.............................................................................................................................................
A termination step
.............................................................................................................................................
5 (a) (ii) State one condition necessary for the initiation of this reaction.
[1 mark]
.............................................................................................................................................
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5 (b) Bromine-containing and chlorine-containing organic compounds may have a role in the
decomposition of ozone in the upper atmosphere.
5 (b) (i) Draw an appropriate displayed formula in the space provided to complete the following
equation to show how CBrF3 may produce bromine atoms in the upper atmosphere.
[1 mark]
CBrF3 + Br
...............................
5 (b) (ii) In the upper atmosphere, it is more likely for CBrF3 to produce bromine atoms than it is
for CClF3 to produce chlorine atoms.
Suggest one reason for this.

[1 mark]
.............................................................................................................................................
.............................................................................................................................................
.............................................................................................................................................
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5 (b) (iii) Bromine atoms have a similar role to chlorine atoms in the decomposition of ozone.
The overall equation for the decomposition of ozone is
2O3 3O2
Write two equations to show how bromine atoms (Br) act as a catalyst in the
Explain how these two decomposition equations show that bromine atoms behave as a
catalyst.
[3 marks]
Equation 1
.............................................................................................................................................
Equation 2
.............................................................................................................................................
Explanation .........................................................................................................................
.............................................................................................................................................
.............................................................................................................................................
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4 (a) Octane (C8H18) is an important compound in petrol.
4 (a) (i) Identify the homologous series to which octane belongs.

[1 mark]
______________________________________________________________________________
4 (a) (ii) Write an equation to show the complete combustion of C8H18

[1 mark]
______________________________________________________________________________
4 (a) (iii) An isomer of octane used to improve the performance of car engines is shown.
CH3 CH3
H3C C CH2 C H
CH3 CH3
Give the IUPAC name of this isomer.

[1 mark]
______________________________________________________________________________
4 (b) Compound X is produced when an alkane is cracked.
H CH2CH3
C C
H H
X
4 (b) (i) Give the IUPAC name for compound X.

[1 mark]
______________________________________________________________________________
4 (b) (ii) One molecule of an alkane is cracked to produce one molecule of compound X, one
molecule of octane and one molecule of ethene.
Deduce the molecular formula of this alkane.

[1 mark]
______________________________________________________________________________
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4 (b) (iii) Name the type of cracking that produces a high yield of compound X.
Give two conditions required for this process.
[2 marks]
Type of cracking _______________________________________________________________
Conditions ____________________________________________________________________
______________________________________________________________________________
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3 Haloalkanes are used as refrigerants, solvents and anaesthetics.
3 (a) Trichloromethane (CHCl3) is a haloalkane that can be formed by heating a mixture of

chloromethane (CH3Cl) and chlorine.
3 (a) (i) Write an overall equation for the formation of trichloromethane by the reaction of
chloromethane with chlorine.
[1 mark]
______________________________________________________________________________
3 (a) (ii) Name the mechanism for this formation of trichloromethane.

[1 mark]
______________________________________________________________________________
3 (a) (iii) Dichloromethane (CH2Cl2) is an intermediate in this formation of trichloromethane.
Write an equation for each of the following steps in the mechanism for the reaction of
dichloromethane with chlorine.
[4 marks]
Initiation step
______________________________________________________________________________
______________________________________________________________________________
______________________________________________________________________________
A termination step leading to the formation of a compound with formula C2H2Cl4
______________________________________________________________________________
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3 (b) Chlorotrifluoromethane (CClF3) is used as a refrigerant, but is being phased out due to
concerns about ozone depletion in the upper atmosphere.
In the upper atmosphere, CClF3 decomposes in the presence of UV light forming a
reactive intermediate that catalyses the decomposition of ozone.
3 (b) (i) Write an equation to show how CClF3 decomposes to form the reactive intermediate.
[1 mark]
______________________________________________________________________________
3 (b) (ii) Write two equations to show how this reactive intermediate is involved in catalysing the
[2 marks]
1 _____________________________________________________________________________
2 _____________________________________________________________________________
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Section B
8 Two reactions of 2-bromopentane, (CH3CH2CH2CHBrCH3) are shown.
reaction 1 reaction 2
C5H10 CH3CH2CH2CHBrCH3 C5H11OH
The C5H10 formed in reaction 1 exists as a mixture of three isomers, one of which is
pent-1-ene. Two of the isomers are a pair of stereoisomers. All three isomers
decolourise bromine.
8 (a) The same reagent is used in both reactions. The product is determined by the choice of
conditions.
State the reagent and the conditions for each of reaction 1 and reaction 2.
State the role of the reagent in each reaction.
Name and outline the mechanism of reaction 1 for the formation of pent-1-ene.
[8 marks]
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(20)
WMP/Jun16/CHEM2

Alkanes and Halogenoalkanes

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Alkanes and

4 There are several oxides of nitrogen.

4 (b) Give one reason why the oxide NO is a pollutant gas.

4 (d) Explain how NO is produced in the engine of a motor vehicle.

7 Chlorine is a useful industrial chemical.

7 (a) Chlorine gas is used in the manufacture of chlorine-containing organic compounds.

First propagation step

Second propagation step

A termination step producing butane.

Essential condition .............................................................................................................

Type of mechanism ...........................................................................................................

4 (a) (ii) Give the general formula for the alkanes.

4 (b) Pentane burns completely in oxygen.

4 (b) (i) Write an equation for this reaction.

4 (d) (i) Write an equation for this cracking reaction.

Question 4 continues on the next page

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

4 (e) (i) Name Q.

7 (a) Consider the following reaction.

7 (a) (i) Name and outline a mechanism for this reaction.

Name of mechanism .................................................................................................

7 (a) (ii) Name the haloalkane in this reaction.

Name and outline a mechanism for this reaction.

Name of mechanism ..........................................................................................................

7 (d) Alkenes can be polymerised to produce poly(alkenes).

7 (d) (i) State the type of polymerisation that alkenes undergo.

Name of alkene .........................................................................................................

H2C CH2 + Cl2 ClCH2CH2Cl

Answer all questions in the spaces provided.

Write an equation to show the complete combustion of methane.

Write an equation to show the complete combustion of methanethiol.

Turn over for the next question

7 Pentane is a member of the alkane homologous series.

7 (b) One of the structural isomers of pentane is 2,2-dimethylpropane.

Draw the displayed formula of 2,2-dimethylpropane.

State the type of structural isomerism shown.

7 (c) A molecule of hydrocarbon Y can be thermally cracked to form one molecule of

Deduce the molecular formula of Y.

Suggest why this solid pollutant is an environmental problem.

Question 7 continues on the next page

C5H12 + Cl2 C5H11Cl + HCl

Calculate the percentage atom economy for the formation of C5H11Cl

Deduce how many straight-chain isomers of C5H11Cl could be formed.

7 (f) Consider the following compound.

Name this compound.

Deduce the empirical formula of this compound.

7 Halogens are used to make halogenated organic compounds.

7 (a) The refrigerant used in air conditioners is a mixture of fluorinated alkanes.

First propagation step

Second propagation step

A termination step leading to the formation of hexafluoroethane.

7 (b) Chlorofluorocarbons (CFCs) were used as refrigerants.

7 (b) (i) An example of a CFC is 1,1,1-trichloro-2,2-difluoroethane.

Bond broken .......................................................................................................................

Name of the reactive intermediate .....................................................................................

Turn over for the next question

9 Organic reaction mechanisms help chemists to understand how the reactions of

Question 9 continues on the next page

9 (b) Name and outline a mechanism for the following conversion.