Barr Beacon School

A-level Chemistry (7404/7405)

3.3.3 Halogenoalkanes
Past Paper Questions

Name _______________________________

Questions All Attempted: 

Green Pen: 
Used examiners report to annotate: 

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Q1.In each of the following questions, you should draw the structure of the compound in the space
provided.

(a) Draw the structure of the alkene that would form 1,2-dibromo-3-methylbutane when
reacted with bromine.

(1)

(b) Draw the structure of the alcohol with molecular formula C4H10O that is resistant to
oxidation by acidified potassium dichromate(VI).

(1)

(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)

(d) Draw the structure of the organic product with Mr = 73, made from the reaction between 2-
bromobutane and ammonia.

(1)
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(Total 4 marks)

Q2. A student read the following passage on the Internet.

Halogenoalkanes contain a polar covalent bond. The carbon atom of the polar covalent
bond can be attacked by nucleophiles. Nucleophilic attack enables halogenoalkanes to
undergo substitution reactions.
A nucleophilic substitution reaction occurs when a halogenoalkane undergoes
hydrolysis; the rate of hydrolysis of the halogenoalkane is influenced by the
carbon–halogen bond enthalpy.

(a) Explain the meaning of each of the following terms in the information given above.

(i) nucleophile

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

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

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

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

(ii) substitution, as applied to nucleophilic substitution in a haloalkane

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

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

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

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

(iii) hydrolysis

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

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

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

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

(iv) bond enthalpy, as applied to a carbon–halogen bond.

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

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

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

(b) Outline a mechanism for the nucleophilic substitution reaction in which

2-bromopropane (CH3CHBrCH3) reacts with potassium hydroxide to form
propan-2-ol.

(2)

(c) Haloalkanes also undergo elimination reactions to produce alkenes.

(i) Outline a mechanism for the elimination reaction in which 2-bromopropane reacts
with potassium hydroxide to form propene.

(3)

(ii) A student obtained the following infrared spectrum for the product from this
elimination reaction.

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)
(Total 11 marks)

Q3. Consider the following scheme of reactions.

(a) Give the IUPAC name for compound P and that for compound Q.

P .....................................................................................................................

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

(b) The conversion of P into Q in Reaction 1 uses HCl

Name and outline a mechanism for this reaction................................................................

(5)

(c) The conversion of Q into R in Reaction 2 uses NH3

Name and outline a mechanism for this reaction...................................................................

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(5)

(d) State the type of reaction shown by Reaction 3.

Identify a reagent for this reaction.

Give one condition necessary for a high yield of product when Q is converted into P.

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

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

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

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

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

(e) Hydrogen bromide (HBr) could be used in the overall conversion of P into R, instead of
using HCl
Hydrogen bromide is made by the reaction of NaBr with concentrated phosphoric acid.
Concentrated sulfuric acid is not used to make HBr from NaBr

Write an equation for the reaction of NaBr with H3PO4 to produce HBr and Na3PO4 only.

Identify two toxic gases that are formed, together with HBr, when NaBr reacts with
concentrated H2SO4

State the role of H2SO4 in the formation of these two toxic gases.

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

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

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

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

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

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

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(4)
(Total 19 marks)

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Q4.Haloalkanes are used in the synthesis of other organic compounds.

(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.

(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)

(ii) Draw the displayed formula for the other isomer that is formed.

(1)

(iii) State the type of structural isomerism shown by these two alkenes.

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

(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.

(i) Draw the displayed formula for X.

(1)

(ii) Suggest one change to the reaction conditions that would increase the yield of X.

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

(iii) State the type of mechanism for the conversion of 2-bromo-3-methylbutane into X.

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

(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.

Wavenumber / cm−1

Feature .................................................................................................

...............................................................................................................
(1)
(Total 10 marks)

Q5. Consider the following reactions.

(a) Name and outline a mechanism for Reaction 1.

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

Mechanism

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(5)

(b) Name and outline a mechanism for Reaction 2.

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

Mechanism

(5)

(c) State the type of reaction in Reaction 3.

Give the name of substance X.

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

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

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

(d) The haloalkane produced in Reaction 1 can be converted back into propene in an
elimination reaction using ethanolic potassium hydroxide.

CH3CHBrCH3 H2C=CHCH3

Outline a mechanism for this conversion.

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(3)
(Total 15 marks)

Q6. (a) Chloromethane can be made by the reaction of chlorine with methane.

(i) Give one essential condition for this reaction.

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

(ii) Name the mechanism for this reaction.

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

(iii) Further substitution can occur during this reaction. Identify the main organic product
when a large excess of chlorine is used in this reaction.

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

(b) Ethanenitrile can be made by reacting chloromethane with potassium cyanide.

(i) Write an equation for this reaction.

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

(ii) Name the mechanism for this reaction.

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

(iii) Explain, in terms of bond enthalpies, why bromomethane reacts faster than
chloromethane with potassium cyanide.

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

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

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

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

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

(c) Ethanenitrile can be hydrolysed to a carboxylic acid by heating it under reflux with a dilute
acid. Identify the carboxylic acid formed in this reaction.

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

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(d) Chloromethane can react with ammonia to produce a primary amine.

(i) What feature of the chloromethane molecule makes it susceptible to attack by an

ammonia molecule?

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

(ii) Name the amine produced in this reaction.

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

(iii) Outline a mechanism for this reaction.

(6)
(Total 13 marks)

Q7. 2-bromo-2-methylpentane is heated with potassium hydroxide dissolved in ethanol. Two

structural isomers are formed.

(a) State the meaning of the term structural isomers.

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

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

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

(b) Name and draw the mechanism for the formation of one of the isomers.

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

Mechanism

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(5)
(Total 6 marks)

Q8. Alkenes are useful intermediates in the synthesis of organic compounds.

(a) (i) Complete the elimination mechanism by drawing appropriate curly arrows.

(3)

(ii) Draw structures for the E and Z stereoisomers of hex-3-ene.

E isomer of hex-3-ene Z isomer of hex-3-ene

(2)

(iii) State the meaning of the term stereoisomers.

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

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

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

(Extra space) ........................................................................................

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

(b) The equation for the first reaction in the conversion of hex-3-ene into hexan-3-ol is shown
below.

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CH3CH2CH=CHCH2CH3 + H2SO4 CH3CH2CH2CH(OSO2OH)CH2CH3

Outline a mechanism for this reaction.

(4)
(Total 11 marks)

Q9. (a) Consider the following reaction.

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

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

Mechanism

(3)

(ii) Name the haloalkane in this reaction.

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

(iii) Identify the characteristic of the haloalkane molecule that enables it to undergo this
type of reaction.

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

(b) An alternative reaction can occur between this haloalkane and potassium hydroxide as
shown by the following equation.

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Name and outline a mechanism for this reaction.

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

Mechanism

(4)

(c) Give one condition needed to favour the reaction shown in part (b) rather than that shown
in part (a).

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

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

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

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

(ii) Name the alkene that gives a polymer with the repeating unit shown below.

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

(1)
(Total 12 marks)

Q10. 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.

(a) When 2-bromopentane reacts with ethanolic KOH, two structurally isomeric alkenes are
formed.

(i) Name and outline a mechanism for the conversion of 2-bromopentane into
pent-2-ene as shown below.

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(4)

(ii) Draw the structure of the other structurally isomeric alkene produced when 2-
bromopentane reacts with ethanolic KOH.

(1)

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

(5)
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(c) Name and outline a mechanism for the following conversion.

(5)
(Total 15 marks)

Q11. Nucleophiles react with bromoethane in substitution reactions. This type of reaction is
illustrated in the following scheme.

(a) State what is meant by the term nucleophile.

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

(b) Outline a mechanism for the reaction of potassium cyanide with bromoethane
(Reaction 1).

(2)

(c) Explain why an excess of ammonia is needed in Reaction 2 to produce a high yield of
ethylamine.
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......................................................................................................................

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

(d) When potassium hydroxide reacts with bromoethane, ethene can also be formed.
Name and outline a mechanism for this reaction.

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

Mechanism

(4)
(Total 8 marks)

Q12. Consider the following reaction in which an alkene is formed from a haloalkane.

(a) Name the haloalkane used in this reaction.

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

(b) Name and outline a mechanism for this reaction.

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

Mechanism

(4)

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(c) Another alkene, which is a structural isomer of but-2-ene, is also formed during this
reaction.

(i) State what is meant by the term structural isomers.

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

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

(ii) Draw the structure of this other alkene.

(2)
(Total 7 marks)

Q13.Trifluoromethane (CHF3) can be used to make the refrigerant chlorotrifluoromethane(CClF3).

(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.

(i) Write an equation for each of the following steps in the mechanism for the reaction
of CHF3 with Cl2

Initiation step

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

First propagation step

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

Second propagation step

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

Termination step to form hexafluoroethane

...............................................................................................................
(4)

(ii) Give one essential condition for this reaction.

...............................................................................................................
(1)
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(b) In some refrigeration systems, CHF3 has replaced CClF3 because of concerns about
ozone depletion.

(i) Identify the species formed from CClF3 that is responsible for the catalytic
decomposition of ozone in the upper atmosphere.

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

(ii) Write an overall equation to represent the decomposition of ozone into oxygen.

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

Q14.Chlorine can be used to make chlorinated alkanes such as dichloromethane.

(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

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

First propagation step

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

Second propagation step

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

The termination step that forms a compound with empirical formula CH2Cl.

........................................................................................................................
(4)

(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

(i) Name the type of reactive intermediate that acts as a catalyst in this reaction.

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

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(ii) Write two equations to show how this intermediate is involved as a catalyst in them
decomposition of ozone.

Equation 1................................................................................................

Equation 2................................................................................................
(2)
(Total 7 marks)

Q15. 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

(a) (i) Give the IUPAC name of CF3Cl

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

(ii) Complete the following equation that shows the formation of a chlorine atom from a
molecule of CF3Cl

(1)

(iii) State what the • represents in Cl•

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

(b) Write two equations that show how chlorine atoms catalyse the decomposition of ozone
into oxygen.

Equation 1 ....................................................................................................

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

(c) An equilibrium is established between oxygen and ozone molecules as shown below.

3O2(g) 2O3(g) ΔH = +284 kJ mol–1

(i) State Le Chatelier’s principle.

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

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

(ii) Use Le Chatelier’s principle to explain how an increase in temperature causes an

increase in the equilibrium yield of ozone.

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

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

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

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

(d) Chemists supported the legislation to ban the use of CFCs. Modern refrigerators use
pentane rather than CFCs as refrigerants.
With reference to its formula, state why pentane is a more environmentally acceptable
refrigerant.

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

......................................................................................................................
(1)
(Total 9 marks)

Mark Scheme
M1.(a) Structure for 3-methylbut-1-ene
H2C=CHCH(CH3)2
Any correct structural representation.
Credit “sticks” and require the double bond.
1

(b) Structure for 2-methylpropan-2-ol

(CH3)3COH
Any correct structural representation.
Credit “sticks”.
1

(c) Structure for propene

H2C=CHCH3
Any correct structural representation.
Credit “sticks” and require the double bond.
1

(d) Structure for 2-aminobutane

CH3CH2CH(NH2)CH 3
Any correct structural representation.
Credit “sticks”.
1
[4]

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M2. (a) (i) Electron pair donor
OR
Species which uses a pair of electrons to form aco-ordinate/covalent bond.
Credit “lone pair” as alternative wording
Credit “electron pair donator”
1

(ii) Replacement of the halogen (atom) (by the nucleophile)

OR
The carbon-halogen bond/C-X breaks and a bond formswith the nucleophile or
between the carbon and the nucleophile
They must describe the idea of substitution in a haloalkane.
Accept the idea that a nucleophile replaces the halogen which
becomes a halide ion
Penalise reference to “halogen molecule” and penalise the idea
that the haloalkane contains a halide
1
(iii) Splitting molecules using/by water
OR
breaking/splitting/dissociating (C¡VX) bond(s)/using/by water
NOT simply the reaction with water or simply the addition of water.
Ignore “compound”
1
(iv) (Heat) energy/enthalpy required/needed/absorbed (at constantpressure) to
break/split it/the (carbon-halogen) bond
OR
(Heat) energy/enthalpy required/needed/absorbed (at constantpressure) for
homolysis of the (C–X/the carbon-halogen) bond
Ignore bond formation Ignore “average”
1
(b)

M1 must show an arrow from the lone pair of electrons on the oxygen atom of the
negatively charged hydroxide ion to the central C atom.
M2 must show the movement of a pair of electrons from theC-Br bond to the Br atom.
Mark M2 independently.
Award full marks for an SN1 mechanism in which M1 is the attack of thehydroxide ion on
the intermediate carbocation.
Penalise M1 if covalent KOH is used
Penalise M2 for formal charge on C or incorrect partial charges
Penalise once only for a line and two dots to show a bond.
Max 1 mark for the wrong reactant
Accept the correct use of “sticks”
2
(c) (i)

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M1 must show an arrow from the lone pair on oxygen of a negatively charged
hydroxide ion to the correct H atom
M2 must show an arrow from the correct C-H bond to the C-C bond and should
only be awarded if an attempt has been made at M1
M3 is independent provided it is from the original molecule
Award full marks for an E1 mechanism in which M2 is on thecorrect carbocation.
Penalise M1 if covalent KOH
Penalise M3 for formal charge on C or incorrect partial charges
Penalise once only for a line and two dots to show a bond.
Max 2 marks for wrong reactant
Accept the correct use of “sticks” for the molecule except for the
C-H being attacked
3
(ii) M1 Stated that the spectrum has an absorption/absorbance/peak in the range
1620 cm–1 to 1680 (cm–1) or specifiedcorrectly in this range from the spectrum
M2 depends on correct range or wavenumber being specified
M2 (Infrared absorption) due to C=C OR carbon-carbon double bond
QoL for correct M1 statement which includes both the word
absorption (or alternative) and the correct range or
wavenumber
Allow “peak” OR “dip” OR “spike” OR “trough”OR “low
transmittance” as alternatives for absorption.
For M2 it is not sufficient simply to state that an alkene has C=C
M2 could be on the spectrum
Ignore reference to other absorptions
2
[11]

M3.(a) P 3,3−dimethylbut−1−ene
OR
accept 3,3−dimethylbutene
Ignore absence of commas, hyphens and gaps
Require correct spelling
Q 3−chloro−2,2−dimethylbutane
OR
accept 2−chloro−3,3−dimethylbutane
In Q, “chloro” must come before “dimethyl”
2

(b) M1 Electrophilic addition

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M2 must show an arrow from the double bond towards the H atom of HCl
M3 must show the breaking of the H−Cl bond
M4 is for the structure of the carbocation
M5 must show an arrow from the lone pair of electrons on the negatively charged
chloride ion towards the positively charged carbon atom on their carbocation.
NB The arrows here are double−headed
M1 both words required
For the mechanism
M3 Penalise incorrect partial charge on H−Cl bond and penalise
formal charges
Ignore partial negative charge on the double bond.
Maximum 3 of 4 marks for a correct mechanism using HBr or
the wrong organic reactant or wrong organic product (if shown) or
a primary carbocation
Penalise once only in any part of the mechanism for a line and two
dots to show a bond
Credit the correct use of “sticks”
For M5, credit attack on a partially positively charged carbocation
structure, but penalise M4
5
(c) M1 Nucleophilic substitution
For M1, both words required.
Accept phonetic spelling

M2 must show an arrow from the lone pair of electrons on the nitrogen atom of an
ammonia molecule to the correct C atom
M3 must show the movement of a pair of electrons from the C− Cl bond to the Cl
atom. Mark M3 independently provided it is from their original molecule
M4 is for the structure of the alkylammonium ion, which could be a condensed
formula. A positive charge must be shown on, or close to, the N atom.
M5 is for an arrow from the N−H bond to the N atom
Award full marks for an SN1 mechanism in which M2 is the attack of the ammonia
on the intermediate carbocation
NB These are double-headed arrows
For the mechanism
Penalise M2 if NH3 is negatively charged.
Penalise M3 for formal charge on C of the C−Cl or incorrect partial
charges on C−Cl
Penalise M3 for an additional arrow from the Cl to something else
The second mole of ammonia is not essential for M5; therefore
ignore any species here

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Penalise once only for a line and two dots to show a bond
Maximum 3 of 4 marks for the mechanism for wrong organic
reactant OR wrong organic product if shown
Accept the correct use of “sticks”
5

(d) M1 (base) elimination

M1 Dehydrohalogenation
M2 KOH OR NaOH
M3 Must be consequential on a correct reagent in M2, but if incomplete or
inaccurate attempt at reagent (e.g. hydroxide ion), penalise M2 only and mark on
Any one from
• high temperature OR hot OR heat / boil under reflux
• concentrated
• alcohol / ethanol (as a solvent) / (ethanolic conditions)
M3 not “reflux” alone
M3 if a temperature is stated it must be in the range 78C to 200 °C
Ignore “pressure”
3

(e) M1
3NaBr + H3PO4 3HBr + Na3PO4
M1 Credit correct ionic species in the equation
M2 and M3
SO2 and Br2 identified
M4
Concentrated sulfuric acid
• is an oxidising agent
• oxidises the bromide (ion) or Br− or NaBr or HBr
• is an electron acceptor
In M2 and M3 the two gases need to be identified. If equations are
used using sulfuric acid and the toxic gases are not identified
clearly, allow one mark for the formulas of SO2 and Br2
• apply the list principle as appropriate but ignore any
reference to HBr
• the marks are for identifying the two gases either by
name or formula
4
[19]

M4.(a) (i) M1 Elimination

M1 Credit “base elimination” but no other prefix.

Penalise M2 if covalent KOH

Penalise M4 for formal charge on C or Br of C−Br or incorrect
partial charges on C−Br
M2 must show an arrow from the lone pair on the oxygen of a negatively
charged hydroxide ion to a correct H atom
Ignore other partial charges
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M3 must show an arrow from a correct C−H bond adjacent to the C−Br bond
to a correct C-C bond. Only award if an arrow is shown attacking the H atom
of a correct adjacent C−H bond in M2
Penalise once only in any part of the mechanism for a line and
two dots to show a bond
M4 is independent provided it is from their original molecule, BUT CE=0 for
the mechanism (penalise M2, M3 and M4 only) if nucleophilic
substitution mechanism is shown
Maximum any 2 of 3 marks for the mechanism for wrong
organic reactant or wrong organic product (if shown).
Credit the correct use of “sticks” for the molecule except for the
C−H being attacked
Award full marks for an E1 mechanism in which M4 is on the correct
carbocation
Penalise M4, if an additional arrow is drawn from Br eg to K+
NB These are double-headed arrows
4

(ii) Displayed formula for 3-methylbut-1-ene

All bonds and atoms must be drawn out, but ignore bond angles
1

(iii) Position(al) (isomerism or isomer)

Penalise any other words that are written in addition to these.
1

(b) (i) Displayed formula for 3-methylbutan-2-ol

All bonds and atoms must be drawn out, but ignore bond angles.
1

(ii) Any one from

• Lower / decreased temperature OR cold
• Less concentrated (comparative) OR dilute KOH
• Water (as a solvent) / (aqueous conditions)
Ignore “pressure”.
1

(iii) Nucleophilic substitution

Both words needed - credit phonetic spelling.
1

(iv) (Strong / broad) absorption / peak in the range 3230 to 3550 cm−1 or specified
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value in this range or marked correctly on spectrum
Allow the words “dip” OR “spike” OR “trough” OR “low
transmittance” as alternatives for absorption.
1
[10]

M5.(a) M1 electrophilic addition

For M1, both words required
Accept phonetic spelling

For the mechanism

M2 Ignore partial negative charge on the double bond
M2 must show an arrow from the double bond towards the H atom of the H–Br
molecule
M3 Penalise partial charges on H–Br bond if wrong way and
penalise formal charges
M3 must show the breaking of the H–Br bond
Penalise once only in any part of the mechanism for a line and two
dots to show a bond
M5 must show an arrow from the lone pair of electrons on the negatively charged
bromide ion towards the correct (positively charged) carbon atom
Maximum any 3 of 4 marks for the mechanism for wrong
(organic) reactant OR wrong organic product (if shown) OR
primary carbocation
Accept the correct use of sticks
NB These are double-headed arrows
5

(b) M1 Nucleophilic substitution

For M1, both words required
Accept phonetic spelling

For the mechanism

Penalise M2 if NH3 is negatively charged
M2 must show an arrow from the lone pair of electrons on the nitrogen atom of an
ammonia molecule to the correct C atom
Penalise M3 for formal charge on C of the C−Br or incorrect partial
charges on C−Br
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Penalise M3 for an additional arrow from the Br to something else
M3 must show the movement of a pair of electrons from the C–Br bond to the Br
atom. Mark M3 independently provided it is from their original molecule
The second mole of ammonia is not essential for M5; therefore
ignore any species here
M4 is for the structure of the alkylammonium ion, which could be a condensed
formula. A positive charge must be shown on / or close to, the N atom
Penalise once only for a line and two dots to show a bond
M5 is for an arrow from the N–H bond to the N atom
Maximum any 3 of 4 marks for the mechanism for wrong
organic reactant OR wrong organic product if shown
Award full marks for an SN1 mechanism in which M2 is the attack of the ammonia
on the intermediate carbocation
Accept the correct use of “sticks”
NB These are double-headed arrows
5

(c) M1 (addition) polymerisation OR poly-addition

Ignore “additional”
Credit polyprop-1-ene and polypropylene
M2 poly(propene) / polypropene
Penalise “condensation polymerisation”
2

(d)

Penalise M1 if covalent KOH

M1 must show an arrow from the lone pair on the oxygen of a negatively charged
hydroxide ion to a correct H atom
Penalise M3 for formal charge on C of C–Br or incorrect partial
charges on C−Br.
M2 must show an arrow from a correct C–H bond adjacent to the C–Br bond to the
appropriate C–C bond. Only award if an arrow is shown attacking the H atom of a
correct C−H bond in M1
Ignore other partial charges
Penalise once only in any part of the mechanism for a line and two
dots to show a bond
M3 is independent provided it is from their original molecule, but CE=0 if
nucleophilic substitution
Maximum any 2 of 3 marks for wrong organic reactant
Award full marks for an E1 mechanism in which M3 is on the correct carbocation.
Accept the correct use of “sticks” for the molecule except for the
C–H being attacked
NB These are double-headed arrows
3
[15]

M6. (a) (i) UV light OR sunlight OR T 450°C (1)

NOT high T

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(ii) (free) radical substitution (1)
(iii) CCl4 (1) OR named
3

(b) (i) CH3Cl + KCN → CH3CN + KCl (1) CN– Cl–

(ii) nucleophilic substitution (1)
(iii) C–Br bond is weaker (than C–Cl bond)OR C–Br bond enthalpy is less than C–Cl (1)
Ignore electronegativity
3

(c) CH3COOH OR ethanoic acid (1)

1

(d) (i) OR C–Cl is polar (1) OR C atom is electron deficient / δ+

(ii) methylamine (1) only
(iii) SN1 scores full marks

6
[13]

M7.(a) (Compounds with the) same molecular formula but different structural / displayed / skeletal
formula
1

(b) (basic) elimination

1

Mechanism points:
Correct arrow from lone pair on :OH– to H on C adjacent to C–Br
1

Correct arrow from C–H bond to C–C

1

Correct arrow from C–Br bond to Br

1

Structure of chosen product

1

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OR

[6]

M8. (a) (i)

Penalise one mark from their total if half-headed arrows are used
Penalise M3 for formal charge on C of the C-Br or incorrect partial
charges on C-Br
Ignore other partial charges

M1 must show an arrow from the lone pair on oxygen of a negatively charged
hydroxide ion to the correct H atom
Penalise once only in any part of the mechanism for a line and two
dots to show a bond.
M2 must show an arrow from the correct C–H bond to the correct C–C bond.Only
award if an arrow is shown attacking the H atom of the correct C–Hbond in M1
M3 is independent but CE=0 if nucleophilic substitution
N.B these are double-headed arrows
3

(ii)
Award 1 mark if both correct stereoisomers but in the wrong
places
Accept no other alkenes.
Be reasonably lenient on the bonds to ethyl (or to CH2CH3) since
the question is about E and Z positions but penalise once only if
connection is clearly to the CH3 of CH2CH3
Accept linear structures
2

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(iii) M1 (Compounds / molecules with) the same structural formula
Penalise M1 if “same structure”
M2 with atoms/bonds/groups arranged differently in space
Ignore references to “same molecular formula” or “same empirical
formula” or any reference to “displayed formula”
ORatoms/bonds/groups that have different spatial arrangements / different
orientation.
Mark independently
2

(b)
M1must show an arrow from the double bond towards the H atom of the H – O bond OR
HO on a compound with molecular formula for H2SO4
M1 could be to an H+ ion and M2 an independent O – H bond break on a compound with
molecular formula for H2SO4
M1 Ignore partial negative charge on the double bond.
M2 must show the breaking of the O – H bond.
M2 Penalise partial charges on O – H bond if wrong way and
penalise formal charges
In M2 do not penalise incorrect structures for H2SO4
M3 is for the structure of the carbocation.
M4 must show an arrow from the lone pair of electrons on the correct oxygen of the
negatively charged ion towards a correct (positively charged) carbon atom.
M4 NOT HSO4–
For M4, credit as shown or –:OSO3H ONLY with the negative
charge anywhere on this ion
OR correctly drawn out with the negative charge placed correctly
on oxygen
Penalise once only in any part of the mechanism for a line and two
dots to show a bond
NB The arrows here are double-headed
Max 3 of any 4 marks for wrong organic reactant or wrong organic
product (if shown)
Accept the correct use of “sticks”
4
[11]

M9. (a) (i) Nucleophilic substitution

1

2
M1 must show an arrow from the lone pair of electrons on theoxygen atom of the
negatively charged hydroxide ion to thecentral C atom.M2 must show the movement
of a pair of electrons from theC-Br bond to the Br atom. Mark M2 independently.
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Penalise M1 if covalent KOH is used
Penalise M2 for formal charge on C or incorrect partial charges
Penalise once only for a line and two dots to show a bond.
Max 1 mark for the mechanism for the wrong reactant and/or
“sticks”
Ignore product
Award full marks for an SN1 mechanism in which M1 is theattack of the hydroxide
ion on the intermediate carbocation.

(ii) 2-bromopropane ONLY

1
(iii) Polar C–Br OR polar carbon–bromine bond OR dipole on C–BrOR δ+ (δ–)C atom
of carbon–bromine bond is δ+/electron deficient OR C―Br
(Credit carbon–halogen bond as an alternative tocarbon–bromine bond)
It must be clear that the discussion is about the carbon atom of the
C–Br bond. NOT just reference to a polar molecule.Ignore X for
halogen
1

(b) Elimination
Credit “base elimination” but NOT “nucleophilic elimination”No
other prefix.
1

3
M1 must show an arrow from the lone pair on oxygen of a negativelycharged hydroxide
ion to the correct H atomM2 must show an arrow from the correct C-H bond to the C-C
bondand should only be awarded if an attempt has been made at M1M3 is independent.
MechanismPenalise M1 if covalent KOH
Penalise M3 for formal charge on C or incorrect partial charges
Penalise once only for a line and two dots to show a bond.
Max 2 marks for the mechanism for wrong reactant and/or
“sticks”
Ignore product
Award full marks for an E1 mechanism in which M2 is on thecorrect carbocation.

(c) Any one condition from this list to favour elimination;

Apply the list principle
• alcohol(ic)/ethanol(ic) (solvent)
• high concentration of KOH/alkali/hydroxide OR concentratedKOH/hydroxide
Ignore “aqueous”
• high temperature or hot or heat under reflux or T = 78 to 100°C
Ignore “excess”
1

(d) (i) Addition (polymerisation) ONLY

Penalise “additional”
1

(ii) But-2-ene ONLY (hyphens not essential)

Ignore references to cis and trans orE/ZIgnore butane
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1
[12]

M10. (a) (i) M1 Elimination

M2 must show an arrow from the lone pair on the oxygenof a negatively charged
hydroxide ion to a correct H atom
M3 must show an arrow from a C-H bond adjacent tothe C-Br bond towards the
appropriate C-C bond.Only award if a reasonable attempt has been madeat the
attack on the H atom of the appropriate adjacent C-H
M4 is independent provided it is from their original molecule

Award full marks for an E1 mechanism in which M3 is on the correct carbocation.

N.B. These are double-headed arrows
For M1, accept “Base elimination” but no other prefix.
Penalise M2 if covalent KOH
Penalise M4 for formal charge on C of C-Br or incorrect partial
charges on C-Br
Ignore other partial charges
Penalise once only in any part of the mechanism for a line and two
dots to show a bond.
Max any 2 of 3 marks for the mechanism for wrong reactant (or
wrong product if shown).
Accept the correct use of “sticks” for the molecule except for the
C-H being attacked
4

(ii) Structure for pent-1-ene

CH3CH2CH2CH=CH2
Penalise C3H7
Accept correct “sticks”
1

(b) M1 Electrophilic addition

M2 must show an arrow from the double bond towards the Br atom of the Br-Br molecule
M3 must show the breaking of the Br-Br bond.
M4 is for the structure of the tertiary carbocation with Br on the correct carbon atom.

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M5 must show an arrow from the lone pair of electrons on the negatively charged bromide
ion towards the positively charged carbon atom.
N.B. These are double-headed arrows
For M1, both words required.
For the mechanism
M2 Ignore partial negative charge on the double bond.
M3 Penalise partial charges on Br-Br bond if wrong way and
penalise formal charges
Penalise once only in any part of the mechanism for a line and two
dots to show a bond
Max any 3 of 4 marks for the mechanism for
wrong organic reactant or wrong organic product (if shown) or
primary carbocation.
If HBr is used, max 2 marks for their mechanism
Accept the correct use of “sticks”
5

(c) M1 Nucleophilic substitution

M2 must show an arrow from the lone pair of electrons on the nitrogenatom of an
ammonia molecule to the C atom.
M3 must show the movement of a pair of electrons from the C-Br bondto the Br atom. M3
is independent provided it is from their original molecule
M4 is for the structure of the alkylammonium ion, which could be acondensed formula. A
positive charge must be shown on/or close to,the N atom.
M5 is for an arrow from the N-H bond to the N atom.

Award full marks for an SN1 mechanism in which M2 is the attackof the ammonia on the
intermediate carbocation.
N.B. These are double-headed arrows
For M1, both words required.
Penalise M2 if NH3 is negatively charged.
Penalise M3 for formal charge on C or incorrect partial charges
The second mole of ammonia is not essential for M5; therefore
ignore any species here.
Penalise once only for a line and two dots to show a bond.
Max any 3 of 4 marks for the mechanism for wrong organic
reactant (or wrong organic product if shown)
Accept the correct use of “sticks”
5
[15]

M11. (a) Electron pair donorORSpecies which uses a pair of electronsto form a co-ordinate /
covalent bond.
QoLCredit “lone pair” as alternative wording
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1

(b)

M1 Must show an arrow from the lone pair of electronson the carbon atom of the
negatively chargedcyanide ion to the central C atom.
M2 Must show the movement of a pair of electrons fromthe C-Br bond to the Br atom.
Mark M2 independently.
Award full marks for an SN1 mechanism in which M1 is theattack of the cyanide ion on the
intermediate carbocation.
Penalise M1 if covalent KCN is used
Penalise M2 for formal charge on C or incorrect partial charges
Penalise once only for a line and two dots to show a bond.
Max 1 mark for the wrong reactant or “sticks”
2

(c) Ethylamine / CH3CH2NH2 is a nucleophileOREthylamine could react furtherOREthylamine

could make secondary / tertiary aminesORTo make reaction with ammonia more
likelyORTo minimise further substitutionORThe idea of releasing free amine from the
saltORThe idea of removing a proton from the intermediatealkylammonium ionORThe
idea that ammonia acts both initially as a nucleophile andthen as a base
Do not credit a simple reference to the equation or the mechanism
requiring two moles of ammonia.
1

(d) Elimination
Credit “base elimination” but NOT “nucleophilic elimination”No
other prefix.

1
M1 Must show an arrow from the lone pair on oxygen of anegatively charged hydroxide
ion to the correct H atom
M2 Must show an arrow from the correct C-H bond to theC-C bond and should only be
awarded if an attempt hasbeen made at M1
M3 Is independent.
Award full marks for an E1 mechanism in which M2 is on thecorrect carbocation.
MechanismPenalise M1 if covalent KOH
Penalise M3 for formal charge on C or incorrect partial charges
Penalise once only for a line and two dots to show a bond.
Max 2 marks for the mechanism for wrong reactant or “sticks”
3
[8]

M12.(a) 2-bromobutane;
1

(b) Elimination;
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 Barr Beacon School
(penalise “nucleophilic” OR “electrophilic” before the word
“elimination”)
1
M1: curly arrow from lone pair on oxygen of hydroxide ion to H atomon correct C-H
adjacent to C-Br;
(penalise M1 if KOH shown as covalent with an arrow breaking the
bond)
1
M2: curly arrow from single bond of adjacent C-H to adjacentsingle bond C-C;
(only credit M2 if M1 is being attempted to correct H atom)
1
M3: curly arrow from C-Br bond to side of Br atom;
(credit M3 independently unless arrows contradict)(Credit possible
repeat error from 2(c)(iii) for M3)(If the wrong haloalkane is used
OR but-1-ene is produced, award MAX. 2 marks for the
mechanism)(If E1 mechanism is used, give full credit in which M1
and M2 are for correct curly arrows on the correct carbocation)

(c) (i) (structural) isomers/hydrocarbons/compounds/they have the samemolecular

formula, but different structural formulas/different structures; 1
(penalise statements which are not expressed in good English and
which do not refer clearly to structural isomers i.e. plural)(penalise
statements which refer to “different (spatial) arrangements”)(credit”
different displayed formulas”)(Q of L mark)
(ii) Correct structure for but-1-ene;
1
[7]

M13.(a) (i) M1 Initiation

Cl2 2Cl•
Penalise absence of dot once only.
M2 First propagation
Cl• + CHF3 CF3• +HCl
Penalise + or − charges every time.
M3 Second propagation
Cl2 + CF3• CClF3 + Cl•
Credit CF3• with the radical dot above / below / to either side.
M4 Termination (must make C2F6)
2 CF3• C2F6 or CF3CF3
Mark independently.
4

(ii) ultra-violet / uv / sun light

OR (very) high temperature
OR 500 °C ≤ T ≤ 1000 °C
OR 773 K ≤ T ≤ 1273 K
1

(b) (i) Cl• OR chlorine atom / chlorine (free−) radical / Cl (atom)

Not ‘chlorine’ alone.
Credit ‘Cl’ alone on this occasion.
1

(ii) 2O3 3O2

Or multiples.
Ignore state symbols.
If the correct answer is on the line OR clearly identified below
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some working, then ignore any working.
1
[7]

M14.(a) InitiationCl2 2Cl•

Penalise absence of dot once only.
First propagationCl• + CH3Cl •CH2Cl + HCl
Credit the dot anywhere on the radical.
Second propagationCl2 + •CH2Cl CH2Cl2 + Cl•
Termination (must make 1,2-dichloroethane)2 •CH2Cl CH2ClCH2Cl
Penalise C2H4Cl2
4

(b) (i) (chlorine free) radical

Ignore formula.
1

(ii) M1 Cl• + O3 ClO• + O2

M2 ClO• + O3 Cl• + 2O2
M1 and M2 could be in either order.
Credit the dot anywhere on the radical.
Penalise absence of dot once only.
Individual multiples acceptable but both need to be doubled if two
marks are to be awarded.
2
[7]

M15. (a) (i) chlorotrifluoromethane

Spelling must be correct but do not penalise “flouro”
Ignore use of 1–
1

(ii) CF3•
May be drawn out with dot on C
OR if as shown dot may be anywhere
1

(iii) An unpaired/non-bonded/unbonded/free/a single/one/loneelectron

NOT “bonded electron” and NOT “paired electron”
NOT “pair of electrons”
NOT “electrons”
Ignore “(free) radical”
1

(b) M1 Cl• + O3 → ClO• + O2

M2 ClO• + O3 → 2O2 + Cl•
Mark independently
Equations could gain credit in either position
The dot can be anywhere on either radical
Penalise the absence of a dot on the first occasion that it is seen
and then mark on. Do not make the same penalty in the next
equation, but penalise the absence of a dot on the other radical.
Apply the list principle for additional equations
2

(c) (i) (If any factor is changed which affects an equilibrium),the (position of) equilibrium
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will shift/move so as to opposethe change.
OR
(When a system/reaction in equilibrium is disturbed),the equilibrium shifts/moves in
a direction which tends toreduce the disturbance
Must refer to equilibrium
Ignore reference to “system” alone
A variety of wording will be seen here and the key part is the last
phrase.
An alternative to shift/move would be the idea of changing/altering
the position of equilibrium
1

(ii) M1 The (forward) reaction/to the right is endothermic ortakes in heat

OR The reverse reaction/to the left is exothermic or gives out heat
M2 The equilibrium moves/shifts to oppose the increase intemperature
M2 depends on a correct statement for M1
For M2 accept
The equilibrium moves/shifts
• to take in heat/lower the temperature
• to promote the endothermic reaction and take in heat/ lower
the temperature
• to oppose the change and take in heat/lower the
temperature
(leading to the formation of more ozone)
2

(d) Any one of

• Pentane does not contain chlorine OR C–Cl (bond)
• Pentane is chlorine-free
• Pentane does not release chlorine (atoms/radicals)
Ignore reference to F OR C–F OR halogen
Ignore “Pentane is not a CFC”
Ignore “Pentane is a hydrocarbon”
Ignore “Pentane only contains C and H”
Ignore “Pentane is C5H12”
1
[9]

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E1.Overall, this question proved accessible for many students with part (c) the highest scoring part.
Many students are being very sensible choosing to draw displayed formulae in questions of this
type. The use of displayed formulae is to be encouraged since these gain full credit and often
result in the student making fewer mistakes. Schools and colleges need to advise students to
be careful about their working. If, in the answer space, they leave additional, incomplete or
incorrect formulae that are not crossed through, this will contradict a correct answer which will
then be penalised.

E2. It was surprising to see that the term “nucleophile” was still not well known when all that was
required was “an electron pair donor”. Part (a)(ii) was well answered but part (a)(iii) was
answered surprisingly poorly given that a similar question was included on the paper in June
2010. The remainder of this question was well answered by most candidates.

E3.Part (a) was answered quite well. The naming of P and Q was a challenge for some with a
demand both for correct spelling and correct use of the alphabet for functional groups and this
led to only 48% scoring both marks. This question included two curly arrow mechanisms and
these questions always result in the best discrimination of student performance. Part (b) and
part (c) provided an excellent distribution across the full range of marks with the usual errors
seen, such as an incorrect carbocation in part (b), a negative charge on ammonia in part (c)
and, in both parts, a failure to use either a lone pair of electrons or a bond as the origin of a pair
of electrons. It was essential in part (d) to identify a reagent, in order to be able to access the
reaction condition mark and some excellent responses were seen. It is worth reminding
students that as a general guide, a reagent is something that you get out of a bottle; for
example, sodium hydroxide and not hydroxide ion. Part (e) also discriminated well with most
students able to write the equation and then to identify sulfur dioxide as one of the toxic gases.

E4.Mechanisms continue to discriminate well and over two-thirds of all students scored at least two
marks in part (a)(i). Two displayed formulas were required in this question in parts (a)(ii) and (b)
(i) and 37% and 25%, respectively, scored the mark in each part. Part (b)(ii) was relatively
demanding, whereas the remainder of part (b) was very high-scoring.

E5.Organic reaction mechanisms discriminate well. Schools and colleges still need to heed the
advice that full marks will only be awarded in a mechanism such as that in part (b) if the positive
charge on the intermediate alkylammonium ion is placed on the N atom and not on or adjacent
to a hydrogen atom. Over 80% scored at least 3 marks on both parts (a) and (b). A surprising
number of students were unable to name substance X correctly in part (c).

E6. This question was well answered by many candidates, although in part (a)(ii) the word
“substitution” was often missed and weaker candidates had problems recognising that
tetrachloromethane would form as the main product when a large excess of chlorine is used. In
part (b)(i) marks were lost through equations not being balanced or through errors in the
formula of ethanenitrile. In part (b)(iii) the idea from the specification that the “carbon-halogen
bond enthalpy influences the rate of hydrolysis” was known and applied in this context by many
candidates. Rather too many answers lacked precision and stated simply that “bromomethane
has weaker bonds” without indicating the relative strengths of the C-Br and C-Cl bonds. Part (c)
was generally answered correctly. In part (d)(i) the demand was for the candidates to
appreciate the polar nature of the C-Cl bond, rather than the more vague response that
“chloromethane is polar”. In (d)(ii), many candidates were able to name methylamine correctly
and attempts at the mechanism in (d)(iii) were generally good. The main problems with many
mechanisms arose from the inclusion either of a negative charge on the ammonia molecule or
curly arrows going the wrong way on the methylammonium ion, which often lacked a positive
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charge. Notwithstanding these difficulties most candidates scored at least two marks.

E8. Providing the students with the basic information for the elimination reaction in part (a)(i)
enabled most students to score at least one mark and more than half scored full marks.
Structures of E and Z isomers were generally well understood and many students could score
at least one mark in their answers to the meaning of the term stereoisomers.
The mechanism in part (b) is demanding and discriminated very well

E9. Candidates are able to tackle organic reaction mechanisms with confidence and this
question was well answered. The most demanding part was part (a)(iii) in which they had to
indicate that the carbon-bromine bond was polar.

E10. Putting three mechanisms together proved to be very discriminating. Weaker candidates
were able to score some marks and the best candidates scored all 15. There is always a
concern that in these longer Section B questions, candidates might forget to record the name of
a mechanism and there was some evidence of that happening here. Partial credit was given in
part (a)(i) for a mechanism that used an incorrect starting or finishing compound with much of
the focus concentrated on the curly arrows. This guiding principle was applied to good effect in
parts (b) and (c). In part (c), centres need to appreciate that full marks will only be awarded in a
mechanism of this type if the positive charge on the intermediate is placed on the N atom and
not on or adjacent to a hydrogen atom.

E11. While some very good answers were seen for all parts of this question, the general
impression was that some candidates found this question demanding. Relatively few candidates
were able to state correctly the meaning of the term nucleophile, but almost 70% could gain at
least half of the marks in the nucleophilic substitution mechanism in part (b). Part (c) was
recognised by examiners to be a difficult question and only a minority of candidates were
successful. Part (d) discriminated very well with the full range of marks seen and more than half
the candidates were able to score at least half of the marks.

E12.This question was often relatively high scoring despite having a mechanism which has caused
problems on previous papers. Part (a) was usually well answered, although it was a surprise to
see "bromine" as an answer on several scripts. The name of the mechanism in part (b) was
often well known, although some candidates incorrectly prefaced the word "elimination" with
electrophilic or nucleophilic. The mechanism itself usually yielded at least one mark from C-Br
bond breakage and some complete and very well presented answers were seen. In part (c),
many candidates struggled to state that structural isomers have the same molecular formula,
but different structural formulae and the mark was often lost from one or the other part of this
statement. Problems arose, because candidates appeared to confuse the idea with
stereoisomers and referred to different (spatial) arrangements of atoms or groups. This latter
point was compounded by some candidates drawing cis and/or trans isomers of but-2-ene in
part (c)(ii), while others chose to draw methylpropene. Even those who knew that the answer
was but-1-ene, too often failed to complete their structure correctly.

E13.Part (a) required a free-radical substitution mechanism for molecules with two different halogens
and it discriminated well. In common with previous questions involving a similar mechanism, the
second propagation step proved to be the most demanding part of this question. The remainder
of the question was relatively high scoring.

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E14.The free-radical substitution mechanism always discriminates well and this was no exception.
Almost three-quarters of all students scored 2 marks but fewer than 10% scored 4 marks. It was
important in the termination step to show clearly that the product is 1,2-dichloroethane.
Some good responses were seen in part (b) perhaps because this is straight from the
specification, although only half of all students scored both marks in part (b)(ii).

E15. This question was not as high scoring as might have been expected. Candidates were
unfamiliar with the equations that show how chlorine atoms catalyse the decomposition of
ozone, even though these are in the specification. The ability to articulate a correct argument
using Le Chatelier’s principle in part (c)(ii) was well done, although candidates should be urged
to refer to the “equilibrium” rather than the “system”.

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