June 14 QP + MS

Tuesday 3 June 2014 – Afternoon
AS GCE CHEMISTRY A
F322/01 Chains, Energy and Resources
* 1 3 9 3 4 3 7 8 3 7 *
Candidates answer on the Question Paper.

OCR supplied materials: Duration: 1 hour 45 minutes
• Data Sheet for Chemistry A (inserted)
Other materials required:
• Scientific calculator
* F 3 2 2 0 1 *
INSTRUCTIONS TO CANDIDATES
• The Insert will be found inside this document.
• Write your name, centre number and candidate number in the boxes above. Please write clearly
and in capital letters.
• Use black ink. HB pencil may be used for graphs and diagrams only.
• Answer all the questions.
• Read each question carefully. Make sure you know what you have to do before starting your
answer.
• Write your answer to each question in the space provided. If additional space is required, you
should use the lined pages at the end of this booklet. The question number(s) must be clearly
shown.
• Do not write in the bar codes.
INFORMATION FOR CANDIDATES

• The number of marks is given in brackets [ ] at the end of each question or part question.
Where you see this icon you will be awarded marks for the quality of written communication
in your answer.
This means for example you should:
• ensure that text is legible and that spelling, punctuation and grammar are accurate so that
meaning is clear;
• organise information clearly and coherently, using specialist vocabulary when appropriate.
• You may use a scientific calculator.
• A copy of the Data Sheet for Chemistry A is provided as an insert with this question paper.
• You are advised to show all the steps in any calculations.
• The total number of marks for this paper is 100.
• This document consists of 24 pages. Any blank pages are indicated.
© OCR 2014 [H/500/7834] OCR is an exempt Charity

DC (NF/SW) 89910/3 Turn over
3
Answer all the questions.
1 This question is about cyclic organic compounds.
The table shows some information about cycloalkanes.
Cycloalkane Skeletal formula Boiling point / °C
Cyclopropane –33
Cyclopentane 49
Cyclohexane 81
(a) These cycloalkanes are members of the same homologous series and have the same general
formula.
(i) What is meant by the term homologous series?
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(ii) State the general formula for these cycloalkanes.
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(iii) Explain the increase in boiling points of the cycloalkanes shown in the table.
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© OCR 2014 Turn over

4
(b) The C–C–C bond angles in cyclohexane are 109.5°.
State and explain the shape around each carbon atom in cyclohexane.
shape .................................................................
explanation ...............................................................................................................................
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[2]
(c) In the absence of ultraviolet radiation, cyclopropane undergoes an addition reaction with
bromine.
Suggest the structure of the organic product formed in this reaction.
[1]
(d) Petrol contains both cyclohexane, C6H12, and hexane.
Cyclohexane can be prepared from hexane.
(i) Construct the equation for this reaction.
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(ii) Suggest one advantage of adding cyclohexane to hexane in petrol.
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(e) Cyclobutane is another cycloalkane.
There are several unsaturated isomers of cyclobutane that are alkenes.
Two of these isomers are stereoisomers.
(i) Explain what is meant by the term stereoisomers.
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(ii) Draw these two stereoisomers.
[2]
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(f) In the presence of ultraviolet radiation, cyclohexane reacts with bromine.
A mixture of cyclic organic compounds is formed, including C6H11Br.
(i) Complete the table below to show the mechanism of the reaction between bromine and
cyclohexane to form C6H11Br.
Include all possible termination steps in your answer.
Step Equation
Initiation
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Propagation
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Termination
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[5]
(ii) The initiation step involves homolytic fission.
Explain why the initiation step is an example of homolytic fission.
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(g) The reaction between cyclohexane and bromine in (f) also forms C6H10Br2.
(i) Write an equation, using molecular formulae, for the reaction of cyclohexane and bromine
in the presence of ultraviolet radiation to form C6H10Br2.
..................................................................................................................................... [1]
(ii) Name one of the structural isomers of C6H10Br2 formed in the reaction between
cyclohexane and bromine.
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[Total: 21]

6
2 1-Bromobutane, CH3CH2CH2CH2Br, reacts with methoxide ions, CH3O−, by nucleophilic substitution.
(a) Suggest how the methoxide ion can act as a nucleophile.
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(b) Using the ‘curly arrow’ model, suggest the mechanism for this reaction.
Show any relevant dipoles.
[3]
(c) 1-Iodobutane also reacts with methoxide ions.
Indicate, by placing a tick in one of the boxes, how the use of 1-iodobutane would affect the
rate of reaction compared with that of 1-bromobutane.
1-Iodobutane does not change the rate

1-Iodobutane increases the rate
1-Iodobutane decreases the rate
Explain your answer.
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(d) The ethanoate ion, CH3COO− also acts as a nucleophile when reacting with 1-bromobutane
in a substitution reaction.
Draw the skeletal formula and give the name of the organic product formed in this reaction.
skeletal formula
name of product .................................................................................................................. [2]

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(e) 1-Bromobutane (Mr, 136.9) can be made from a reaction of butan-1-ol, C4H9OH, as shown in
the equation below.
C4H9OH + KBr + H2SO4 C4H9Br + KHSO4 + H2O
(i) Calculate the atom economy for the formation of 1-bromobutane in this reaction.
atom economy = ..................................................... % [1]
(ii) Suggest a reactant, other than a different acid, that could be used to improve the atom
economy of making 1-bromobutane by the same method.
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(iii) A student prepares a sample of 1-bromobutane.
5.92 g of butan-1-ol are reacted with an excess of sulfuric acid and potassium
bromide. After purification, 9.72 g of 1-bromobutane are collected.
Calculate the percentage yield.
Give your answer to three significant figures.
percentage yield = ...................................................... % [3]
[Total: 12]

8
3 Hydrogen iodide, HI, is a colourless gas that can be made from the reaction of hydrogen, H2, and
iodine, I2.
This reversible reaction is shown in equilibrium 3.1 below.
H2(g) + I2(g) 2HI(g) ΔH = −9 kJ mol−1 equilibrium 3.1
The activation energy for the forward reaction is 173 kJ mol−1.
(a) Complete the enthalpy profile diagram below for the forward reaction in equilibrium 3.1.
On your diagram:
• Label the activation energy, Ea
• Label the enthalpy change of reaction, ΔH
• Include the formulae of the reactants and products.
enthalpy
progress of reaction
[2]
(b) Calculate the activation energy, Ea, for the reverse reaction.
Ea (reverse reaction) = ............................................ kJ mol−1 [1]
(c) When the reverse reaction takes place hydrogen iodide, HI, decomposes to form iodine and
hydrogen.
Calculate the enthalpy change when 336 dm3 of hydrogen iodide, measured at room
temperature and pressure, decomposes.
Include the sign for enthalpy change in your answer.
enthalpy change .................................................... kJ [2]

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(d) A student mixes hydrogen and iodine at room temperature and pressure and allows the
mixture to reach dynamic equilibrium.
H2(g) + I2(g) 2HI(g) ΔH = −9 kJ mol−1 equilibrium 3.1
(i) A closed system is required for dynamic equilibrium to be established.
State one other feature of this dynamic equilibrium.
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(ii) The student heats the equilibrium mixture keeping the volume constant.
Predict how the composition of the equilibrium mixture changes on heating.
Explain your answer.
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(iii) Predict and explain what effect, if any, an increase in the pressure would have on the
position of the equilibrium.
effect ..................................................................................................................................
explanation ........................................................................................................................
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(e) Calculate the bond enthalpy for the H–I bond in equilibrium 3.1, given the following
information.
Bond Bond Enthalpy / kJ mol−1

H–H 436
I–I 151
bond enthalpy ........................................... kJ mol−1 [2]

[Total: 11]
10
4 This question is about the determination of enthalpy changes.
(a) A student carries out an experiment to find the enthalpy change of reaction, ΔHr , for the
reaction below.
Na2CO3(s) + 2HCl(aq) 2NaCl(aq) + CO2(g) + H2O(l)
In the experiment, 3.18 g of Na2CO3 are added to 50.0 g of 2.00 mol dm−3 HCl, an excess.
The temperature of the reaction mixture increases by 5.5 °C.
Calculate ΔHr , in kJ mol−1.
Give your answer to three significant figures.
The specific heat capacity, c, of the reaction mixture is 4.18 J g−1 K−1.
ΔHr = ........................................... kJ mol−1 [4]
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(b) The booster rocket of a spacecraft uses a mixture of aluminium and ammonium chlorate(VII),
NH4ClO4, as a fuel. The equation and some enthalpy changes are shown below.
3Al(s) + 3NH4ClO4(s) Al 2O3(s) + AlCl 3(s) + 6H2O(g) + 3NO(g) ΔH = –2677 kJ mol−1
Standard enthalpy change of

Substance
formation, ΔHf / kJ mol−1
NH4ClO4(s) –295
Al 2O3(s) –1676
AlCl 3(s) –704
H2O(g) –242
(i) What is meant by the term standard enthalpy change of formation?
Give the standard conditions.
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(ii) Write the equation, including state symbols, for the reaction that represents the standard
enthalpy change of formation of NH4ClO4(s).
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(iii) Calculate the enthalpy change of formation of NO(g) using the data above.
enthalpy change of formation of NO(g) = ........................................... kJ mol−1 [3]

[Total: 12]
12
5 Chloroethene, CH2CHCl, can be polymerised to form poly(chloroethene).
(a) Write an equation, using displayed formulae, to show the formation of this polymer.
[2]
(b) Incineration of plastics containing poly(chloroethene) produces waste gases that can damage
the environment.
Incineration carried out in the presence of oxygen produces carbon dioxide, carbon monoxide
and hydrogen chloride as waste gases and one other non-toxic product.
(i) Write an equation for the incineration of the monomer, chloroethene, with oxygen.
[1]
(ii) Chemists have developed ways of removing hydrogen chloride from these waste gases.
Sodium hydrogencarbonate, NaHCO3(s), is frequently used in industry for this purpose.
Explain how sodium hydrogencarbonate removes hydrogen chloride.
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(c) Carbon dioxide is a greenhouse gas that is linked to global warming.
The greenhouse effect of carbon dioxide in the atmosphere is dependent on two factors.
What are these two factors?
1 ...............................................................................................................................................
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2 ...............................................................................................................................................
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[2]
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(d) Chemists are trying to minimise climate change as a result of global warming.
One way is to use Carbon Capture and Storage (CCS). One method of CCS is to react the
carbon dioxide with metal oxides.
(i) Write an equation to illustrate this method of CCS.
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(ii) State one other method of CCS.
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[Total: 8]

14
6 (a) Reaction rates can be increased or decreased by changing conditions of temperature and
pressure.
(i) Explain how increasing the temperature increases the rate of reaction.
Include a labelled sketch of the Boltzmann distribution, on the grid below.
Label the axes.
Your answer needs to be clear and well organised using the correct terminology.
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(ii) Describe and explain the effect of decreasing the pressure on the rate of a reaction.
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(b) Catalysts are used to speed up chemical reactions.
(i) Write an equation for an industrial preparation of ethanol which involves the use of an
enzyme in yeast.
State a suitable temperature for this reaction and one other essential condition.
equation ............................................................................................................................
temperature .......................... °C.
condition ............................................................................................................................
[2]
(ii) Catalytic converters are used to decrease the emission of nitrogen monoxide and carbon
monoxide from the internal combustion engine. These two gases react together on the
surface of the catalyst.
Write an equation for this reaction.
..................................................................................................................................... [1]
[Total: 9]

16
7 The flowchart shows how 2-methylbut-2-ene can be converted into a number of organic products.
(a) Complete the flowchart by drawing an organic structure in the box below.
H3C CH3
C C reagent A
H3C H
2-methylbut-2-ene
KOH(aq) / warm
reaction R
CH3 CH3
mixture of two
alcohols H3C C C H
OH OH
[1]
(b) Identify reagent A.
............................................................................................................................................. [1]
(c) In the flowchart, reaction R forms a mixture of two alcohols that are structural isomers of
C5H12O.
(i) State the reagents and conditions needed for reaction R.
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(ii) What is meant by the term structural isomers?
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(iii) Draw the two structural isomers of C5H12O formed in reaction R.
[2]
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(iv) Suggest why 2-methylbut-2-ene is less soluble in water than either of the structural
isomers formed.
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(d) Describe the oxidation reactions of propan-1-ol when using a suitable oxidising agent.
Indicate how the use of different reaction conditions can control which organic product forms.
Include reagents, observations and equations in your answer.
In your equations, use structural formulae and use [O] to represent the oxidising agent.
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[Total: 14]

18
8 (a) Compound B, CxHyO, can be oxidised to form a ketone C.
0.035 mol of B has a mass of 2.59 g.
Compound B reacts with compound D, C3H6O2, in the presence of an acid catalyst to form
two compounds E and F.
• Calculate the molar mass of compound B.
• Give the structures of compounds B, C, D, E and F.
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BLANK PAGE
Question 8 continues on page 20
PLEASE DO NOT WRITE ON THIS PAGE

20
(b) Compound G is a branched-chain organic compound that does not have E and Z isomers.
Elemental analysis of compound G gave the following percentage composition by mass:

C, 55.8%; H, 7.0%; O, 37.2%.
The mass spectrum and infrared spectrum of compound G are shown below.
Mass spectrum
100
X
80
60
relative
intensity
40
20 Y
0
10 20 30 40 50 60 70 80 90 100
m /z
Infrared spectrum
100
transmittance
(%)
50
0
4000 3000 2000 1500 1000 500
wavenumber / cm–1
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• Calculate the empirical and molecular formulae for compound G.
• Write the formulae for the particles responsible for peak X and peak Y in the mass
spectrum.
• Draw the structure of compound G.
Explain fully how you arrive at a structure for compound G using all the evidence provided.
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[Total: 13]
END OF QUESTION PAPER
© OCR 2014
F322 Mark Scheme June 2014
Question Answer Mark Guidance

1 (a) (i) (series of compounds with the) 2 IGNORE references to physical properties
same functional group IGNORE has same general formula (in question)
OR same/similar chemical properties
OR same/similar chemical reactions  DO NOT ALLOW have the same empirical formula OR
have the same molecular formula
each successive/subsequent member differing by CH2 
(ii) CnH2n  1
(iii) 2 Both answers need to be comparisons
ALLOW ORA throughout
More carbons (in ring) ALLOW has more electrons

OR OR larger (carbon) ring
more (surface area of) contact OR higher molecular mass
IGNORE bigger molecule
AND IGNORE chain instead of ring
DO NOT ALLOW ‘more contact between atoms’
more van der Waals forces
OR stronger van der Waals forces  ALLOW ‘VDW’ for van der Waals
‘More intermolecular forces’ is not sufficient
More energy needed to break the intermolecular forces  ALLOW it is harder to overcome the intermolecular forces
ALLOW intermolecular bonds / van der Waals bonds
ALLOW more energy is needed to separate molecules
IGNORE more energy is needed to break bonds
5

(b) tetrahedral  2 Mark each point independently
four bonding pairs repel OR four bonds repel  IGNORE surrounded by four atoms
IGNORE four areas of electron charge repel
IGNORE four electron pairs repel (one could be lp)
DO NOT ALLOW atoms repel
(c) 1 ALLOW correct structural OR displayed OR skeletal formula
OR mixture of the above (as long as unambiguous)
H H H
ALLOW structure of 1,2-isomer

Br C C C Br H H H
H H H Br C C C H

H Br H
IGNORE molecular formula

DO NOT ALLOW, structure of 1,1-isomer OR 2,2-isomer
H H H
Br C C C H
Br H H
(d) (i) C6H14  C6H12 + H2  1 ALLOW correct structural OR displayed OR skeletal formula
OR mixture of the above (as long as unambiguous)
ALLOW any correct multiple
IGNORE state symbols
6

(ii) Cyclohexane will burn more efficiently  1 KEY IDEA IS COMBUSTION OR BURNING
Assume ‘it’ refers to cyclohexane

ALLOW ORA for hexane
ALLOW cyclohexane allows smoother burning

OR promotes more efficient combustion
OR increases octane number
OR reduces knocking OR less likely to produce pre-ignition
OR burns better OR easier to burn OR combusts more easily
OR improves combustion
OR burns more cleanly
DO NOT ALLOW cyclohexane ignites more easily
IGNORE cyclohexane increase volatility of fuel
IGNORE reference to boiling points
IGNORE cyclohexane gives a better fuel
(e) (i) (Compounds with the) same structural formula but a 1 ALLOW different spatial arrangement of atoms.
different arrangement (of atoms) in space  DO NOT ALLOW different displayed formula.
(ii) 2 ALLOW displayed OR skeletal formula OR mixture of the

H CH 3 H H above.
C C C C ALLOW structures in either order
IGNORE molecular formula
H3 C H H3 C CH 3
IGNORE structural formula
  IGNORE names
IGNORE E/Z and cis/trans labels
ALLOW 1 mark for a pair of E/Z isomers of an incorrect
hydrocarbon structure with four C atoms e.g. C, or CH or
CH2 instead of CH3 groups.
7

(f) (i) 5
Step Equation IGNORE state symbols
Initiation
(1 mark) Br2  2Br•  IGNORE dots
C6H12 + Br•  C6H11• + HBr 
Propagation If an incorrect hydrocarbon with six C atoms is used:
(2 marks) DO NOT ALLOW any marks for the propagation steps but
C6H11• + Br2  C6H11Br + Br• 
ALLOW ECF for termination steps (i.e. 3 max)
C6H11• + Br•  C6H11Br
C6H11 • + C6H11 •  C12H22

Termination
(2 marks) Br• + Br•  Br2
Two correct 
All three correct 
(ii) The breaking of a (Br-Br) bond AND forms (two) radicals 1 ALLOW ‘the breaking of a covalent bond’
OR ALLOW the splitting of the bond in bromine
the breaking of a (Br-Br) bond AND one electron (from the
bond pair) goes to each atom/bromine  ALLOW the breaking of a covalent bond where each atom
keeps one of the bonding electrons
IGNORE particle for atom
ALLOW one electron goes to each product / species
DO NOT ALLOW molecule or compound for atom
IGNORE homolytic fission equations
(g) (i) C6H12 + 2Br2  C6H10Br2 + 2HBr  1 ALLOW molecular formula only.
(ii) 1,1-dibromocyclohexane 1 Locant numbers MUST lowest possible e.g. DO NOT

OR 1,2-dibromocyclohexane ALLOW 2,4-dibromocyclohexane etc.
OR 1,3-dibromocyclohexane
OR 1,4-dibromocyclohexane  IGNORE structures
Total 21
8

2 (a) It is an electron pair donor OR can donate a lone pair  1
(b) 3 ANNOTATE ANSWER WITH TICKS AND CROSSES ETC
C3H7 C3H 7
IGNORE connectivity to C3H7 throughout
  --
H C Br H3CO C H (+
+ Br
Br)
H H
OCH3 IGNORE alkyl group in first marking point.

Curly arrow must start from C–Br bond and not from C atom.
Dipole shown on the C-Br bond, C and Br- and curly arrow Dipole must be partial charge and not full charge
from the C-Br bond to the Br atom 
Curly arrow from :OCH3 to carbon atom in the C-Br bond  CH3O– curly arrow must come from one lone pair on O of
CH3O– ion OR from negative sign on O of the CH3O– ion
Correct organic product  ALLOW arrow from lone pair on O in OCH3–
Lone pair not required
SN1 mechanism DO NOT ALLOW CH3O-
DO NOT ALLOW incorrect connectivity of CH3O group in the
C3H7 C3H7 final product –CH3O

IGNORE Br- as a product

H C Br H C+ + Br-
H H ALLOW SN1 mechanism

Dipole shown on the C–Br bond, C and Br- and curly arrow
from C–Br bond to the Br atom 
C3H7 C3H7 curly arrow from CH3O– to carbonium ion
correct organic product 
H C+ H3CO C H
OCH3 H
H
9

(c) 1
1-Iodobutane increases the rate

AND
C—I bonds are weaker (than C—Br) All statements must be comparative
OR C—I bond has a lower bond enthalpy ALLOW ORA
OR C—I bond needs a smaller amount of energy to break IGNORE C—I bond is longer
OR C—I bond is easier to break  IGNORE polarity and references to electronegativity
(d) 2
O ALLOW only skeletal formula
O 
butyl ethanoate  DO NOT ALLOW ECF from incorrect structure.

ALLOW butylethanoate
ALLOW butanyl for butyl
DO NOT ALLOW butly
(e) (i) ( 136.9 × 100 ) = 47% 1 ALLOW 47 up to calculator value correctly rounded.
291.1 47.0 or 47.03 or 47.029 will be correct common answers
IGNORE any working shown.

(e) (ii) NaBr OR LiBr  1 ALLOW correct name or formula
DO NOT ALLOW HBr (it is an acid)
(e) (iii) Look at answer if 88.8% AWARD 3 marks Answer MUST be to 3 significant figures.
if 88.75% AWARD 2 marks (not 3 sig. fig.) 3
ALLOW ECF but do not allow a yield >100%
Moles of butan-1-ol = 0.08(00) 
Moles of 1-bromobutane = 0.071(0)  ALLOW Mass of 1-bromobutane expected = 10.952 g
% yield = 88.8% 
Total 12
10

3 (a) There are 3 marking points required for 2 marks 2 ANNOTATE ANSWER WITH TICKS AND CROSSES ETC
IGNORE state symbols.
Ea:
ALLOW (+)173 only as an alternative label for Ea
ALLOW no arrowhead or arrowheads at both ends of
Ea activation energy line
The Ea line must point to maximum (or near to the
maximum) on the curve OR span approximately 80%
H2(g) + I2(g)
of the distance between reactants and maximum
regardless of position
 ALLOW AE or AE for Ea
2HI(g)
ΔH:
IF there is no ∆H labelled ALLOW –9 as an alternative
label for ∆H.
IF ∆H is labelled IGNORE any numerical value.
DO NOT ALLOW –∆H.

ALLOW this arrow even if it has a small gap at the top
H2 and I2 on LHS and bottom i.e. does not quite reach reactant or
product line
AND 2HI on RHS
AND correctly labelled Ea 
ΔH labelled with product below reactant

AND arrow downwards 
(b) (+)182  1 This is the ONLY acceptable answer
11

(c) Look at answer if +63 kJ AWARD 2 marks 2
If 63 (no sign) OR-63 (incorrect sign) AWARD 1 mark ALLOW one mark for +126 kJ
No of moles of HI = 14 moles 
Enthalpy Change = +63 kJ  Sign and value required.

ALLOW ECF from incorrect number of moles of HI
(d) (i) Rate of the forward reaction is equal to the rate of the reverse 1 ALLOW both reactions occur at same rate
reaction 
OR
concentrations do not change IGNORE conc. of reactants = conc. of products
(ii) 2 Mark each point independently
More H2 and I2 OR less HI  ALLOW more reactants OR less products
(equilibrium position shifts) to the left Note: ALLOW suitable alternatives for to the left e.g.
AND towards reactants
(Forward) reaction is exothermic OR towards H2 / I2
OR reverse reaction is endothermic OR in reverse direction
OR in the endothermic direction OR favours the left.
ALLOW gives out heat for exothermic

ALLOW takes in heat for endothermic
IGNORE responses in terms of rate

(iii) No effect 1
AND
Same number of (gaseous) moles on both sides  ALLOW same number of molecules on each side
12

(e) Look at answer if (+)298 AWARD 2 marks 2
If answer is -298 AWARD 1 mark (incorrect sign)
2 x H-I bond enthalpy correctly calculated

(436 +151-(-9) =) (+)596 
ALLOW 1 mark for (+)293.5 kJ mol-1 (bonds broken divided
H-I bond enthalpy correctly calculated by 2)
ALLOW 1 mark for (+)289 kJ mol-1 (incorrect expression
(Bond energy for H-I (+)596 =) (+)298 kJ mol-1  i.e. [436 +151+(-9)])
2 2
Total 11
13

4 (a) FIRST, CHECK THE ANSWER ON ANSWER LINE 4 ANNOTATE ANSWER WITH TICKS AND CROSSES ETC
IF answer = –38.3 (kJ mol-1) award 4 marks
IF answer = (+)38.3 (kJ mol-1) award 3 marks (incorrect
sign)
IF answer = -38,300 (kJ mol-1) award 3 marks (used J
instead of kJ).
Energy Note: q = 50.0 × 4.18 × 5.5

q calculated correctly = 1149.5(J) OR 1.1495 (kJ)  ALLOW 1149.5 OR correctly rounded to 3 sig figs (J)
IGNORE sign
IGNORE working
ALLOW 53.18 × 4.18 × 5.5 OR 1222.6082 OR 1220 OR
correctly rounded to 3 or more sig figs in J or kJ
Moles
Amount, n, of Na2CO3 calculated correctly= 0.03(00)  IGNORE working
IGNORE trailing zeros
Calculating H
correctly calculates H in kJ mol-1 to 3 or more sig figs
IGNORE sign at this intermediate stage
ALLOW ECF from incorrect q and/or incorrect n
Rounding and Sign
calculated value of H rounded to 3 sig. fig. with minus
sign Final answer must have correct sign and three sig figs
ALLOW –40.8 kJ mol–1 if 53.18 used in calculation of q

ALLOW –40.7 kJ mol–1 if q is rounded to 1220 from 53.18
earlier
(b) (i) (Enthalpy change) when one mole of a compound  3 ALLOW energy required OR energy released
ALLOW one mole of substance OR one mole of product
is formed from its elements  DO NOT ALLOW one mole of element
298 K / 25 °C AND 1 atm / 100 kPa / 101 kPa / 1 bar  IGNORE reference to concentration
14

(ii) 2
½N2(g) + 2H2(g) + ½Cl2(g) + 2O2(g)  NH4ClO4(s)
correct species 
Second mark can only be awarded if all species in the
correct state symbols and balancing  equation are correct
DO NOT ALLOW multiples of this equation

(iii) FIRST, CHECK THE ANSWER ON ANSWER LINE 3 ANNOTATE ANSWER WITH TICKS AND CROSSES ETC
IF answer = (+)90 award 3 marks
IF answer = –90 award 2 marks
IF answer = 270 award 2 marks
IF answer = 2947 award 1 mark
Processing Hf values
(3832 – 885) 2947 Note: 2947 =  [–1676 + (–704) + (6 x –242)] – (3 x –295)]
OR
 (3832 – 885)
subtraction using H reaction
(2947-2677)= 270 
Calculation of H formation NO
ALLOW ECF for dividing by 3 from working that includes at
least one Hf and one balancing number and H (-2677) for
270/3 = (+)90 
1 mark
Total 12
15

5 (a) 2
H H Displayed formulae MUST be used to award each mark
H H
n C C C C
Cl H
Cl H n
Correct polymer with side links 
Balanced equation for formation of correct polymer - n on LHS can be at any height to the left of formula
correct use of n in the equation and brackets  AND n on the RHS must be a subscript
(essentially below the side link)
(b) (i) CH2CHCl + 2O2 CO + CO2 + HCl + H2O  1 ALLOW any other correctly balanced equation with the same
reactants and products
ALLOW C2H3Cl for CH2CHCl
(ii) Sodium hydrogencarbonate neutralises HCl  1 Assume that ‘it’ refers to sodium hydrogencarbonate but
DO NOT ALLOW other chemicals e.g. sodium
ALLOW NaHCO3 is a base

ALLOW forms a salt or sodium chloride or NaCl
ALLOW equation to show formation of NaCl from NaHCO3
and HCl even if not balanced.
IGNORE reacts
16

(c) ANY TWO from 2
abundance (in atmosphere) OR amount (in atmosphere)

OR (atmospheric) concentration OR percentage (in air) 
OR
ability to absorb infrared/IR (radiation) ALLOW absorption of infrared/IR
OR
residence time 
(d) (i) Any balanced equation between a metal oxide and carbon 1 ALLOW MO for metal oxide
dioxide to form a carbonate
e.g CaO + CO2 CaCO3 
(ii) ANY ONE FROM 1 Assume that ‘it’ refers to carbon dioxide but
DO NOT ALLOW carbon
deep in oceans
OR in geological formations DO NOT ALLOW reacted with oxides or stored as
OR (deep) in rocks carbonates.
OR in mines
OR in oil wells
OR in gas fields 
Total 8
17

6 (a) (i) 4 ANNOTATE ANSWER WITH TICKS AND CROSSES
ETC
Number
of Candidates do not need Ea on graph
Molecules
T1
T2
ALLOW particles instead of molecules on the y axis

Eact
Energy
DO NOT ALLOW atoms instead of particles/molecules
ALLOW ECF for the incorrect use of atoms (instead of
axes labelled (number of) molecules and (kinetic) energy  molecules/particles)
DO NOT ALLOW enthalpy on the x-axis
DO NOT ALLOW increase of more than one small

square at high energy end of curve.
Correct drawing of a two Boltzmann distributions
i.e. both curves must start within the first small square nearest to the
origin AND must not touch the x axis at high energy  Maximum of curve for higher temperature to right
AND lower than maximum of lower temperature curve
AND above lower temp line at higher energy
Higher temp line should intersect lower temp line once
Drawing of Boltzmann distribution at two different
temperatures with higher and lower temperature clearly DO NOT ALLOW lower activation energy
identified ( ie T2>T1)  QWC requires more molecules have or exceed
activation energy/Ea.
IGNORE more molecules have enough energy to
QWC - (At a higher temperature) more molecules have energy react for the QWC mark (as not linked to Ea)
above activation energy ORA if states the effect when the temperature is lower
IGNORE (more) successful collisions
OR greater area under the curve above the activation energy
18

(a) (ii) (Decreasing the pressure) decreases the rate of reaction 2 Correct effect on rate must be linked to reason for
the first marking point.
AND
Decreased concentration of molecules

OR ALLOW molecules are further apart
Number of molecules remains the same but the volume increases IGNORE less crowded
OR ALLOW particles or atoms for molecules
Less molecules per (unit) volume  ALLOW ‘space’ for volume
DO NOT ALLOW area instead of volume
Less frequent collisions  ALLOW collisions occur less often

OR decreased rate of collision
IGNORE less chance of collisions
‘less collisions’ alone is not sufficient

IGNORE successful
(b) (i) 2 ALLOW correct molecular OR structural OR displayed
C6H12O6 2C2H5OH + 2CO2  OR skeletal formula OR mixture of the above (as long
as unambiguous)
Temperature: Between 20 °C and 45 °C inclusive DO NOT ALLOW acidic or alkaline conditions

AND If there is a contradiction or an incorrect answer in
Condition: Absence of oxygen OR anaerobic  any condition given then do not award this mark.
ALLOW conditions shown in the equation
A limited supply of oxygen is not sufficient
IGNORE pressure
IGNORE yeast (in question)
ALLOW Lack of oxygen
(b) (ii) 2NO + 2CO 2CO2 + N2  1 ALLOW multiples
Total 9
19

7 (a) 1 ALLOW correct structural OR displayed OR skeletal
CH3 CH3 formula OR mixture of the above
H3 C C C H DO NOT ALLOW molecular formula
ALLOW dichloro or diiodo compound instead of the

Br Br  dibromo compound as the only alternatives.
(b) Reagent A: correct halogen e.g. Br2 / bromine 1 ALLOW Cl2 if dichloro compound drawn
ALLOW I2 if diiodo compound drawn

Answer must match box from (a) to score
(c) (i) Steam AND acid catalyst  1 ALLOW H+ / named acid / H2SO4 / H3PO4
ALLOW H2O(g)
ALLOW water only if a temperature of 100 °C or
above is quoted.
IGNORE any temperature given with steam
IGNORE pressure
(ii) (compounds or molecules) having the same molecular formula but 1 ALLOW different structure OR different displayed
different structural formulae  formula OR different skeletal formula for structure
Same formula is not sufficient

Different arrangement of atoms is not sufficient
(iii) 2 ALLOW correct structural OR displayed OR skeletal
CH3 CH3 CH3 CH3 formula OR mixture of the above
ALLOW any vertical bond to OH
H3C C C H H3C C C H DO NOT ALLOW OH–
OH H  H OH 
(iv) Does not contain OH group(s) 2 ALLOW ORA throughout
OR does not contain hydroxyl group(s) DO NOT ALLOW OH– (ions) / hydroxide (ions)
OR is not an alcohol 
Does not form hydrogen bonds with water  ‘Does not form hydrogen bonds’ is not sufficient
20

(d) Reagents: Acid/H and (potassium or sodium) dichromate/Cr2O72-
+
6 ANNOTATE ANSWER WITH TICKS AND CROSSES
seen once ETC
Observations: Orange to Green OR Orange to Blue

ALLOW H2SO4 and K2Cr2O7
Distillation / Distil produces aldehyde/CH3CH2CHO: 

ALLOW correct displayed formula OR correct
CH3CH2CH2OH + [O] CH3CH2CHO + H2O  structural formula OR skeletal formula OR a mixture of
the above
DO NOT ALLOW molecular formulae
ALLOW C3H7OH for propan-1-ol in equations
DO NOT ALLOW CH3CH2COH for aldehyde
Reflux (of propan-1-ol) produces carboxylic acid/CH3CH2COOH

IGNORE further oxidation of aldehyde
CH3CH2CH2OH + 2[O] CH3CH2COOH + H2O 
ALLOW CH3CH2CO2H for carboxylic acid
Total 14
21

8 (a) Molar mass of B = 74  6 ANNOTATE ANSWER WITH TICKS AND CROSSES ETC
B-F clearly identified Check and annotate page 19 below this response
B/alcohol: Molar mass = 2.59 = 74

H H OH H 0.035
For structure of B, C, D or E/F ALLOW correct displayed OR

H C C C C H
correct structural formula OR correct skeletal formula OR
mixture of the above as long as unambiguous.
H H H H 
DO NOT ALLOW missing H atom(s) in a displayed formula
C/ketone: for one structure but ALLOW missing H atoms in subsequent
H H O H
structures.
H C C C C H IGNORE names of organic compounds
H H H 
D/carboxylic acid:
H H O
H C C C E and F can be identified either way round
O H ALLOW H2O or displayed formula for mark

H H 
For E and F – ALLOW the two optical isomers
E and F:
H H O O
O C 2 H5 C 2 H5
CH3 H H
H C C C C
O C C C H C C C
CH 3 H 3C O C 2 H5
H H C2 H5 O
H H H H H

H2O/water 
22

8 (b) 7 ANNOTATE ANSWER WITH TICKS AND CROSSES ETC
Molecular formula for G: 2 marks
55.8 7.0 37.2
Mole ratio C : H : O = : :
12.0 1.0 16.0
ALLOW mass of C = 0.558 x 86 or 48 AND mass of H =
OR 4.65 : 7.0 : 2.33/2.325 OR 2 : 3 : 1 OR C2H3O 
0.07 x 86 or 6 AND mass of O = 0.372 x 86 = 32
Molecular formula of G C4H6O2 
Mass spectrum for G: 2 marks
Peak X or peak 41 indicates C3H5+ 

+ charge required for each response
Peak Y or peak 45 indicates COOH+ 
ALLOW one mark if both formulae are correct but with no
charge/incorrect charge
ALLOW any possible fragments that contain C, H and/or O

that have the correct mass. E.g. Peak X indicates C2OH+,
Peak Y indicates C2H5O+
Unfeasible fragments are not allowed e.g. C3H9+ (too many H
Infrared for G: 1 mark
atoms)
Peak at 1640–1750 cm-1 indicates presence of C=O
LOOK ON THE SPECTRUM for labelled absorbance which
AND
can be given credit
Peak at 2500–3300 cm-1 (indicates the presence of) –OH
Candidates must link absorbance to bond in order to gain the
group linked carboxylic acid/COOH QWC 
mark
ALLOW 1700 cm-1
For 2500–3300 cm-1, ALLOW 2900 cm-1 or any stated

wavenumber with range 2500–3300 cm-1
ALLOW wavenumber range up to 2400–3500 cm-1
23
Structure of G: 2 marks
Correct structure: ALLOW structural, skeletal or displayed formula.

CH 3 O
H
DO NOT ALLOW ECF from incorrect molecular formula
C C C
H O H 
1 mark for one of the following structures of C4H6O2:
OR
OR
Total 13
24

June 14 QP + MS

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June 14 QP + MS

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Tuesday 3 June 2014 – Afternoon

Candidates answer on the Question Paper.

INFORMATION FOR CANDIDATES

© OCR 2014 [H/500/7834] OCR is an exempt Charity

1 This question is about cyclic organic compounds.

The table shows some information about cycloalkanes.

Cycloalkane Skeletal formula Boiling point / °C

(i) What is meant by the term homologous series?

(ii) State the general formula for these cycloalkanes.

© OCR 2014 Turn over

Suggest the structure of the organic product formed in this reaction.

(d) Petrol contains both cyclohexane, C6H12, and hexane.

Cyclohexane can be prepared from hexane.

(i) Construct the equation for this reaction.

(ii) Suggest one advantage of adding cyclohexane to hexane in petrol.

(e) Cyclobutane is another cycloalkane.

There are several unsaturated isomers of cyclobutane that are alkenes.

Two of these isomers are stereoisomers.

(i) Explain what is meant by the term stereoisomers.

(ii) Draw these two stereoisomers.

A mixture of cyclic organic compounds is formed, including C6H11Br.

Include all possible termination steps in your answer.

(ii) The initiation step involves homolytic fission.

Explain why the initiation step is an example of homolytic fission.

© OCR 2014 Turn over

(a) Suggest how the methoxide ion can act as a nucleophile.

Show any relevant dipoles.

(c) 1-Iodobutane also reacts with methoxide ions.

1-Iodobutane does not change the rate

Explain your answer.

name of product .................................................................................................................. [2]

C4H9OH + KBr + H2SO4 C4H9Br + KHSO4 + H2O

atom economy = ..................................................... % [1]

(iii) A student prepares a sample of 1-bromobutane.

Calculate the percentage yield.

Give your answer to three significant figures.

percentage yield = ...................................................... % [3]

© OCR 2014 Turn over

This reversible reaction is shown in equilibrium 3.1 below.

H2(g) + I2(g) 2HI(g) ΔH = −9 kJ mol−1 equilibrium 3.1

The activation energy for the forward reaction is 173 kJ mol−1.

Ea (reverse reaction) = ............................................ kJ mol−1 [1]

Include the sign for enthalpy change in your answer.

enthalpy change .................................................... kJ [2]

H2(g) + I2(g) 2HI(g) ΔH = −9 kJ mol−1 equilibrium 3.1

(i) A closed system is required for dynamic equilibrium to be established.

State one other feature of this dynamic equilibrium.

Predict how the composition of the equilibrium mixture changes on heating.

Explain your answer.

Bond Bond Enthalpy / kJ mol−1

bond enthalpy ........................................... kJ mol−1 [2]

Na2CO3(s) + 2HCl(aq) 2NaCl(aq) + CO2(g) + H2O(l)

Calculate ΔHr , in kJ mol−1.

Give your answer to three significant figures.

ΔHr = ........................................... kJ mol−1 [4]

3Al(s) + 3NH4ClO4(s) Al 2O3(s) + AlCl 3(s) + 6H2O(g) + 3NO(g) ΔH = –2677 kJ mol−1

Standard enthalpy change of

(i) What is meant by the term standard enthalpy change of formation?

Give the standard conditions.

enthalpy change of formation of NO(g) = ........................................... kJ mol−1 [3]