Practice Paper

_Please write clearly in block capitals

Centre number_ Candidate number_

Surname ___________________________________________________

Forename(s) ___________________________________________________

Candidate signature ___________________________________________________

I declare this my own work

A-level
CHEMISTRY
Paper 2 Organic and Physical Chemistry
Time allowed: 2 hours

Materials For Examiner’s Use

For this paper, you must have:
• the Periodic Table/Data Booklet, provided as an insert Question Mark
• a ruler with millimetre measurements
• a scientific calculator 1

Instructions 2
• Use black ink or ball-point pen.
• Fill in the boxes at the top of this page. 3
• You must answer all questions.
• You must answer the questions in the spaces provided. Do not 4
• write outside the box around each page or on blank pages.
• If you need extra space for your answer(s), use the lined page(s) 5
• at the back of this book, clearly indicating the question number.
• All working must be shown. 6
• Do all rough work in this book. Cross through any work you do
7
• not want to be marked.
Information 8
• The marks for questions are shown in brackets.
• The maximum mark for this paper is 105. 9

Disclaimer 10
• This paper is not official material produced by AQA. Interpret the
• paper as you will, but the questions should not be taken to be 11
• accurate predictions for the upcoming exam series.
TOTAL
 2

_01 Skatole is the compound that is most responsible for the smell of faeces.
Figure 1 shows the skeletal formula of skatole.
Figure 1

_01.1 Write down the molecular formula of skatole.

[1 mark]

________________________________________________________________

_01.2 Calculate the number of atoms in 2.0 grams of skatole, giving your answer to an
appropriate number of significant figures.

[3 marks]

________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________

Number of atoms = _____________

 3

_01.3 Predict the shape of the nitrogen atom in a molecule of skatole.

Justify your answer.

[3 marks]

_Shape of nitrogen atom:

________________________________________________________________

_Justification:

________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________

_01.4 Draw the displayed formula of skatole in the space below.

[1 mark]
 4

_02.1 Three organic compounds are to be identified using test tube reactions.
In no particular order, the compounds are known to be cyclohexene, butanoic acid and
oct-2-enoic acid.
Two test tube reactions are proposed to assist with the identification of these compounds:
(1) Heat the sample gently with ethanol and a few drops of concentrated sulphuric acid.
(2) Add a few drops of a solution containing starch and iodine to the sample.
Describe what would be observed when each of the organic compounds undergo the
proposed tests and include equations for any reactions that may occur.

[6 marks]

________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
 5

________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
 6

_03 This question concerns the chemistry of the following organic nitrogen compounds:

_03.1 Write down the structural formula of the above organic nitrogen compound with the
highest melting point.

[1 mark]

________________________________________________________________

_03.2 Explain your answer to question 03.1.

[5 marks]

________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
 7

_03.3 Explain which of the four listed organic nitrogen compounds acts as the strongest base.

[3 marks]

________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________

_03.4 Tetrapropylammonium chloride is formed when one of the four listed organic nitrogen
compounds reacts with a suitable chloroalkane.
Circle the structure of the organic nitrogen compound required and identify the suitable
chloroalkane and the condition required to form tetrapropylammonium chloride.
Suggest a possible use of tetrapropylammonium chloride.

[4 marks]

_Chloroalkane required:

________________________________________________________________
_Condition:

________________________________________________________________
_Use of tetrapropylammonium chloride:

________________________________________________________________
________________________________________________________________
________________________________________________________________
 8

_03.5 Amines can be produced by heating an amide with bromine and sodium hydroxide.
The side products of this reaction are carbon dioxide, water and sodium bromide:
RCONH2 + 2NaOH + Br2 → RNH2 + CO2 + H2O + 2NaBr
Organic compound A is heated and refluxed with acidified potassium dichromate to form
the organic compound B, which is then heated with bromine and sodium hydroxide to form
organic compound C.
Figure 2 shows the structure of the product formed when organic compound C is treated
with a stoichiometric quantity of dilute sulphuric acid solution.
Figure 2

Identify organic compounds A and B and write down an equation showing the conversion
of organic compound A to organic compound B.
You may represent the potassium dichromate as [O] and state symbols are not required.

[3 marks]

_Identity of organic compound A:

________________________________________________________________
_Identity of organic compound B:

________________________________________________________________
_Equation:

________________________________________________________________
________________________________________________________________
 9

_04.1 Cisplatin binds to guanine in DNA after a series of ligand exchange reactions.
State why this makes cisplatin an effective anticancer drug.

[1 mark]

________________________________________________________________
________________________________________________________________
________________________________________________________________

_04.2 Figure 3 shows a complementary pair of DNA nucleotides

Figure 3

Describe how DNA nucleotides join to form a molecule of DNA.

[3 marks]

________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
 10

_05 A primary chloroalkane is hydrolysed using dilute sodium hydroxide.

_05.1 Give the name and an outline of the mechanism in this reaction, including relevant
dipoles, curly arrows and lone pairs.
In your answer, you should represent the primary chloroalkane as R-CH2-Cl.

[5 marks]

_Name of mechanism:

________________________________________________________________

_Outline of mechanism:

________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
__________________________________
_05.2 It is given that the first step of the mechanism in question 05.1 is the rate-determining step
of the reaction.
Write down a suitable rate equation for this reaction in terms of t, [R-CH2-Cl], [OH-] and k,
where t is the time elapsed and k is a rate constant.

[1 mark]

________________________________________________________________
 11

_06.1 Give four reasons why TMS is a suitable standard for 13C nmr spectroscopy.

[4 marks]

________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________

_06.2 Give one advantage and one disadvantage of using deuterated water as a solvent in 1H
nmr spectroscopy.

[2 marks]

_Advantage:

________________________________________________________________
________________________________________________________________
________________________________________________________________
_Disadvantage:

________________________________________________________________
________________________________________________________________
________________________________________________________________
 12

_06.3 Compare and contrast the integrated 1H nmr spectra of propan-1-ol and propan-2-ol.
In your answer, you should include the peak area ratios for each spectrum.

[6 marks]

________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
 13

________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
 14

_07 This question concerns the chemistry of benzene and cyclohexene.

_07.1 Outline the mechanism for the reaction of cyclohexene with iodine monobromide.

[3 marks]

________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________

_07.2 Cyclohexene can undergo polymerisation to form poly(cyclohexene).

Draw two repeat units of the polymer poly(cyclohexene).

[1 mark]

________________________________________________________________
________________________________________________________________
________________________________________________________________
 15

_07.3 Some enthalpy change data is shown in table 1.

Table 1

Enthalpy change
/ kJ mol-1

6C (s) + 3H2 (g) → C6H6 (l) +49

6C (s) + 6H2 (g) → C6H12 (l) -156

C6H10 (l) + H2 (g) → C6H12 (l) -119

The Kekulé model would suggest that the enthalpy of hydrogenation of benzene would be
expected to be around triple the enthalpy of hydrogenation of cyclohexene.
Using the data in table 1, explain why a delocalised model for the structure of benzene is
favoured over the Kekulé model.

[5 marks]

________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
 16

_07.4 Compare and contrast the reactions of benzene and cyclohexene with chlorine.

[4 marks]

________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
 17

There are no questions printed on this page

DO NOT WRITE ON THIS PAGE

ANSWER IN THE SPACES PROVIDED
 18

_08 Hydrogen can be used to reduce nitrogen monoxide.

It is proposed that the reaction proceeds by the following three-step mechanism:

1. 2NO (g) ⇌ N2O2 (g) fast

2. N2O2 (g) + H2 (g) → N2O (g) + H2O (l) slow

3. N2O (g) + H2 (g) → N2 (g) + H2O (l) fast

_08.1 It can be inferred from the proposed mechanism that the rate equation for the reaction can
be given by the expression:
Rate = k [N2O2] [H2]
By considering a suitable equilibrium constant, find a rate equation for this reaction in
terms of [NO] and [H2].
Considering this rate equation in terms of [NO] and [H2], state the overall order of reaction.

[3 marks]

_Rate equation:

________________________________________________________________

________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
Overall order of reaction: _____________
 19

_08.2 Table 2 shows data collected for a series of experiments performed at the same
temperature, in which the concentrations of nitrogen monoxide and hydrogen are varied.
Table 2

Experiment [NO] [H2] Initial rate

/ mol dm-3 / mol dm-3 / mol dm-3 s-1

1 0.10 0.10 4.50 × 10-5

2 0.10 0.20 9.00 × 10-5

3 0.20 0.30 5.40 × 10-4

Considering these results, comment on the validity of the proposed mechanism.

[4 marks]

________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________

________________________________________________________________
________________________________________________________________
________________________________________________________________
 20

_08.3 The concentration of hydrogen in the reaction mixture can be monitored at any given time,
because water is produced as a product of the reaction.
Describe how one could use this to determine the initial rate of reaction.

[5 marks]

________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
 21

There are no questions printed on this page

DO NOT WRITE ON THIS PAGE

ANSWER IN THE SPACES PROVIDED
 22

_09 The Arrhenius equation can be expressed as

Figure 3 shows an Arrhenius plot for a reaction.

Figure 3

_09.1 Explain why a graph of ln k against T-1 would be a straight line.

[1 mark]

________________________________________________________________
________________________________________________________________
________________________________________________________________
 23

_09.2 Use the Arrhenius plot to calculate the activation energy for this reaction and hence,
extrapolate the value of the rate constant at -223 °C.
The gas constant R = 8.31 J K-1 mol-1

[6 marks]

________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
Activation energy: ____________ kJ mol-1_

Rate constant at -270 °C: ____________ units_

 24

_10 This question concerns factors that affect rate of the reduction of nitrogen monoxide by
hydrogen and the Maxwell-Boltzmann distribution:
2NO (g) + 2H2 (g) → N2 (g) + 2H2O (l)

_10.1 Explain the effect of increasing the pressure on the rate of this reaction.

[2 marks]

________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________

_10.2 When a reaction mixture contains a large excess of nitrogen monoxide compared to
hydrogen, the rate of reaction can be found using the following expression:
Rate = k × p(H2)
Where p(H2) is the partial pressure of hydrogen.
Since the partial pressure of hydrogen itself is directly proportional to the total pressure, it
can be said that the rate of reaction is directly proportional to the total pressure.
Explain why this relationship is only valid when there is a large excess of nitrogen
monoxide compared to hydrogen.

[2 marks]

________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
 25

_10.3 Explain, in terms of the Maxwell-Boltzmann distribution, how the decreasing the
temperature of the system, adding more hydrogen and nitrogen monoxide to the system
and adding a catalyst to the system affects the rate of reaction.
You may include diagrams to illustrate your answer.

[7 marks]

________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
 26

_11 Compound E can be produced by the following reaction

2A (g) + 2D (g) ⇌ E (g)

_11.1 A mixture of compounds A and D is heated to a temperature of 1000 K in a container of

volume 125 dm3. At equilibrium, the pressure is 166.20 kPa.
The initial concentrations of A and D are both 0.016 mol dm-3.
By letting the moles of E at equilibrium be x, calculate the value of Kc for this reaction at
1000 K.
Give your answer to three significant figures and include a suitable unit.

[10 marks]

________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
 27

Value of Kc = ____________ Unit: _____________

END OF QUESTIONS
 28

There are no questions printed on this page

DO NOT WRITE ON THIS PAGE

ANSWER IN THE SPACES PROVIDED
 29

There are no questions printed on this page

DO NOT WRITE ON THIS PAGE

ANSWER IN THE SPACES PROVIDED
 30

ADDITIONAL PAGE, IF REQUIRED

Write the question number(s) in the left-hand margin

______________________________________________________
______________________________________________________
______________________________________________________
______________________________________________________
______________________________________________________
______________________________________________________
______________________________________________________
______________________________________________________
______________________________________________________
______________________________________________________
______________________________________________________
______________________________________________________
______________________________________________________
______________________________________________________
______________________________________________________
______________________________________________________
______________________________________________________
______________________________________________________
______________________________________________________
______________________________________________________
______________________________________________________
______________________________________________________
 31

ADDITIONAL PAGE, IF REQUIRED

Write the question number(s) in the left-hand margin

______________________________________________________
______________________________________________________
______________________________________________________
______________________________________________________
______________________________________________________
______________________________________________________
______________________________________________________
______________________________________________________
______________________________________________________
______________________________________________________
______________________________________________________
______________________________________________________
______________________________________________________
______________________________________________________
______________________________________________________
______________________________________________________
______________________________________________________
______________________________________________________
______________________________________________________
______________________________________________________
______________________________________________________
______________________________________________________
 32

ADDITIONAL PAGE, IF REQUIRED

Write the question number(s) in the left-hand margin

______________________________________________________
______________________________________________________
______________________________________________________
______________________________________________________
______________________________________________________
______________________________________________________
______________________________________________________
______________________________________________________
______________________________________________________
______________________________________________________
______________________________________________________
______________________________________________________
______________________________________________________
______________________________________________________
______________________________________________________
______________________________________________________
______________________________________________________
______________________________________________________
______________________________________________________
______________________________________________________
______________________________________________________
______________________________________________________
 33

The next page contains the mark scheme.

 34

PAPER 2 MARK SCHEME: ORGANIC AND PHYSICAL CHEMISTRY:

Question Answers Mark: Additional Comments/Guidance

01.1 C9H9N 1

Question Answers Mark: Additional Comments/Guidance

01.2 Moles of skatole calculated 1 n(C9H9N) = (2.0 g)/(131 g mol-1) = 0.015… mol

Multiplication by 19 in answer 1 n(atoms) = 19(0.015… mol) = 0.29… mol

Correct answer to two significant figures 1 (0.29… mol)(6.02 × 1023 mol-1) = 1.7 × 1023

Question Answers Mark: Additional Comments/Guidance

01.3 Shape: Trigonal pyramid(al) 1

3 bonding pairs around nitrogen atom 1

1 lone pair on nitrogen 1

Question Answers Mark: Additional Comments/Guidance

01.4 1 Allow a delocalised ring for 6-membered ring.

 35

Question Answers Mark: Additional Comments/Guidance

02.1 With ethanol and a few drops of conc. H2SO4:

Both butanoic acid and oct-2-enoic acid give a fruity 1

smell

CH3(CH2)2COOH + CH3CH2OH ⇌ 1 Condone use of ‘→‘ instead of ‘⇌’ for both esterification
CH3(CH2)2COOCH2CH3 + H2O equations

CH3CH=CH(CH2)4COOH + CH3CH2OH ⇌ 1
CH3CH=CH(CH2)4COOCH2CH3 + H2O

With starch-iodine solution:

Both cyclohexene and oct-2-enoic acid turn the solution 1

from blue-black to colourless

C6H10 + I2 → C6H10I2 1

CH3CH=CH(CH2)4COOH + I2 → CH3(CHI)2(CH2)4COOH 1

Question Answers Mark: Additional Comments/Guidance

03.1 NH2CH2COOH 1
 36

Question Answers Mark: Additional Comments/Guidance

03.2 NH2CH2COOH/Glycine can form zwitterions in the solid 1

state.

So there are strong ionic bonds between the zwitterions 1

The strongest intermolecular interactions in 1

NH2(CH2)2CH3 and CH3NHCH2CH3 are hydrogen bonds

The strongest intermolecular forces in N(CH3)3 are 1

permanent dipole-dipole interactions

Ionic bonds are stronger than hydrogen bonds and 1

permanent dipole-dipole interactions, so more thermal
energy is needed to overcome them.

Question Answers Mark: Additional Comments/Guidance

03.3 N(CH3)3/trimethylamine 1

3 alkyl/methyl groups have strong (positive) inductive 1

effect/push electrons onto nitrogen

So lone pair is more available than in other 3 compounds 1

 37

Question Answers Mark: Additional Comments/Guidance

03.4 Circles structure of 1-aminopropane at start of question 1

Chloroalkane: 1-chloropropane 1

Condition: excess chloroalkane/1-chloropropane used 1 Allow ‘make 1-aminopropane the limiting

reactant/reagent’

Use: (cationic) surfactant/disinfectant 1 Allow ‘reagent’/’used in synthesis’

Question Answers Mark: Additional Comments/Guidance

03.5 Compound A: NH2COCH2CH2OH 1 Allow 3-hydroxypropanamide

Compound B: NH2COCH2COOH 1 Allow 3-amino-3-oxopropanoic acid (though this would

not be expected at A level)

Equation: 1
NH2COCH2CH2OH + 2[O] → NH2COCH2COOH + H2O

Question Answers Mark: Additional Comments/Guidance

04.1 It prevents DNA replication 1

 38

Question Answers Mark: Additional Comments/Guidance

04.2 A condensation reaction/condensation polymerisation 1

Occurs between the phosphate and hydroxyl groups (on 1

the sugar/deoxyribose units) to form a single strand

Hydrogen bonding between the complementary bases 1

joins two adjacent strands

Question Answers Mark: Additional Comments/Guidance

05.1 Name of mechanism: nucleophilic substitution 1 Example of acceptable mechanism:

Correct dipole on R-CH2-Cl (δ+ C-Cl δ-) 1

Lone pair on OH- donated to carbon in R-CH2-Cl 1

Correct intermediate formed with curly arrow showing 1

lysis of C-Cl or simply lysis of C-Cl without intermediate
shown.

Correct final products 1

Question Answers Mark: Additional Comments/Guidance

05.2 1/t = k [R-CH2-Cl] [OH-] or 1/t ∝ [R-CH2-Cl] [OH-] 1

 39

Question Answers Mark: Additional Comments/Guidance

06.1 Each of the following scores 1 mark, with a maximum of 1 (x4)

four marks:

-All four carbons/methyl groups are identical

environments

-TMS is volatile/easy to remove from sample

-TMS is nontoxic

-TMS is inert

-TMS mixes well with most organic compounds

Question Answers Mark: Additional Comments/Guidance

06.2 A suitable advantage, i.e doesn’t give additional signals, 1

good solvent for polar compounds etc

A suitable disadvantage, i.e expensive to use, not all 1

compounds dissolve well in it, loss of O-H peaks etc
 40

Question Answers Mark: Additional Comments/Guidance

06.3 This question is marked using levels of response. Stage 1: Numbers of signals:

Level 3 All stages covered and the explanation 1a: Propan-1-ol has 4 signals
5 - 6 marks of each stage is correct and virtually 1b: Propan-2-ol has 3 signals
complete.
Answer is communicated coherently Stage 2: Splitting patterns and shifts:
and shows a logical progression from
stage 1 to stage 2 to stage 3 2a: Both spectra have a singlet peak due to O-H in
region 0.5 - 5.0 ppm
Level 2 All stages covered but the explanation 2b: Both spectra have a triplet peak due to -CH3 groups
3 - 4 marks of each is incomplete or contains in region 0.7 - 1.2 ppm
inaccuracies. OR two stages are 2c: Both spectra have R-O-C-H peaks in region 3.1 - 3.9
covered and the explanations are ppm, though it is a triplet for propan-1-ol and a septet for
correct and virtually complete. propan-2-ol
2d: Propan-1-ol has a sextet peak due to -CH2- in region
Answer is mainly coherent and shows 1.2 - 1.4 ppm, whereas propan-2-ol does not.
progression from stage 1 to stage 2 6
and/or stage 3 Stage 3: Integration curve/peak areas:
Level 1 Two stages are covered but the 3a: The sum of the peak areas in both spectra are
1 - 2 marks explanation of each stage may be identical
incomplete or may contain 3b: Ratio of peak areas/integration ratio in 1H spectrum
inaccuracies. OR one stage is covered of propan-1-ol (in order of increasing shift values):
and the explanations are correct and 3:2:1:2
virtually complete. 3c: Ratio of peak areas/integration ratio in 1H spectrum
Answer includes isolated statements of propan-2-ol (in order of increasing shift values): 6:1:1
and these are presented in a logical
order.

Level 0 Insufficient correct chemistry to gain a

0 marks mark.
 41

Question Answers Mark: Additional Comments/Guidance

07.1 I-Br with correct dipole and heterolytic fission shown with 1 Example of acceptable mechanism:
a curly arrow

Correct intermediate formed - do not allow an 1

intermediate carbocation with a bromine atom attached
to the cyclohexane ring and a free iodide ion.

Curly arrow leading from lone pair on bromide ion, 1

resulting in formation of final product.

Question Answers Mark: Additional Comments/Guidance

07.2 1 Ignore brackets, but do not allow n, as the question

asks for two repeat units.
 42

Question Answers Mark: Additional Comments/Guidance

7.3 Estimated enthalpy change = -357 kJ mol-1 1 3(-119 kJ mol-1) = -357 kJ mol-1

Attempt at Hess’ law seen for calculation of actual 1 e.g ΔH = (-49 kJ mol-1) + (-156 kJ mol-1)
enthalpy change

Actual enthalpy change = -205 kJ mol-1 1

The actual enthalpy change is much less exothermic 1 Allow the actual enthalpy change is less exothermic or is
than is expected greater than than the estimated by 152 kJ mol-1

So there must be a structural feature/delocalisation that 1

adds stability to the ring.
 43

Question Answers Mark: Additional Comments/Guidance

7.4 Similarities:

Each of the following scores 1 mark, with a maximum of 1 (x2)

two marks:

-In both reactions, chlorine acts as an electrophile.

-Both reactions involve the formation of an intermediate.

-In both reactions, a heterolytic bond fission occurs.

Differences:

Each of the following scores 1 mark, with a maximum of 1 (x2)

two marks:

-There is no requirement for a catalyst and heating with

cyclohexane, but a catalyst and heating are needed for
benzene.

-With cyclohexene, it is addition. With benzene, it is (a

single) substitution.

-There are no side products in the reaction with

cyclohexene, but with benzene, HCl is produced as a
product.

-The product produced with benzene is aromatic,

whereas the product produced with cyclohexane is not.
 44

Question Answers Mark: Additional Comments/Guidance

08.1 Kc = [N2O2]/[NO]2 ⇒ Kc[NO]2 = [N2O2] 1

So rate = kKc[NO]2[H2] 1 Where kKc = overall rate constant

Overall order of reaction = 2 + 1 = 3 1

Question Answers Mark: Additional Comments/Guidance

08.2 Order wrt H2 = 1 1 0.20/0.10 = 2, (9.00 × 10-5)/(4.50 × 10-5) = 2 ⇒ 1st order

Calculates factor by which rate increases when 1 (5.40 × 10-4)/(4.50 × 10-5) = 12

comparing 1 and 3 or 2 and 3 or (5.40 × 10-4)/(9.00 × 10-5) = 6

Order wrt NO = 2 1 Fbw [H2] increases = (0.2)/(0.1) = 2 or (0.3)/(0.2) = 1.5

Fbw [NO] increases = (0.2)/(0.1) = 2
⇒ Fbw [NO] affects rate = 12/3 or 6/1.5 = 4 ⇒ 2nd order
(Fbw is a shorthand for ‘factor by which’)

Since the order wrt NO is 2 and the order wrt H2 is 1 1 TE on their 08.1
from the proposed mechanism, this result is consistent
and so the proposed mechanism is valid.
 45

Question Answers Mark: Additional Comments/Guidance

08.3 Record volume/mass of water produced at regular 1

intervals of time.

Plot a graph of volume/mass of water (y-axis) against 1

time (x-axis)

Draw a tangent to the graph 1

At t = 0 1

And calculate the gradient 1

Question Answers Mark: Additional Comments/Guidance

09.1 Correctly compares (rewritten) equation to y = mx + c 1

ln(k) = -Ea/R (T-1) + ln(A)

y = m x + c
 46

Question Answers Mark: Additional Comments/Guidance

09.2 Clear attempt to calculate the gradient seen 1 (15 - -65)/(0.0000 K-1 - 0.0100 K-1)

Gradient = -8000 K 1 = -8000 K

Multiplication by -R 1 (-8000 K)(-8.31 J K-1 mol-1) = +66,840 J mol-1

Activation energy = (+)66.8 kJ mol-1 1 Allow +66.84 or +67, positive sign does not need to be
shown, but do not accept a negative activation energy

Attempt at use of the given formula or the exponential 1 ln(k) = (-8000 K)/(50 K) + 15 = -145
form of Arrhenius’ equation with ln(A) = 15 or A = e15 and k = (e15)exp[(-8000 K)/(50 K)]
T = 50 K

Rate constant = 1.06 × 10-63 units 1 Allow 1.1 × 10-63 or better

Question Answers Mark: Additional Comments/Guidance

10.1 The molecules are forced closer together, so there is a 1

greater probability of successful collisions.

So more frequent, successful collisions per second/unit 1

time.
 47

Question Answers Mark: Additional Comments/Guidance

10.2 (As there is a large excess of nitrogen monoxide,) the 1 Do not allow an answer that suggests all of the hydrogen
number of moles of nitrogen monoxide are (virtually) molecules have reacted.
constant throughout the reaction.

So the partial pressure of nitrogen monoxide is also 1

(virtually) constant throughout the reaction

Question Answers Mark: Additional Comments/Guidance

10.3 The area under a Maxwell-Boltzmann distribution is 1

directly proportional to the total number of molecules

Therefore the greater the area past the activation energy 1

line, the more molecules that are able to react

Adding more hydrogen and nitrogen monoxide increases 1

the area past the activation energy line

Adding a catalyst decreases Ea, so the area past the 1 May be shown using a diagram with an Ea (catalysed)
activation energy line is also greater than before. line drawn to the left of the Ea line

So there are more molecules with E ≥ Ea than before 1

after both changes

So there are more frequent, successful collisions per 1

second/unit time

And as a result of both changes, the rate of reaction 1

increases.
 48

Question Answers Mark: Additional Comments/Guidance

11.1 Initial moles of both reactants found 1 mol A = mol D = (125 dm3)(0.016 mol dm-3) = 2 mol

Finds moles of each gas at equilibrium, in terms of x mol 1 mol A = mol D = (2 - 2x) mol

Total moles of gas at equilibrium = (4 - 3x) mol 1 (2 - 2x) mol + (2 - 2x) mol + x mol = (4 - 3x) mol

Attempt at use of pV = nRT 1 pV = nRT ⇒ pV/RT = n

n = (166.20 kPa)(125 dm3)/(8.31 J K-1 mol-1)(1000 K)

Total moles of gas at equilibrium = 2.5 mol 1 = 2.5 mol

x = 0.5 mol 1 4 - 3x = 2.5 ⇒ x = 0.5 mol

Concentrations of each gas found 1 [A] = [D] = (1 mol)/(125 dm3) = 0.008 mol dm-3
[E] = (0.5 mol)/(125 dm3) = 0.004 mol dm-3

Correct Kc expression 1 Kc = [E] / [A]2[D]2

Kc = 977,000 (must be to 3 sf to score the mark) 1 Kc = (0.004) / (0.008)2(0.008)2 = 977,000 (3 sf)

Unit = mol-3 dm9 1 Unit = (mol dm-3) / (mol dm-3)2(mol dm-3)2 = mol-3 dm9