Please write clearly in block capitals.

Centre number Candidate number

Surname

Forename(s)

Candidate signature
I declare this is 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 (enclosed) Question Mark
• a ruler with millimetre measurements
1
• a scientific calculator, which you are expected to use where appropriate.
2
Instructions 3
• Use black ink or black ball-point pen. 4
• Fill in the boxes at the top of this page.
5
• Answer all questions.
• You must answer the questions in the spaces provided. Do not write outside 6
the box around each page or on blank pages. 7
• If you need extra space for your answer(s), use the lined pages at the end of 8
this book. Write the question number against your answer(s).
• All working must be shown. 9
• Do all rough work in this book. Cross through any work you do not want to 10
be marked.
TOTAL

Information
• The marks for questions are shown in brackets.
• The maximum mark for this paper is 105.

*Jun217405201*
IB/M/Jun21/E12 7405/2
 2
Do not write
outside the
Answer all questions in the spaces provided. box

0 1 Coconut oil contains a triester with three identical R groups.

This triester reacts with potassium hydroxide.

0 1 . 1 Complete the equation by drawing the structure of the other product of this reaction in
the box.

Name the type of compound shown by the formula RCOOK

Give one use for this type of compound.

[3 marks]

Type of compound

Use

0 1 . 2 The triester in coconut oil has a relative molecular mass, Mr = 638.0

In the equation shown at the start of Question 01, R represents an alkyl group that
can be written as CH3(CH2)n

Deduce the value of n in CH3(CH2)n

Show your working.
[3 marks]

*02*
IB/M/Jun21/7405/2
 3
Do not write
outside the
0 1 . 3 A 1.450 g sample of coconut oil is heated with 0.421 g of KOH in aqueous ethanol box

until all of the triester is hydrolysed.

The mixture is cooled.
The remaining KOH is neutralised by exactly 15.65 cm3 of 0.100 mol dm–3 HCl

Calculate the percentage by mass of the triester (Mr = 638.0) in the coconut oil.
[6 marks]

Percentage by mass

Turn over ►

*03*
IB/M/Jun21/7405/2
 4
Do not write
outside the
0 1 . 4 Suggest why aqueous ethanol is a suitable solvent when heating the coconut oil box

with KOH.

Give a safety precaution used when heating the mixture.

Justify your choice.
[3 marks]

Reason

Safety precaution

Justification
15

*04*
IB/M/Jun21/7405/2
 5
Do not write
outside the
0 2 This question is about fuels. box

0 2 . 1 The petrol fraction obtained from crude oil can be used as fuel in cars.

State the meaning of fraction, as used in the term petrol fraction.

[1 mark]

0 2 . 2 Hexadecane (C16H34) can be cracked at high temperature to form petrol.

Complete the equation to show the cracking of one molecule of hexadecane to form
hexane and cyclopentane only.

Give the name of a catalyst used in this cracking reaction.

[3 marks]

C16H34 → +

Catalyst

0 2 . 3 Carbon dioxide is formed when petrol is burned.

Carbon dioxide acts as a greenhouse gas when it absorbs infrared radiation.

Give a reason why carbon dioxide absorbs infrared radiation.

[1 mark]

Question 2 continues on the next page

Turn over ►

*05*
IB/M/Jun21/7405/2
 6
Do not write
outside the
0 2 . 4 Compound Z (HOCH2CH2NH2) can be used to remove carbon dioxide from the box

mixture of waste gases produced in some power stations.

Figure 1 shows part of a suggested mechanism for the reaction of Z with

carbon dioxide.

Figure 1

Draw two curly arrows to complete the mechanism in Figure 1.

Name compound Z (HOCH2CH2NH2)

Deduce the role of Z in step 2 of the mechanism.

[4 marks]

Name

Role

*06*
IB/M/Jun21/7405/2
 7
Do not write
outside the
0 2 . 5 HOCH2CH2NH2 can be represented as XNH2 box

[HOCH2CH2NH3]+ can be represented as [XNH3]+

Draw the shape of XNH2 and of [XNH3]+

State whether the H–N–H bond angle in XNH2 is greater than, the same as, or smaller
than that in [XNH3]+

Explain your answer.

[4 marks]

Shape of XNH2 Shape of [XNH3]+

Bond angle

Explanation

Question 2 continues on the next page

Turn over ►

*07*
IB/M/Jun21/7405/2
 8
Do not write
outside the
0 2 . 6 Bioethanol is used as an alternative to fossil fuels. box

This statement appeared on a website.

“The fact that bioethanol is a carbon-neutral fuel outweighs the environmental

disadvantages of producing bioethanol.”

Evaluate this statement.

In your answer you should include:

• an outline of how bioethanol is produced
• relevant equations
• analysis of the environmental impacts.
[6 marks]

*08*
IB/M/Jun21/7405/2
 9
Do not write
outside the
box

19

Turn over ►

*09*
IB/M/Jun21/7405/2
 10
Do not write
outside the
0 3 A student does an experiment to determine a value for the enthalpy of combustion of box

heptane.
Figure 2 shows some of the apparatus used.

Figure 2

0 3 . 1 Design a table to record all the readings necessary to determine an experimental

value for the enthalpy of combustion for heptane in this experiment.
[2 marks]

0 3 . 2 The student considered using a glass beaker on a tripod and gauze instead of the
clamped copper calorimeter.

Suggest two disadvantages of using a glass beaker on a tripod and gauze.

[2 marks]

Disadvantage 1

Disadvantage 2

*10*
IB/M/Jun21/7405/2
 11
Do not write
outside the
0 3 . 3 Suggest two reasons why the value of enthalpy of combustion from this experiment is box

less exothermic than a data book value.

[2 marks]

Reason 1

Reason 2

0 3 . 4 Suggest one addition to this apparatus that would improve the accuracy of the
enthalpy value obtained.
[1 mark]

Turn over for the next question

Turn over ►

*11*
IB/M/Jun21/7405/2
 12
Do not write
outside the
box

0 4 Kekulé suggested this structure for benzene.

Benzene is now represented by this structure.

.
Figure 3 shows the relative stability of compared to

Figure 3

*12*
IB/M/Jun21/7405/2
 13
Do not write
outside the
0 4 . 1 Use Figure 3 and the data shown in Table 1 to calculate H2 box

[3 marks]

Table 1

H / kJ mol–1
Enthalpy of atomisation for carbon +715
Enthalpy of atomisation for hydrogen +218
Bond enthalpy (C–C) +348
Bond enthalpy (C=C) +612
Bond enthalpy (C–H) +412

H2 kJ mol–1

0 4 . 2 Explain, in terms of structure and bonding, why

is more thermodynamically stable than

[1 mark]

Turn over ►

*13*
IB/M/Jun21/7405/2
 14
Do not write
outside the
0 4 . 3 A mixture of concentrated nitric acid and concentrated sulfuric acid reacts with box

benzene.

Figure 4 shows the incomplete mechanism for this reaction.

Name the mechanism.

Complete the mechanism in Figure 4 by adding

• any lone pairs of electrons involved in each step
• two curly arrows in step 1
• a curly arrow in step 2
• a curly arrow in step 3
• a curly arrow in step 4.
[5 marks]

Name of mechanism

Figure 4

*14*
IB/M/Jun21/7405/2
 15
Do not write
outside the
0 5 This question is about equilibrium. box

0 5 . 1 1 mol of a diester with molecular formula C7H12O4 is added to 1 mol of water in the
presence of a small amount of catalyst.
The mixture is left to reach equilibrium at a constant temperature.

C7H12O4(l) + 2 H2O(l) ⇌ 2 CH3COOH(l) + HO(CH2)3OH(l)

At equilibrium, 𝒳𝒳 mol of ethanoic acid are present in the mixture.

Complete Table 2 by deducing the amounts, in terms of 𝒳𝒳 ,

of the diester, water and diol present in the equilibrium mixture.
[3 marks]

Table 2

Amount in the mixture / mol

Diester Water Acid Diol

At the start 1 1 0 0

At equilibrium 𝒳𝒳

0 5 . 2 Deduce the structure of the diester in Question 05.1

[1 mark]

Question 5 continues on the next page

Turn over ►

*15*
IB/M/Jun21/7405/2
 16
Do not write
outside the
0 5 . 3 A new equilibrium mixture of the substances from Question 05.1 is prepared at a box

different temperature.

C7H12O4(l) + 2 H2O(l) ⇌ 2 CH3COOH(l) + HO(CH2)3OH(l)

Table 3 shows the amount of each substance in this new equilibrium mixture.

Table 3

Amount in the mixture / mol

Diester Water Acid Diol
To be
At equilibrium 0.971 0.452 0.273
calculated

The value of the equilibrium constant, Kc is 0.161 at this temperature.

Calculate the amount of water, in mol, in this new equilibrium mixture.

Show your working.
[3 marks]

7
Amount of water mol

*16*
IB/M/Jun21/7405/2
 17
Do not write
outside the
0 6 This question is about isomers with the molecular formula C5H10O box

0 6 . 1 Draw the skeletal formula of a branched chain aldehyde with molecular formula
C5H10O that is optically active.
[1 mark]

0 6 . 2 Describe how you distinguish between separate samples of the two enantiomers of
the branched chain aldehyde C5H10O
[2 marks]

0 6 . 3 Draw the E and Z forms of a structural isomer of C5H10O that shows both
optical and geometric isomerism.
[2 marks]

E isomer Z isomer

Question 6 continues on the next page

Turn over ►

*17*
IB/M/Jun21/7405/2
 18
Do not write
outside the
0 6 . 4 Isomer J is cyclic and has an ether functional group (C–O–C) box

Isomer J has only three peaks in its 13C NMR spectrum.

Isomer J

Draw two other cyclic isomers of C5H10O that have an ether functional group and only
three peaks in their 13C NMR spectra.
[2 marks]

*18*
IB/M/Jun21/7405/2
 19
Do not write
outside the
0 7 This question is about spectroscopy. box

0 7 . 1 Compound K has molecular formula C4H8O

Figure 5 shows the infrared spectrum of K.

Figure 5

Which functional group does K contain?

Tick () one box.

[1 mark]

Functional Group

alcohol alkene amine carbonyl nitrile

Question 7 continues on the next page

Turn over ►

*19*
IB/M/Jun21/7405/2
 20
Do not write
outside the
0 7 . 2 Compound L has molecular formula C4H7NO box

Figure 6 shows the infrared spectrum of L.

Figure 6

L reacts with H2 in the presence of a nickel catalyst to give compound M.

Suggest three ways in which the infrared spectrum of M is different from the infrared
spectrum of L.
[3 marks]

*20*
IB/M/Jun21/7405/2
 21
Do not write
outside the
0 7 . 3 Figure 7 shows the 1H NMR spectrum of Q, C3H7ClO box

Figure 7

Table 4 shows the chemical shifts (δ values) and integration values for each peak.

Table 4

δ value / ppm 3.95 3.65 3.35

Integration value 0.6 0.6 0.9

Deduce the structure of Q.

Explain your answer.

[5 marks]

Turn over ►

*21*
IB/M/Jun21/7405/2
 22
Do not write
outside the
0 8 This question is about making a diester from cyclohexanol. box

0 8 . 1 State the type of reaction in step 1.

Give the name of the reagent needed for step 1.

[2 marks]

Type of reaction

Reagent

0 8 . 2 State the reagents needed and give equations for step 2 and step 3.

Show the structure of Compound G in your equations.

[4 marks]

Step 2 reagent

Step 2 equation

Step 3 reagent

Step 3 equation

*22*
IB/M/Jun21/7405/2
 23
Do not write
outside the
0 8 . 3 Cyclohexane-1,2-diol reacts with ethanedioyl dichloride. box

Give the name of the mechanism for this reaction.

Complete the mechanism to show the formation of one ester link in the first step of
this reaction.
[5 marks]

Mechanism name

Mechanism

0 8 . 4 Suggest why chemists usually aim to design production methods

• with fewer steps
• with a high percentage atom economy.
[2 marks]

Fewer steps

High percentage atom economy

13

Turn over ►

*23*
IB/M/Jun21/7405/2
 24
Do not write
outside the
0 9 This question is about the ozone layer in the upper atmosphere. box

0 9 . 1 State why the ozone layer is beneficial for living organisms.

[1 mark]

0 9 . 2 State how chlorofluorocarbons (CFCs) form chlorine atoms in the

upper atmosphere.
[1 mark]

0 9 . 3 Give equations to show how chlorine atoms catalyse the decomposition of ozone.
[2 marks]

0 9 . 4 Hydrochlorofluorocarbons (HCFCs) have been used in place of CFCs.

In the mechanism to make an HCFC from a fluoroalkane, two incomplete steps are
shown.

Complete each step in the mechanism.

Give the name of the type of step shown by both these equations.
[3 marks]

●CHF2 + HCl

●CHF2 + Cl2

7
Type of step

*24*
IB/M/Jun21/7405/2
 25
Do not write
outside the
1 0 This question is about rates of reaction. box

Iodine and propanone react together in an acid-catalysed reaction

CH3COCH3(aq) + I2(aq) CH3COCH2I(aq) + HI(aq)

A student completed a series of experiments to determine the order of reaction with

respect to iodine.

Method
• Transfer 25 cm3 of 1.0 mol dm–3 propanone solution into a conical flask.
• Add 10 cm3 of 1.0 mol dm–3 HCl(aq)
• Add 25 cm3 of 5.0 × 10–3 mol dm–3 I2(aq) and start a timer.
• At intervals of 1 minute, remove a 1.0 cm3 sample of the mixture and add each
sample to a separate beaker containing an excess of NaHCO3(aq)
• Titrate the contents of each beaker with a standard solution of
sodium thiosulfate and record the volume of sodium thiosulfate used.

1 0 . 1 Suggest why the 1.0 cm3 portions of the reaction mixture are added to an excess of
NaHCO3 solution.
[2 marks]

1 0 . 2 Suggest why the order of this reaction with respect to propanone can be ignored in
this experiment.
[2 marks]

Question 10 continues on the next page

Turn over ►

*25*
IB/M/Jun21/7405/2
 26
Do not write
outside the
The volume of sodium thiosulfate solution used in each titration is proportional to the box

concentration of iodine in each beaker.

Table 5 shows the results of the experiment.

Table 5

Time / minutes Volume of sodium thiosulfate solution

/ cm3

1 41

2 35

3 24

4 22

5 16

6 10

1 0 . 3 Use the results in Table 5 to draw a graph of volume of sodium thiosulfate solution
against time.

Draw a line of best fit.

[3 marks]

*26*
IB/M/Jun21/7405/2
 27
Do not write
outside the
1 0 . 4 Explain how the graph shows that the reaction is zero-order with respect to iodine in box

the reaction between propanone and iodine.

[2 marks]

Question 10 continues on the next page

Turn over ►

*27*
IB/M/Jun21/7405/2
 28
Do not write
outside the
1 0 . 5 The Arrhenius equation can be written as box

−Ea
In k = + In A
RT

1
Figure 8 shows a graph of ln k against for the reaction
T

2 HI(g) H2(g) + I2(g)

Figure 8

*28*
IB/M/Jun21/7405/2
 29
Do not write
outside the
Use Figure 8 to calculate a value for the activation energy (Ea), in kJ mol 1, for box

this reaction.

The gas constant R = 8.31 J K

[3 marks]

12
Ea kJ mol 1

END OF QUESTIONS

*29*
IB/M/Jun21/7405/2
 30
Do not write
outside the
There are no questions printed on this page box

DO NOT WRITE ON THIS PAGE

ANSWER IN THE SPACES PROVIDED

*30*
IB/M/Jun21/7405/2
 31
Do not write
outside the
box
Question Additional page, if required.
number Write the question numbers in the left-hand margin.

*31*
IB/M/Jun21/7405/2
 32
Do not write
outside the
box
Question Additional page, if required.
number Write the question numbers in the left-hand margin.

Copyright information

For confidentiality purposes, all acknowledgements of third-party copyright material are published in a separate booklet. This booklet
is published after each live examination series and is available for free download from www.aqa.org.uk.

Permission to reproduce all copyright material has been applied for. In some cases, efforts to contact copyright-holders may have
been unsuccessful and AQA will be happy to rectify any omissions of acknowledgements. If you have any queries please contact the
Copyright Team.

Copyright © 2021 AQA and its licensors. All rights reserved.

*216A7405/2*

*32*
IB/M/Jun21/7405/2