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Pearson Edexcel International Advanced Level

Wednesday 8 January 2025
Afternoon (Time: 1 hour 45 minutes) Paper
reference WCH14/01
Chemistry  

International Advanced Level

UNIT 4: Rates, Equilibria and Further
Organic Chemistry

You must have: Total Marks

Scientific calculator, Data Booklet, ruler

Instructions
•• Use black ink or ball-point pen.
If pencil is used for diagrams/sketches/graphs it must be dark (HB or B).
• Fill in the boxes at the top of this page with your name,
centre number and candidate number.
•• Answer all questions.
Answer the questions in the spaces provided
– there may be more space than you need.

Information
•• The total mark for this paper is 90.
The marks for each question are shown in brackets
– use this as a guide as to how much time to spend on each question.
• toIn the question marked with an asterisk (*), marks will be awarded for your ability
structure your answer logically, showing how the points that you make are
related or follow on from each other where appropriate.
• A Periodic Table is printed on the back cover of this paper.
Advice
•• Read each question carefully before you start to answer it.
Show all your working in calculations and include units where appropriate.
•• Try to answer every question.
Check your answers if you have time at the end.
Turn over

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 SECTION A

Answer ALL the questions in this section.

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You should aim to spend no more than 20 minutes on this section.

For each question, select one answer from A to D and put a cross in the box . If you change
your mind, put a line through the box and then mark your new answer with a cross .

1 Which reducing reagent is used to convert carboxylic acids to alcohols?

A acidified potassium dichromate(VI)

B concentrated sulfuric acid

C hydrogen gas with a nickel catalyst

D lithium tetrahydridoaluminate(III) in dry ether

(Total for Question 1 = 1 mark)

2 A polyester is made from pentane-1,5-diol and pentanedioic acid.

Which is the repeat unit of this polyester?

A B

O O O O

[O C (CH2)3 C O (CH2)5 O [ [O C (CH2)5 C O (CH2)5 O [

C D

O O O O

[C (CH2)3 C O (CH2)5 O [ [C (CH2)5 C O (CH2)5 O [

(Total for Question 2 = 1 mark)
Use this space for any rough working. Anything you write in this space will gain no credit.

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3 When ammonia dissolves in water, an equilibrium results.
The equation for this equilibrium is shown.

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NH3 + H2O  NH+4 + OH–

Which of these species act as a Brønsted–Lowry acid in this equilibrium?

A H2O only

B NH3 and OH–

C NH+4 only

D NH+4 and H2O

(Total for Question 3 = 1 mark)

4 A strong monoprotic acid, of concentration 0.0100 mol dm–3, has a pH = 2.0.

What is the decrease in pH if the concentration is increased to 0.0110 mol dm–3?

A 0.001
B 0.04

C 1.04

D 1.96
(Total for Question 4 = 1 mark)
Use this space for any rough working. Anything you write in this space will gain no credit.

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 5 One of the stages in the manufacture of sulfuric acid involves the oxidation of
sulfur dioxide to sulfur trioxide.
The equation for this reaction can be written in either of the two ways shown.
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Equation 1 2SO2 + O2  2SO3

Equation 2 SO2 + ½O2  SO3
The value of Kp at 25°C using Equation 1 is 4.0 × 1024 atm–1.

(a) What is the numerical value of Kp at 25°C using Equation 2?

(1)
A 2.0 × 1012

B 2.0 × 1022

C 2.0 × 1024

D 4.0 × 1024

(b) The relationship between Kp and Kc is shown.

Kp
Kc 
R  T 
Δn

where T is the temperature in kelvin,

R is the gas constant 0.082 dm3 atm mol–1 K–1 and
∆n = moles of product – moles of reactants.
What is the value of Kc at 25°C for the equilibrium using Equation 1?
(1)
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A 1.64 × 10

B 1.95 × 1024

C 8.20 × 1024

D 9.77 × 1025
(Total for Question 5 = 2 marks)
Use this space for any rough working. Anything you write in this space will gain no credit.

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6 Which equation represents the standard enthalpy change of atomisation of iodine?

A ½I2(s) → I(g)

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B ½I2(g) → I(g)

C I2(s) → 2I(g)

D I2(g) → 2I(g)
(Total for Question 6 = 1 mark)

7 Which equation represents the second electron affinity of oxygen?

A O–(g) + e– → O2–(g)

B O(g) + 2e– → O2–(g)

C O+(g) → O2+(g) + e–

D O(g) → O2+(g) + 2e–

(Total for Question 7 = 1 mark)

8 Which compound has the greatest covalent character?

A CaBr2

B CaI2

C MgBr2

D MgI2
(Total for Question 8 = 1 mark)
Use this space for any rough working. Anything you write in this space will gain no credit.

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 9 Which pair of values will always give a thermodynamically feasible reaction?
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Entropy change of the system Enthalpy change of reaction

A negative positive
B negative negative
C positive negative
D positive positive

(Total for Question 9 = 1 mark)

Use this space for any rough working. Anything you write in this space will gain no credit.

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10 This question is about the effect of changes on a system at equilibrium.
(a) The equation for the reaction between hydrogen and iodine is shown.

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H2(g) + I2(g)  2HI(g)
What is the effect, if any, of an increase in pressure on the appearance of the
equilibrium mixture?
(1)
A no change

B the mixture becomes more purple

C the mixture becomes more brown

D the mixture becomes less brown

(b) The equation for the manufacture of ammonia by the Haber process is shown.

N2(g) + 3H2(g)  2NH3(g)   ∆H = –92.2 kJ mol–1

(1)
Kp = 6.76 × 105 atm–2 at 298 K

Which change(s), if any, will result in an increase in the value of Kp?

A an increase in pressure only

B a decrease in temperature only

C an increase in pressure and an increase in temperature

D no changes in pressure or temperature will affect the value of Kp

(c) The equation for the equilibrium between nitrogen dioxide and
dinitrogen tetroxide is shown.

N2O4(g)  2NO2(g)
A change in conditions results in Kp increasing from 0.115 atm to 3.89 atm.
What can be deduced about the change in position of the equilibrium?
(1)
A the equilibrium position has shifted towards the products

B the equilibrium position has shifted towards the reactants

C the equilibrium position is unchanged

D there is almost complete conversion of reactants into products

(Total for Question 10 = 3 marks)

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 11 What is the pH of a 0.100 mol dm–3 solution of sodium hydroxide at 283 K?
[pKw = 14.53 at 283 K]
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A 13.00

B 13.53

C 14.43

D 14.53
(Total for Question 11 = 1 mark)

12 The pH of a dilute solution of a weak carboxylic acid can be calculated from its
Ka value.
Which is not a relevant assumption in the calculation of pH?

A the ionisation of water is insignificant

B the initial and equilibrium concentrations of the acid are the same
C the concentrations of the protons and carboxylate ions are the same

D the dissociation of the carboxylic acid is almost complete

(Total for Question 12 = 1 mark)

13 This is a question about buffers.

(a) The Henderson–Hasselbalch equation can be used to determine the pH of a
buffer solution. This equation is shown.
[salt]
pH  pK a  log
[acid]

What is the pH of a buffer solution containing 0.100 mol dm–3 ethanoic acid and
0.200 mol dm–3 sodium ethanoate?
[Ka(ethanoic acid) = 1.7 × 10–5 mol dm–3 at 298 K]
(1)
A 4.47

B 4.77

C 5.07

D 5.46

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 (b) What is the best reason for the use of buffers in foods?
(1)

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A to improve taste

B to help digestion of the food

C to prevent deterioration by fungal activity

D to enhance the colour and appearance of the food

(c) The carbonic acid/hydrogencarbonate ion buffer system in the blood involves the
equilibria shown.

CO2(g) + H2O(l)  H2CO3(aq)  H+(aq) + HCO3–(aq)

How is the pH of blood affected by increased exercise?
(1)
A there is no effect because the equilibria are not affected by activity

B the pH will decrease due to the equilibria shifting to the left

C the pH will decrease due to the equilibria shifting to the right

D the pH is constant because it is a buffer system

(Total for Question 13 = 3 marks)

14 Which has the greatest molar entropy?

A Hg(l)
B H2O(l)

C NO(g)

D NO2(g)
(Total for Question 14 = 1 mark)

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 15 A graph of the concentration of Q during decomposition is shown.

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[Q]
/ 10 mol dm–3
–3 5

0
0 30 60 90 120 150 180 210 240 270 300
Time / minutes

What is the half-life for this decomposition?

A 93 minutes
B 132 minutes

C 146 minutes

D 291 minutes
(Total for Question 15 = 1 mark)

TOTAL FOR SECTION A = 20 MARKS

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 SECTION B
Answer ALL the questions. Write your answers in the spaces provided.
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16 This question is about pentan-2-one, CH3COCH2CH2CH3 .

(a) Explain why pentan-2-one has a lower boiling temperature than pentan‑2‑ol.
(2)

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(b) Give a chemical test which distinguishes between pentan‑2‑one and

pentan‑3‑one, CH3CH2COCH2CH3 .
Include the results for both substances.
(2)

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(c) Give a different chemical test which distinguishes between pentan‑2‑one and
pentanal, CH3CH2CH2CH2CHO .
Include the results for both substances.
(2)

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 (d) Pentan‑2‑one, pentan-3-one and pentanal react in a similar way with one test
reagent to form solid products.
Identify the reagent and describe how these solid products may be used to

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distinguish the original compounds.
(3)

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(e) Pentan‑2‑one and pentan-3-one both react with hydrogen cyanide in the
presence of KCN. With pentan‑2‑one a racemic mixture is formed but with
pentan‑3‑one there is only one product.
Explain this difference by referring both to the reaction mechanism and to the
structures of the two molecules.
(4)

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(Total for Question 16 = 13 marks)

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 17 Esters are difficult to distinguish from each other using chemical tests, so NMR
spectroscopy is often used.
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(a) There are four ester isomers with the molecular formula C4H8O2 . Their displayed
formulae are shown.

H H H
O O
H H H
H C C H C C C
O C C H O C H
H H H
H H H

Ester P Ester Q

O O
H H H H H
H C H C
O C C C H O C C H

H H H C H
H H
H
Ester R
Ester S

Explain which of the four esters can be distinguished from the other three by the
numbers of peaks in the carbon-13 (13C) NMR spectra.
Justify your answer by labelling any equivalent carbon atoms.
(3)

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15
 *P78458RA01532* Turn over
 (b) There are nine ester isomers with the molecular formula C5H10O2 .
(i) The displayed formulae of two of these esters are shown.

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H H H
H
O
H C H C H
O H C C
H
H C C O C H
C H H
O
C C
H H H H H
H H

Ester W Ester X

Esters W and X both have one peak with a relative area of 3 in their
low‑resolution proton NMR spectra.
Explain how these peaks can be used to distinguish these two esters.
(2)

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16
*P78458RA01632* 
 (ii) The displayed formulae of two different esters are shown in the boxes.
Label the displayed formulae of the two esters Y and Z to show the
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proton environments and the splitting patterns of the peaks in the

high‑resolution proton NMR spectra.
Clearly indicate any equivalent proton environments.
For any multiplet, you may refer to the number of separate peaks in the
multiplet rather than giving a name.
(4)

H H H
O
C H H
H C
O C C C H
H H H

Ester Y

O
H H H
H C
O C C C H
H C H
H H H

Ester Z

(iii) Draw the displayed formula of the C5H10O2 ester which has only 2 peaks in its
low-resolution proton NMR structure.
(1)

(Total for Question 17 = 10 marks)

17
 *P78458RA01732* Turn over
18 This question is about reaction kinetics.
*(a) Halogenoalkanes are hydrolysed by aqueous alkali to form alcohols.

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RX + OH– → ROH + X–

The rate equations for these reactions with two halogenoalkanes are shown.

1-bromobutane rate = k[CH3CH2CH2CH2Br][OH−]

2-bromo-2-methylpropane rate = k[(CH3)3CBr]

Explain how these rate equations can be used to deduce the different reaction
mechanisms of the reaction of hydroxide ions with these halogenoalkanes.
(6)

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18
*P78458RA01832* 
 ................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .

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

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19
 *P78458RA01932* Turn over
 (b) An initial-rates method may be used to investigate the kinetics of the reaction
between hydrogen peroxide and iodide ions in acid solution.
The equation for this reaction is shown.

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H2O2(aq) + 2I–(aq) + 2H+(aq) → I2(aq) + 2H2O(l)

The reaction mixture contains a small amount of thiosulfate ions which reduce
the iodine back to iodide ions.
The equation for this reduction is shown.

I2(aq) + 2S2O32–(aq) → 2I−(aq) + S4O62−(aq)

As soon as the thiosulfate is used up, the iodine that is further produced reacts
with the starch present and results in a colour change. The time taken for this
colour change is noted and the reciprocal of this time is used as a measure of
reaction rate.
The results from a series of experiments where the volume of the
hydrogen peroxide was changed are given in the table.

Reaction rate / s−1 0.9 × 10−2 1.8 × 10−2 2.5 × 10−2 3.7 × 10−2 4.6 × 10−2

Volume of H2O2 / cm3 10 20 30 40 50

(i) Give the colour change after all the thiosulfate is used up.
(2)

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(ii) Plot a graph of reaction rate against volume of hydrogen peroxide.

(3)

20
*P78458RA02032* 
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(iii) State and justify the reaction order with respect to hydrogen peroxide by
using your graph.
(1)

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21
 *P78458RA02132* Turn over
 (c) The continuous monitoring method was used to investigate the kinetics of
the reaction between magnesium and sulfuric acid at different temperatures.
The equation for the reaction is shown.

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Mg(s) + H2SO4(aq) → MgSO4(aq) + H2(g)

(i) The graph shows the results of an experiment at 80°C.

80

70

60

50
Volume of
hydrogen 40
/ cm3
30

20

10

0
10 20 30 40 50 60 70 80 90
Time / s

Calculate the reaction rate at 15 seconds using the tangent shown.

Give your answer to two significant figures and include units, if any.
(2)

22
*P78458RA02232* 
 (ii) The temperature of the reaction was changed to 75°C.
Draw a line on the graph to show the possible results if this was the only
change. Justify any similarities and differences in the lines.
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(2)

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

(Total for Question 18 = 16 marks)

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19 Many effervescent products such as vitamin tablets are solids which contain
citric acid, C6H8O7 , and sodium hydrogencarbonate. Only when these tablets are
added to water is fizzing observed. The equation for the reaction is shown.

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C6H8O7 + 3NaHCO3 → 3H2O + 3CO2 + Na3C6H5O7
(a) Give two reasons why this reaction is thermodynamically feasible when
considering the entropy of the system.
(2)

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(b) Describe, in terms of the particles involved, why the reaction does not occur until
the tablets are dissolved in water.
(3)

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(c) For the reaction at 25°C, the standard entropy change of the surroundings,
∆S surroundings = −234.9 J K−1 mol−1 .
Calculate the enthalpy change of the reaction.
Include a sign and units in your answer.
(2)

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*P78458RA02432* 
 (d) The enthalpy change of solution, ∆solH , of sodium hydrogencarbonate is
+18.6 kJ mol−1 .
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Sketch the enthalpy level diagram to show the relationship between the enthalpy
change of solution, lattice energy and enthalpies of hydration for the dissolving of
sodium hydrogencarbonate in water.
Fully label your diagram.
(3)

Enthalpy, H

(Total for Question 19 = 10 marks)

TOTAL FOR SECTION B = 49 MARKS

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 SECTION C
Answer ALL the questions. Write your answers in the spaces provided.

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20
Oxalic acid
Oxalic acid has the IUPAC name ethanedioic acid and a molar mass = 90 g mol−1 .
HO O

O OH

The name oxalic acid originated from the fact that it was first isolated from plants
of the genus Oxalis. The formation of oxalic acid in plants involves the hydrolysis of
2‑oxobutanedioic acid.
O
HO O O
OH
+ H2O +
HO
O OH OH
O O

Plants can also form oxalic acid from glycolic acid, HOCH2COOH.
Oxalic acid can be manufactured by oxidising sucrose using nitric acid in the
presence of a vanadium(V) oxide catalyst. Over 100,000 tonnes of oxalic acid are
produced each year.
Much of the oxalic acid produced is used for cleaning or bleaching, because it
converts insoluble iron compounds into soluble iron salts.

(a) Calculate the atom economy, by mass, for the formation of oxalic acid from the
hydrolysis of 2‑oxobutanedioic acid.
(2)

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 (b) Give the laboratory reagents and conditions required to convert
glycolic acid, HOCH2COOH, to oxalic acid.
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Do not consider nitric acid.

(2)

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(c) Sucrose is oxidised by concentrated nitric acid to form oxalic acid.

(i) Complete the equation for the reaction of one mole of sucrose with nitric acid.
(2)

HO O
C12H22O11 + 36HNO3 . . . ............................ + ............................... NO2 + ............ . . . . . . . . . . . . . . . . . . . H2O

O OH

(ii) Give one observation that would be seen during this reaction.
(1)

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 (d) A solution of sodium hydroxide was titrated against 25.0 cm3 of oxalic acid
solution. Both solutions were of equal concentrations.

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(i) A student sketched a curve to show the changing pH during the titration.

14

13

12

11

10

8
pH
7

0 10 20 30 40 50 60

Volume of NaOH(aq) added / cm3

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*P78458RA02832* 
 Select one indicator for each equivalence point from this titration graph.
Include the colour at the end-point for each indicator.
Use your Data Booklet.
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(2)
First indicator

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Colour at the end-point

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Second indicator

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Colour at the end-point

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(ii) Suggest a difficulty that would occur if both indicators were present in the
same mixture.
(1)

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(iii) Determine, by using the graph, the two Ka values for oxalic acid.
You must show your working on the graph.
(5)

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 (e) Spinach is one plant source of oxalic acid. Approximately 700 mg of oxalic acid
can be extracted from 100 g of spinach.

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(i) High-performance liquid chromatography, HPLC, is used for analysis in the
extraction process. The HPLC equipment is connected to a detector which
records peaks when substances pass through the HPLC column.
Suggest how a pure sample of oxalic acid would be used to identify the
oxalic acid peak in the chromatogram of the spinach extract.
(1)

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(ii) A 0.558 mol dm−3 solution of oxalic acid is used for cleaning.
Calculate the mass of spinach required to make 500 cm3 of this oxalic acid
cleaning solution.
[Data: Mr oxalic acid = 90]
(3)

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*P78458RA03032* 
 (f ) Write the equation for the reaction of oxalic acid with excess
phosphorus(V) chloride.
(2)
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(Total for Question 20 = 21 marks)

TOTAL FOR SECTION C = 21 MARKS

TOTAL FOR PAPER = 90 MARKS

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
*P78458RA03232*
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