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Centre Number Candidate Number

Pearson Edexcel
International
Advanced Level

Monday 13 January 2020

Afternoon (Time: 1 hour 45 minutes) Paper Reference WCH14/01

Chemistry
International Advanced Level
Unit 4: Rates, Equilibria and Further Organic Chemistry
(including synoptic assessment)
Candidates must have: Scientific calculator Total Marks
Data Booklet
Ruler

Instructions
• Use black ink or black ball-point pen.
• centre
Fill in the boxes at the top of this page with your name,
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.
• ability
In the question marked with an asterisk (*), marks will be awarded for your
to 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.
• Checkallyouryouranswers
Show working in calculations and include units where appropriate.
• if you have time at the end.

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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 This question is about four organic compounds each with five carbon atoms but
different functional groups.

Compound Skeletal formula

Cl
1
O

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O
2

O
3

NH2
4
O

(a) Which of these, when mixed with water, produces the solution with the lowest pH?
(1)
A compound 1
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B compound 2
C compound 3
D compound 4

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(b) Which of these reacts with ethylamine, CH3CH2NH2 , to form an N-substituted amide?
(1)
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A compound 1
B compound 2
C compound 3
D compound 4

(c) Which of these reacts with iodine and sodium hydroxide in solution to produce a
pale yellow precipitate?
(1)
A compound 1
B compound 2
C compound 3
D compound 4
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(Total for Question 1 = 3 marks)

2 Which of these molecules can rotate the plane of plane-polarised light?

A H2NCH2COOH
B HOCH2CH2COOH
C ClCH2C(CH3)(Cl)COOH
D H2NC(CH3)2COOH

(Total for Question 2 = 1 mark)

3 A polymer is prepared by the reaction between hexanedioyl dichloride and

hexane-1-6-diamine.
What type of polymerisation occurs?
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A addition
B condensation
C hydrolysis
D substitution

(Total for Question 3 = 1 mark)

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4 The compound HOOCCH CHCOOH reacts with excess sodium hydroxide solution.
What is the organic product formed in the reaction?

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A NaOOCCH CHCOONa
B HOOCCH CHCOONa
C NaOOCC(OH)HC(OH)HCOONa
D NaOOCCH CHCHO

(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 Which diagram shows the mechanism for the second order reaction between
1-bromoethane and potassium hydroxide in aqueous solution?
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Diagram 1
H H H
H H H
H į+ H H
C C+ C
C Br į– C C
–•• OH
H H OH H
H H + Br– H

Diagram 2
H H H
H H H
H į+ H H
C C+ C
C Br į– C –
OH C
•• OH
H H H
H H H
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–
+ Br

Diagram 3
–
H ⎡ H ⎤ H
H –•• ⎢ H Br ⎥ H
H į+ OH
C ⎢H C ⎥ H C
C Br į–
⎢ C OH ⎥ C
OH
H ⎢ H ⎥ H
H ⎣ H ⎦ H + Br–

Diagram 4
H ⎡ H ⎤
– H
H H H
H į+ –••
⎢ Br ⎥
H
C OH ⎢H C ⎥ C
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C Br į–
⎢ C OH ⎥ C
OH
H ⎢ H ⎥ H
H ⎣ H ⎦ H + Br–

A Diagram 1
B Diagram 2
C Diagram 3
D Diagram 4

(Total for Question 5 = 1 mark)

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6 Which of these reacts directly with ethanoic acid to form ethanoyl chloride?
A chlorine

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B chloroethane
C hydrogen chloride
D phosphorus(V) chloride

(Total for Question 6 = 1 mark)

7 Which of these changes has the largest increase in the entropy of the system?
A H2O(s) → H2O(l)
B Hg(l) → Hg(g)
C H2O(l) + HCl(g) → H3O+(aq) + Cl–(aq)
D C(graphite) → C(diamond)

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(Total for Question 7 = 1 mark)

8 Equal amounts of W and X are mixed and allowed to reach equilibrium.

W+XUY+Z
The value of the equilibrium constant is Kc = 4.85. At equilibrium, the mixture
will contain
A almost all Y and Z
B almost all W and X
C W, X, Y and Z but there is less Y and Z than W and X
D W, X, Y and Z but there is more Y and Z than W and X

(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 What does X represent on the diagram?

Li+(g) + Cl–(g)
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LiCl(s)

Li+(aq) + Cl–(aq)

A sum of enthalpy changes of hydration of the gaseous ions

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B enthalpy change of formation of LiCl

C enthalpy change of solution of LiCl
D lattice energy of LiCl

(Total for Question 9 = 1 mark)

10 How are 20 cm3 of 0.05 mol dm–3 H2SO4(aq) and 20 cm3 of 0.10 mol dm–3 CH3COOH(aq) alike?
Both solutions
A have the same pH
B have the same total concentration of ions
C have the same total concentration of negative ions
D require 20 cm3 of 0.10 mol dm–3 NaOH(aq) for complete reaction
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(Total for Question 10 = 1 mark)

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11 Which two solutions, both of concentration 0.10 mol dm–3, have been used to
produce this titration curve?

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pH 7

0
Volume of alkali added

A HCl(aq) and KOH(aq)

B HCOOH(aq) and KOH(aq)
C HCl(aq) and NH3(aq)

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D HCOOH(aq) and NH3(aq)

(Total for Question 11 = 1 mark)

12 A solution of sodium hydroxide of concentration 0.0080 mol dm–3 has a pH

A between 7 and 9
B between 9 and 11
C between 11 and 13
D above 13

(Total for Question 12 = 1 mark)

Use this space for any rough working. Anything you write in this space will gain no credit.
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13 A student carried out an experiment to determine the equilibrium constant for the
reaction to form ethyl ethanoate from ethanol and ethanoic acid.
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CH3COOH + CH3CH2OH U

CH3COOCH2CH3 + H2O

Different amounts of each substance were added to conical flasks, each containing
2.0 cm3 of 1.0 mol dm−3 hydrochloric acid.

Volume added / cm3

Conical
flask HCl H 2O CH3COOH CH3COOCH2CH3 CH3CH2OH
(aq) (l) (l) (l) (l)
1 2.0 1.0 0 2.0 0

2 2.0 0 5.0 0 5.0

3 2.0 0 4.0 0 3.0

4 2.0 0 0 3.0 0
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The flasks were then stoppered and left for a week to reach equilibrium.
Each mixture was then titrated with 1.0 mol dm−3 sodium hydroxide.

(a) In which flask(s) was the equilibrium approached from the right-hand side of the
equation?
(1)
A flask 1 only
B flask 4 only
C flasks 1 and 4 only
D flasks 2 and 3 only

(b) Which of these statements explains why it is possible to titrate the reaction
mixture directly to find the equilibrium concentrations?
(1)
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A the equilibrium reaction is slow

B the sodium hydroxide quickly hydrolyses the ester
C all the reactant concentrations remain constant during the titration
D a buffer solution forms in the reaction

(Total for Question 13 = 2 marks)

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14 A reactant Q is converted into two products. Which of these graphs shows that this
reaction is first order with respect to Q?

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Graph 1 Graph 2

[Q] Rate

time [Q]

Graph 3 Graph 4

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Rate [Q]

[Q] time

A Graph 1
B Graph 2
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D Graph 4

(Total for Question 14 = 1 mark)

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

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15 This question is about the kinetics of the reaction between nitrogen monoxide and oxygen.

2NO(g) + O2(g) → 2NO2(g)

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The rate equation for the reaction is rate = k[NO]2[O2]

(a) Which statement is not correct?
(1)
A the reaction is third order overall
B the units of the rate of the reaction are mol dm−3 s−1
C the rate of the reaction increases when the pressure is increased
D when the concentration of nitrogen monoxide doubles and the concentration
of oxygen quadruples, the rate increases by a factor of 8

(b) What are the units of the rate constant, k , for this reaction?
(1)
A dm9 mol−3 s−1
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B mol3 dm−9 s−1

C mol2 dm−6 s−1
D dm6 mol−2 s−1

(c) An experiment was carried out using 1.10 × 10−2 mol dm−3 of oxygen and some
nitrogen monoxide.
The numerical value of the initial rate and rate constant were:
• initial rate = 3.20 × 10−3
• rate constant, k = 1.70 × 103
What was the initial concentration, in mol dm−3, of the nitrogen monoxide used in
the experiment?
(1)
A 1.31 × 10−2
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B 1.71 × 10−4
C 2.02 × 10−3
D 4.50 × 10−2

(Total for Question 15 = 3 marks)

TOTAL FOR SECTION A = 20 MARKS

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SECTION B

Answer ALL the questions.

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Write your answers in the spaces provided.

16 The compound ethyl 3-oxobutanoate, which is used in food flavouring, has the
formula CH3COCH2COOCH2CH3.
The high resolution proton (1H) NMR spectrum of this compound is

x
w

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5 4 3 2 1 0

Chemical shift, į / ppm

(a) (i) Identify which groups of hydrogen atoms are responsible for each peak in the
spectrum by adding the labels w, x, y and z to the appropriate parts of this
displayed formula to match the letters on the spectrum.
(2)

H O H O H H

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

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(ii) Explain the splitting patterns of the peaks at 4.2 ppm and 1.3 ppm.
(2)
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(iii) The carbon-13 (13C) NMR spectrum of ethyl 3-oxobutanoate has six peaks.
Draw the structure of an isomer of ethyl 3-oxobutanoate that contains a
carboxylic acid group and a ketone functional group, but only has four peaks in its
carbon-13 NMR spectrum.
(1)
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(b) A chemist synthesising ethyl 3-oxobutanoate looked for its presence in the reaction
mixture using thin-layer chromatography. The solvent used was a mixture of
ethoxyethane, C2H5OC2H5, which is polar, and hexane.

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Under these conditions, the Rf value for ethyl 3-oxobutanoate was 0.45.
(i) Complete the diagram below, showing a chromatogram for ethyl 3-oxobutanoate,
including appropriate labels.
(3)

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(ii) Suggest why the Rf value for ethyl 3-oxobutanoate is significantly lower than 0.45
when just hexane is used as the solvent.
(2)

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(Total for Question 16 = 10 marks)

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*17 Compare and contrast the reactions of propanal and propanone with one oxidising agent,
one reducing agent and 2,4-dinitrophenylhydrazine.

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In your answer include any relevant observations for the reactions you discuss and
equations for any reactions classified as oxidation, using [O] for the oxygen from the
oxidising agent.

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(Total for Question 17 = 6 marks)

*P60472A01732*
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18 The rate constant for the reaction to convert cyclopropane to propene was
determined at five different temperatures.

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CH2 CH
H2C CH3
H 2C CH2

The results are shown in the table.

Temperature (T) 1 / Temperature (1 / T) Rate constant (k)

ln k
/K / K−1 / s−1
719 1.39 × 10−3 2.49 × 10−5 –10.60

746 1.34 × 10−3 1.23 × 10−4 –9.00

791 1.26 × 10−3 1.66 × 10−3

840 1.83 × 10−2 –4.00

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889 1.12 × 10−3 1.65 × 10−1 –1.80

(a) (i) Complete the table.

(1)
(ii) Plot a graph of ln k against 1 / T.
(3)

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(iii) Use your graph to determine the activation energy, Ea , in kJ mol−1.

You should include the value and units of the gradient of the line.
The Arrhenius equation is
E 1
ln k = – a × + constant
R T (3)
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*P60472A01932*
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(b) The activation energy for many reactions is around +50 kJ mol–1.
Given this information, comment on your value for Ea.

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(2)

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(c) Explain the trend in the value of the rate constant k as the temperature increases.
(3)

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*P60472A02132*
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19 This question is about halides.

(a) Silicon tetrachloride, SiCl4 , is used in the manufacture of optical fibres. It can

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be made by the reaction of silicon carbide, SiC, with hydrogen chloride using a
catalyst of nickel(II) chloride.

SiC(s) + 4HCl(g) → SiCl4 (l) + CH4(g) ¨H = –631.3 kJ mol−1

The standard molar entropies S 9 , of the substances are shown in the table.

Substance SiC(s) HCl(g) SiCl4 (l) CH4(g)

S 9 / J K−1 mol−1 +16.5 +186.8 +239.7 +186.2

(i) Calculate the total entropy change, ¨Stotal , for this reaction, at 298 K, using the
information given.
Include a sign and units in your answer which should be given to an
appropriate number of significant figures.

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(5)

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(ii) In industry, the reaction is carried out at 700 °C.

By considering entropy and other relevant factors, justify the use of this temperature.
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(3)

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(iii) Use your answer from (a)(i) to calculate the equilibrium constant for the
reaction at 298 K.
(2)
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(b) The following data can be used in a Born-Haber cycle for calcium iodide, CaI2.

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Letter Energy change Value / kJ mol–1

A Enthalpy change of atomisation of calcium +178.2

B First ionisation energy of calcium +590

C Second ionisation energy of calcium +1145

D Enthalpy change of atomisation of iodine (½I2(s) → I(g)) +106.8

E Electron affinity of iodine –295.4

F Lattice energy of calcium iodide –2074

(i) Complete the Born-Haber cycle by adding letters in the boxes for the energy
changes, relevant species on the blank lines and arrowheads to show the
direction of each energy change.

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(3)

Ca(g) + 2I(g)
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D ×2
Ca(g) + I2(g)

A
Ca(s) + I2(g)
Enthalpy change
of formation of
CaI2(s) calcium iodide

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(ii) Use the data to calculate the value for the enthalpy change of formation of
calcium iodide.
(2)
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(iii) The value for the lattice energy of calcium iodide determined experimentally
by using the Born-Haber cycle differs significantly from the theoretical
calculated value.
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Explain why the Born-Haber and the theoretical values for the lattice energies
are similar for calcium fluoride but significantly different for calcium iodide.
(4)

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(c) The electron affinity of iodine is –295.4 kJ mol–1.

Explain how the electron affinity of chlorine differs from that of iodine.

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(3)

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(Total for Question 19 = 22 marks)

TOTAL FOR SECTION B = 50 MARKS

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*P60472A02632*
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SECTION C

Answer ALL the questions.

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Write your answers in the spaces provided.

20 This question is about ethanoic acid and some of its compounds.

(a) Three students, A, B and C, carried out an investigation to determine the amount
of isoamyl acetate, an ester of ethanoic acid, in a banana food flavouring.
They hydrolysed the ester with excess sodium hydroxide solution.
CH3COOCH2CH2CH(CH3)2 + NaOH → CH3COONa + (CH3)2CHCH2CH2OH
The amount of sodium hydroxide remaining was determined by titrating the
reaction mixture with hydrochloric acid.
(i) Give the systematic name for isoamyl acetate.
(1)
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(ii) 6.06 × 10–3 mol of sodium hydroxide reacted with the ester present in 1.07 g of
the flavouring.
Calculate the percentage by mass of the ester in the food flavouring.
(3)
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(iii) The students used 25.0 cm3 of sodium hydroxide solution with concentration
0.980 mol dm–3 for the hydrolysis.

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Calculate the pH of the reaction mixture when the hydrolysis is complete.
Assume the total volume is 25.0 cm3.
[Ionic product of water, Kw = 1.0 × 10–14 mol2 dm–6]
(3)

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(iv) Two indicators, methyl orange and phenolphthalein, were available for this titration.
Student A thought only methyl orange could be used.
Student B thought only phenolphthalein could be used.
Student C suggested either indicator could be used.
Explain which student is correct.
(2)

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(v) Describe how the sodium ethanoate in the final reaction mixture could be
converted into ethanoic acid.
(1)
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*P60472A02932*
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(b) Ethanoic acid can be used to form buffer solutions.

(i) Calculate the pH of the buffer solution formed when 50.0 cm3 of ethanoic acid

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with concentration of 0.150 mol dm–3 is mixed with 30.0 cm3 of
sodium hydroxide solution with concentration of 0.142 mol dm–3.
[Ka for ethanoic acid = 1.70 × 10–5 mol dm–3]
(5)

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(ii) Small amounts of sodium hydroxide and hydrochloric acid are added to
separate samples of the buffer solution in (b)(i).
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Explain why these samples resist change in pH.

Illustrate your answer with at least two equations.
(5)

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(Total for Question 20 = 20 marks)

TOTAL FOR SECTION C = 20 MARKS

TOTAL FOR PAPER = 90 MARKS

*P60472A03132*
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*P60472A03232*
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