WCH04 01 Que 20190605

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Pearson Edexcel
International
Advanced Level
Tuesday 4 June 2019

Afternoon (Time: 1 hour 40 minutes) Paper Reference WCH04/01
Chemistry
Advanced
Unit 4: General Principles of Chemistry I – Rates,
Equilibria and Further Organic Chemistry
(including synoptic assessment)
Candidates must have: Scientific calculator Total Marks
Data Booklet
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.
• written
Questions labelled with an asterisk (*) are ones where the quality of your
communication will be assessed
– you should take particular care with your spelling, punctuation and grammar, as
well as the clarity of expression, on these questions.
• 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 give units where appropriate.
• Check your answers if you have time at the end.
Turn over
P56131A
©2019 Pearson Education Ltd.
2/1/1/1/1/
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SECTION A
Answer ALL the questions in this section. You should aim to spend no more than 20 minutes on
DO NOT WRITE IN THIS AREA

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 The rate equation for the reaction of a bromoalkane, RBr, with hydroxide ions is
rate = k[RBr]
The bromoalkane that is hydrolysed according to this rate equation is most likely to be
A 1-bromohexane.
B 1-bromo-2-methylpentane.
C 2-bromo-2-methylpentane.
D 2-bromo-3-methylpentane.

(Total for Question 1 = 1 mark)
2 Which method is most suitable for comparing the rate of hydrolysis of a primary iodoalkane
and a tertiary iodoalkane in aqueous silver nitrate?
A Measuring the increase in pH.
B Measuring the change in mass.
C Measuring the time to form a precipitate.
D Taking samples followed by titrating with sodium thiosulfate.

Use this space for any rough working. Anything you write in this space will gain no credit.
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3 The chemical equation and the rate equation for the reaction of iodine with excess propanone
in the presence of an acid catalyst are shown.
I2 + CH3COCH3 o CH3COCH2I + HI
rate = k[CH3COCH3][H+]
Which of the following sketch graphs is correct for this reaction?
A rate
[I2]
B rate
[I2]
C [I2]
time
D [I2]
time

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4 The Arrhenius equation is

Ea 1
ln k = − × + constant
R T
The activation energy, E a , is determined from the gradient of the graph shown.
x axis
Ea
gradient = −
R
y axis
The axes on the graph are

x axis y axis
1
A ln k
T
1
B ln k −
T
1
C ln k
T
1
D − ln k
T
5 What are the signs of the entropy changes at 273 K when water freezes?
H2O(l) o H2O(s)
ǻSsystem ǻSsurroundings
A negative positive
B positive negative
C negative negative
D positive positive
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6 Which are the Brønsted-Lowry acids in the following equilibrium?
CH3COOH + C2H5COOH U CH3COO− + C2H5COOH2+

A CH3COOH and C2H5COOH

B CH3COOH and C2H5COOH2+
C C2H5COOH and CH3COO−
D CH3COO− and C2H5COOH2+
7 In a titration of hydrochloric acid with aqueous ammonia, which indicator would be

most suitable to detect the end-point?
Refer to your Data Booklet.
A Azolitmin (litmus)
B Bromocresol purple
C Phenolphthalein
D Alizarin yellow R
8 A solution of hydrochloric acid has pH = 2.

The solution is diluted to one tenth of its original concentration.
What is the pH of the diluted solution?
A 0.70
B 1.0
C 2.7
D 3.0

5
9 Equal amounts of three compounds were placed in separate beakers and the same
volume of water was added to each.

Compound 1 CH3COOH
Compound 2 CH3COCl
Compound 3 CH3COONa
Which shows the order of increasing pH in the mixtures?
A CH3COOH CH3COCl CH3COONa
B CH3COCl CH3COOH CH3COONa
C CH3COONa CH3COOH CH3COCl
D CH3COCl CH3COONa CH3COOH
10 What are the units of Kc for the following equilibrium?

Cu(s) + 2Ag+(aq) U Cu2+(aq) + 2Ag(s)
A mol dm−3
B dm3 mol−1
C mol2 dm−6
D no units

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11 The graph shows the percentage yield of a product in a gaseous equilibrium under
different conditions.
80
70 350 °C
60
50
% yield of 450 °C
product at 40
equilibrium
30
550 °C
20
10
0
0 100 200 300 400
pressure / atm
The forward reaction in the equilibrium is

A exothermic with the number of moles of gas decreasing.
B exothermic with the number of moles of gas increasing.
C endothermic with the number of moles of gas decreasing.
D endothermic with the number of moles of gas increasing.
12 Which is the correct expression for R ln K ?
A R ln K = ǻSsystem − ǻH/T
B R ln K = ǻSsystem + ǻH/T
C R ln K = ǻSsystem − TǻH
D R ln K = ǻSsystem + TǻH

7
13 Which compound is most soluble in water?
A C4H9Cl

B C4H9Br
C C3H7COOH
D CH3COOC2H5
14 Which compound reacts with phosphorus(V) chloride to form ethanoyl chloride?
A CH3CHO
B CH3CH2OH
C CH3COCH3
D CH3COOH

15 Which two compounds react together to make the compound shown?
A Ethanoyl chloride and ethylamine

B Ethanoyl chloride and propylamine
C Propanoyl chloride and ethylamine
D Propanoyl chloride and propylamine
(Total for Question 15 = 1 mark) DO NOT WRITE IN THIS AREA
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16 The repeat unit of a polymer is shown.
O O
C (CH2)2 C O (CH2)2 O
Which monomers react to make this polymer?

A HOOC(CH2)2COOH and Cl(CH2)2Cl
B ClOC(CH2)2COCl and HO(CH2)2OH
C ClOC(CH2)2COCl and HOOC(CH2)2COOH
D HOOC(CH2)2COOCH3 and ClOC(CH2)2COCl
17 The retention time in gas chromatography is the time it takes for a compound to pass
through the chromatography column.
A column is packed with a stationary phase that is polar.
Which of the following will have the longest retention time in the column?
A hexane
B hex-1-ene
C pentane
D pentan-1-ol
18 A compound has the structure
CH3(CH2)4CH2 CH2(CH2)6CH2OH
C C
H H
The systematic name of the compound is

A E-hexadec-7-en-1-ol
B Z-hexadec-7-en-1-ol
C E-hexadec-9-en-1-ol
D Z-hexadec-9-en-1-ol
9
19 Fats, such as the one shown, can be converted into fuels for biodiesel by transesterification.
CH2OOCC17H33

CHOOCC17H33
CH2OOCC17H33
Which compound is used as a fuel, following the transesterification of this fat with methanol?
A C17H33COOCH3
B C17H33COOH
C CH2OOCCH3
CHOOCCH3
CH2OOCCH3
D CH2OH

CHOH
CH2OH
20 The type of radiation used in nmr spectroscopy is

A infrared.
B microwave.
C radio waves.
D ultraviolet.
TOTAL FOR SECTION A = 20 MARKS

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

21 When nitrogen(II) oxide, NO, reacts with hydrogen at high temperatures, the products
are nitrogen and water.
(a) Write an equation for this reaction. State symbols are not required.
(1)
(b) The table shows the results of a series of experiments to measure the rate of this reaction.
Experiment Initial concentration / mol dm−3

Initial rate / mol dm−3 s−1
number [NO(g)] [H2(g)]

1 0.0020 0.020 5.5 × 10−3
2 0.0040 0.040 4.4 × 10−2
3 0.0080 0.020 8.8 × 10−2
(i) Deduce the order of reaction with respect to nitrogen(II) oxide and to hydrogen.
Justify your answers by referring to data from the table.
(3)
Order with respect to NO . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ..............................................
Order with respect to H2 . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .............................................
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(ii) Write the rate equation for the reaction.
(1)
(iii) Calculate the value of the rate constant and give its units.
(2)
(c) There is more than one step in the reaction mechanism.

(i) Suggest why the reaction is unlikely to take place in a single step.
(1)
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(ii) The first step of a three-step reaction mechanism is shown.
2NO(g) o N2O2(g)
The second step of the mechanism is the rate determining step.

Suggest an equation for the rate determining step.
Justify your suggestion.
(2)
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(Total for Question 21 = 10 marks)
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22 Propanoic acid is a weak acid with Ka = 1.30 × 10−5 mol dm−3.
(a) (i) Write the expression for the acid dissociation constant, Ka , of propanoic acid.

(1)
(ii) Calculate the pH of a solution of propanoic acid with a concentration of

0.120 mol dm−3.
(3)

(b) 25.00 cm3 of propanoic acid, with a concentration of 0.120 mol dm−3, was pipetted
into a conical flask.
This solution was titrated with sodium hydroxide of concentration 0.150 mol dm−3.
CH3CH2COOH + NaOH o CH3CH2COONa + H2O
(i) Use the value of Ka to calculate the pH of the mixture in the flask when
enough sodium hydroxide has been added to react with half of the acid.
(2)
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*P56131A01428*
*(ii) In the region where the acid is half neutralised, the pH of the titration mixture
changes more gradually than it does when the end-point is approached.
Explain the reason for this gradual change in pH.

(3)
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(iii) Calculate the minimum volume of sodium hydroxide required to react with
all of the propanoic acid.
(2)
(iv) Calculate the pH when 40 cm3 of sodium hydroxide (an excess) was added.
(3)
15
(c) In another titration, a solution of aqueous ammonia with a concentration of
0.120 mol dm−3 was added to 25.00 cm3 propanoic acid with a concentration of
0.120 mol dm−3.

(i) Sketch the shape of the titration curve on the grid.
(2)
14
10.5
pH
7
3.5

0 10 20 30 40
volume of ammonia / cm3
(ii) Explain why an indicator cannot be used to determine the end-point of this reaction.
(1)
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23 This question is about some reactions involving ethanal, CH3CHO.

CH3CHO
Reaction A Reaction B Reaction C

I2 + NaOH HCN + KCN
CH3CH2OH Two organic Product C

products
(a) Ethanal is a carbonyl compound.

Describe the test for a carbonyl compound and give the result.
(2)
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(b) Identify, by name or formula, the reagent needed to carry out Reaction A.
(1)
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(c) (i) Identify the two organic products of Reaction B.

(2)
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(ii) State what you would see when Reaction B is carried out.
(1)
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18
*P56131A01828*
(d) (i) Name the reaction type and mechanism that occurs in Reaction C.
(1)
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(ii) Draw the mechanism for Reaction C.

Include curly arrows, and all the relevant dipoles and lone pairs.
(4)
(iii) The organic product of Reaction C is a racemic mixture.

State the meaning of ‘racemic mixture’.
(1)
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*(iv) By referring to the mechanism of Reaction C, explain why a racemic mixture

forms in this reaction.
(2)
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19
24 This question is about compounds of iodine.
(a) Potassium iodate(V) can be decomposed by heating.

KIO3(s) o KI(s) + 1½O2(g)
(i) Use data from your Data Booklet to calculate the enthalpy change for this reaction.
(2)

(ii) Calculate the standard entropy change of the system, ǻS system .
[The standard molar entropy of ½O2(g) is 102.5 J mol−1 K−1]
(2)
20
*P56131A02028*
(iii) Use your answers to (a)(i) and (a)(ii) to calculate the minimum temperature for
this reaction to be spontaneous.
Show your working clearly.

(2)
(iv) Explain why some reactions which are thermodynamically favourable do not
occur spontaneously.
(1)
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21
(b) Some data about potassium iodide and its ions are shown.
Enthalpy change of solution of KI = +20.3 kJ mol−1

Ion Enthalpy change of hydration / kJ mol−1
K+(g) −320
I−(g) –308
(i) Use these data to calculate the lattice energy of potassium iodide.
(2)

*(ii) Explain why the lattice energy of sodium iodide is more exothermic than that
of potassium iodide.
(2)
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TOTAL FOR SECTION B = 52 MARKS
22
*P56131A02228*
SECTION C
Answer ALL the questions. Write your answers in the spaces provided.
25 This question is about the chemistry of methanol.

(a) Methanol can be synthesised by the reaction of carbon monoxide with hydrogen.
CO(g) + 2H2(g) U CH3OH(g)
A mixture of 18.5 mol of carbon monoxide and 13.5 mol of hydrogen was allowed
to reach equilibrium at 550 K and 60 atm pressure.
At equilibrium the mixture contained 5.5 mol of methanol.
(i) Write the expression for the equilibrium constant in terms of pressure, Kp , for
this reaction.
(1)
(ii) Calculate the number of mol of carbon monoxide and hydrogen remaining
at equilibrium.
Hence calculate the value of Kp at 550 K.
Give your answer to three significant figures and include the units.
(5)
23
(iii) The value of Kp is greater when the reaction is carried out at a lower temperature.
Use this information to deduce the sign of ǻSsurroundings for the forward reaction.

Give your reasoning.
(2)
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(b) An organic compound, P, has the molecular formula C5H8O3 .

A molecule of P has a carbon chain that is not branched, and contains
two different functional groups.
(i) P reacts with sodium carbonate solution, forming bubbles of a colourless gas.
There is no colour change when P is warmed with a mixture of
potassium dichromate(VI) and sulfuric acid.
Use all the information provided to identify, by name or formulae, the
two functional groups present in P.
(2)
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(ii) The mass spectrum of P has a strong peak at m / e = 43.

Suggest the structural formula of the fragment causing this peak.
(1)
24
*P56131A02428*
*(iii) When P is heated with methanol, in the presence of dilute sulfuric acid, a
pleasant smelling compound, Q, is formed.
The high resolution proton nmr spectrum of Q is shown.

The numbers show the relative areas of the peaks.
3 3
2 2
4.4 4.0 3.6 3.2 2.8 2.4 2.0 1.6
į / ppm
Draw the structure of Q. Justify your answer by considering the relative areas
of the four peaks, and their splitting patterns.
(4)
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25
(iv) Write an equation using structural formulae to show the reaction of P with
methanol in the presence of dilute sulfuric acid to form Q.
(2)

(v) The reaction of P with methanol does not give a 100% yield of Q because of
the equilibrium position which is reached.
Suggest the formula of a compound which would react with methanol to
form Q in a reaction which is not reversible.
(1)

TOTAL FOR SECTION C = 18 MARKS

TOTAL FOR PAPER = 90 MARKS
26
*P56131A02628*
BLANK PAGE
*P56131A02728*
27
*P56131A02828*
BLANK PAGE
28

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Please check the examination details below before entering your candidate information

Candidate surname Other names

Centre Number Candidate Number

Tuesday 4 June 2019

DO NOT WRITE IN THIS AREA

DO NOT WRITE IN THIS AREA

(Total for Question 2 = 1 mark)

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Which of the following sketch graphs is correct for this reaction?

(Total for Question 3 = 1 mark)

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The axes on the graph are

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(Total for Question 4 = 1 mark)

(Total for Question 5 = 1 mark)

CH3COOH + C2H5COOH U CH3COO− + C2H5COOH2+

A CH3COOH and C2H5COOH

(Total for Question 6 = 1 mark)

7 In a titration of hydrochloric acid with aqueous ammonia, which indicator would be

(Total for Question 7 = 1 mark)

8 A solution of hydrochloric acid has pH = 2.

(Total for Question 8 = 1 mark)

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(Total for Question 9 = 1 mark)

10 What are the units of Kc for the following equilibrium?

DO NOT WRITE IN THIS AREA

(Total for Question 10 = 1 mark)

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The forward reaction in the equilibrium is

(Total for Question 11 = 1 mark)

12 Which is the correct expression for R ln K ?

(Total for Question 12 = 1 mark)

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(Total for Question 13 = 1 mark)

14 Which compound reacts with phosphorus(V) chloride to form ethanoyl chloride?

DO NOT WRITE IN THIS AREA

15 Which two compounds react together to make the compound shown?

A Ethanoyl chloride and ethylamine

(Total for Question 15 = 1 mark) DO NOT WRITE IN THIS AREA

Which monomers react to make this polymer?

(Total for Question 16 = 1 mark)

(Total for Question 17 = 1 mark)

18 A compound has the structure

The systematic name of the compound is

(Total for Question 18 = 1 mark)

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20 The type of radiation used in nmr spectroscopy is

(Total for Question 20 = 1 mark)

TOTAL FOR SECTION A = 20 MARKS

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Experiment Initial concentration / mol dm−3

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Order with respect to NO . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ..............................................

Order with respect to H2 . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .............................................

(c) There is more than one step in the reaction mechanism.

(ii) The first step of a three-step reaction mechanism is shown.

The second step of the mechanism is the rate determining step.

(Total for Question 21 = 10 marks)