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Pearson Edexcel International Advanced Level

Wednesday 7 June 2023
Morning (Time: 1 hour 45 minutes) Paper
reference WCH15/01
Chemistry
 

International Advanced Level

UNIT 5: Transition Metals and Organic
Nitrogen Chemistry
You must have: Total Marks
Scientific calculator, Data Booklet

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

Information
• The total mark for this paper is 90.
• – usemarks
The for each question are shown in brackets
this as a guide as to how much time to spend on each question.
• Into 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.
• Checkanswer
Try to every question.
• your answers if you have time at the end. Turn over

*P71943A0136*
P71943A
©2023 Pearson Education Ltd.

N:1/1/1/1/
 SECTION A
Answer ALL the questions in this section.
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 The equation for a redox reaction is shown.

2V2+(aq) + Cu2+(aq) → 2V3+(aq) + Cu(s)

What is the cell diagram for this reaction?

A V(s) | V3+(aq), V2+(aq) | | Cu(s) | Cu2+(aq)

B V(s) | V2+(aq), V3+(aq) | | Cu2+(aq) | Cu(s)

C Pt(s) | V3+(aq), V2+(aq) | | Cu(s) | Cu2+(aq)

D Pt(s) | V2+(aq), V3+(aq) | | Cu2+(aq) | Cu(s)

(Total for Question 1 = 1 mark)

2 Some standard electrode potentials are shown.

Right-hand electrode system E /V

Mg2+ + 2e–  Mg –2.37

Ce3+ + 3e–  Ce –2.33

Mn2+ + 2e–  Mn –1.19

  Mn3+ + e–  Mn2+ +1.49

  Ce4+ + e–  Ce3+ +1.70

Which reaction is thermodynamically feasible?

A 2Ce + 3Mg2+ → 2Ce3+ + 3Mg

B 4Ce3+ → Ce + 3Ce4+

C 3Mn2+ → Mn + 2Mn3+

D Mg + 2Ce4+ → Mg2+ + 2Ce3+

(Total for Question 2 = 1 mark)

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*P71943A0236* 
3 In a chemical reaction, E cell is directly proportional to

A Kc

B rH

C Ssystem

D Stotal

(Total for Question 3 = 1 mark)

4 For the reaction shown, E cell = +0.89 V.

4V3+(aq) + O2(g) + 2H2O(l) → 4VO2+(aq) + 4H+(aq)

Which statement can be deduced from this information only?

A the reaction will not occur under any conditions

B the reactants are kinetically stable with respect to the products

C the reactants are thermodynamically unstable with respect to the products

D an aqueous solution of V3+ will oxidise rapidly on standing in air

(Total for Question 4 = 1 mark)

5 Which reaction occurs at the negative electrode in a hydrogen-oxygen fuel cell?

A H2 + 2OH– → 2H2O + 2e–

B 2H+ + 2e– → H2

C O2 + 4H+ + 4e– → 2H2O

D 4OH– → O2 + 2H2O + 4e–

(Total for Question 5 = 1 mark)

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

3
 *P71943A0336* Turn over
6 Which electronic configuration is correct?

A Ti2+ [Ar]4s2

B Cr [Ar]3d44s2

C Fe3+ [Ar]3d34s2

D Cu [Ar]3d104s1

(Total for Question 6 = 1 mark)

7 The structure of the complex Cr2(CH3CO2)4(H2O)2 is shown.

CH3

C CH3
O OC
O O
H2O Cr Cr OH2
O
O
CO O
CH3 C

CH3

What is the coordination number of chromium in this complex?

A two
B four

C six

D twelve

(Total for Question 7 = 1 mark)

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

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*P71943A0436* 
8 Which complex contains only monodentate ligands?

A [Fe(CN)6]4–

B [Cr(C2O4)3]3–

C [Ni(EDTA)]2–

D [Co(NH2CH2CH2NH2)2Cl2]

(Total for Question 8 = 1 mark)

9 Which complex has a ligand-metal-ligand bond angle of 109.5°?

A [CuCl4]2–

B [Fe(EDTA)]–

C [Ag(NH3)2]+

D [Pt(NH3)2Cl2]

(Total for Question 9 = 1 mark)

10 Which ion is not blue?

A VO2+

B [Co(H2O)6]2+

C [Cr(H2O)6]2+

D [Cu(H2O)6]2+

(Total for Question 10 = 1 mark)

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

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 *P71943A0536* Turn over
11 Which equation shows a redox reaction in which the solution turns yellow?

A Fe + 2HCl → FeCl2 + H2

B VO3– + 2H+ → VO2+ + H2O

C Cr2O72– + 2OH– → 2CrO42– + H2O

D 2Cr(OH)3 + 3H2O2 + 4KOH → 2K2CrO4 + 8H2O

(Total for Question 11 = 1 mark)

12 Aqueous ammonia is added in excess to an aqueous solution of Cu2+.

What is the equation for the overall reaction?

A [Cu(H2O)6]2+ + 2NH3 → [Cu(H2O)4(OH)2] + 2NH4+

2+
B [Cu(H2O)6]2+ + 2NH3 → [Cu(NH3)2(H2O)4] + 2H2O

C [Cu(H2O)6]2+ + 4NH3 → [Cu(NH3)4(H2O)2]2+ + 4H2O

D [Cu(H2O)6]2+ + 6NH3 → [Cu(NH3)6]2+ + 6H2O

(Total for Question 12 = 1 mark)

13 Which equation shows the formation of a precipitate?

A     [Zn(OH)4]2– + 2H3O+ → [Zn(H2O)4(OH)2]

B    [Zn(H2O)6]2+ + 4OH– → [Zn(OH)4]2– + 6H2O

C [Cr(H2O)3(OH)3] + 3H3O+ → [Cr(H2O)6]3+ + 3H2O

D [Cr(H2O)3(OH)3] + 3OH– → [Cr(OH)6]3– + 3H2O

(Total for Question 13 = 1 mark)

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

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*P71943A0636* 
14 What is the sequence of oxidation number changes for vanadium when V2O5 is used
in the contact process?
A +2 → +1 → +2

B +2 → +5 → +2

C +5 → +4 → +5

D +5 → +6 → +5

(Total for Question 14 = 1 mark)

15 What is the total number of delocalised electrons in anthracene?

anthracene
A 6
B 10

C 14

D 18

(Total for Question 15 = 1 mark)

16 Which statement explains why bromine reacts more readily with phenol than
with benzene?

A the O H bond in phenol is polar

B the oxygen atom in phenol is very electronegative

C a lone pair of electrons on oxygen in phenol is delocalised into the ring

D the electron density in the ring is greater in benzene than in phenol

(Total for Question 16 = 1 mark)

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

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 *P71943A0736* Turn over
17 Which reaction can form a secondary amine?

N
LiAlH4
A

C2H5Br
B
C2H5NH2

C C2H5Br
(C2H5)2NH

O NaOH
D
NH

(Total for Question 17 = 1 mark)

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

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*P71943A0836* 
18 Compound X reacts with excess nitrous acid, followed by coupling with
excess phenol to form an azo dye.

OCH3

H2N NH2

H3CO

compound X
What is the structure of the azo dye?

HO

OCH3
A

H2N NH2

H3CO

HO

OCH3

B H2N NH2

H3CO

OH

OCH3

C H2N N
N OH
H3CO

OCH3
HO N
D N N
N OH
H3CO

(Total for Question 18 = 1 mark)

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 *P71943A0936* Turn over
19 Four amino acids are dissolved in deionised water to form separate
0.05 mol dm–3 solutions.
Which amino acid will give the solution with the lowest pH?

A HO OH

NH2

O O

B HO OH

NH2

O
H2N
C OH

NH2

D OH

NH NH2

(Total for Question 19 = 1 mark)

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

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*P71943A01036* 
20 Which carbonyl compound and Grignard reagent would not react to form
compound Y?

OH

compound Y

Carbonyl compound Grignard reagent

O
BrMg
A

O
B
BrMg

O
C BrMgCH3

O
D BrMg

(Total for Question 20 = 1 mark)

TOTAL FOR SECTION A = 20 MARKS

11
 *P71943A01136* Turn over
 BLANK PAGE

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*P71943A01236* 
 SECTION B
Answer ALL the questions. Write your answers in the spaces provided.
21 This question is about mercury, Hg, and its compounds.
Mercury is a liquid element in the same group of the Periodic Table as zinc.
The electronic configuration of mercury is [Xe]4f 145d106s2.
(a) Mercury forms compounds in either the +1 or +2 oxidation states.
Explain why mercury is classified as a d-block element but is not a
transition element.
(3)

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 (b) Mercury reacts with nitric acid to form an aqueous solution of Hg(NO3)2 and
nitrogen monoxide gas.
The unbalanced equation is shown.

Hg(l) + HNO3(aq) → Hg(NO3)2(aq) + NO(g) + H2O(l)

(i) Explain, using oxidation numbers, why this is a redox reaction.

(2)

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(ii) Deduce the ionic half-equations for this reaction.

State symbols are not required.
(2)

(iii) Complete the equation for this reaction by adding the

stoichiometric coefficients.
(1)

............. . . . Hg(l) + ................ HNO3(aq) → ................ Hg(NO3)2(aq) + ................ NO(g) + .............. . . H2O(l)

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*P71943A01436* 
 (c) Mercury(II) fulminate, Hg(CNO)2 , is an explosive.
(i) It is produced in the reaction between Hg(NO3)2 and ethanol. The other
products of the reaction are ethanal and water.
Write the equation for the reaction of one mole of Hg(NO3)2 with ethanol to
form mercury(II) fulminate.
State symbols are not required.
(2)

(ii) Hg(CNO)2 decomposes as shown.

3Hg(CNO)2(s) → Hg(CN)2(s) + 2Hg(s) + 2CO2(g) + 2CO(g) + 2N2(g)

Calculate the total volume, in cm3, of gas produced when

1.00 g of Hg(CNO)2 decomposes at room temperature and pressure.
(3)

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 *P71943A01536* Turn over
 (d) Mercury(I) chloride, Hg2Cl2 , is also known as calomel.
A saturated calomel electrode may be used as an alternative to the
standard hydrogen electrode.

glass tube

Hg(l)

saturated KCl

porous glass Hg2Cl2 (paste)

membrane

KCl crystals

The half-equation for the calomel electrode is

Hg2Cl2(s) + 2e–  2Hg(l) + 2Cl–(aq)

The standard electrode potential of the calomel electrode is E = +0.24 V.

(i) Suggest why KCl crystals are needed in the outer tube of the electrode.
(1)

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*P71943A01636* 
 (ii) A calomel electrode was used to measure the standard electrode potential of
the Sn2+(aq) | Sn(s) half‑cell.

– +
V

Sn(s)

1.0 mol dm–3 Sn2+(aq)

The reading on the voltmeter in this cell was +0.37 V.

Deduce the standard electrode potential for the Sn2+(aq) | Sn(s) half‑cell.
(1)

(iii) Write the overall equation for the cell reaction.

(1)

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 (iv) Add labels to complete the diagram of a standard hydrogen electrode.
Include details of any essential conditions.
(3)

salt bridge
KNO3(aq)

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(v) Suggest one advantage of using a calomel electrode, in place of a

standard hydrogen electrode, when measuring a cell potential.
(1)

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(Total for Question 21 = 20 marks)

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*P71943A01836* 
22 The amount of calcium ethanedioate, CaC2O4 , present in a sample of spinach is
determined by redox titration.
11.4 g of spinach leaves are stirred in 50.0 cm3 of a warm acidified solution
of 0.0100 mol dm–3 potassium manganate(VII), KMnO4 , oxidising all the
ethanedioate ions, C2O42– .

16H+ + 2MnO4– + 5C2O42– → 2Mn2+ + 10CO2 + 8H2O

The excess manganate(VII) ions, MnO4– , are then titrated with an acidified solution of
0.0500 mol dm–3 iron(II) sulfate, FeSO4 .

5Fe2+ + 8H+ + MnO4– → 5Fe3+ + Mn2+ + 4H2O

25.95 cm3 of iron(II) sulfate solution was needed for complete reaction.
Calculate the percentage by mass of CaC2O4 present in the spinach leaves.
Give your answer to an appropriate number of significant figures.

(Total for Question 22 = 6 marks)

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*23 Some thermochemical, X-ray diffraction and bromination information on benzene
and cyclohexene is shown.
Thermochemical data

Compound Enthalpy of hydrogenation / kJ mol–1

benzene –208

cyclohexene –120

X-ray diffraction data

a a f e

a a f d
a a f e

Benzene bond a Cyclohexene bond d e f

Bond length / pm 139 Bond length / pm 129 150 153

Bromination

Compound Reaction conditions Organic product

benzene FeBr3 , heat bromobenzene

cyclohexene room temperature 1,2-dibromocyclohexane

Explain how all this information provides evidence that the electrons in the π-bonds
of benzene are delocalised.
(6)

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*P71943A02036* 
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(Total for Question 23 = 6 marks)

21
 *P71943A02136* Turn over
24 This question is about polymers.
(a) Polyacrylamide (PAM) and polyacrylic acid (PAA) are water-absorbent
addition polymers.
O NH2 O OH

n n

PAM PAA

(i) PAM is made from the acrylamide monomer.

O

NH2

acrylamide

Give the IUPAC name for acrylamide.

(1)

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(ii) Explain why PAM is able to absorb large amounts of water.

Include a diagram in your answer.
(3)

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22
*P71943A02236* 
 (iii) The structure of PAA in aqueous solution is pH-dependent.
Below pH 4, the structure of PAA is compact due to the formation of
intramolecular hydrogen bonds.
Above pH 8, PAA has an open coil structure.

compact structure open coil structure

below pH 4 above pH 8

Suggest why PAA exists as an open coil structure above pH 8.

(2)

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23
 *P71943A02336* Turn over
 (b) Polyvinylpyrrolidone (PVP) is an addition polymer used in the
pharmaceutical industry. The average molar mass of PVP is 90 000 g mol–1.

O
N

PVP

(i) Draw the structure of the vinylpyrrolidone monomer used to make PVP.
(1)

(ii) Calculate the number of monomers needed to make one molecule of PVP
polymer with a molar mass of 90 000 g mol–1.
Give your answer to the nearest whole number.
(2)

(iii) A 740 mg tablet of a painkiller contains 4.0 % PVP by mass.

Calculate the number of molecules of PVP polymer in the tablet.
(3)

24
*P71943A02436* 
 (c) All types of nylon are condensation polymers.
(i) State what is meant by the term condensation polymer.
(2)

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(ii) The structure of nylon 6,6 is shown.

O H

N
N n
O H

nylon 6,6

Nylon 6,6 is made from two monomers.

Deduce the structural formulae of these two monomers.
(2)

structural formula of monomer 1

structural formula of monomer 2

25
 *P71943A02536* Turn over
 (iii) Caprolactam can be directly converted to give a different polymer, nylon 6, in
a ring-opening polymerisation reaction.

NH

caprolactam

Draw two repeat units of nylon 6.

(2)

(Total for Question 24 = 18 marks)

TOTAL FOR SECTION B = 50 MARKS

26
*P71943A02636* 
 BLANK PAGE

27
 *P71943A02736* Turn over
 SECTION C
Answer ALL the questions. Write your answers in the spaces provided.
25 The synthetic drugs of the ’Caine’ family are used as local anaesthetics.
Caine drugs prevent nerve activity by binding to sodium channel receptors in the
lipid cell membranes of neurons.

O O
N
O O

H2N H2N

benzocaine procaine

O
S
O
O
N NH
NH

O NH
lidocaine

articaine

(a) Name the three functional groups present in benzocaine.

(2)

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

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

28
*P71943A02836* 
 (b) Procaine can react with hydrochloric acid to form a monohydrochloride salt.
(i) Write an equation, using molecular formulae, for this reaction.
State symbols are not required.
(2)

(ii) Explain by considering both nitrogen atoms in procaine which nitrogen is

more likely to be protonated in the reaction with hydrochloric acid.
(2)

O
N
O

H2N

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

(c) When benzocaine and procaine are hydrolysed, one of the products formed is the
same in both reactions.
Give the structure of this product.
(1)

29
 *P71943A02936* Turn over
 (d) Lidocaine can be prepared in the synthesis shown.

Step 1 Step 2
conc. HNO3
conc. H2SO4
30 °C NO2 NH2

2,6-dimethylnitrobenzene

Step 3

Step 4
O O
N Cl
NH NH NH

lidocaine

(i) Give the mechanism for Step 1.

Include an equation for the formation of the electrophile.
(4)

30
*P71943A03036* 
 (ii) A low yield of 2,6-dimethylnitrobenzene is obtained in Step 1 due to the
formation of additional organic products.
Give possible structures for two additional organic products.
(2)

(iii) Give the reagents for Step 2.

(1)

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

(iv) Deduce the skeletal formula of the reagent for Step 3.

(1)

(v) State the type and mechanism of reaction occurring in Step 4.

(1)

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31
 *P71943A03136* Turn over
 (e) Articaine is a chiral molecule.
Indicate any chiral centres on the structure of articaine.
(1)

O
S
O

NH

O NH

articaine

(f ) Articaine is metabolised in the body with a half-life of 20 minutes.

A patient is given a dose of 100 mg of articaine.
Calculate the mass of articaine in micrograms, μg, remaining in the body
after 4 hours.
[1 μg = 10–3 mg]
(3)

(Total for Question 25 = 20 marks)

TOTAL FOR SECTION C = 20 MARKS

TOTAL FOR PAPER = 90 MARKS

32
*P71943A03236* 
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33
 *P71943A03336*
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34
*P71943A03436* 
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35
 *P71943A03536*
36
*P71943A03636* 