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Pearson Edexcel International Advanced Level

Friday 12 January 2024
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, 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.
• structure
In the question marked with an asterisk (*), marks will be awarded for your ability to
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

P73457RA
©2024 Pearson Education Ltd.
S:1/1/1/
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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 The apparatus can be used to measure E cell for the reaction shown.

2Cr3+(aq) + Zn(s) → 2Cr2+(aq) + Zn2+(aq)

V
electrode 1 electrode 2

salt bridge

Zn2+(aq) Cr2+(aq) and Cr3+(aq)

(a) Which electrodes are used for this cell?

(1)

electrode 1 electrode 2

A platinum platinum

B platinum chromium

C zinc chromium

D zinc platinum

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 (b) A student wishes to measure the standard cell potential, E cell , of this cell.
The right‑hand cell requires Cr3+ and Cr2+ ions.
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What mass of Cr2(SO4)3 ·18H2O must be dissolved in 1.00 dm3 of deionised water to
give the concentration of Cr3+ ions required to measure this E cell ?
(1)
A 52.0 g

B 196 g

C 358 g

D 716 g

(c) What can be deduced from the fact that, for this reaction, E cell is positive?
(1)
A ΔStotal and ln K are positive

B ΔStotal and ln K are negative

C ΔStotal is positive and ln K is negative

D ΔStotal is negative and ln K is positive

(Total for Question 1 = 3 marks)

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

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2 The half‑equations for a hydrogen‑oxygen fuel cell in alkaline solution are shown.

        2H2O(l) + 2e– → H2(g) + 2OH–(aq)    E = –0.83 V

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½O2(g) + H2O(l) + 2e– → 2OH–(aq)            E = +0.40 V

(a) The equation for the overall cell reaction is

(1)
A 3H2O(l) + ½O2(g) → H2(g) + 4OH–(aq)

B H2(g) + 4OH–(aq) → 3H2O(l) + ½O2(g)

C H2(g) + ½O2(g) → H2O(l)

D H2O(l) → H2(g) + ½O2(g)

(b) Calculate E cell for the reaction occurring in the hydrogen‑oxygen fuel cell, under
alkaline conditions.
(1)
A –1.23 V
B –0.43 V

C +0.43 V

D +1.23 V

(Total for Question 2 = 2 marks)

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

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 3 Which successive ionisation energies (in kJ mol–1) are most likely to be those of a
transition element?
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A 578 1817 2745 11 578 14 831

B 759 1561 2958   5290   7236

C 789 1577 3232   4356 16 091

D 801 2427 3660 25 026 32 828

(Total for Question 3 = 1 mark)

4 Which sequence shows the ions in order of increasing strength as a reducing agent?
Refer to your Data Booklet.

A V2+ < Fe2+ < Cr2+

B Cr2+ < Fe2+ < V2+

C Cr2+ < V2+ < Fe2+

D Fe2+ < V2+ < Cr2+
(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 This question concerns the chemistry of copper.
In the reaction sequence, the substances P, Q, R, S, T and U contain copper in various

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oxidation states.

P
blue
NaOH(aq) solution

Q KI(aq)
pale blue
solid
T
H2SO4(aq) pink solid
aqueous CuI and
solution X U
blue solution

R aqueous
dark blue solution X
solution

vigorous S
shaking colourless
solution

(a) What are the electronic structures of the three copper species?
(1)

Cu Cu+ Cu2+

A [Ar] 3d9 4s2 [Ar] 3d9 4s1 [Ar] 3d9

B [Ar] 3d9 4s2 [Ar] 3d8 4s2 [Ar] 3d7 4s2

C [Ar] 3d10 4s1 [Ar] 3d9 4s1 [Ar] 3d8 4s1

D [Ar] 3d10 4s1 [Ar] 3d10 [Ar] 3d9

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 (b) Which rows show the substances with their correct oxidation states?
(1)
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Cu(0) Cu(I) Cu(II)

A S U P

B S R Q

C T S P

D T U Q

(c) Aqueous solution X contains

(1)
A H2SO4

B KI

C NaOH
D NH3
(Total for Question 5 = 3 marks)

6 The diagram shows the skeletal structure of theobromine, which has a bitter taste
and is found in chocolate and tea leaves.

N
N

O N N

Which of the functional groups listed is not present in the structure?

A alkyl

B amide

C amine

D ketone
(Total for Question 6 = 1 mark)

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7 Peptides are short chains of amino acids linked by peptide bonds.

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COOH
NH
COOH
O O O O
H H H
H2N N N N
N N N N COOH
H H H H
O O O
COOH COOH COOH

How many different types of amino acid have joined to form the octapeptide?

A 4

B 5

C 6
D 8
(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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 8 Which shows the structure of the amino acid lysine as a solid, and in solution at
high pH?
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Solid High pH solution

O O
H2N H2N
OH O–

NH2 NH2

O O
H3N+ H2N
O– O–

NH2 NH2

O O
H2N H3N+
OH O–

NH2 NH3+

O O
H3N+ –
H3N+
O OH

NH2 NH3+

(Total for Question 8 = 1 mark)

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9 A dipeptide has the molecular formula C7H12N2O3 .
The dipeptide is hydrolysed to form two amino acids. One of the amino acids

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produced does not have a chiral centre.
What is the structure of the other amino acid which does have a chiral centre?

S
A
OH

NH2

B
OH

NH2

C
OH

NH

D
OH

NH2

(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 The aroma of strawberries is due to a number of volatile compounds, including the
four isomeric esters shown.
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O O

O O

ester P ester Q

O O

O O

ester R ester S

(a) Which of the esters have five peaks in their 13C NMR spectrum?
(1)
A P only
B Q and R only

C R and S only

D Q, R and S only

(b) Which of the esters will not have a doublet in its high resolution proton
NMR spectrum?
(1)
A P

B Q

C R

D S

(c) Which of the esters could rotate the plane of plane‑polarised

monochromatic light?
(1)
A Q only

B Q and R

C Q, R and S

D R and S
(Total for Question 10 = 3 marks)

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11 The formulae of three synthetic polymers, X, Y and Z, are shown.

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N

n n n
Cl O
O NH2

X Y Z

Which are made by addition polymerisation reactions?

A X, Y and Z

B X and Y

C X and Z

D Y and Z

(Total for Question 11 = 1 mark)

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

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 12 Sodium thiosulfate can be used to determine the concentration of an iodine solution
by titration using starch indicator.
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(a) 5.00 g of sodium thiosulfate was dissolved in deionised water and the solution
made up to 250.0 cm3 in a volumetric flask.
The volumetric flask has an uncertainty of ± 0.25 cm3.
What is the minimum uncertainty of the balance required to match the
uncertainty of the volumetric flask?
Assume two weighings are needed.
(1)
A ± 0.0025 g

B ± 0.005 g

C ± 0.01 g

D ± 0.05 g

(b) The titration was carried out with sodium thiosulfate in the burette and starch
was added just before the end‑point.
What would be the colour of the solution in the conical flask at the end‑point?
(1)
A blue‑black

B brown

C colourless
D yellow

(Total for Question 12 = 2 marks)

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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13 In 1865, Friedrich August Kekulé suggested a structure for benzene which consisted
of alternating single and double carbon–carbon bonds.

Kekulé structure

However, modern analytical techniques indicate a structure in which the electrons

are delocalised.

delocalised structure

(a) Explain how the results of X‑ray diffraction experiments on benzene suggest a
delocalised structure rather than the Kekulé structure.
(2)

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 (b) The compound 1,2‑dichlorobenzene exists as only one structure.
Explain how this supports the delocalised structure of benzene rather than the
Kekulé structure.
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(2)

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(c) State how the enthalpy changes of hydrogenation for cyclohexene and benzene
provide evidence for the delocalised structure.

+ H2 →         ΔH = –118 kJ mol–1

+ 3H2 →         ΔH = –205 kJ mol–1

(1)

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 (d) Describe the structure of benzene in terms of the atomic orbitals involved,
the bonds formed and the delocalised electrons.
(3)

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(Total for Question 13 = 8 marks)

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*P73457RA01636* 
 14 N‑phenylethanamide, historically used as a painkiller, can be synthesised from
benzene as shown.
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NO2 NH2

benzene nitrobenzene phenylamine

H
N

N‑phenylethanamide

(a) Concentrated nitric acid reacts with a second reagent to produce an electrophile.
This electrophile reacts with benzene to form nitrobenzene.
(i) Identify, by name or formula, the second reagent and the electrophile.
(2)

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 (ii) Draw the mechanism for the reaction between the electrophile and
benzene to form nitrobenzene.
(3)

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(b) (i) Identify, by name or formula, the reagent(s) required to convert
nitrobenzene into phenylamine.
(1)

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(ii) State the type of reaction occurring during this step.

(1)

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*P73457RA01836* 
 *(c) In the final step of the synthesis, phenylamine reacts with either
ethanoyl chloride or ethanoic anhydride.
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phenylamine + ethanoyl chloride → N‑phenylethanamide + hydrogen chloride

phenylamine + ethanoic anhydride → N‑phenylethanamide + ethanoic acid

Ethanoyl chloride is considerably more reactive than ethanoic anhydride.

Hazard symbols for reactants and products are shown.

Compound Hazards Compound Hazards

phenylamine N‑phenylethanamide

ethanoic
ethanoic acid
anhydride

ethanoyl
hydrogen chloride
chloride

Assess the advantages and disadvantages of the use of ethanoic anhydride rather
than ethanoyl chloride for this reaction.
Consider the hazards associated with the reactants and products, and the atom
economy of each reaction.
(6)

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

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

19
 *P73457RA01936* Turn over
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................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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20
*P73457RA02036* 
 (d) The overall yield for the synthesis of N‑phenylethanamide from benzene was
found to be 35.2%.
Calculate the minimum volume of benzene, in cm3, required to make
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10.0 g of N‑phenylethanamide.
[Density of benzene = 0.879 g cm–3]
(4)

(e) Another painkiller, paracetamol, can be synthesised from phenol in a similar

sequence. Phenol is nitrated by dilute nitric acid.

H
NO2 NH2 N

O
HO HO HO HO
phenol 4‑nitrophenol 4‑aminophenol paracetamol

Explain why the nitration of phenol requires much milder conditions than the
formation of nitrobenzene.
(2)

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(Total for Question 14 = 19 marks)

21
 *P73457RA02136* Turn over
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
*P73457RA02236*
BLANK PAGE

22
 15 (a) Gingerol is a compound found in fresh ginger that activates spice receptors on
the tongue, giving raw ginger a hot taste.
The skeletal formula of gingerol is shown.
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O OH

HO
O

gingerol

(i) Give the molecular formula of gingerol.

(1)

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(ii) The OH group is shown attached to the carbon chain by a

wedge‑shaped bond.
Suggest why the bond between the carbon chain and the OH group is shown
as a wedge.
(2)

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23
 *P73457RA02336* Turn over
 (b) Cooking fresh ginger converts gingerol into zingerone, which is less pungent and
has a sweeter flavour.

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Zingerone can be formed in a four‑step synthesis from coniferyl alcohol.
Step 2 in the synthesis involves a Grignard Reagent, while Steps 1, 3 and 4 are
redox reactions.
The synthesis is shown with the structures of the intermediate
compounds incomplete.
Complete this four‑step synthesis of zingerone from coniferyl alcohol.
Include in your answer completed structures of the intermediate compounds and
the reagents and conditions required.
(7)

Step 1

OH Reagents and conditions

HO .............................................................................. HO
O ..............................................................................
O

coniferyl alcohol intermediate 1

Step 2

Reagents and conditions

.............................................................................. HO

..............................................................................
O

intermediate 1 intermediate 2

24
*P73457RA02436* 
 Step 3
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Reagents and conditions

.............................................................................. HO

..............................................................................
O

intermediate 2 intermediate 3

Step 4
O

Reagents and conditions

.............................................................................. HO

..............................................................................
O

intermediate 3 zingerone

(Total for Question 15 = 10 marks)

25
 *P73457RA02536* Turn over
16 A Latimer diagram for a chemical element is a summary of the
standard electrode potential data for that element.

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In a Latimer diagram, the form of the element with the highest oxidation state is on
the left, with successively lower oxidation states to the right.
A Latimer diagram for manganese at pH = 0 is shown.

1.69 V 1.23 V

+0.90 V +1.28 V +2.90 V +0.95 V +1.50 V 2+–1.18 V

MnO–4 HMnO–4 H3MnO4 MnO2 Mn3+ Mn Mn

1.51 V

The diagram shows that the standard electrode potential for the reduction of
MnO–4 to MnO2 , in acidic conditions, is +1.69 V.

MnO–4 + 4H+ + 3e–  MnO2 + 2H2O      E = +1.69 V

(a) (i) Justify the assignment of the oxidation state of +5 to manganese in H3MnO4
using oxidation numbers.
(1)

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

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(ii) Write an equation for the reaction of H3MnO4 in acidic solution to give ions
containing manganese(VI) and manganese(IV).
Use the Latimer diagram to obtain the formulae of the ions produced.
State symbols are not required.
(2)

26
*P73457RA02636* 
 (iii) Deduce whether or not this disproportionation reaction is thermodynamically
feasible by calculating E for the reaction.
(2)
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27
 *P73457RA02736* Turn over
 (b) Before use in titration experiments, potassium manganate(VII) solutions must be
standardised. One method uses ethanedioate ions to find the exact concentration
of the manganate(VII) ions.

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250.0 cm3 of a standard solution contained 1.915 g of
sodium ethanedioate, Na2C2O4 .
A potassium manganate(VII) solution of approximately 0.02 mol dm–3 was
standardised using this solution.
Excess sulfuric acid was added to 25.0 cm3 portions of the
potassium manganate(VII) solution which were titrated with the
sodium ethanedioate solution.
The mean titre was 22.95 cm3.
The relevant ionic half‑equations are shown.

MnO–4 + 8H+ + 5e– → Mn2+ + 4H2O

C2O42– → 2CO2 + 2e–

(i) State the colour change at the end‑point of the titration.

(1)

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

(ii) Calculate the accurate concentration of the potassium manganate(VII),

in mol dm–3, giving your answer to an appropriate number of
significant figures.
(4)

28
*P73457RA02836* 
 (iii) A second titration carried out without the addition of sulfuric acid resulted in
the formation of a brown suspension.
Explain how the value of the mean titre would be affected, if at all, by the
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reaction that forms this suspension.

Use the Data Booklet as a source of information.
There is no need to calculate Ecell values.
(3)

(Total for Question 16 = 13 marks)

TOTAL FOR SECTION B = 50 MARKS

29
 *P73457RA02936* Turn over
 SECTION C

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

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17 Transition metal compounds can show a number of different types of isomerism.
Hydration isomerism is where different numbers of water molecules act as ligands.
The name chromium(III) chloride is given to several chemical compounds with the
formula CrCl3·xH2O , including a number of hydration isomers.
(a) Anhydrous chromium(III) chloride, CrCl3 , is a violet solid which can react with
water to produce three isomers.
[Cr(H2O)6]3+3Cl– is violet.
[Cr(H2O)5Cl]2+2Cl–·H2O is pale green.
[Cr(H2O)4Cl2]+Cl–·2H2O is dark green.
(i) Explain why the three isomers have different colours.
(3)

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

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

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

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

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

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

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

30
*P73457RA03036* 
 (ii) You are provided with three equimolar solutions of the three isomers.
Suggest how you would quantitatively determine the relative numbers of free
chloride ions in the three isomers using the standard test for a chloride ion.
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(5)

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

31
 *P73457RA03136* Turn over
 (b) Complexes can exhibit both cis‑trans and optical isomerism. The cis‑ and
trans‑isomers of diamminedichloroplatinum(II) are commonly known as
cis‑platin and trans‑platin.

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NH3 NH3

Cl Pt NH3 Cl Pt Cl

Cl NH3

cis‑platin trans‑platin

In chemotherapy medication, cis‑platin is used to treat a number of cancers

including testicular cancer and breast cancer, while trans‑platin has no beneficial
effect against cancer. The cis‑isomer is effective because it binds with the
deoxyribonucleic acid (DNA) molecules in a cancerous cell through adenine and
guanine groups. This interferes with the replication of the cell and results in
its destruction.

H
N
DNA strand
H2N N DNA strand

N N
G NH3
Adenine H3N Pt
A G NH3
H H3N Pt A
G

H G NH3
Pt
G NH3
N
H3N A cis‑platin bound to
O N DNA strand Pt
H3N G 2 guanine groups

HN N
Guanine DNA strand
NH2 G

This works in three steps.

Step 1 Slow substitution of one chloride ligand by a water.
Step 2 This water ligand is easily displaced by guanine or adenine in the
DNA strand.
Step 3 Finally the second chloride ligand is displaced by a different guanine or
adenine from a different part of the strand.

32
*P73457RA03236* 
 (i) Write the balanced equation for Step 1.
State symbols are not required.
(1)
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(ii) Describe how guanine and adenine can bind to the platinum ion.
(1)

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

(iii) trans‑Platin binds to DNA.

Suggest why this does not damage the DNA.
(2)

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

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

33
 *P73457RA03336* Turn over
 (c) Reinecke’s salt has the formula NH4[Cr(SCN)x(NH3)y] · zH2O. The anion exists
as a trans‑isomer.
It contains 14.67% chromium, 36.23% sulfur, 4.51% oxygen and

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27.65% nitrogen by mass.
(i) Calculate the values x, y and z in Reinecke’s salt.
You must show your working.
(3)

(ii) Draw a diagram of the anion of Reinecke’s salt showing its

three‑dimensional shape.
(2)

34
*P73457RA03436* 
 (d) (i) Explain why the tetrahedral complex [Co(NH3)ClBrI] exists as two
optical isomers.
(2)
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................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .

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

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

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

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

(ii) Complete the diagram showing the two optical isomers of the
tetrahedral complex.
(1)

Co Co

(Total for Question 17 = 20 marks)

TOTAL FOR SECTION C = 20 MARKS

TOTAL FOR PAPER = 90 MARKS

35
 *P73457RA03536*
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
*P73457RA03636*
36