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Pearson Edexcel International Advanced Level

Friday 25 October 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

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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 What is the electronic configuration of the chromium atom?

A [Ar] 3d4 4s2

B [Ar] 3d5 4s1

C [Ar] 3d6

D [Ar] 3d1 4s2 4p3

(Total for Question 1 = 1 mark)

2 Which ion shows the typical property of transition metals by forming

coloured complexes?

A Cu+

B Ni2+

C Sc3+

D Zn2+
(Total for Question 2 = 1 mark)

3 The formula of a chromium compound is [Cr(H2O)4Cl2]+Cl– .

The molar mass of the compound is 230.5 g mol−1.
What is the percentage by mass of chlorine in the complex ion?

A 18.2%

B 30.8%

C 36.4%

D 46.2%
(Total for Question 3 = 1 mark)
Use this space for any rough working. Anything you write in this space will gain no credit.

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4 The reaction between peroxodisulfate ions and iodide ions is shown.

S2O82− + 2I− → 2SO42− + I2

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The reaction has a high activation energy but is catalysed by iron(II) ions.
(a) What is the best explanation for the high activation energy of this reaction?
(1)
A the peroxodisulfate ion is a weak oxidising agent

B the iodide ion is a weak reducing agent

C peroxodisulfate ions and iodide ions are both negatively charged

D the reaction involves three reactant ions

(b) Which property of iron(II) ions enables them to function as a catalyst for
this reaction?
(1)
A iron(II) ions can be easily reduced to metallic iron
B iron(II) ions effectively adsorb the reactants

C iron(II) ions can be easily oxidised and then reduced

D iron(II) ions can be easily reduced and then oxidised

(Total for Question 4 = 2 marks)

5 Chromium(III) hydroxide, Cr(OH)3(H2O)3 , is amphoteric.

This means that chromium(III) hydroxide dissolves in

A water

B strong acid only

C strong alkali only

D strong acid and strong alkali

(Total for Question 5 = 1 mark)
Use this space for any rough working. Anything you write in this space will gain no credit.

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6 Naphthalene is an aromatic molecule with two aromatic rings joined together.
It can be nitrated at position 1 as shown.

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NO2

+ HNO3  + H2O

naphthalene 1-nitronaphthalene
Molar mass = 128 g mol–1 Molar mass = 173 g mol–1

(a) In an experiment, a 2.00 g sample of naphthalene was nitrated and produced

2.57 g of 1-nitronaphthalene.
What is the percentage yield of 1-nitronaphthalene?
(1)
A 95.1%

B 77.8%
C 74.0%

D 57.6%

(b) A student carrying out this experiment calculated the percentage yield of the
reaction to be greater than 100%.
What is the most likely explanation for this result?
(1)
A there was unreacted naphthalene present

B the naphthalene was impure

C the sample of 1-nitronaphthalene was damp

D other isomers of 1-nitronaphthalene were produced

(Total for Question 6 = 2 marks)
Use this space for any rough working. Anything you write in this space will gain no credit.

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7 This question is about the azo dye, chrysoidine, which has the structure shown.

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NH2

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N
N

NH2

(a) In the production of chrysoidine, phenylamine is first reacted with nitrous acid.
Which equation shows the formation of nitrous acid from sodium nitrite?
(1)
A NaNO2 + HCl → HNO2 + NaCl

B NaNO3 + HCl → HNO3 + NaCl

C NaNO3 + HCl → HNO2 + NaClO

D NaNO2 + HCl → HNO2 + Na + ½Cl2

(b) The reaction of phenylamine with nitrous acid produces the

benzenediazonium ion.
Which is the structure of the benzenediazonium ion?
(1)

+ +
:N N N N:

   A    B

+ +
:N N N N:

   C    D

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(c) Which reactant is required for the coupling reaction with the
benzenediazonium ion to form chrysoidine?
(1)
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NH2

   A

NH2

NH2

HO
   B

NH2

NH2

H2N
   C

NH2

NH2

Cl–N+2
    D

NH2

(Total for Question 7 = 3 marks)

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

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8 The amino acid serine has the structure shown.

H H O

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N C C
H OH
CH2
OH

(a) The IUPAC name for serine is

(1)
A 2-amino-2-carboxyethanol

B 2-amino-1-hydroxyethanoic acid

C 2-amino-1-hydroxypropanoic acid

D 2-amino-3-hydroxypropanoic acid

(b) Which is the organic product of the reaction between serine and
sodium hydroxide solution?
(1)
H H O
N C C
   A
H CH2 O–Na+

OH

H H O
N C C
   B
H CH2 O–Na+

O–Na+

H H O
H N+ C C
   C
H CH2 O–Na+

OH

H H O
H N+ C C
   D
H CH2 O–Na+

O–Na+

(Total for Question 8 = 2 marks)

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9 The cumene process is the main industrial method for making phenol.
The overall equation for this process is shown.
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OH
O

+ + O O  +

What is the atom economy by mass of the cumene process for making phenol?

A 61%

B 62%

C 94%

D 95%
(Total for Question 9 = 1 mark)

10 An aromatic compound with a ten-carbon ring has the structure shown.

(a) Evidence for the aromaticity of this compound is that the carbon-carbon bonds in
the ten-carbon ring
(1)
A alternate in length between single and double bonds

B all have similar lengths

C have no regular pattern of bond length

D are all similar to the carbon-carbon double bond length

(b) The aromaticity is due to the formation of pi (π) bonds as a result of overlap of
(1)
A s and p orbitals

B p and d orbitals

C p orbitals

D d orbitals
(Total for Question 10 = 2 marks)

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11 The polymer, nylon 6-10, is made from a six-carbon diamine and a ten-carbon
dicarboxylic acid.

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Which is the repeat unit of this nylon?

O O
   A N (CH2)10 N C (CH2)6 C

H H

O O
   B N (CH2)6 N C (CH2)10 C

H H

O O
   C N (CH2)10 N C (CH2)4 C

H H

O O
   D N (CH2)6 N C (CH2)8 C

H H

(Total for Question 11 = 1 mark)

12 Car exhaust gases react on the surface of a catalytic converter.

2CO + 2NO → 2CO2 + N2

Which interactions could not occur between the gases and the catalytic converter in
this process?

A covalent bonds

B hydrogen bonds

C London forces

D permanent dipole-induced dipole forces

(Total for Question 12 = 1 mark)

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13 Which pair of equations shows the most likely mechanism for vanadium(V) oxide
acting as a catalyst in the contact process?
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A V2O5 + ½O2 → V2O6 then V2O6 + SO2 → V2O5 + SO3

B V2O5 + SO2 → V2O + 1½O2 + SO3 then V2O + 2O2 → V2O5

C V2O5 + ½O2 → 2VO3 then 2VO3 + SO2 → V2O5 + SO3

D V2O5 + SO2 → V2O4 + SO3 then V2O4 + ½O2 → V2O5

(Total for Question 13 = 1 mark)

14 The formation of carbon dioxide from the reaction between manganate(VII) ions and
ethanedioate ions is autocatalysed by manganese(II) ions.
The equation for this reaction is shown.

2MnO4− + 5C2O2−
4 + 16H+ → 10CO2 + 2Mn2+ + 8H2O
Which graph for the complete reaction shows the autocatalysis of this reaction by the
manganese(II) ions?

   A    B

Volume of Volume of
carbon dioxide carbon dioxide

Time Time

   C    D

Volume of Volume of
carbon dioxide carbon dioxide

Time Time

(Total for Question 14 = 1 mark)

TOTAL FOR SECTION A = 20 MARKS

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

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15 This question is about butylamine, C4H9NH2 .
The boiling temperature of butylamine is 78°C, which is much higher than alkanes of
similar molar mass.
(a) Butylamine is miscible with water. Draw a labelled diagram to show one of the
intermolecular interactions between a butylamine molecule and a molecule
of water.
Include relevant lone pairs and dipoles.
(2)

(b) Butylamine has a fishy, ammonia-like smell. The exposure limit or safety level in
the atmosphere for butylamine is 15 mg m−3 .
Calculate the maximum number of butylamine molecules that are allowed
per cubic metre.
[Avogadro constant, L = 6.02 × 1023 mol−1]
(2)

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(c) Butylamine reacts with ethanoyl chloride to form N-butylethanamide.
Write an equation for this reaction using displayed formulae.
(2)
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(d) Explain why butylamine is a stronger base than ammonia.

(3)

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(Total for Question 15 = 9 marks)

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16 Iron is generally prescribed when a person is suffering from anaemia. Many people
find it easier to take medicine in liquid form rather than solid tablets.

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An iron solution, advertised for this purpose, contains iron as Fe2+ .
An adult is advised to take 90.0 mg of iron daily.
A 25.0 cm3 sample of the solution was made up to 100.0 cm3 using sulfuric acid and
deionised water.
25.0 cm3 samples of the diluted iron(II) solution were titrated with a
0.0125 mol dm−3 potassium manganate(VII) solution.
The mean titre was 16.20 cm3 .
The reaction is shown.

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

Calculate the volume of iron solution required to obtain a 90.0 mg dose of iron.
Give your answer to an appropriate number of significant figures.

Volume required by an adult to obtain a 90.0 mg dose ..................................... . . . . . . . . . . . . . . . . . . . . . . . . . cm3

(Total for Question 16 = 6 marks)

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17 This question is about electrochemical cells.
*(a) Describe how you would carry out an experiment to determine the standard

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electrode potential of the electrode system shown.

Co2+(aq) + 2e−  Co(s)

Assume that you have access to the equipment and chemicals that you need,
describing their use in your answer.
You may include a labelled diagram.
(6)

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(b) Acidified potassium dichromate(VI) is an oxidising agent.
The acid commonly used is sulfuric acid.

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Explain, using reference to the electrode potentials shown, why concentrated
hydrochloric acid should not be used to acidify potassium dichromate(VI).

Electrode system E /V

Cr2O72− + 14H+ + 6e−  2Cr3+ + 7H2O +1.33

Cl2 + 2e−  2Cl− +1.36

(3)

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(c) The cell diagram for an electrochemical cell is shown.

Ag(s) | Ag+(aq) || [VO+2 (aq) + 2H+(aq)], [VO2+(aq) + H2O(l)] | Pt(s)

Write the reduction half-equation for this electrochemical cell.

State symbols are not required.
(1)

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(d) The Direct Methanol Fuel Cell (DMFC) uses methanol and oxygen to generate
electricity. When the cell operates, the methanol reacts with water at one
electrode to produce carbon dioxide and hydrogen ions.
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At the other electrode the oxygen reacts with hydrogen ions to form water.
(i) Write the oxidation half-equation for this fuel cell.
State symbols are not required.
(1)

(ii) Write the overall equation for this fuel cell.

State symbols are not required.
(1)

(iii) The reduction half-cell in the DMFC has a standard electrode potential
E = +1.23 V .
When the solution concentration changes, the electrode potential changes
so that E = +1.20 V.
The relationship between these values is given by the equation

E = E + 4.277 × 10−3 ln X

where X is the concentration of the solution in mol dm−3 .

Calculate the value of X in the non-standard half-cell.
(1)

(Total for Question 17 = 13 marks)

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18 This question is about coloured transition metal complex ions.
(a) The [Fe(H2O)6]2+ complex ion is green and the [Fe(H2O)6]3+ complex ion is yellow.

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(i) Explain why the [Fe(H2O)6]2+ complex ion is coloured.
(3)

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(ii) Explain why the two iron complex ions are different colours.
(2)

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(b) The thiocyanate ion, SCN−, forms a ‘blood-red’ coloured complex ion with
iron(III) ions.
(i) The dot-and-cross diagram for the thiocyanate ion can be drawn in more
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than one way. For example, the negative charge can be on the nitrogen atom
as shown.

 –

*
*
*
S C N
*
*
*

Complete the alternative dot-and-cross diagram of the thiocyanate ion where

the negative charge is on the sulfur atom.
Use () for the nitrogen electrons, (×) for the carbon electrons,
(*) for the sulfur electrons and () for the extra electron.
(2)

S C N

(ii) 12.8 cm3 of 0.05 mol dm−3 iron(III) chloride solution reacted with
8.0 cm3 of 0.08 mol dm−3 ammonium thiocyanate to form a complex ion.
Deduce the formula of the octahedral complex ion that iron(III) ions form
with thiocyanate ions in aqueous solution.
You must show your working.
(3)

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Formula

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(c) Colorimetry was used to determine the concentration of a solution
of copper(II) sulfate.
Six solutions of copper(II) sulfate of known concentration were prepared and their

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absorbance at a wavelength of 635 nm measured. The results are shown.

Concentration of
0.00 0.10 0.20 0.30 0.40 0.50
CuSO4(aq) / mol dm−3

Absorbance at 635 nm 0.00 0.28 0.55 0.83 1.10 1.38

(i) Plot a graph of absorbance against concentration using the data in the table.
(3)

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(ii) 50.0 cm3 of a solution of copper(II) sulfate of unknown concentration was
pipetted into a 250.0 cm3 volumetric flask and the volume made up to the
mark with deionised water.
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The absorbance at a wavelength of 635 nm for this

diluted copper(II) sulfate solution was 0.72.
Determine the concentration of the original copper(II) sulfate solution.
You must show your working on the graph.
(2)

(iii) Give one possible reason why any concentrations of

copper(II) sulfate determined from the graph of values
over 0.50 mol dm−3 are uncertain.
(1)

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(d) The complex ion formed from cobalt(III) ions and ethane-1,2-diamine is a
yellow‑orange colour.
The equation for the formation of this complex ion is shown.

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[Co(H2O)6]3+ + 3H2NCH2CH2NH2 → [Co(H2NCH2CH2NH2)3]3+ + 6H2O

(i) Give a reason, by referring to the equation, why the formation of the diamine
complex from the aqueous complex ion is thermodynamically favoured.
(1)

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

(ii) Explain, by reference to the structure of ethane-1,2-diamine, why it is a

bidentate ligand.
(2)

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

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

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

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

(iii) Explain how the H N H bond angles would be expected to change in

ethane-1,2-diamine when the complex ion is formed.
(3)

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

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

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

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

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

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

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

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

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

(Total for Question 18 = 22 marks)

TOTAL FOR SECTION B = 50 MARKS

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SECTION C
Answer ALL the questions. Write your answers in the spaces provided.
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19

Raspberry ketone
Over two hundred different compounds contribute to the smell of raspberries, including the
one known as raspberry ketone.
O

HO

Raspberry ketone is also found in other fruits such as cranberries and blackberries. It can
be extracted from fruit but it is present in a very low percentage and so it is prepared
industrially by a variety of methods.
The two-step method shown gives a 99% yield.
O O
H2
(CH3)2CO
O rhodium /
NaOH
alumina
HO HO HO
catalyst

Two other compounds which contribute to the characteristic smell of raspberries are shown.

O O

α-ionone β-ionone

(a) Give the empirical formula of the raspberry ketone.

(1)

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(b) Raspberry ketone can be synthesised in the laboratory from phenol using a
Friedel–Crafts reaction. The overall reaction is shown.

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O
O

+ Cl + HCl
HO HO

(i) Draw the mechanism for this reaction, using appropriate curly arrows.
Include equations showing the formation of the electrophile and the
regeneration of the catalyst at the end of the reaction.
(5)

(ii) Give a reason why the yield of the raspberry ketone by this method is not high.
(1)

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

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

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(c) Raspberry ketone can also be synthesised in the laboratory using a
Grignard reagent via a multi-step process. The overall reaction is shown.
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OH O

HO HO

Devise this multi-step synthesis.

Give the reagents and conditions for each step in the synthesis, including the
formation of the Grignard reagent and the structures of the intermediates.
(7)

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(d) The second step of the industrial preparation of the raspberry ketone involves the
reduction shown.

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O O

H2
catalyst
HO HO

Suggest why the choice of reducing agent is particularly important in

this reaction.
(1)

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

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

(e) The α-ionone and β-ionone molecules are structural isomers.

O O

α-ionone β-ionone

(i) Compare and contrast the stereoisomerism of these two molecules.

On the structures, circle any features of the molecules that give rise
to stereoisomerism.
(3)

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

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

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(ii) Identify with an asterisk (*) the carbon atom environment in
α-ionone which would be expected to produce a peak with
a quartet splitting pattern in a high resolution proton NMR spectrum.
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(1)

α-ionone

(iii) Predict the number of peaks in the carbon-13 NMR spectrum of β-ionone,
which has the molecular formula C13H20O .
Justify your answer.

β-ionone
(1)

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

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

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

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

(Total for Question 19 = 20 marks)

TOTAL FOR SECTION C = 20 MARKS

TOTAL FOR PAPER = 90 MARKS

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