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Pearson Edexcel International Advanced Level

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 black ball‑point pen.
• centrethe
Fill in boxes at the top of this page with your name,
number and candidate number.
• Answer all questions.
• Answer the questions in the spaces provided
– there may be more space than you need.

Information
• The total mark for this paper is 90.
• The marks for each question are shown in brackets
– use this as a guide as to how much time to spend on each question.
• 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.
• 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.
You should aim to spend no more than 20 minutes on this section.
For each question, select one answer from A to D and put a cross in the box . If you change
your mind, put a line through the box and then mark your new answer with a cross .

1 This question is about transition metal complexes.

(a) The bonding within the complex [Cu(NH3)4(H2O)2]2+ is
(1)
A covalent, dative covalent and ionic

B covalent and dative covalent only

C covalent only

D dative covalent only

(b) Which complex is tetrahedral?

(1)
A [Pt(NH3)2Cl2]

B [Cu(H2O)4(OH)2]

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

D [CoCl4]2−

(c) Which complex contains a bidentate ligand?

(1)
A [Co(NH2CH2CH2NHCH2CH2NH2)2]3+

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

C [Ni(NH2CH2CH2NH2)3]2+

D [Mn(EDTA)]2−

(Total for Question 1 = 3 marks)

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

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2 A hydrogen‑oxygen fuel cell is used to provide electrical energy for an electric motor
in a car.
(a) The electrolyte in the fuel cell is acidic. What is the half‑equation at the anode?
(1)
A ½O2(g) + 2H+(aq) + 2e− → H2O(l)

B H2O(l) → ½O2(g) + 2H+(aq) + 2e−

C H2(g) → 2H+(aq) + 2e−

D 2H+(aq) + 2e− → H2(g)

(b) Hydrogen‑oxygen fuel cells have advantages over methanol‑oxygen fuel cells
in vehicles.
Which of these is an advantage of the hydrogen‑oxygen fuel cell?
(1)
A more energy is released per mole of fuel used

B emissions do not contribute to climate change

C hydrogen is easier to store than methanol

D only hydrogen can be obtained from renewable resources

(Total for Question 2 = 2 marks)

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

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3 An electrochemical cell is made from the electrode systems shown by these
half‑equations.

Ag+(aq) + e−  Ag(s) E = +0.80 V

VO+2 (aq) + 2H+(aq) + e−  VO2+(aq) + H2O(l) E = +1.00 V

The apparatus used to measure the value for E cell under standard conditions is shown.

voltmeter

silver platinum

1 mol dm−3 electrolyte
Ag+(aq)
salt
bridge

(a) Which silver compound could be used as the electrolyte in the left‑hand half‑cell?
(1)
A silver nitrate

B silver hydroxide

C silver chloride

D silver carbonate

(b) The electrolyte in the right‑hand half‑cell is prepared using equal volumes of
(1)
A 1 mol dm−3 acidified VO2+(aq) and 1 mol dm−3 acidified VO2+(aq)

B 2 mol dm−3 acidified VO2+(aq) and 2 mol dm−3 acidified VO2+(aq)

C 1 mol dm−3 VO2+(aq) and 1 mol dm−3 HCl(aq)

D 1 mol dm−3 VO2+(aq) and 1 mol dm−3 HCl(aq)

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(c) Which is the equation for the overall cell reaction under standard conditions?
(1)
A VO2+(aq) + Ag+(aq) + H2O(l) → VO2+(aq) + Ag(s) + 2H+(aq)

B VO2+(aq) + Ag(s) + 2H+(aq) → VO2+(aq) + Ag+(aq) + H2O(l)

C VO2+(aq) + 3Ag(s) + 2H+(aq) → VO2+(aq) + 3Ag+(aq) + H2O(l)

D VO2+(aq) + 3Ag+(aq) + H2O(l) → VO2+(aq) + 3Ag(s) + 2H+(aq)

(d) Which is the value of E cell in volts?

(1)
A −1.80

B −0.20

C +0.20

D +1.80

(e) Which is the cell diagram for this cell, using the conventional representation of
half‑cells?
(1)
A Ag(s) | Ag+(aq) | | [VO2+(aq) + 2H+(aq)] | [VO2+(aq) + H2O(l)] | Pt(s)

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

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

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

(Total for Question 3 = 5 marks)

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

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4 A mass of 4.179 g of hydrated iron(III) sulfate, Fe2(SO4)3·H2O , was dissolved in
deionised water and the solution made up to 200 cm3.
What is the concentration of sulfate ions, SO42− , in the solution, in mol dm−3?
[Molar mass of Fe2(SO4)3·H2O = 417.9 g mol−1]

A 0.01

B 0.05

C 0.10

D 0.15

(Total for Question 4 = 1 mark)

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

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5 The infrared spectrum of a compound X is shown.

100
90
80
70
% Transmittance 60
50
40
30
20
4000 3500 3000 2500 2000 1500 1000 500

Wavenumber / cm−1

Which could be compound X?

A   
OH

OH
B   

C   
H

D   
CH3

(Total for Question 5 = 1 mark)

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6 Methylbenzene reacts with a mixture of concentrated nitric acid and concentrated
sulfuric acid to form 2,4,6‑trinitromethylbenzene.

O2N NO2

NO2

(a) What is the number of peaks in the 13C NMR spectrum of methylbenzene?
(1)
A seven

B six

C five

D four

(b) What type of reaction takes place?

(1)
A nucleophilic addition

B nucleophilic substitution

C electrophilic addition

D electrophilic substitution

(c) Which expression shows the mass in grams of 2,4,6‑trinitromethylbenzene formed

from 10 g of methylbenzene if the yield of the reaction is 85 %?
[Mr values: methylbenzene = 92       2,4,6‑trinitromethylbenzene = 227]
(1)
A (10 × 85 × 227) ÷ (92 × 100)

B (10 × 100 × 227) ÷ (92 × 85)

C (10 × 100 × 227) ÷ (92 × 115)

D (10 × 115 × 227) ÷ (92 × 100)

(Total for Question 6 = 3 marks)

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7 The mass spectrum of the compound shown is obtained using a high resolution
mass spectrometer.

What is the mass to charge ratio, m / z, of the molecular ion of this compound?
[ Ar values: H = 1.0078     C = 12.0000     O = 15.9949]

A 92.0261

B 92.0312

C 93.0339

D 93.0390

(Total for Question 7 = 1 mark)

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

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8 A group of students carry out an experiment to find the concentration of
chlorine, Cl2(aq), in a solution.

Excess potassium iodide solution is added to a 10.0 cm3 sample of the

chlorine solution.

Cl2(aq) + 2I −(aq) → 2Cl−(aq) + I2(aq)

The iodine produced is titrated with a solution of thiosulfate ions of known

concentration, using starch indicator.

2S2O32−(aq) + I 2(aq) → S4O62−(aq) + 2I −(aq)

The concentration of the Cl2(aq) is between 0.038 and 0.042 mol dm−3 .

(a) What concentration of thiosulfate ions, in mol dm−3 , is required to give a titre of
approximately 20 cm3 ?
(1)
A 0.010

B 0.020
C 0.040

D 0.080

(b) What is the most suitable volume of 0.1 mol dm−3 potassium iodide solution,
in cm3 , to add to the 10.0 cm3 of chlorine solution?
(1)
A 7.6
B 8.0

C 8.4

D 10.0

(c) What is the colour change at the end‑point of the titration?

(1)
A colourless to pale yellow

B pale yellow to colourless

C colourless to blue‑black

D blue‑black to colourless

(Total for Question 8 = 3 marks)

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9 The formulae of four ions are shown.

Formula of ion

CrO42−

AlO2−

[Fe(CN)6]4−

[CrCl2(H2O)4]+

How many of these ions contain a metal with an oxidation number of +3?

A one

B two

C three
D four

(Total for Question 9 = 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.

10 This question is about silver and silver compounds.

Glass decorations are made reflective by coating their inner surface with silver. This is
achieved by using the reaction between silver nitrate solution, ammonia and glucose,
under alkaline conditions.
Initially the colourless complex ion diamminesilver(I), [Ag(NH3)2]+ , forms.
(a) (i) Explain the shape of [Ag(NH3)2]+ .
(3)

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(ii) Explain why [Ag(NH3)2]+ is colourless.

(2)

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(b) The diamminesilver(I) complex then reacts with glucose forming silver and an
organic compound, Y. Two other products also form.
(i) Complete the equation for the reaction.
(2)

OH OH O

HO
H + ................  [Ag(NH3)2]+ + ................  OH−

OH OH

glucose

C6H12O7 + ................  Ag + .............................................................. + ............................................................. .

Y
(ii) Draw the structure of Y.
(1)

(c) The overall reaction in a silver cell used in watch batteries is

Ag2O(s) + H2O(l) + Zn(s) → 2Ag(s) + Zn(OH)2(s)

The half‑equation for the reaction at the positive electrode is

Ag2O(s) + H2O(l) + 2e− → 2Ag(s) + 2OH−(aq)

Deduce the half‑equation for the reaction at the negative electrode.

State symbols are not required.
(1)

(Total for Question 10 = 9 marks)

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11 Chlorpheniramine is an amine used in the treatment of hayfever.

Cl amine group

(a) Deduce the classification of the labelled amine group.

(1)

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(b) The compound pyridine is used in the synthesis of chlorpheniramine.

N
pyridine

Like many amines, pyridine is miscible with water and the solution formed
is alkaline.
Explain each of these properties of pyridine.
(4)

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(c) A student suggested that the final step in the synthesis of chlorpheniramine starts
with the reaction between monodesmethylchlorpheniramine and chloromethane.
Assuming the reaction is similar to that between ammonia and chloromethane,
complete the mechanism for this proposed reaction.
Some of the organic structures shown have been simplified.
Include curly arrows, and any relevant dipoles and lone pairs of electrons.
(4)

H
H Cl
HN + C
R
H
monodesmethyl-
chlorpheniramine chloromethane

H
N H
R C + HCl

(Total for Question 11 = 9 marks)

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12 This question is about polymers.
(a) The diagram shows part of the structure of a polymer formed by a
condensation reaction between two amino acids.

H2N O

H O

N
N

H O

Predict the structures of the two monomers that produce this polymer.
(2)

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(b) The diagram shows a repeat unit of an addition polymer used in some
food wraps. It is formed from two different monomers.

Cl H Cl H
C C C C
Cl H H H

Deduce the structures of the two monomers that produce this polymer.
(2)

(c) A synthetic rubber polymer has the structure shown.

H2 H H2
C C C H
C C C
H H2

The molar mass of the synthetic rubber is approximately 300 000 g mol−1.

Calculate the approximate number of repeat units in the polymer.
(2)

(Total for Question 12 = 6 marks)

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13 The hydride of arsenic, arsine, is a toxic gas used in the production of semiconductors.
(a) Draw a dot‑and‑cross diagram for arsine, AsH3 .
(1)

(b) Arsine is a reducing agent and reacts with cerium(IV) sulfate solution,

forming arsenic.
The data from an experiment are shown.
Volume of arsine gas = 350 cm3 at 115 000 Pa and 20 °C
Volume of cerium(IV) sulfate solution = 488 cm3
Concentration of cerium(IV) sulfate solution = 0.102 mol dm−3
(i) Complete the half‑equation.
(1)

AsH3 → As

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(ii) Calculate the final oxidation state of the cerium ion formed in the reaction.
(6)

(Total for Question 13 = 8 marks)

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*14 Describe the reactions of separate samples of aqueous cobalt(II) sulfate
with aqueous sodium hydroxide, excess aqueous ammonia and
concentrated hydrochloric acid.
For each reaction, link your description to an appropriate equation.
State symbols are not required.
(6)

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20
*P69508A02032* 


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(Total for Question 14 = 6 marks)

21
 *P69508A02132* Turn over

BLANK PAGE

22
*P69508A02232* 


15 A compound Q contains the elements carbon, hydrogen and oxygen only.

(a) Combustion analysis of 4.91 g of Q produces 14.6 g of carbon dioxide and
3.58 g of water.
Show that the molecular formula of Q is C10H12O .
You must show all your working.
[ Mr of Q = 148]
(4)

23
 *P69508A02332* Turn over

(b) The high resolution proton NMR spectrum of Q is shown.

Area under curve 5 2 2 3

10 9 8 7 6 5 4 3 2 1 0

δ (ppm)

Deduce the structure of Q. Justify your answer by considering the relative peak
areas, the chemical shifts and the splitting patterns.
You will find it helpful to refer to page 8 of the Data Booklet.
The peak at 3.6 ppm is due to a proton environment on a carbon bonded to the
benzene ring. The peak is not where it might be expected from the general values
in the Data Booklet.
(7)

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*P69508A02432* 


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

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

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

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

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

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

(Total for Question 15 = 11 marks)

TOTAL FOR SECTION B = 49 MARKS

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

16 Benzoic acid is a white crystalline solid with the structure shown.

HO O
C

It is found in many plants as it is an important building block for the biosynthesis of a

variety of compounds, such as plant hormones and attractants for pollinators.
The role of benzoic acid in the chemical industry is also widespread and
approximately 500 000 tonnes are produced annually. It is used in the synthesis of
many compounds, including medicines, dyes and insect repellents.
Such synthetic dyes are often classified as aryl azo dyes. These dyes have a range of
vivid colours and a wide range of uses in many industries, including food and textiles.
Their synthesis involves the formation of a diazonium ion. This ion then reacts with a
phenol in a coupling reaction, to form the dye. The relative simplicity of the reactions
involved and ready availability of starting materials make azo dyes cheap to produce.
Salts of benzoic acid, such as calcium benzoate and sodium benzoate, are used in the
food industry as preservatives.

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(a) Devise a reaction scheme to produce benzoic acid from benzene,

via bromobenzene and then a Grignard reagent.
Include the reagents and essential conditions for each step and give the name or
structure of each of the intermediate compounds.
Details of practical procedures and reaction mechanisms are not required.
(6)

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(b) Benzoic acid can be used in the synthesis of azo dyes.
In Step 1, benzoic acid reacts with concentrated nitric acid to form
(i)
3‑nitrobenzoic acid.

HO O HO O
C C
conc.
H2SO4 catalyst
+ concentrated HNO3

NO2

benzoic acid 3‑nitrobenzoic acid

Draw the mechanism for the reaction, using appropriate curly arrows.
Include equations showing the role of the catalyst and how it is regenerated.
(5)

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In Step 2, the 3‑nitrobenzoic acid reacts to form 3‑aminobenzoic acid.

(ii)

HO O HO O
C C

NO2 NH2

3‑nitrobenzoic acid 3‑aminobenzoic acid

State the reagents required for this reaction.

(1)

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

In Step 3, the 3‑aminobenzoic acid reacts with sodium nitrite and

(iii)
dilute hydrochloric acid, forming a diazonium ion.

HO O HO O
C C

NaNO2

HCl(aq) +
NH2 N N

3‑aminobenzoic acid diazonium ion

State a temperature at which this reaction should take place, giving

one reason for your answer.
(2)

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

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

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

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

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

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(iv) Draw the structure of the azo dye formed when the diazonium ion reacts
with phenol.
(1)

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(c) Hydrated calcium benzoate is used as a preservative in soft drinks.

It has the formula Ca(C6H5COO)2·xH2O.
2.60 g of hydrated calcium benzoate was dissolved in deionised water.
Excess lead(II) nitrate solution was added, forming a precipitate of
lead(II) benzoate, Pb(C6H5COO)2(s). This precipitate was removed and dried.
The mass of the dry solid was 3.89 g.
Calculate the molar mass of hydrated calcium benzoate and hence deduce the
value of x.
(6)

(Total for Question 16 = 21 marks)

TOTAL FOR SECTION C = 21 MARKS

TOTAL FOR PAPER = 90 MARKS

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