Ilovepdf Merged (2) Removed

PMT
Please check the examination details below before entering your candidate information
Candidate surname Other names
Centre Number Candidate Number
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
Instructions
• Use black ink or 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.
• toIn 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.
• Try to answer every question.
• Check your answers if you have time at the end.
Turn over
*P71873A0132*
P71873A
©2022 Pearson Education Ltd.
B:1/1/1/
PMT
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 When copper is added to concentrated nitric acid, a brown gas is given off and the
final solution is blue.
In terms of oxidation number and electron transfer, how does the nitrogen change in
this reaction?
Oxidation number Electron transfer
A decreases gains electrons
B decreases loses electrons
C increases gains electrons
D increases loses electrons
(Total for Question 1 = 1 mark)
2 What is the pressure of hydrogen gas used in the standard hydrogen electrode?
A 1 Pa
B 100 Pa
C 1 000 Pa
D 100 000 Pa

Use this space for any rough working. Anything you write in this space will gain no credit.
2
*P71873A0232* 
PMT
3 An electrochemical cell is set up using the electrode systems shown.
Cr2O72− + 14H+ + 6e−  2Cr3+ + 7H2O
TiO2+ + 2H+ + e−  Ti3+ + H2O
(a) What materials will be used for the electrodes in this cell?
(1)
Cr2O72− , Cr3+ TiO2+ , Ti3+
A chromium titanium
B chromium platinum
C platinum titanium
D platinum platinum
(b) The reaction between Cr2O72− ions and Ti3+ ions has E cell = +1.14 V.
The standard electrode potential for the Cr2O72− , Cr3+ electrode system is +1.33 V.
What is the standard electrode potential for the TiO2+ , Ti3+ electrode system?
(1)
A −2.47 V
B −0.19 V
C +0.19 V
D +2.47 V
(Total for Question 3 = 2 marks)

3
 *P71873A0332* Turn over
PMT
4 The possibility of a reaction between potassium dichromate(VI) and hydrochloric acid

may be assessed using standard electrode potentials but also depends on the
activation energy, Ea , of the reaction.
Cr2O72− + 14H+ + 6Cl− → 2Cr3+ + 7H2O + 3Cl2 E cell = −0.03 V
When potassium dichromate(VI) and hydrochloric acid are mixed, very little chlorine
is formed under standard conditions but a significant amount of chlorine is produced
when concentrated hydrochloric acid is used.
What is the effect on Ecell and on Ea of using concentrated hydrochloric acid?
Ecell Ea
A less positive decreased
B less positive unchanged
C more positive decreased
D more positive unchanged
5 The element zinc is not classified as a transition metal. This is because
A the 3d subshell of a zinc atom is full
B zinc only forms one stable ion
C the only stable zinc ion has the electronic configuration [Ar] 3d10
D neither zinc nor zinc ions show catalytic properties
6 What is the electronic configuration of the Fe2+ ion?
A [Ar] ↑ ↑ ↑ ↑ ↑ ↑
B [Ar] ↑↓ ↑ ↑ ↑ ↑
C [Ar] ↑ ↑ ↑ ↑ ↑↓
D [Ar] ↑↓ ↑↓ ↑ ↑
3d 4s
4
*P71873A0432* 
PMT
7 Platinum forms a complex with the formula Pt(NH3)2Cl2 which is used in

cancer treatment. Three possible structures of this complex are shown.
Cl
Cl NH3 Cl NH3
Pt Pt Pt
Cl
Cl NH3 H3N Cl H3N
NH3
X Y Z
The complex used in cancer treatment contains
A structure X only
B structure Y only
C structure Z only
D an equimolar mixture of structures X and Y only
8 When oxygen binds to the haem group in haemoglobin, each oxygen molecule
A bonds reversibly to an iron(II) ion
B bonds irreversibly to an iron(II) ion

C replaces an iron(II) ion in a reversible reaction
D replaces an iron(II) ion in an irreversible reaction

5
 *P71873A0532* Turn over
PMT
9 The sequence shown is the mechanism for a reaction in aqueous solution.

Step 1 Ag+ + Ce4+ → Ag2+ + Ce3+
Ti+
Step 2 + Ag2+ → Ti2+ + Ag+
Ti2+ + Ce4+ → Ti3+
Step 3 + Ce3+
In the overall reaction
A the oxidation of Ag+ is catalysed by Ce4+ ions
B the oxidation of Ag+ is catalysed by Ti2+ ions
C the oxidation of Ti+ is catalysed by Ag+ ions
D the oxidation of Ti+ is catalysed by Ag2+ ions
10 How many σ bonds and π bonds are there in a molecule of benzene?
σ bonds π bonds
A 6 3
B 6 6
C 12 3
D 12 6
11 Benzene reacts with fuming sulfuric acid to form benzenesulfonic acid.

Fuming sulfuric acid is
A sulfuric acid with a concentration of 98 %
B pure sulfuric acid
C concentrated sulfuric acid containing dissolved sulfur dioxide
D concentrated sulfuric acid containing dissolved sulfur trioxide

6
*P71873A0632* 
PMT
12 The structure of the amino acid isoleucine is shown.
OH
NH2
(a) What is the systematic name of isoleucine?

(1)
A 2‑amino‑3‑ethylbutanoic acid
B 2‑amino‑3‑methylpentanoic acid
C 3‑amino‑2‑ethylbutanoic acid
D 3‑amino‑2‑methylpentanoic acid
(b) What is the structure of isoleucine in a solution of pH = 2?

(1)
O O
A B
O− OH
NH2 NH+3
O O
C D
OH+2 O−
NH2 NH+3

7
 *P71873A0732* Turn over
PMT
13 When dilute hydrochloric acid is added to butylamine and the solution is allowed to
evaporate to dryness, a white solid forms.
What is the formula of the white solid?
A CH3CH2CH2CH2Cl
B CH3CH2CH2CH2NH3Cl
C CH3CH2CH2CONH2
D CH3CH2CH2COOH
14 Amines may be prepared by the reduction of nitriles.

Identify the nitrile and the reducing agent used to prepare butylamine.
Nitrile Reducing agent
A propanenitrile lithium tetrahydridoaluminate(III)
B propanenitrile tin and concentrated hydrochloric acid
C butanenitrile lithium tetrahydridoaluminate(III)
D butanenitrile tin and concentrated hydrochloric acid

8
*P71873A0832* 
PMT
15 The structure of crotonamide is shown.
H C NH2
C C
CH3 H
What is the repeat unit of the polymer formed from crotonamide?
NH2 H H H
H C O C C C
A B
C C H H C O
CH3 H NH2
H H O H H H O
C C C C N D C C C C N
CH3 H H H H H H
16 The structure of a hydrocarbon is shown.
How many peaks will there be in the 13C NMR spectrum of this compound?
A four
B five
C six
D seven
9
 *P71873A0932* Turn over
PMT
17 The structures of cocaine and its metabolite benzoylecgonine are shown.
O O
O OH
N N
O O
O O
cocaine benzoylecgonine
How would you expect the solubility of cocaine in water and the pH of its
aqueous solution to compare with benzoylecgonine?
Solubility in water pH of aqueous solution
A cocaine more soluble cocaine higher pH
B cocaine more soluble cocaine lower pH
C cocaine less soluble cocaine higher pH
D cocaine less soluble cocaine lower pH

10
*P71873A01032* 
PMT
18 The use of recrystallisation to purify a chemical compound depends on how its

solubility in the chosen solvent varies with temperature.
How should the solubility of the chemical compound depend on temperature?
High temperature Low temperature
A soluble soluble
B soluble insoluble
C insoluble soluble
D insoluble insoluble
TOTAL FOR SECTION A = 20 MARKS
11
 *P71873A01132* Turn over
PMT
SECTION B
Answer ALL the questions. Write your answers in the spaces provided.
19 This question is about the chemistry of vanadium.

The standard electrode potentials of some vanadium species are shown.
Electrode system E /V
V2+(aq) + 2e−  V(s) −1.18
V3+(aq) + e−  V2+(aq) −0.26
VO2+(aq) + 2H+(aq) + e−  V3+(aq) + H2O(l) +0.34
VO−3 (aq) + 4H+(aq) + e−  VO2+(aq) + 2H2O(l) +1.00
(a) Explain the highest stable oxidation state formed by vanadium, by referring to its
electronic configuration.
(3)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
12
*P71873A01232* 
PMT
(b) A student suggests that the ion VO2+ may be converted into V3+ using
sodium thiosulfate, Na2S2O3 , with no other vanadium species being formed
by reduction.
(i) Justify the use of sodium thiosulfate for this reaction by writing the relevant
equations and calculating their E cell values.
Use the standard electrode potentials given in the table and values from your
Data Booklet.
State symbols are not required in the equations.
(4)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(ii) Explain why nickel, Ni, is not a suitable reagent to convert VO2+ into V3+, with
no other vanadium species being formed.
(2)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
13
 *P71873A01332* Turn over
PMT
(c) Most vanadium produced is used to make a steel alloy called ferrovanadium.
The vanadium content of ferrovanadium may be determined by a
titration method.
Procedure
• The sample of ferrovanadium is dissolved in chloric(V) acid.
The vanadium species formed is VO−3 .
• The resulting solution is transferred to a 250.0 cm3 volumetric flask, washings
added and the solution made up to the mark with distilled water and mixed.
• Using a pipette, 25.0 cm3 of the solution is transferred to a conical flask and
25.0 cm3 of a 0.250 mol dm−3 solution of iron(II) sulfate, FeSO4 , is added.
The iron(II) ions react with the VO−3 ions:
VO−3 + 4H+ + Fe2+  VO2+ + 2H2O + Fe3+
• The resulting solution is titrated against potassium manganate(VII) to

determine the amount of iron(II) ions remaining.
MnO−4 + 8H+ + 5Fe2+ → Mn2+ + 5Fe3+ + 4H2O
In an experiment, the mass of ferrovanadium used was 4.87 g, the concentration

of potassium manganate(VII) was 0.0195 mol dm−3 and a mean titre of 22.50 cm3
was obtained.
(i) Give the colour of the solution at the end‑point of the titration.
(1)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(ii) Suggest why the VO2+ ions formed do not affect the titration.
(2)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
14
*P71873A01432* 
PMT
(iii) Calculate the percentage by mass of vanadium in the ferrovanadium.

(7)
(d) In the manufacture of sulfuric acid, vanadium(V) oxide, V2O5 , is the catalyst used
in the conversion of sulfur dioxide to sulfur trioxide:
2SO2 + O2  2SO3
Write two equations to show a possible mechanism for this reaction.

State symbols are not required.
(2)
15
 *P71873A01532* Turn over
PMT
*20 Delocalised electron systems are important in determining the chemical properties of
some compounds.
Compare and contrast the chemical reactions of bromine with benzene and
cyclohexene, and with benzene and phenol, by considering the effects of
delocalised electrons.
Detailed descriptions of the bonds or of the reaction mechanisms involved are
not required.
(6)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
16
*P71873A01632* 
PMT
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
17
 *P71873A01732* Turn over
PMT
21 Coniine is the toxic compound present in poison hemlock.

The structure of coniine is shown, with R representing an alkyl group.
N R
H
coniine
(a) A sample of 0.235 g of coniine was vaporised at 185 °C and 105 000 Pa.
The volume of the vapour was 67.1 cm3.
(i) Show by calculation that the molar mass of coniine is 127 g mol−1.
(4)
(ii) Deduce the molecular formula of the alkyl group R, using the structure of
coniine and its molar mass. You must show your working.
(2)
18
*P71873A01832* 
PMT
(b) The table summarises the low resolution proton NMR data for the R group
in coniine.
Proton environment Chemical shift / ppm Peak area
1 0.90 3
2 1.33 2
3 1.37 2
(i) Explain why only one of the two possible structural formulae of R can give
these data.
(3)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
19
 *P71873A01932* Turn over
PMT
(ii) In the high resolution proton NMR data for the R group in coniine, the peak
for proton environment 2 is a sextet.
Deduce the splitting patterns for proton environments 1 and 3, using this
information and the information in the table.
(3)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
20
*P71873A02032* 
PMT
(c) Explain, using a diagram, which type of stereoisomerism is shown by coniine.

In your diagram use R to represent the alkyl group.
(2)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
21
 *P71873A02132* Turn over
PMT
22 Many oxides of transition metals are used as coloured pigments.

(a) Viridian is a blue‑green pigment with the formula M2O3·2H2O ; M is not the symbol
of the element.
When a sample of viridian is heated until all the water of crystallisation is
removed, the mass is reduced by 19.15 %.
Identify element M.
(4)
22
*P71873A02232* 
PMT
(b) Cobalt(II) oxide is used in the ceramics industry as an additive to produce

blue glazes and enamels. Cobalt(II) oxide dissolves in sulfuric acid to give a
pink aqueous solution of cobalt(II) sulfate. When concentrated hydrochloric acid is
added to aqueous cobalt(II) sulfate, a dark blue solution forms.
(i) Name the type of reaction that occurs when concentrated hydrochloric acid is
added to aqueous cobalt(II) sulfate.
(1)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(ii) Write an ionic equation for the reaction that occurs when
concentrated hydrochloric acid is added to aqueous cobalt(II) sulfate.
(2)
(iii) Explain why the shape of the complex ion changes when
concentrated hydrochloric acid is added.
(2)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
TOTAL FOR SECTION B = 50 MARKS
23
 *P71873A02332* Turn over
PMT
SECTION C
23 Chemicals from Plants
Plants are a rich source of useful chemicals, although their applications have often
pre‑dated the identification of the active compound. One of the best known
examples of this is the use of willow bark extracts to reduce pain and fevers, a
practice that is at least two thousand years old. The active compound in willow bark
is salicin.
OH
OH
HO O
O
HO
OH
salicin
In the body, salicin is changed into salicylaldehyde and then salicylic acid.
Salicylic acid may in turn be converted into 2‑acetoxybenzenecarboxylic acid,
a compound which is better known as aspirin, one of the most widely used
medications in the world.
H O HO O HO O
C C C
HO HO O
C
O
salicylaldehyde salicylic acid 2‑acetoxybenzenecarboxylic acid
24
*P71873A02432* 
PMT
(a) Calculate the percentage composition by mass of the elements in salicin.

(4)
(b) The first stage in the breakdown of salicin results in the formation of
salicyl alcohol.
OH
HO
salicyl alcohol
Salicyl alcohol is readily oxidised in the laboratory to form salicylic acid.

(i) State the reagents and conditions needed for this oxidation.
(2)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
25
 *P71873A02532* Turn over
PMT
(ii) The boiling temperature of salicylaldehyde is 197 °C.

Suggest why this makes it very difficult to obtain salicylaldehyde by
oxidising salicyl alcohol.
.(2)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(c) Aromatic aldehydes such as salicylaldehyde may be prepared in the laboratory by

electrophilic substitution.
For example, benzaldehyde may be obtained by reacting benzene with
a mixture of carbon monoxide and hydrogen chloride in the presence of
aluminium chloride.
The mixture of carbon monoxide and hydrogen chloride reacts like
methanoyl chloride.
(i) Write an equation for the formation of the electrophile from
methanoyl chloride. Use displayed formulae.
(1)
(ii) Draw the mechanism of the formation of benzaldehyde from benzene using
the electrophile from (c)(i).
(3)
26
*P71873A02632* 
PMT
(d) Salicylaldehyde may be used in the synthesis of coumarin, a compound which

occurs in many plants. Coumarin is in turn used to prepare warfarin, a compound
prescribed to reduce blood clotting.
O O
coumarin
One suggested synthesis of coumarin from salicylaldehyde involves the formation

of an intermediate compound, F.
C
O
OH
OH
salicylaldehyde compound F
Devise a synthesis of F using salicylaldehyde and bromoethane as the only

organic starting materials.
Include any other reagents and intermediate compounds, and give essential
reaction conditions.
(4)
27
 *P71873A02732* Turn over
PMT
(e) Salicylaldehyde combines with 1,2‑diaminoethane in a condensation reaction to

form salen ligand.
N N
OH HO
salen ligand
Salen ligand reacts with many metal ions to form very stable complexes which are
useful catalysts.
(i) Draw a diagram of the complex that one salen ligand forms with a Ni2+ ion,
showing the type of bonding involved.
(2)
(ii) Explain why the salen ligand complex of the Ni2+ ion is much more stable than
the aqua complex of the same ion.
(2)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
TOTAL FOR SECTION C = 20 MARKS

TOTAL FOR PAPER = 90 MARKS
28
*P71873A02832* 
PMT

Paper
reference WCH15/01
Chemistry
 

Nitrogen Chemistry
Scientific calculator, Data Booklet, ruler
Instructions
• Use black ink or ball-point pen.
• centrethe
Information
• toIn the question marked with an asterisk (*), marks will be awarded for your ability
Advice
Turn over
*P70956A0132*
P70956A
Q:1/1/1/1/
PMT
SECTION A
1 This question is about catalysts.

(a) Some standard electrode potentials are shown.
Right-hand electrode system E /V
Cu2+ + e−  Cu+ +0.15
I2 + 2e−  2I − +0.54
Fe3+ + e−  Fe2+ +0.77
Cl2 + 2e−  2Cl− +1.36
S2O82− + 2e−  2SO42− +2.01
Which of these ions is most likely to catalyse the reaction between S2O82− and I − ?
S2O82− + 2I − → 2SO42− + I2
(1)
A Cl−
B Fe2+
C Cu2+
D Cu+
(b) Which term best describes the type of catalyst for the reaction in (a)?
(1)
A autocatalyst
B biocatalyst
C heterogeneous
D homogeneous
2
*P70956A0232* 
PMT
(c) Which substance is manufactured in a process involving a reaction catalysed by

vanadium(V) oxide?
(1)
A ammonia
B nitric acid
C sodium hydroxide
D sulfuric acid
2 This question is about alkaline hydrogen-oxygen fuel cells.

(a) What is the half-equation at the negative electrode?
(1)
A H2(g) + 2OH−(aq) → 2H2O(l) + 2e−
B 2H2O(l) + 2e− → H2(g) + 2OH−(aq)

C O2(g) + 2H2O(l) + 4e− → 4OH−(aq)
D 4OH−(aq) → O2(g) + 2H2O(l) + 4e−
(b) Which statement is correct for an alkaline hydrogen-oxygen fuel cell when
compared with an acidic hydrogen-oxygen fuel cell?
(1)
A E cell is greater
B ΔS total is greater
C the catalyst is more efficient
D Kc is greater

Use this space for rough working. Anything you write in this space will gain no credit.
3
 *P70956A0332* Turn over
PMT
3 Excess aqueous sodium thiosulfate is added to an aqueous solution of

ammonium vanadate(V).
What colour is the mixture when the reaction is complete?
Refer to page 10 of the Data Booklet.
A yellow
B blue
C green
D violet

4
*P70956A0432* 
PMT
4 Which transition metal complex is commonly used as a treatment for cancer?
Cl 2–
A Cu
Cl
Cl Cl
+
NCCH3
B Cu
NCCH3
H3CCN NCCH3
Cl NH3
C Pt
Cl NH3
H3N Cl
D Pt
Cl NH3
5 Which reagent, when added to aqueous sodium dichromate(VI), Na2Cr2O7(aq), causes

a shift in equilibrium resulting in the formation of a yellow solution?
A NaOH(aq)
B HCl(aq)
C Zn(s)
D H2O2(aq)
5
 *P70956A0532* Turn over
PMT
6 A titre has an uncertainty of 0.32 %.

The uncertainty of each burette reading is ±0.05 cm3 .
What is the most likely value of the titre in cm3 ?
A 6.40
B 15.60
C 31.25
D 32.00
7 This question is about polymers.

(a) A repeat unit of the polymer PET has the structure shown.
O O
O
O
What is the percentage by mass of carbon in the repeat unit?

(1)
A 57.1 %
B 62.5 %
C 65.2 %
D 66.7 %
6
*P70956A0632* 
PMT
(b) One of the monomers used to make PET is benzene-1,4-dicarboxylic acid.
O O
HO OH
How many peaks are there in the 13C NMR spectrum of

benzene‑1,4‑dicarboxylic acid?
(1)
A 2
B 3
C 4
D 6
(c) The repeat unit of another polymer has the structure shown.
H CH3
C C H H
H C O C C OH
O
H H
This polymer is formed from

(1)
A a single type of monomer by an addition reaction
B a single type of monomer by a condensation reaction
C two different types of monomer by an addition reaction
D two different types of monomer by a condensation reaction

7
 *P70956A0732* Turn over
PMT
8 Which ion is formed when a mixture of sodium nitrite, NaNO2 , and dilute
hydrochloric acid reacts with phenylamine at a temperature of 5°C?
H
+
A N H
+
B N N
H
+
C N
+
D N N

8
*P70956A0832* 
PMT
9 This question is about a Grignard reagent, 2-methylpropylmagnesium bromide.
MgBr
This Grignard reagent can be prepared by refluxing 1-bromo-2-methylpropane with

magnesium in a flask containing a dry solvent and anti-bumping granules.
(a) Which solvent is used in this preparation?
(1)
A ethanol
B ether
C pentane
D propanone
(b) Why are anti-bumping granules added to the flask?

(1)
A to lower the boiling temperature of the solvent
B to prevent the solvent evaporating
C because the solvent is highly flammable
D to ensure the solvent boils smoothly
(c) The structure of 2-methylpropylmagnesium bromide is shown.
MgBr
Which statement best describes the circled carbon atom?

(1)
A positive and electrophilic
B positive and nucleophilic
C negative and electrophilic
D negative and nucleophilic
9
 *P70956A0932* Turn over
PMT
(d) Which compound reacts with 2‑methylpropylmagnesium bromide to form

4‑ethyl‑2‑methylheptan‑4‑ol?
OH
MgBr
2‑methylpropylmagnesium bromide 4‑ethyl‑2‑methylheptan‑4‑ol

(1)
A hexan‑3‑one
B hexan‑2‑one
C hexan‑3‑ol
D hexan‑2‑ol

10
*P70956A01032* 
PMT
10 This question is about the amino acid serine.
HO OH
NH2
serine
(a) Which ion is most likely to form if serine is dissolved in

sodium carbonate solution?
(1)
O
A
HO OH
NH
+ 3
B
HO O−
NH
+ 3
C −
O O−
NH2
D
HO O−
NH2
11
 *P70956A01132* Turn over
PMT
(b) Serine has a melting temperature in the region of 200–300 °C.

This high melting temperature is mainly due to the formation of
(1)
A hydrogen bonds
B ionic bonds
C London forces
D peptide bonds
11 Which is correct for the reaction of bromine with phenol when compared
with benzene?
Reactivity of phenol Electron density of the ring in phenol
A more reactive higher electron density
B more reactive lower electron density
C less reactive higher electron density
D less reactive lower electron density
12
*P70956A01232* 
PMT
SECTION B
12 This question is about 2‑ethanoylaminobenzoic acid.
Crystals of this compound emit flashes of light when crushed.
2‑ethanoylaminobenzoic acid can be synthesised using benzene as a
starting material.
CH3 CH3
Step 1 Step 2
CH3Cl conc. HNO3
AlCl3 catalyst conc. H2SO4 NO2
<30 °C
alkaline
Step 3
KMnO4
CO2H CO2H CO2H

Step 5 Step 4
CH3COCl
NHCOCH3 NH2 NO2
2‑ethanoylaminobenzoic acid compound A
(a) A student proposed a mechanism for Step 1.
+
CH3Cl + AlCl3 CH3 + AlCl4−
CH3 CH3
+
CH3 + H + H+
H+ + AlCl4− HCl + AlCl3
(i) Identify two errors in the mechanism by circling them.

(2)
14
*P70956A01432* 
PMT
(ii) State how the errors identified in (a)(i) should be corrected.

Justify your answer in terms of the structures involved.
(2)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(b) Give a reason why it is important to keep the temperature below 30 °C in Step 2.
(1)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(c) State the type of reaction in Step 3.

(1)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(d) Identify, by name or formula, the reagents needed for Step 4.

(1)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
15
 *P70956A01532* Turn over
PMT
(e) Explain how the structures of ethanoyl chloride, CH3COCl, and compound A
enable them to react forming 2‑ethanoylaminobenzoic acid in Step 5.
(3)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(f ) Calculate the volume of benzene required to form 5.92 g of

2‑ethanoylaminobenzoic acid, assuming the overall yield for the synthesis
is 28.2 %.
Give your answer to an appropriate number of significant figures.
[Density of benzene = 0.879 g cm−3]
(4)
16
*P70956A01632* 
PMT
*13 Compare and contrast the reactions in aqueous solution of nickel(II) sulfate with
sodium hydroxide and with ammonia.
For each reaction include
• what would be seen
• the equation (state symbols are not required)
• the type of reaction.
(6)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
18
*P70956A01832* 
PMT
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
19
 *P70956A01932* Turn over
PMT
14 A compound, Q, is a pale yellow liquid that is the main constituent of cinnamon oil.
Q contains the elements carbon, hydrogen and oxygen only.
(a) Complete combustion of 6.02 g of Q produces 18.07 g of carbon dioxide and
3.30 g of water.
Determine the empirical formula of Q.
(4)
20
*P70956A02032* 
PMT
(b) Tests on samples of Q show that it

• burns in air with a very sooty flame
• forms an orange precipitate with Brady’s reagent
(2,4-dinitrophenylhydrazine solution)
• forms a silver precipitate with Tollens’ reagent
• decolourises bromine water
• exists as a pair of geometric isomers.
Deduce a structure for Q, explaining how each piece of information supports
your answer.
(6)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
21
 *P70956A02132* Turn over
PMT
15 This question is about transition metal compounds and their quantitative analysis.
(a) Potassium dichromate(VI), K2Cr2O7, is present in very small amounts in cement, to
help increase the time for the cement to set.
A 50.0 g sample of cement was washed with portions of deionised water to
dissolve the potassium dichromate(VI). Any insoluble residues were removed by
filtration and the filtrate was transferred to a volumetric flask. The volume was
made up to 100.0 cm3 , using 2 mol dm−3 sulfuric acid.
50.0 cm3 of this solution was transferred to a conical flask and titrated
with a solution of ammonium iron(II) sulfate, (NH4)2Fe(SO4)2(aq),
of concentration 3.24 × 10−4 mol dm−3 .
The indicator N-phenylanthranilic acid was used, which gave an intense red-violet
colour at the end-point.
The mean titre of ammonium iron(II) sulfate was 10.90 cm3 .
The ionic equation for the redox reaction in the titration is shown.
6Fe2+(aq) + Cr2O72−(aq) + 14H+(aq) → 2Cr3+(aq) + 7H2O(l) + 6Fe3+(aq)
(i) State the colour of each chromium species in the reaction.
(1)
Cr2O72− . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
Cr3+ .. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(ii) Suggest a reason why an indicator is needed in this titration.

(1)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
22
*P70956A02232* 
PMT
(iii) Calculate the percentage by mass of potassium dichromate(VI) in the

cement sample.
(5)
23
 *P70956A02332* Turn over
PMT
(b) N‑phenylanthranilic acid has the structure shown.
O OH
H
N
The solution used as an indicator was prepared by mixing 100 mg of this acid in
5 cm3 of sodium hydroxide solution, NaOH(aq).
The mixture was then diluted to 100 cm3 with deionised water.
Explain why the N‑phenylanthranilic acid is added to the sodium hydroxide
solution before it is mixed with water in the preparation of this solution.
(2)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(c) The concentration of chromium(VI) in aqueous solution may also be determined

using a colorimeter.
On adding 1,5‑diphenylcarbazide, DPC, to a solution of chromium(VI) ions, an
intensely coloured octahedral complex forms.
The formula of the complex is Cr(DPC)36+.
(i) The structure of DPC is shown.
O
H H
N N
N N
H H
Describe how DPC is able to act as a bidentate ligand, using your diagram to
show the atoms involved.
(3)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
24
*P70956A02432* 
PMT
(ii) The intense colour of this complex is due to the transfer of electrons from the
ligand to the chromium(VI) ion.
Suggest a possible reason why the colour is not due to the transfer of
electrons between split d-orbitals in the ion.
Refer to the electronic configuration of the chromium(VI) ion.
(1)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(d) The concentration of nickel(II) ions, Ni2+(aq), can be determined by forming a

complex with the ligand dimethylglyoxime, C4H8N2O2 .
[Ni(H2O)6]2+ + 2C4H8N2O2 + 2OH− → [Ni(C4H7N2O2)2(H2O)2] + 6H2O
Explain why the formation of the dimethylglyoxime complex is favoured, in terms

of entropy.
(2)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
25
 *P70956A02532* Turn over
PMT
16 The ester ethyl 2‑methylbutanoate is found in wild berries such as bilberries.

Devise a synthesis to convert but‑2‑ene into ethyl 2‑methylbutanoate in four steps.
but‑2‑ene ethyl 2‑methylbutanoate
Include the reagents and essential conditions for each step and the name or structure
of each of the intermediate compounds.
Details of practical procedures are not required.
26
*P70956A02632* 
PMT
SECTION C
17
Gilding Metal
Gilding metal is a type of brass alloy that consists of copper and a small amount of
zinc, ranging from 5 % to 11 % by mass. Copper is very malleable and is hardened
by the addition of zinc.
Gilding metal is much less susceptible to cracking due to corrosion than brasses
with a higher percentage of zinc.
It has a warm, golden colour and can be used to coat materials using electrolysis.
It is also used to make test pieces in jewellery manufacture because it has similar
properties to silver but is less expensive.
The proportions of copper and zinc determine the exact properties of the gilding
metal and can be determined by chemical analysis.
(a) 2.72 g of a type of brass is dissolved in excess concentrated nitric acid, forming a
solution containing both Cu2+ and Zn2+ ions.
A solution containing hydrogensulfate(IV) ions, HSO3− , is then added.
2Cu2+(aq) + HSO3−(aq) + H2O(l) → 2Cu+(aq) + HSO4−(aq) + 2H+(aq)

The addition of ammonium thiocyanate, NH4SCN, gives a precipitate of
copper(I) thiocyanate, CuSCN.
Cu+(aq) + SCN−(aq) → CuSCN(s)

The precipitate of copper(I) thiocyanate is collected, dried and found to have a
mass of 4.69 g.
(i) Determine whether or not this type of brass is a gilding metal, by calculating
its percentage by mass of copper.
(4)
27
 *P70956A02732* Turn over
PMT
(ii) Explain, by considering both thermodynamic and kinetic factors, why HSO3−
reduces Cu2+ to Cu+ but does not then reduce Cu+ to Cu.
Use the data in the table.
(3)
Right-hand electrode system E /V
Cu2+ + e−  Cu+ +0.15
HSO4− + 2H+ + 2e–  HSO3− + H2O +0.17
Cu+ + e−  Cu +0.52
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
28
*P70956A02832* 
PMT
(b) After the copper(I) thiocyanate is precipitated, Zn2+ ions remain in solution.
A student suggested that these Zn2+ ions can be precipitated by adding a large
excess of aqueous sodium hydroxide.
Comment on this suggestion by describing the reactions that take place as a
large excess of aqueous sodium hydroxide is gradually added.
(4)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(c) Suggest why gilding metals are less malleable than pure copper, by considering
their structure.
(2)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
29
 *P70956A02932* Turn over
PMT
(d) Zinc and copper are also used in electrochemical cells.

(i) Draw a labelled diagram of the apparatus used to measure the emf of a cell
with copper and zinc electrodes under standard conditions.
(3)
30
*P70956A03032* 
PMT
(ii) The Nernst equation describes the relationship between the concentration of
metal ions in a half-cell and its electrode potential.
0.0260
E=E + × ln [ion]
z
E = electrode potential under non-standard concentrations
z = the number of positive charges on the metal ion
A cell is set up with Cu2+ ions of concentration 1.00 mol dm−3 and
Zn2+ ions of unknown concentration. The emf of the cell is +1.09 V.
Calculate the concentration of the zinc ions.
Use the data on page 10 of the Data Booklet.
(3)

31
 *P70956A03132*
PMT
32
*P70956A03232* 
PMT

Paper
reference WCH15/01
Chemistry
 

Nitrogen Chemistry
Instructions
• Use black ink or black ball‑point pen.
• centrethe
Information
• Into the question marked with an asterisk (*), marks will be awarded for your ability
Advice
Turn over
*P69508A0132*
P69508A
L:1/1/1/1/
PMT
SECTION A
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−

2
*P69508A0232* 
PMT
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

3
 *P69508A0332* Turn over
PMT
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)
4
*P69508A0432* 
PMT
(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)

5
 *P69508A0532* Turn over
PMT
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

6
*P69508A0632* 
PMT
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
7
 *P69508A0732* Turn over
PMT
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)
8
*P69508A0832* 
PMT
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

9
 *P69508A0932* Turn over
PMT
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
10
*P69508A01032* 
PMT
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
11
 *P69508A01132* Turn over
PMT
SECTION B
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)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(ii) Explain why [Ag(NH3)2]+ is colourless.

(2)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
12
*P69508A01232* 
PMT
(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.

(1)
13
 *P69508A01332* Turn over
PMT
11 Chlorpheniramine is an amine used in the treatment of hayfever.
Cl amine group
(a) Deduce the classification of the labelled amine group.

(1)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(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)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
14
*P69508A01432* 
PMT
(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
15
 *P69508A01532* Turn over
PMT
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)
16
*P69508A01632* 
PMT
(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)
17
 *P69508A01732* Turn over
PMT
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
18
*P69508A01832* 
PMT
(ii) Calculate the final oxidation state of the cerium ion formed in the reaction.
(6)
19
 *P69508A01932* Turn over
PMT
*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.
(6)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
20
*P69508A02032* 
PMT
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
21
 *P69508A02132* Turn over
PMT
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
PMT
(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)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
24
*P69508A02432* 
PMT
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
25
 *P69508A02532* Turn over
PMT
SECTION C
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.
26
*P69508A02632* 
PMT
(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)
27
 *P69508A02732* Turn over
PMT
(b) Benzoic acid can be used in the synthesis of azo dyes.

(i) In Step 1, benzoic acid reacts with concentrated nitric acid to form
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)
28
*P69508A02832* 
PMT
(ii) In Step 2, the 3‑nitrobenzoic acid reacts to form 3‑aminobenzoic acid.
HO O HO O
C C
NO2 NH2
3‑nitrobenzoic acid 3‑aminobenzoic acid
State the reagents required for this reaction.

(1)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(iii) In Step 3, the 3‑aminobenzoic acid reacts with sodium nitrite and
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)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
29
 *P69508A02932* Turn over
PMT
(iv) Draw the structure of the azo dye formed when the diazonium ion reacts
with phenol.
(1)
30
*P69508A03032* 
PMT
(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)

31
 *P69508A03132*
PMT

Paper
reference WCH15/01
Chemistry
 

UNIT 5: Transition Metals and Organic Nitrogen
Chemistry
Instructions
• Use black ink or black ball‑point pen.
• centrethe
Information
• 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
Advice
Turn over
*P67131A0132*
P67131A
E:1/1/1/1/1/E2/
PMT
SECTION A
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 shown was used to measure the standard electrode potential for the
reduction of Cr2O 2–
7 ions to Cr
3+
ions in acid solution:
7 (aq) + 14H (aq) + 6e → 2Cr (aq) + 7H2O(l)

Cr2O 2– + – 3+
V
H2 gas at salt bridge
100 kPa KNO3(aq)
electrode 1 electrode 2
solution 1 solution 2
(a) Which material should be used for each electrode?

(1)
Electrode 1 Electrode 2
A Na2Cr2O7 Cr2O3
B H2 Cr
C Pt Cr
D Pt Pt
2
*P67131A0232* 
PMT
(b) Solution 1 is
(1)
A 0.33 mol dm–3 H3PO4(aq)
B 0.50 mol dm–3 H2SO4(aq)
C 1.00 mol dm–3 HCl(aq)
D 1.00 mol dm–3 CH3COOH(aq)
(c) Solution 2 contains 14.71 g of K2Cr2O7 .

What mass of Cr2(SO4)3⋅18H2O should also be used?
[Mr values: K2Cr2O7 = 294.2 Cr2(SO4)3⋅18H2O = 716.3]
(1)
A 8.95 g
B 17.91 g
C 19.62 g
D 35.82 g
(d) Solution 2 is best acidified with

(1)
A H2SO4
B HCl
C HBr
D H2CrO4

3
 *P67131A0332* Turn over
PMT
2 The equation for a redox reaction is
5Fe2+(aq) + MnO 4–(aq) + 8H+(aq) → 5Fe3+(aq) + Mn2+(aq) + 4H2O(l)

d
Which is the correct cell diagram to measure E cell for this reaction?
A Fe | Fe2+, Fe3+ || [MnO 4– + 8H+], [Mn2+ + 4H2O] | Mn
B Fe | Fe2+, Fe3+ || [Mn2+ + 4H2O], [MnO 4– + 8H+] | Mn
C Pt | Fe2+, Fe3+ || [MnO 4– + 8H+], [Mn2+ + 4H2O] | Pt
D Pt | Fe2+, Fe3+ || [Mn2+ + 4H2O], [MnO 4– + 8H+] | Pt
3 Some standard electrode potentials are shown.
Electrode system Ed / V
Bk3+ + e–  Bk2+ –2.80
Cu2+ + e–  Cu+ +0.15
Bk4+ + e–  Bk3+ +1.67
Au+ + e–  Au +1.69
Au2+ + e–  Au+ +1.80
Ag3+ + e–  Ag2+ +1.80
Ag2+ + e–  Ag+ +1.98
Cu3+ + e–  Cu2+ +2.40
Which of these disproportionation reactions is thermodynamically feasible under

standard conditions?
A 2Bk3+ → Bk2+ + Bk4+
B 2Cu2+ → Cu+ + Cu3+
C 2Au+ → Au + Au2+
D 2Ag2+ → Ag+ + Ag3+
4
*P67131A0432* 
PMT
4 Which is true of a hydrogen‑oxygen fuel cell?
A the cathode has a more positive potential than the anode
B hydrogen is oxidised at the cathode
C oxygen is reduced at the negative electrode
D the cell potential is different when operating under alkaline or

acidic conditions
5 Which of the following statements best explains carbon monoxide poisoning?
A carbon monoxide binds irreversibly to haemoglobin
B carbon monoxide forms stronger dative covalent bonds with haemoglobin

than oxygen does
C the formation of carboxyhaemoglobin leads to a large increase in the
entropy of the system
D carbon monoxide has a triple bond whereas oxygen has a double bond
6 Aqueous ammonia is added drop by drop to a solution of cobalt(II) chloride,

CoCl2(aq), until in excess.
What would be the sequence of observations?
A blue solution → pink precipitate → dark blue solution
B pink solution → blue precipitate
C blue solution → pink precipitate
D pink solution → blue precipitate → yellow‑brown solution
5
 *P67131A0532* Turn over
PMT
7 Some nickel(II) complex ions are formed by the addition of complexing agents to
nickel(II) ions, [Ni(H2O)6]2+ , in aqueous solution.
On formation, which of these leads to the most positive increase in ΔSsystem?
A [NiCl4]2–
B [Ni(EDTA)]2–
C [Ni(C2O4)2 ]2–
D [Ni(H2NCH2CH2NH2)3 ]2+
8 Which of the following is not true of the reactions occurring in the catalytic converter
fitted to a car exhaust?
A they involve heterogeneous catalysis
B carbon monoxide is adsorbed onto the surface of the catalyst

C nitrogen is desorbed from the surface of the catalyst
D the products cause no harm to the environment
9 The reaction of ethanedioate ions, C2O 42– , with manganate(VII) ions, MnO 4– , in
acidic solution involves autocatalysis.
2MnO 4– + 16H+ + 5C2O 42– → 2Mn2+ + 10CO2 + 8H2O
The catalyst in this reaction is
A MnO 4–
B H+
C Mn2+
D CO2
6
*P67131A0632* 
PMT
10 Iodide ions, I–, are oxidised by peroxodisulfate(VI) ions, S2O 82– .
2I–(aq) + S2O 82–(aq) → I2(aq) + 2SO 42–(aq)
Which of the following statements is true of this reaction?
A both Fe2+(aq) and Fe3+(aq) catalyse the reaction
B Fe2+(aq) catalyses the reaction but Fe3+(aq) does not
C Fe3+(aq) catalyses the reaction but Fe2+(aq) does not
D neither Fe2+(aq) nor Fe3+(aq) catalyses the reaction
11 Which of these could not be formed when excess benzene is heated with
trichloromethane, CHCl3, in the presence of an aluminium chloride catalyst?
Cl
A B
Cl
Cl
C D
7
 *P67131A0732* Turn over
PMT
12 What is the molar mass, in g mol–1, of the organic product when phenol reacts with
excess bromine water?
A 156.9
B 172.9
C 330.7
D 488.5
13 Which sequence shows these compounds in order of decreasing basicity?
A C6H5NH2 > CH3CH2CH2NH2 > NH3
B NH3 > CH3CH2CH2NH2 > C6H5NH2
C CH3CH2CH2NH2 > NH3 > C6H5NH2
D C6H5NH2 > NH3 > CH3CH2CH2NH2
14 Which amine could not be prepared by the reduction of a nitrile?
A B
H2N
H2N
C H2N D H2N
8
*P67131A0832* 
PMT
15 How many different amino acids form the repeat unit of the polymer shown?
HO
O O O



HN HN HN 
HN HN HN




O O HS O
A 3
B 4
C 5
D 6
16 Grignard reagents react with
A water giving primary alcohols
B all aldehydes giving secondary alcohols
C ketones giving secondary or tertiary alcohols
D carbon dioxide giving carboxylic acids
17 The melting temperature is determined for impure crystals of an organic compound.

When compared with a data book value for the pure compound, the measured
melting temperature
A will be the same as the true value
B will be higher than the true value
C will be lower than the true value
D could be higher or lower than the true value
9
 *P67131A0932* Turn over
PMT
SECTION B
18 A series of reactions with iron and iron complexes was carried out.
Reaction 1 A sample of iron was heated with hydrochloric acid and a pale green
hydrated salt A with molar mass 198.8 g mol–1 was crystallised from
the solution.
Reaction 2 Salt A was dissolved in water forming a pale green solution containing
complex ion B. On addition of excess aqueous potassium cyanide, KCN,
the solution turned yellow due to the formation of complex ion C.
Reaction 3 Chlorine gas was bubbled through the solution containing
complex ion C forming a red solution of complex ion D.
Salt E, the potassium salt of complex ion D, was then crystallised from
the solution.
(a) Deduce the formula of the hydrated salt A.
You must show your working.
(2)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(b) Give the formula of complex ion B.

(1)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
10
*P67131A01032* 
PMT
(c) Complex ion C has six cyanide ligands.

Draw the structure of C, clearly showing its three‑dimensional shape.
(1)
(d) The percentage composition by mass of salt E is
K = 35.6 % Fe = 17.0 % C = 21.9 % N = 25.5 %
Calculate the empirical formula of salt E.

(3)
11
 *P67131A01132* Turn over
PMT
(e) Write the ionic equation for the reaction of complex ion C with chlorine to form
complex ion D.
(2)
(f ) Complete the table, using  as appropriate, to identify the type of each reaction.
(2)
Neutralisation Ligand exchange Redox
Reaction 2
Reaction 3
12
*P67131A01232* 
PMT
19 This question is about benzene, C6H6 , a colourless liquid first isolated in 1825, and
some related compounds.
Three C6H6 structures proposed in the 1860s are shown.
Kekulé structure Dewar structure Ladenburg structure
The delocalised model for the structure of benzene has been accepted since the
1930s following the study of its X‑ray diffraction pattern and the understanding of
electron delocalisation in bonding theory.
The Dewar and Ladenburg structures have since been

isolated as stable compounds but there is no compound
with the Kekulé structure.
benzene
(a) Describe a chemical test, including the result, that could distinguish the
Dewar structure from benzene.
(2)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(b) State one similarity and one difference you would expect in the low resolution
proton NMR spectrum of the Ladenburg structure and that of benzene.
You must include data from the Data Booklet to support your answer.
(2)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
13
 *P67131A01332* Turn over
PMT
(c) Explain how X‑ray diffraction shows that benzene has a delocalised structure and
not a Kekulé structure.
(2)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(d) The Ladenburg and Dewar structures both isomerise to benzene.

The enthalpy changes are –376 kJ mol–1 and –297 kJ mol–1 respectively.
(i) Draw a labelled enthalpy level diagram showing the relative thermodynamic
stability of the Ladenburg structure, the Dewar structure and benzene.
Include the enthalpy change values in kJ mol–1.
Your diagram does not need to be to scale.
(2)
H / kJ mol–1
14
*P67131A01432* 
PMT
(ii) Give a possible reason why the isomerisation of the Dewar structure to
benzene has a lower activation energy than that of the Ladenburg structure
to benzene.
(1)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(e) The enthalpy change of hydrogenation of hex‑3‑ene is –118 kJ mol–1.
+ H2
The table shows the enthalpy changes of hydrogenation of two further alkenes
containing six carbon atoms.
Enthalpy change of hydrogenation

Alkene
/ kJ mol–1
–236
E‑hexa‑1,4‑diene
–214
E‑hexa‑1,3‑diene
Use your knowledge of benzene thermochemistry to suggest explanations

for both of these enthalpy changes of hydrogenation in relation to
the value for hex‑3‑ene.
(2)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
15
 *P67131A01532* Turn over
PMT
(f ) Methylbenzene, C6H5CH3 , reacts with ethanoyl chloride, CH3COCl, in the presence

of the catalyst aluminium chloride, AlCl3 , to form a mixture of organic products
with the formula CH3COC6H4CH3 .
C6H5CH3 + CH3COCl → CH3COC6H4CH3 + HCl
(i) Draw the skeletal formulae of three different arenes with the formula
CH3COC6H4CH3 .
(2)
(ii) The 13C NMR spectrum of one of these arenes, compound X, is shown.
two peaks very close in chemical shift
200 180 160 140 120 100 80 60 40 20 0

δ / ppm
Identify compound X.
Use the number of peaks on the 13C NMR spectrum to justify your answer.
(2)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
16
*P67131A01632* 
PMT
(iii) Complete the diagram, including curly arrows, to show the mechanism for the
formation of compound X in this reaction.
Include an equation for the regeneration of the catalyst.
(4)
CH3COCl + AlCl3 → CH3CO+ + AlCl 4–
17
 *P67131A01732* Turn over
PMT
20 This question is about titanium(III) chloride, TiCl3 .

(a) Titanium(III) chloride is used as a catalyst in the production of poly(propene).
State the property of transition metals, such as titanium, that makes their
compounds effective catalysts.
(1)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(b) When dissolved in tetrahydrofuran (THF), titanium(III) chloride forms a blue

solution containing complex Y.
Cl Cl
Ti3+
Cl
THF complex Y
(i) THF acts as a monodentate ligand in complex Y.

State the meaning of the terms monodentate and ligand.
(2)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
18
*P67131A01832* 
PMT
(ii) Complex Z is a stereoisomer of complex Y.

Complete the diagram to show the arrangement of the ligands in complex Z.
(1)
Cl
Ti3+
complex Z
19
 *P67131A01932* Turn over
PMT
(c) A student determines the change in oxidation number of nitrogen when

a solution of magnesium nitrate, Mg(NO3)2 , is titrated with aqueous
titanium(III) chloride.
Procedure
Step 1 Using a volumetric flask, prepare 100.0 cm3 of an aqueous solution
containing 0.750 g of solid Mg(NO3)2∙6H2O.
Step 2 Pipette 10.0 cm3 of the solution from Step 1 into a conical flask and
add a few drops of alizarin indicator.
Add 2 cm3 of concentrated hydrochloric acid and heat the mixture.
Step 3 Fill a burette with 0.0850 mol dm–3 aqueous titanium(III) chloride and
titrate the contents of the conical flask from Step 2 while continuing to
heat the mixture.
During the titration, Ti3+ ions are oxidised to TiO2+ ions
Ti3+ + H2O → TiO2+ + 2H+ + e–
Alizarin indicator is green in the presence of aqueous Ti3+ and yellow in the
presence of aqueous TiO2+.
The end‑point of the titration is reached on the addition of 20.70 cm3 of aqueous
titanium(III) chloride.
(i) State the colour change that would be observed at the end‑point of
the titration.
(1)
From . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ....................................... to ............................................................................................ . .
20
*P67131A02032* 
PMT
(ii) Use the results to determine the final oxidation state of nitrogen in
the titration.
[Mr value: Mg(NO3)2∙6H2O = 256.3]
(5)
21
 *P67131A02132* Turn over
PMT
(iii) Write the overall ionic equation for the titration reaction using your answer to
(c) (ii) and the relevant half‑equations from the list below.
(2)
TiO2+ + 2H+ + e–  Ti3+ + H2O E d = +0.10 V

NO3– + 2H+ + e–  NO2 + H2O E d = +0.80 V
NO3– + 3H+ + 2e–  HNO2 + H2O E d = +0.94 V
NO3– + 4H+ + 3e–  NO + 2H2O E d = +0.96 V
d
(iv) Use the electrode potential data provided to calculate E cell for the
overall titration reaction.
(1)
(v) Suggest why the contents of the conical flask are heated.
(1)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
22
*P67131A02232* 
PMT
*(vi) The student’s teacher said,

2+
“As TiCl3 is blue and TiO ions are colourless in aqueous solution, the titration can
be carried out without an alizarin indicator.”
Assess the teacher’s statement.
In your answer you should
• identify, by name or formula, a coloured complex ion expected to be
present when TiCl3 dissolves in water
• explain how the colour of this complex ion arises
• suggest why the titration may be more accurate with an alizarin indicator.
(6)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
23
 *P67131A02332* Turn over
PMT
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
24
*P67131A02432* 
PMT
SECTION C
21 Organic molecules are an important source of colour both in the natural world and in
a wide range of industrial applications.
Curcumin contributes to the yellow colour of turmeric spice and is used as an
additive in cosmetics and foods. It has been suggested that curcumin can act as an
antioxidant and anticancer agent, through reactions with free radicals and proteins,
and may also inhibit Alzheimer’s disease by complexing to toxic metal ions.
O OH
O O
HO OH
curcumin
Azo dyes are synthetic compounds that do not occur naturally. They can be used to
colour textiles such as cotton. The acid‑base indicator methyl red is an azo dye.
O
HO N=N
methyl red
Indigotin is used to dye denim a blue colour and coumarin 440 is used to generate
blue light in lasers. Both dyes occur naturally in plants but can be synthesised in
the laboratory.
O H
N
N
H O H2N O O
indigotin coumarin 440
25
 *P67131A02532* Turn over
PMT
(a) The equation shows the reaction between a free radical T • and curcumin (shown
by a simplified structure).
O X O X
TH +
T H
O O
curcumin
Complete the left‑hand side of the equation by adding curly half‑arrows.

(1)
(b) Selenide anions attached to protein side‑chains may undergo
nucleophilic addition reactions with curcumin.
Complete the mechanism for one of the steps in such a reaction,
adding curly arrows to the simplified structures shown.
(2)
Protein Se– Protein

O Se O–
Y Z Y Z
curcumin
26
*P67131A02632* 
PMT
(c) Curcumin anions can act as bidentate ligands in metal‑curcumin (M‑curc)

complexes. The oxygen atoms of the curc ligand occupy adjacent coordination
sites in the complex, as shown.
–
O O
P Q
curcumin anion
Complete the table relating to two M‑curc complexes.

(2)
[Au(curc)2]+ [Al(curc)(C2H5OH)2(NO3)2]
Coordination number 4
O–M–O bond angle 90°
Shape octahedral
Charge on metal ion +3
27
 *P67131A02732* Turn over
PMT
(d) An incomplete synthesis for methyl red starting from 2‑nitrobenzaldehyde and
phenylamine is shown.
O HO O
NO2 NO2
Step X Sn and concentrated HCl
compound A
heat under reflux
2‑nitrobenzaldehyde
Step Y
O
NH2
OH
excess CH3I
compound B N+ N
heat
Cl–
phenylamine
Step Z
O
HO N=N
methyl red
28
*P67131A02832* 
PMT
(i) State the reagents and conditions needed in Step X.

(2)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(ii) Draw the structure of compound A.

(1)
(iii) State the reagents needed in Step Y.

(1)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(iv) Draw the structure of compound B.

(1)
(v) The temperature used in Steps Y and Z should be kept as close to 5 °C

as possible. State why the temperature should be neither higher nor lower
than 5 °C.
(2)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
29
 *P67131A02932* Turn over
PMT
(e) Indigotin can be synthesised from 2‑nitrobenzaldehyde and propanone in

aqueous sodium hydroxide.
O H
N
N
H O
indigotin
(i) Complete the equation for this reaction.

(2)
O O
O H O
2 + + NaOH N + + H2O
NO2 ........ ........ N ........ ........
ONa
H O
(ii) Calculate the mass of 2‑nitrobenzaldehyde required to make 10.0 g of

indigotin from this reaction when the percentage yield is 85.0 % .
(3)
30
*P67131A03032* 
PMT
(f ) Give the structure of the organic product of each of the following reactions of
coumarin 440.
H2N O O
coumarin 440
(i) Hydrolysis with excess aqueous sodium hydroxide.

(2)
(ii) Condensation with ethanoyl chloride.

(1)

31
 *P67131A03132*
PMT
Pearson Edexcel Centre Number Candidate Number

International
Advanced Level

Paper
reference WCH15/01
Chemistry
UNIT 5: Transition Metals and
Organic Nitrogen Chemistry
You must have: Scientific calculator, Total Marks

Data Booklet
Instructions
• Use black ink or black ball-point pen.
• Fill in the boxes at the top of this page with your name,
centre number and candidate number.
Information
• – usemarks
The for each question are shown in brackets
this as a guide as to how much time to spend on each question.
• The question labelled with an asterisk (*) is one where the quality of your written
communication will be assessed – you should take particular care with your spelling,
punctuation and grammar, as well as the clarity of expression, on this question.
Advice
• Checkallyouryouranswers
Show working in calculations and include units where appropriate.
• Good luck with yourifexamination.
you have time at the end.
•
Turn over
*P64627A0136*
P64627A
1/1/1/1/1
PMT
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 In which of the following pairs does the metal have different oxidation numbers?
A CrO42− and Cr2O72−
B CrO42− and CrO3Cl−
C V2O5 and VO43−
D VO+2 and VO2+
2 This question is about the reaction

2Fe3+(aq) + Ti(s) → 2Fe2+(aq) + Ti2+(aq) Ecell
O = +2.40 V
(a) The electrode potential for the Fe3+/ Fe2+ electrode system is +0.77 V.
What is the electrode potential for the Ti2+/Ti electrode system?
(1)
A −3.17 V
B −1.63 V
C +1.63 V
D +3.17 V
2
*P64627A0236*
PMT
(b) What metals should be used for the electrodes in the cell for this reaction?
(1)
Metals used for the electrode

Fe3+/ Fe2+ electrode system Ti2+/ Ti electrode system
A iron titanium
B iron platinum
C platinum titanium
D platinum platinum
(c) The half-cell for the Fe3+/ Fe2+ electrode system is prepared by mixing equal
volumes of solutions of iron(II) sulfate, FeSO4, and iron(III) sulfate, Fe2(SO4)3.
What concentrations of the original solutions are needed for the resulting
mixture to be standard?
(1)
Concentration of the original solution
FeSO4 Fe2(SO4)3
A 1 mol dm–3 0.5 mol dm–3

B 1 mol dm–3 1 mol dm–3
C 2 mol dm–3 1 mol dm–3
D 2 mol dm–3 2 mol dm–3
3
*P64627A0336* Turn over
PMT
3 What is the electronic configuration of a chromium atom?

3d 4s
A (Ar) ↑ ↑ ↑ ↑ ↑ ↑
B (Ar) ↑ ↑ ↑ ↑ ⇅
C (Ar) ⇅ ⇅ ↑ ↑
D (Ar) ⇅ ↑ ↑ ⇅
4 A ligand must be an
A electron-pair donor
B electron-pair donor and negatively charged

C electron-pair acceptor
D electron-pair acceptor and negatively charged
5 Diamminecopper(I) ions are not coloured because
A the d orbitals in copper(I) cannot be split

B the energy difference between the split d orbitals is outside the visible
region of the spectrum
C d—d transitions are not possible because the d orbitals are fully occupied
D copper(I) complexes are readily oxidised
4
*P64627A0436*
PMT
6 Copper(II) ions form a complex with 1,2-diaminoethane (symbol ‘en’) with the formula Cu(en)32+.
What type of ligand is 1,2-diaminoethane, and what is the coordination number of
copper(II) in the complex?
Type of ligand Coordination number

A bidentate 3
B bidentate 6
C tridentate 3
D tridentate 6
7 Aqueous sodium hydroxide was added to aqueous iron(II) sulfate and the mixture
allowed to stand.
What would be observed?
Observations
Immediately after adding
After standing
sodium hydroxide
A brown precipitate no change
B green precipitate no change
C brown precipitate precipitate turns green
D green precipitate precipitate turns brown
5
PMT
8 When aqueous ammonia is added to an aqueous solution of zinc sulfate, a white

precipitate forms which dissolves in excess ammonia to give a colourless solution.
What types of reaction are occurring?
Type of reaction
Formation of white Formation of colourless
precipitate solution
A deprotonation ligand exchange
B deprotonation deprotonation
C ligand exchange deprotonation
D ligand exchange ligand exchange
9 Benzene is sometimes represented by a Kekulé structure.
Kekulé structure of benzene

If this were the only structure of benzene, what would be the total number of
isomers of dichlorobenzene?
A two
B three
C four
D five
6
*P64627A0636*
PMT
10 What is the product when benzene reacts with fuming sulfuric acid?
A S O
O
S OH
B
O
C S OH
OH
D S OH
7
PMT
11 Hydrogen bonds are formed when methylamine dissolves in water.

Which structure best represents a hydrogen bond between methylamine and water?
H H
O
A H C N H H
H H
H H
B H C N H O
H
H H
H H H
C O H C N
H H H
H H
D H O H C N
H
H H
12 Which type of compound cannot be a monomer in the formation of polyamides?
A amides
B amino acids
C diacyl chlorides
D diamines
8
*P64627A0836*
PMT
13 Alanine is an amino acid.

(a) Which structure best represents alanine at high pH?
(1)
NH2 OH
A H3C C C
H O
NH2 O–
B H3C C C
H O
NH3+ OH
C H3C C C
H O
NH3+ O–
D H3C C C
H O
(b) Alanine is a crystalline solid at room temperature.

What are the main forces broken when alanine melts?
(1)
A London forces
B hydrogen bonds
C covalent bonds
D ionic bonds
9
PMT
14 An aliphatic organic compound has the infrared spectrum shown.

100
Transmittance / %
P
50
0
4000 3000 2000 1500 1000 500
Wavenumber / cm –1
What are the bond stretches responsible for the peaks P and Q in the spectrum?
P Q
A O—H carboxylic acid C O carboxylic acid
B O—H carboxylic acid C O aldehyde
C C—H aldehyde C O carboxylic acid
D C—H aldehyde C O aldehyde
10
*P64627A01036*
PMT
15 How many peaks are there in the carbon-13 (13C) NMR spectrum of methylcyclohexane?
methylcyclohexane
A one
B three
C five
D seven
16 In the high resolution proton NMR spectrum of propan-2-ol, CH3CHOHCH3 there are
A one singlet, one doublet and a heptet
B one singlet, two doublets and a heptet
C two singlets and two triplets
D three singlets and a quartet
11
PMT
17 What is the minimum volume of oxygen gas, measured at room temperature and
pressure, required for the complete combustion of 9.2 g of C3H8O3 (Mr = 92)?
[Molar volume of gas at room temperature and pressure = 24.0 dm3 mol−1]
A 4.8 dm3
B 8.4 dm3
C 12.0 dm3
D 16.8 dm3
12
*P64627A01236*
PMT
SECTION B
18 This question is about manganese compounds. Some data are given below.
Electrode reaction EO / V
1 MnO4− + e− ⇌ MnO42− +0.56
2 MnO42− + 2H2O + 2e− ⇌ MnO2 + 4OH− +0.59
3 Fe3+ + e− ⇌ Fe2+ +0.77
4 MnO2 + 4H+ + 2e− ⇌ Mn2+ + 2H2O +1.23
5 MnO4− + 8H+ + 5e− ⇌ Mn2+ + 4H2O +1.51
6 MnO4− + 4H+ + 3e− ⇌ MnO2 + 2H2O +1.70
7 MnO42− + 4H+ + 2e− ⇌ MnO2 + 2H2O +2.26
(a) (i) Write the ionic equation for the disproportionation of manganate(VI) ions, MnO42−,
in acidic conditions, using relevant half-equations from the table.
(2)
O for the disproportionation of manganate(VI) ions in acidic

(ii) Calculate Ecell
conditions, stating whether or not the reaction is thermodynamically feasible.
(2)
14
*P64627A01436*
PMT
(iii) Using the standard electrode potentials in the table, assess the
thermodynamic feasibility of preparing manganate(VI) by reacting
manganate(VII) and manganese(IV) oxide in alkaline conditions.
(4)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
15
PMT
(b) Steel is an alloy of iron and carbon. A group of students determined the iron
content of a sample of steel wire by a titration method.
A known mass of the wire was dissolved in dilute sulfuric acid and the resulting
solution made up to 250.0 cm3 with more dilute sulfuric acid and mixed thoroughly.
Fe + H2SO4 → FeSO4 + H2
25.0 cm3 samples of the resulting solution were titrated with 0.0195 mol dm−3
potassium manganate(VII) solution.
(i) State the colour change at the end-point of the titration.
(1)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(ii) One student used 1.53 g of the wire (weighed directly on the balance pan)
and obtained a mean titre of 27.35 cm3.
Using half-equations 3 and 5 from the table, calculate the percentage of iron
in the steel wire. Give your answer to three significant figures.
(5)
16
*P64627A01636*
PMT
(iii) A second student carried out the same experiment but used distilled water to
make up the solution in the volumetric flask.
A brown suspension formed during the titration.
Explain how, if at all, the titre value would be affected by this student’s error.
(3)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(c) The uncertainties of the apparatus used in the experiment in (b) are shown.
Uncertainty on each Percentage uncertainty on

Apparatus Value measured
reading value measured / %
Balance 1.53 g ±0.005 g 0.65
Burette 27.35 cm3 ±0.05 cm3
Pipette 25.0 cm3 ±0.06 cm3
Volumetric flask 250.0 cm3 ±0.3 cm3
(i) Complete the table.

(2)
(ii) A third student obtained a value of 95.863% for the proportion of iron in the wire.
State whether or not this student has given their answer to an appropriate
number of significant figures. Justify your answer in terms of the total percentage
uncertainty of the experiment.
(2)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
17
PMT
19 This question is about the investigation of an organic compound X.

X is a liquid at room temperature and pressure, which turns damp red litmus paper blue.
(a) (i) Name the functional group present in X.
(1)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(ii) When 0.493 g of X was vaporised, 157 cm3 of dry air was displaced, measured
at 15°C and 103 000 Pa.
Calculate the molar mass of X, using the ideal gas equation.
(4)
18
*P64627A01836*
PMT
(b) X reacted vigorously with ethanoyl chloride forming steamy fumes and
a white solid Y.
(i) Identify the steamy fumes, by name or formula.
(1)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ........................................................................................................................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ........................................................................................................................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(ii) Suggest the functional group present in Y.

(1)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ........................................................................................................................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(iii) Analysis of Y showed that its composition by mass was 62.6 % carbon;
11.3 % hydrogen; 12.2 % nitrogen; 13.9 % oxygen.
Determine the empirical formula of Y. You must show your working.
(3)
19
PMT
*(c) A simplified high resolution proton NMR spectrum of Y is shown.

The relative peak areas are given near each peak.
3
TMS
1
12.0 10.0 8.0 6.0 4.0 2.0 0.0

Chemical shift (δ) / ppm
Deduce the structure of Y, using the NMR spectrum and the other information in
the question.
(6)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
20
*P64627A02036*
PMT
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
21
O
PMT
(d) Draw the structure of compound X.

(1)
22
*P64627A02236*
PMT
20 This question is about benzene and some related compounds.

(a) Some standard enthalpies of combustion are shown.
Standard enthalpy of
Compound Structure
combustion, ∆cH O / kJ mol−1
cyclohexene −3752
cyclohexa-1,4-diene −3584
benzene −3267
(i) Using the standard enthalpies of combustion of cyclohexene and

cyclohexa-1,4-diene, calculate a value for the enthalpy of combustion of the
theoretical compound ‘cyclohexa-1,3,5-triene’.
(2)
cyclohexa-1,3,5-triene
24
*P64627A02436*
PMT
(ii) Explain the difference between the enthalpy of combustion of

‘cyclohexa-1,3,5-triene’ calculated in (a)(i) and the enthalpy of combustion
of benzene given in the table.
(3)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(b) Bromine reacts with cyclohexene to form 1,2-dibromocyclohexane, and with

benzene to form bromobenzene.
Compare and contrast these reactions, considering the type and mechanism of
each reaction and the conditions required.
You are not required to draw the mechanisms of the reactions.
(4)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
25
PMT
(c) Bromine also reacts with phenol.

(i) Identify, by name or formula, the organic product when phenol reacts with
excess bromine.
(1)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(ii) Explain why bromine reacts much faster with phenol than with benzene.
(2)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
26
*P64627A02636*
PMT
SECTION C
21
Iron Chemistry
Iron is a typical transition metal. Due to the similar energies of the 3d and
4s electrons, iron forms compounds in a number of oxidation states.
Iron(II) and iron(III) are the most common oxidation states, and iron(III) is
the most stable.
Iron ions form many complexes, including that in haemoglobin which is
responsible for oxygen transport in the blood of most vertebrates.
The haemoglobin-iron complex with oxygen is responsible for the red colour
of blood.
Iron(III) ions may be detected in solution by the addition of thioglycolic acid
(HSCH2COOH). All the water ligands of the iron(III) ion are replaced giving
a complex with an intense red colour which can be detected in
very low concentrations.
The complexes of iron(II) and iron(III) usually have a coordination number of
six and are octahedral but the chloro complexes have a coordination number
of four and are tetrahedral.
Iron and its compounds can act as catalysts. The element catalyses the Haber
process, acting as a typical heterogeneous catalyst. However, the compounds
and complexes of iron are usually homogeneous catalysts.
(a) Explain, in terms of electronic structure, why iron(III) compounds are more stable
than iron(II) compounds.
(2)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
27
PMT
(b) The third ionisation energy of iron is 2958 kJ mol−1.

(i) Write the equation for the third ionisation energy of iron.
Include state symbols.
(1)
(ii) Explain how stable iron(III) ions can be formed from iron(II) ions in
aqueous solution. Refer to the relevant energy changes of these ions only.
(3)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
28
*P64627A02836*
PMT
(c) Invertebrates use a copper complex, haemocyanin, to transport oxygen.

Blue oxyhaemocyanin gives invertebrate blood its characteristic colour.
Explain why oxyhaemocyanin and oxyhaemoglobin have different colours.
(3)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
29
PMT
(d) The presence of iron in sodium carbonate can affect its properties; the higher the
quality of the sodium carbonate, the lower the proportion of iron.
The proportion of iron in a laboratory grade anhydrous sodium carbonate was
listed as less than 20 ppm by mass.
In an experiment to check this specification, 20 g of the sodium carbonate was
dissolved in sulfuric acid, and thioglycolic acid added in excess to form the
iron(III) thioglycolic acid complex, Fe(HSCH2COOH)33+. The solution was made up
to 500 cm3 in a volumetric flask and thoroughly mixed.
Colorimeter calibration graph
2
1.5
log (% transmittance)
1
0.5
0 0.5 1 1.5
Concentration of iron / mg dm–3
The transmittance of the resulting solution was determined using a colorimeter

and found to be 39.8 %.
(i) Using the calibration graph, determine whether or not the iron concentration
in this sample of sodium carbonate meets the stated specification.
(4)
30
*P64627A03036*
PMT
(ii) Suggest what type of ligand thioglycolic acid is in the iron(III) thioglycolic acid
complex. Justify your answer.
(2)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(e) Iodide ions are oxidised to iodine by peroxodisulfate ions.

2I−(aq) + S2O2−
8 (aq) → I2(aq) + 2SO42−(aq)
Iron(II) ions act as a homogeneous catalyst for this reaction.
(i) State why the catalyst is described as ‘homogeneous’.
(1)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(ii) Write two equations to show how iron(II) ions catalyse this oxidation.
(2)
(iii) Suggest how iron(II) ions lower the activation energy of this reaction.
(1)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
31
PMT
(f ) Give a possible reason why the chloro complexes of iron ions have a coordination
number of four rather than six.
(1)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .

32
*P64627A03236*
PMT

International
Advanced Level
Monday 18 January 2021

Morning (Time: 1 hour 45 minutes) Paper Reference WCH15/01
Chemistry
Unit 5: Transition Metals and Organic Nitrogen Chemistry

Scientific calculator, Data booklet
Instructions
• Use black ink or ball-point pen.
• centrethe
Information
• Inability
the question marked with an asterisk (*), marks will be awarded for your
to structure your answer logically showing how the points that you make
are related or follow on from each other where appropriate.
Advice
Turn over
*P67819A0128*
P67819A
1/1/1/1/1
PMT
SECTION A
1 When an alkene is added to a solution of potassium manganate(VII),
the purple solution turns colourless.
In terms of electron transfer and oxidation number, how does the manganese change
in this reaction?
Electron transfer Oxidation number
A gains electrons increases
B gains electrons decreases
C loses electrons increases
D loses electrons decreases
2 The standard hydrogen electrode uses an electrode of platinum coated in a

finely divided form of the metal called platinum black.
What is the purpose of this coating?
A t o increase the rate of the equilibrium between the hydrogen gas and the
hydrogen ions
B to provide an inert protective coating for the electrode
C to increase the electrical conductivity of the electrode
D to ensure that the conditions remain standard
2
*P67819A0228*
PMT
3 An electrochemical cell is set up to measure E cell

d
for the reaction
Fe(s) + Sn2+(aq) → Fe2+(aq) + Sn(s)
(a) What is the cell diagram for this cell?
(1)
A Fe(s) | Fe2+(aq) || Sn(s) | Sn2+(aq)
B Fe2+(aq) | Fe(s) || Sn2+(aq) | Sn(s)
C Fe(s) | Fe2+(aq) || Sn2+(aq) | Sn(s)
D Fe2+(aq) | Fe(s) || Sn(s) | Sn2+(aq)

(b) The standard electrode potential for the Fe / Fe2+ electrode system is −0.44 V and
d
E cell for the reaction is +0.30 V.
What is the standard electrode potential for the Sn / Sn2+ electrode system?
(1)
A −0.74 V
B −0.14 V
C +0.14 V
D +0.74 V
3
PMT
4 Hydrogen-oxygen fuel cells can operate in acidic or alkaline conditions.

What is the reaction at the anode in an alkaline hydrogen-oxygen fuel cell?
A O2(g) + 2H2O(l) + 4e− → 4OH−(aq)
B 4OH−(aq) → O2(g) + 2H2O(l) + 4e−
C 2H2O(l) + 2e− → H2(g) + 2OH−(aq)
D H2(g) + 2OH−(aq) → 2H2O(l) + 2e−
5 Which of these has the greatest number of unpaired electrons in each of its atoms?
A chromium
B iron
C manganese
D vanadium
6 Nickel is classified as a transition metal. This is because nickel
A is a d block element
B has partially filled d orbitals
C forms stable ions with partially filled d orbitals

D forms stable compounds in which it has different oxidation states
4
*P67819A0428*
PMT
7 Platinum forms a complex with the formula Pt(NH3)2Cl2 and chromium forms
−
a complex with the formula CrCl4 .
(a) What are the shapes of these complexes?
(1)
A both complexes are square planar
B both complexes are tetrahedral

−
C Pt(NH3)2Cl2 is tetrahedral and CrCl4 is square planar
−
D Pt(NH3)2Cl2 is square planar and CrCl4 is tetrahedral
(b) What is the bonding between the ligands and the central atom in
these complexes?
(1)
A the bonding in both complexes is ionic
B the bonding in both complexes is dative covalent

−
C the bonding in Pt(NH3)2Cl2 is dative covalent and in CrCl4 is ionic
−
D the bonding in Pt(NH3)2Cl2 is ionic and in CrCl4 is dative covalent
8 Cobalt chloride is used as a test for the presence of water.

This test depends on the fact that
A anhydrous cobalt(II) chloride is blue and hydrated cobalt(II) chloride is pink

B anhydrous cobalt(II) chloride is pink and hydrated cobalt(II) chloride is blue
C cobalt(II) chloride is blue and cobalt(III) chloride is pink
D cobalt(II) chloride is pink and cobalt(III) chloride is blue
5
PMT
9 Iodide ions are oxidised by peroxodisulfate ions in aqueous solution.

8 → I2 + 2SO4
2I− + S2O2− 2−
This reaction is catalysed by adding Fe2+ ions to the solution.

This catalysis is effective because
A Fe2+ reacts with iodide ions and with peroxodisulfate ions
B Fe2+ has many electrons in its outermost subshells
C Fe2+ has many active sites on which the reaction can occur
D Fe2+ is readily oxidised to Fe3+ which is then reduced to Fe2+
10 The delocalised electrons in benzene result from the overlap of
A s orbitals to form σ bonds
B s orbitals to form π bonds

C p orbitals to form σ bonds
D p orbitals to form π bonds
11 The reaction of ethene with bromine occurs under normal laboratory conditions but
the reaction of benzene with bromine to form bromobenzene requires heat and the
presence of a catalyst.
The best explanation for the difference in reactivity is that the delocalised electrons
in benzene
A repel electrophiles
B result in a kinetic barrier to intermediate formation
C result in benzene having an endothermic enthalpy of formation
D make benzene thermodynamically stable with respect to the formation of

bromobenzene
6
*P67819A0628*
PMT
12 What is the name of the compound shown?

O
NH2
A 1-methylpropanamide
B 3-methylpropanamide
C 2-methylbutanamide
D 3-methylbutanamide
13 Separate 0.1 mol dm−3 aqueous solutions of ammonia, butylamine and phenylamine
were prepared.
Which of the following sequences shows the solutions in order of increasing pH?
A butylamine, phenylamine, ammonia
B ammonia, butylamine, phenylamine
C phenylamine, ammonia, butylamine
D ammonia, phenylamine, butylamine
7
PMT
14 The repeat unit of a polymer is shown.
O NH2
What is the structure of the monomer?
O
A
NH2
O
B
NH2
C
NH2
D
NH2
8
*P67819A0828*
PMT
15 The repeat unit of a polymer is shown.

O H O H H H H H
C C C N C C C N
CH3 H H H
This polymer could be
A both a polypeptide and a polyamide
B neither a polypeptide nor a polyamide
C a polypeptide but not a polyamide
D a polyamide but not a polypeptide
16 The structure of a hydrocarbon is shown.
How many peaks will there be in the 13C NMR spectrum of this compound?
A four
B five
C seven
D eight
9
PMT
17 When a sample of a hydrocarbon is burned completely in oxygen,

2.64 g of carbon dioxide and 0.81 g of water are formed.
Which of these could be the molecular formula of the hydrocarbon?
A C2H3
B C4H3
C C4H6
D C12H9
18 Benzenecarboxylic acid may be produced from benzene in a two-step synthesis.
O OH
CH3 C
Step 1 Step 2
Yield 45% Yield 60%
benzene methylbenzene benzenecarboxylic acid

Mr = 78 Mr = 92 Mr = 122
8.24 g of benzenecarboxylic acid was formed in this synthesis.

What mass of benzene was used?
A 3.48 g
B 5.27 g
C 19.51 g
D 30.52 g
10
*P67819A01028*
PMT
BLANK PAGE
11
PMT
SECTION B
19 The diagram summarises some reactions of copper compounds.
KI(aq) H2SO4(aq)
CuSO 4(aq) copper(I) iodide P (pink solid) + Q (blue solution)
NH3(aq) NH3(aq)
NH3(aq)
R (pale blue solid) T (dark blue solution) V (colourless solution)
heat vigorous shaking

HNO3(aq)
S (black solid) W (blue solution)
(a) Identify, by name (including the oxidation state) or formula, the species in the
sequence that contain copper.
(7)
P ....... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ........................................................................................................................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
Q ....... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
R ....... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
S ......... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ........................................................................................................................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
T ....... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
V ....... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
W . ..... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(b) T and V are the same type of chemical species.

(i) Name this type of chemical species.
(1)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
12
*P67819A01228*
PMT
(ii) Explain why T is coloured while V is colourless.

A detailed explanation of the fact that T is coloured is not required.
(3)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(iii) Suggest an explanation for the change of V into T on shaking.

(2)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(c) The reaction between copper(I) iodide and sulfuric acid is a disproportionation.
(i) Write the ionic equation for this disproportionation reaction.
(1)
(ii) Show that the reaction in (c)(i) is thermodynamically feasible.

Use the standard electrode potentials of the relevant half-cells
from the Data Booklet.
(2)
13
PMT
(d) The rare mineral mitscherlichite has the chemical formula K2CuCl4⦁nH2O.
4.26 g of mitscherlichite was dissolved in distilled water and the solution made up
to 250.0 cm3. Excess potassium iodide solution was added to a 25.0 cm3 portion
of this solution and the iodine formed was titrated against a solution of
sodium thiosulfate with a concentration of 0.0500 mol dm−3.
This procedure was repeated until concordant results were obtained.
The mean accurate titre was 26.65 cm3.
The equations for the reactions are
2Cu2+ + 4I− → 2CuI + I2
2S2O32− + I2 → S4O62− + 2I−
Calculate the value of n, the number of moles of water of crystallisation per mole
of mitscherlichite.
(6)
14
*P67819A01428*
PMT
20 Ketones are useful starting compounds in organic synthesis.

This question is about butanone.
C CH3
H3C CH2
butanone
(a) The mass spectrum of butanone has significant peaks at m / z = 43 and

at m / z = 57.
(i) Give the structures of the species responsible for these two peaks.
(2)
(ii) Give the structure of one other species that you would expect to produce
a peak at a different m / z value in the mass spectrum of butanone.
(1)
15
PMT
(b) Devise a reaction scheme to prepare propan-1-ol from butanone, using no more
than four steps.
Identify the reagents and essential conditions for each step and give the name or
(4)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
16
*P67819A01628*
PMT
(c) Devise a reaction scheme to prepare 2-methylbut-2-ene from butanone, using no

more than four steps.
Identify the reagents and essential conditions for each step and give the name or
(5)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
17
PMT
21 A yellow crystalline solid E dissolved in distilled water to give a yellow solution.

Addition of dilute sulfuric acid to this solution produced an orange solution F.
Warming F with ethanol resulted in a green solution G, and the formation of ethanal.
A standard cell was set up using solutions of F and G for the right-hand electrode and
ethanol and ethanal for the left-hand electrode.
d
E cell was found to be +1.94 V.
CH3CHO(aq) + 2H+(aq) + 2e− ⇌ C2H5OH(aq) E d = − 0.61 V
(a) Deduce the formulae of the ions responsible for the colours of F and G, using the
standard electrode potential and E d given, and the values in the Data Booklet.
(2)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(b) Write the overall equation for the reaction in the cell.
(2)
(c) Write the ionic equation for the reaction of the aqueous solution of E
with dilute sulfuric acid. State symbols are not required.
(1)
18
*P67819A01828*
PMT
22 Using excess oxygen, 25 cm3 of a gaseous hydrocarbon CxHy was burned completely.
After cooling to room temperature the total gas volume was measured and found to
be 75 cm3 less than the total gas volume before the mixture was ignited.
When the product gases were shaken with potassium hydroxide solution, the total
gas volume decreased by a further 100 cm3.
All gas volumes were measured at room temperature and pressure.
A general equation for the combustion of a hydrocarbon is
𝑦𝑦 𝑦𝑦
Cx Hy + x+ O2 → xCO2 + H2O
4 2
(a) Determine the molecular formula of CxHy . You must show your working.
(3)
(b) When CxHy was added to a little bromine water and the mixture shaken, the
bromine water remained yellow.
Suggest two possible structures for CxHy .
(2)
19
PMT
*23 Compare and contrast the mechanism of the action of platinum as a catalyst in the
removal of pollutants from car engine exhaust fumes with that of vanadium(V) oxide
as a catalyst in the Contact Process for the manufacture of sulfuric acid.
General definitions of catalysts are not required.
(6)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
20
*P67819A02028*
PMT
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
21
PMT
SECTION C
Coffee Chemistry
24 There are over a thousand chemical compounds in coffee and their physiological
effects are the subject of considerable speculation and research. The verdict on coffee
is contradictory: some of the compounds have been identified as toxic and even
carcinogenic but others are antioxidants associated with cancer prevention. Recent
research has identified compounds in coffee that might be used in the treatment of
prostate cancer.
By far the best known compound in coffee is caffeine, the most widely consumed
psychoactive drug in the world. In small amounts it is a stimulant but doses in excess
of 10 g per day are toxic. Caffeine contains amide and amine groups.
N
N
N
O N
caffeine
Chlorogenic acid is responsible for the acidic taste of coffee. It is an antioxidant and
has also been shown to slightly decrease blood pressure.
OH
HO
O
O
HO O
OH
OH
OH chlorogenic acid
Caffeic acid, quinic acid and acetoin are also present in coffee.
22
*P67819A02228*
PMT
(a) Another way of drawing the structure of caffeine is shown.
N
N
N
O N
(i) The bonding represented by this diagram of caffeine differs from that given in
the passage.
Explain what this diagram indicates about the bonding in caffeine, stating the
effect on the structure of caffeine.
(3)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(ii) Suggest why caffeine is a much weaker base than a primary amine such as
ethylamine, even though the right-hand ring has two amine groups.
(2)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
23
PMT
(b) A 200 cm3 cup of coffee contains approximately 85 mg of caffeine.

(i) Calculate the concentration, in mol dm−3, of caffeine in this cup of coffee.
Give your answer to an appropriate number of significant figures.
(4)
(ii) The removal of caffeine from the body is a first order reaction with a half-life
of between three and seven hours for an adult.
An adult drinks coffee containing a total of 160 mg of caffeine.
Calculate to the nearest hour the minimum time needed for the amount of
caffeine in their body to drop to 20 mg.
(2)
24
*P67819A02428*
PMT
(c) Chlorogenic acid is an ester of caffeic acid, a compound that is present in all plants.
HO
OH
OH caffeic acid
(i) A student suggested that caffeic acid could be synthesised by an electrophilic

substitution of 1,2-dihydroxybenzene.
Draw the mechanism of this electrophilic substitution, including the formation
of a suitable electrophile.
(5)
25
PMT
(ii) Deduce the structure of quinic acid which combines with caffeic acid to form
chlorogenic acid.
(1)
HO
OH
OH caffeic acid
OH
HO
O
O
HO O
OH
OH
OH chlorogenic acid
quinic acid
26
*P67819A02628*
PMT
(d) The structure of acetoin is shown with one of the proton environments labelled.
A OH
acetoin
(i) Identify the other proton environments of acetoin on the structure and label
them B, C etc.
(1)
(ii) Complete the table to show the splitting pattern in the high resolution
proton NMR spectrum of acetoin.
(2)
Proton environment Splitting pattern

27
*P67819A02728*
PMT
28
*P67819A02828*

International
Advanced Level
Tuesday 9 June 2020

Morning (Time: 1 hour 40 minutes) Paper Reference WCH05/01
Chemistry
Advanced
Unit 5: General Principles of Chemistry II – Transition
Metals and Organic Nitrogen Chemistry
(including synoptic assessment)
Candidates must have: Scientific calculator Total Marks
Data Booklet
Instructions
• Use black ink or black ball-point pen.
• centre
Fill in the boxes at the top of this page with your name,
• Answer allthequestions.
Answer
• – there may bequestions in the spaces provided
more space than you need.
Information
• written
Questions labelled with an asterisk (*) are ones where the quality of your
communication will be assessed
– you should take particular care with your spelling, punctuation and grammar,
as well as the clarity of expression, on these questions.
Advice
• Show all your working in calculations and give units where appropriate.
Turn over
*P64618A0128*
P64618A
1/1/1/1/1/
SECTION A
Answer ALL the questions in this section. You should aim to spend no more than 20 minutes
on this section. For each question, select one answer from A to D and put a cross in the box .
If you change your mind, put a line through the box and then mark your new answer with
a cross .
1 A reaction of benzene produces benzenesulfonic acid:
OH
O S O
This reaction is carried out using

A concentrated nitric acid and concentrated sulfuric acid.
B concentrated sulfuric acid.
C fuming sulfuric acid.
D sulfur dioxide and steam.
2 It may be deduced that benzene is unsaturated because it
A decolourises bromine water.

B turns acidified potassium dichromate(VI) green on heating.
C burns with a smoky flame.
D forms separate layers when added to water.

2
*P64618A0228*
3 Which is/are the organic product(s) of the reaction of phenol with excess
aqueous bromine?
A B
OH OH
Br Br Br Br
Br Br
Br Br
C D
OH OH OH
Br Br Br
mixture of and
Br Br
Br Br
4 Which molecule has an amine functional group?
O
O
A B
HN H2N
O
H2N
C D
NH O

3
5 Methyl orange is an indicator with the structure
N N
N SO−3 Na+
(a) Methyl orange is an azo dye. The benzenediazonium intermediate can be made using
(1)
A HNO2
B HNO3
C H2SO4 and HNO3
D HCl only
(b) The reaction conditions for the formation of methyl orange from the
benzenediazonium intermediate are
(1)
A reflux at 50–55 °C.
B heat with AlCl3.
C LiAlH4 in dry ether.
D ice-cold alkaline solution.
6 An example of an addition polymer is
H2N O
C
CH2 CH
Which of these is the monomer of this polymer?

A CH3CH2CONH2
B CH2CHCONH2
C H2NCHCHCOOH
D CH3CH(OH)CONH2
4
*P64618A0428*
7 The amino acid lysine has the structure
NH2
CH2 CH2 CH O
H2N CH2 CH2 C
OH
(a) Which of these could be a repeat unit for poly(lysine)?

(1)
O O
A N CH C B CH C
n n
H (CH2)4NH2 (CH2)4NH2
O O
C CH C O D N CH C O
n n
(CH2)4NH2 H (CH2)4NH2
(b) The reaction of lysine with excess hydrochloric acid produces

(1)
A B
NH2 NH+3 Cl−
CH2 CH2 CH O CH2 CH2 CH O

H2N CH2 CH2 C H2N CH2 CH2 C
Cl OH
C D
NH+3 Cl− NH+3 Cl−
CH2 CH2 CH O CH2 CH2 CH O

+ +
−
Cl H3N CH2 CH2 C −
Cl H3N CH2 CH2 C
OH Cl
5
(c) The presence of amino acids such as lysine can be detected by the use of
(1)
A 2,4-dinitrophenylhydrazine (Brady’s reagent).
B iodine.
C ninhydrin.
D Tollens’ reagent.
(d) Lysine is a crystalline solid with a high melting temperature.

The best explanation is that
(1)
A each lysine molecule has strong London forces due to the high number of electrons.
B each lysine molecule can form hydrogen bonds at both ends.
C proton transfer within the molecules results in ionic bonding.
D the molecular shape allows the molecules to pack together closely.
d
8 The reaction of aluminium with oxygen has E cell = +2.17 V.
Aluminium is corrosion-resistant in air because
A aluminium does not react with oxygen.
B aluminium forms a stable oxide coating.
C the reaction is not carried out under standard conditions.
D the reaction is not thermodynamically feasible.
9 A disadvantage of the use of methanol in a fuel cell is that methanol is

A difficult to store.
B difficult to transport.
C flammable.
D made from fossil fuels.
6
*P64618A0628*
10 The colour of the complex [CrCl4]− in aqueous solution is due to the
A movement of electrons to a higher quantum shell.
B return of excited electrons to the ground state.
C splitting of a d orbital.
D promotion of electrons between d orbitals.
11 The reaction shown is between aqueous chromium(III) ions and excess concentrated
hydrochloric acid.
[Cr(H2O)6]3+ + 4Cl− → [CrCl4]− + 6H2O
(a) This reaction is an example of

(1)
A amphoteric behaviour.
B ligand exchange.
C oxidation of the chromium ion.
D reduction of the chromium ion.
(b) What are the coordination numbers of the chromium ion in each complex?
(1)
[Cr(H2O)6]3+ [CrCl4]−
A 1 1
B +3 −1
C 6 6
D 6 4

7
12 The advantage of steam distillation over distillation is that
A it is cheaper to use steam.
B the neutrality of the steam does not affect organic molecules.
C the process is gentler with temperature-sensitive substances.
D a safety valve or outlet is not required from the condenser.
13 Ammonia, butylamine and phenylamine all form alkaline aqueous solutions.

The order of increasing pH of equimolar solutions is
A phenylamine < butylamine < ammonia
B ammonia < butylamine < phenylamine
C ammonia < phenylamine < butylamine
D phenylamine < ammonia < butylamine
14 Which of the following is not a bidentate ligand?
NH
A H2N NH2 B H2N NH2
−
O− O−
O O
C D O O
8
*P64618A0828*
d d
15 The relationship of E cell with ∆S and E cell with ln Kc is
∆S ln Kc
A directly proportional directly proportional
B directly proportional indirectly proportional
C indirectly proportional directly proportional
D indirectly proportional indirectly proportional
9
SECTION B
16 This is a question about gold, Au.

Some electrode potentials for gold are shown in the table. You will need these in
addition to the values in the Data Booklet.
Right-hand electrode system E d/ V

Au3+(aq), Au+(aq) | Pt +1.29
Au3+(aq) | Au(s) +1.41
Au+(aq) | Au(s) +1.69
(a) An electrochemical cell is set up by connecting two half-cells, with electrodes of

gold and silver dipping into separate solutions of gold(III) ions and silver(I) ions.
Both solutions have a concentration of 1 mol dm−3.
d
(i) Draw a labelled diagram of the apparatus to measure E cell for this
electrochemical cell.
(3)
d
(ii) Write the equation for the cell reaction, including state symbols, and calculate E cell.
(2)
d
E cell =
10
*P64618A01028*
(iii) Explain, using the electrode potential data in the table, why aqueous solutions
of gold(I) ions are unstable, giving an equation for the reaction that occurs.
(2)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(b) Solutions containing gold(I) ions are stabilised by the addition of cyanide ions.
The reaction is
Au+(aq) + 2CN−(aq) → [Au(CN)2]−(aq)
(i) Suggest the shape of the [Au(CN)2]− ion.

(1)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(ii) During the production of gold from its ore, zinc is added to a solution
containing [Au(CN)2]− ions. The reaction is
2[Au(CN)2]−(aq) + Zn(s) → 2Au(s) + [Zn(CN)4]2−(aq)
Explain which species is the reducing agent in this reaction, illustrating your
answer with a half-equation.
(2)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
11
17 Chromium is a transition metal with many of the typical properties of these elements.
(a) State the meaning of the term ‘transition metal’.
(1)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(b) Chromium and copper have the same outermost electronic configuration.
Give this outermost electronic configuration.
(1)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(c) Use your knowledge of the oxidation states of chromium to predict the formulae
of two chromium oxides.
(1)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
*(d) Green precipitates can be formed by the addition of a small volume of

sodium hydroxide solution to separate aqueous solutions of Cr3+ ions, Fe2+ ions
and Ni2+ ions.
Explain how separate samples of these precipitates can be distinguished.
(3)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
12
*P64618A01228*
(e) On addition of excess ammonia, chromium(III) ions form
hexaamminechromium(III), [Cr(NH3)6]3+ .
(i) Draw a diagram to show the three-dimensional shape of this complex ion.
(2)
(ii) State the H N H bond angle in this complex ion.

Justify your answer.
(2)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(iii) When EDTA is added to an aqueous solution of the [Cr(NH3)6]3+ complex, the
formation of the EDTA complex is favoured.
Explain why this is so.
(2)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
13
(f ) Sodium chromate(VI), Na2CrO4 , often contains impurities.
A procedure to determine the percentage purity by mass of a sample of
sodium chromate(VI) involves:
• conversion of chromate(VI) ions into dichromate(VI) ions in acidic conditions
• use of the dichromate(VI) ions in acidic solution as an oxidising agent to
convert Fe2+ to Fe3+
Procedure
Step 1 1.59 g of the sodium chromate(VI) sample is weighed out.
Step 2 The sample is transferred to a 250.0 cm3 volumetric flask and 100 cm3 of
dilute sulfuric acid is added. The dichromate(VI) solution formed is made
up to the mark with deionised water and thoroughly mixed.
Step 3 A burette is filled with the dichromate(VI) solution.
Step 4 25.0 cm3 of a 0.0492 mol dm−3 solution of ammonium iron(II) sulfate, (NH4)2Fe(SO4)2 ,
is pipetted into a conical flask.
Step 5 Sulfuric acid and phosphoric acid are added to the conical flask followed
by a few drops of a diphenylamine indicator.
Step 6 The dichromate(VI) solution is added from the burette into the conical
flask with swirling until an intense blue-violet colour forms.
Step 7 The titration was repeated until concordant results are obtained.
(i) Write a balanced ionic equation for the conversion of the chromate(VI) ions
into dichromate(VI) ions in acidic solution to show the 2:1 molar ratio.
(1)
14
*P64618A01428*
(ii) Calculate the percentage purity by mass of the sodium chromate(VI) sample if
the mean titre is 10.80 cm3.
The reaction between the dichromate(VI) ions and the iron(II) ions is
Cr2O72− + 6Fe2+ + 14H+ → 2Cr3+ + 6Fe3+ + 7H2O

(6)
15
(g) There are a number of different industrial catalysts which contain chromium.
One of these is copper(II) chromite(III), Cu2Cr2O5 which is a solid used in organic
synthetic pathways.
Suggest how a heterogenous catalyst, such as copper(II) chromite(III), speeds up
the rate of a chemical reaction.
(3)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
16
*P64618A01628*
18 This is a question about an unknown organic compound, X.
X is an unbranched cyclic hydrocarbon.
The complete combustion of a 4.10 g sample of X formed 7.20 dm3 of carbon dioxide
and 4.50 g of water at room temperature and pressure.
(a) Use the combustion data to show that the molecular formula of X could be C6H10 .
(3)
(b) The organic compound Y is formed when X reacts with excess liquid bromine.
The molecular formula of Y is C6H10Br2.
Write the displayed formulae of X and Y.
(2)
(c) When X reacts with bromine water, a different organic compound Z is formed
which has optical isomers.
(i) Draw the skeletal formula of Z.
(1)
17
(ii) Describe how the presence of a single optical isomer could be detected,
including the expected result.
(2)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(d) Give the wavenumber ranges of two absorptions that you would expect in the
infrared spectrum of X, indicating the bonds responsible.
(2)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(e) X is used to make a number of intermediates in industrial synthetic processes.

Examples of such intermediates are adipic acid and maleic acid.
O O
O
OH HO
O
OH OH
adipic acid maleic acid

(i) State the systematic name of adipic acid.
(1)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
18
*P64618A01828*
(ii) Write an equation for the formation of a nylon polymer using adipic acid and
an amine of your choice.
(3)
(iii) Maleic acid can undergo an elimination reaction, losing a water molecule.
A mechanism has been partly drawn for this reaction but four curly arrows are missing.
Complete the mechanism by adding the curly arrows.
(2)
O O O +
O O O
O O O O
¨
H H H + H2O + H+
H+
O O O O¨ −
+
¨
O O O O+ H
+ H
H H H H
19
(iv) Draw the geometric isomer of maleic acid and suggest why this isomer is
much less likely to undergo dehydration.
(2)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
20
*P64618A02028*
SECTION C
19 Aspirin, ibuprofen and paracetamol are common pain relievers that can be obtained
without a doctor’s prescription. Their structures are
OH
HO O
O O N
H
O OH O
aspirin ibuprofen paracetamol
These pharmaceutical drugs are included in the World Health Organization’s model
list of essential medicines. However, none of these drugs is without hazards. For
example, possible side effects of taking aspirin include stomach bleeding and
stomach ulcers.
These drugs may be taken in tablet or liquid form.
Adults can take ibuprofen and paracetamol at the same time if necessary. This is not
recommended for children. The advice is to take ibuprofen with food or after having
just eaten.
A compound related to aspirin is found in the bark of the willow tree. The health
benefits of willow bark have been known for over 2000 years. Ibuprofen was
discovered after many years of drug research into finding an anti-inflammatory drug
to treat rheumatoid arthritis. Paracetamol was initially discovered in the 1880s, but
it was not until the 1940s that it was further investigated by the pharmaceutical
industry, which led to its worldwide use today.
(a) Name the functional group that is present in both aspirin and ibuprofen but not
paracetamol.
(1)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ........................................................................................................................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(b) Give the molecular formula of ibuprofen.

(1)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ........................................................................................................................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
21
(c) A simplified synthetic pathway for ibuprofen is shown.
Step 1
O
molecule A molecule B
OH
(i) Use your knowledge of electrophilic substitution reactions to write the

mechanism for the reaction of benzene in Step 1 with the electrophile shown.
(3)
O electrophile
+
22
*P64618A02228*
(ii) Identify, by name or formula, an organic compound that could be used to
form the electrophile given in (c)(i).
(1)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(iii) Give a reason why lithium tetrahydridoaluminate(III) in dry ether cannot be

used to convert molecule A into molecule B.
(1)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
23
(d) Paracetamol can be synthesised from phenol.
A summarised synthetic pathway is shown.
OH OH OH
Step 1 Step 2 Intermediate Step 3

Q
NO2 N CH3
H C
Intermediate P
O
*(i) Step 1 does not require a mixture of concentrated nitric acid and
concentrated sulfuric acid, which is required for the nitration of benzene.
Explain why the nitration of phenol (Step 1) occurs in much milder conditions
than the nitration of benzene. State the reagents and conditions required.
(3)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
24
*P64618A02428*
(ii) State the reagents and conditions required to convert intermediate P into
paracetamol in Steps 2 and 3. Identify intermediate Q.
(3)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ........................................................................................................................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ........................................................................................................................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ........................................................................................................................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ........................................................................................................................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ........................................................................................................................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ........................................................................................................................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(e) Aspirin is only slightly soluble in water.

(i) Calculate the volume of aspirin solution, of concentration 0.0161 mol dm−3,
required to give the same dose of aspirin as two 300 mg tablets of aspirin.
Give your answer to three significant figures and include units.
(3)
25
(ii) Give the skeletal formula of the sodium salt of aspirin.
(1)
(iii) Give a reason why the sodium salt of aspirin is used when the drug is required
in liquid form.
(1)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(f ) At times, a stereo-specific drug molecule needs to be synthesised.

Give two reasons why a single enantiomer may be required.
(2)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .

26
*P64618A02628*

Ilovepdf Merged (2) Removed

Uploaded by

Copyright:

Available Formats

Ilovepdf Merged (2) Removed

Uploaded by

Document Information

Copyright

Available Formats

Share this document

Share or Embed Document

Sharing Options

Did you find this document useful?

Is this content inappropriate?

Copyright:

Available Formats

Ilovepdf Merged (2) Removed

Uploaded by

Copyright:

Available Formats

PMT

Centre Number Candidate Number

Pearson Edexcel International Advanced Level

International Advanced Level

Answer ALL the questions in this section.

You should aim to spend no more than 20 minutes on this section.

Oxidation number Electron transfer

A decreases gains electrons

B decreases loses electrons

C increases gains electrons

D increases loses electrons

(Total for Question 1 = 1 mark)

(Total for Question 2 = 1 mark)

3 An electrochemical cell is set up using the electrode systems shown.

Cr2O72− + 14H+ + 6e−  2Cr3+ + 7H2O

TiO2+ + 2H+ + e−  Ti3+ + H2O

Cr2O72− , Cr3+ TiO2+ , Ti3+

(Total for Question 3 = 2 marks)

4 The possibility of a reaction between potassium dichromate(VI) and hydrochloric acid

Cr2O72− + 14H+ + 6Cl− → 2Cr3+ + 7H2O + 3Cl2 E cell = −0.03 V

A less positive decreased

B less positive unchanged

C more positive decreased

D more positive unchanged

(Total for Question 4 = 1 mark)

5 The element zinc is not classified as a transition metal. This is because

A the 3d subshell of a zinc atom is full

B zinc only forms one stable ion

(Total for Question 5 = 1 mark)

6 What is the electronic configuration of the Fe2+ ion?

(Total for Question 6 = 1 mark)

7 Platinum forms a complex with the formula Pt(NH3)2Cl2 which is used in

The complex used in cancer treatment contains

(Total for Question 7 = 1 mark)

A bonds reversibly to an iron(II) ion

B bonds irreversibly to an iron(II) ion

D replaces an iron(II) ion in an irreversible reaction

(Total for Question 8 = 1 mark)

9 The sequence shown is the mechanism for a reaction in aqueous solution.

A the oxidation of Ag+ is catalysed by Ce4+ ions

B the oxidation of Ag+ is catalysed by Ti2+ ions

C the oxidation of Ti+ is catalysed by Ag+ ions

D the oxidation of Ti+ is catalysed by Ag2+ ions

(Total for Question 9 = 1 mark)

10 How many σ bonds and π bonds are there in a molecule of benzene?

(Total for Question 10 = 1 mark)

11 Benzene reacts with fuming sulfuric acid to form benzenesulfonic acid.

A sulfuric acid with a concentration of 98 %

B pure sulfuric acid

C concentrated sulfuric acid containing dissolved sulfur dioxide

D concentrated sulfuric acid containing dissolved sulfur trioxide

(Total for Question 11 = 1 mark)

12 The structure of the amino acid isoleucine is shown.

(a) What is the systematic name of isoleucine?

(b) What is the structure of isoleucine in a solution of pH = 2?

(Total for Question 12 = 2 marks)

(Total for Question 13 = 1 mark)

14 Amines may be prepared by the reduction of nitriles.

Nitrile Reducing agent

A propanenitrile lithium tetrahydridoaluminate(III)