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Pearson Edexcel International Advanced Level

Monday 12 June 2023
Morning (Time: 1 hour 20 minutes)
Paper
reference WCH16/01
Chemistry  
International Advanced Level

UNIT 6: Practical Skills in Chemistry II
You must have: Total Marks

Scientific calculator, ruler
Instructions
• Use black ink or ball-point pen.
•• IfFillpencil is used for diagrams/sketches/graphs it must be dark (HB or B).
in the boxes at the top of this page with your name,
centre number and candidate number.
•• Answer all questions.
Answer the questions in the spaces provided
– there may be more space than you need.
Information
•• The total mark for this paper is 50.
The marks for each question are shown in brackets
– use this as a guide as to how much time to spend on each question.
• You will be assessed on your ability to organise and present information, ideas,
descriptions and arguments clearly and logically, including your use of grammar,
punctuation and spelling.
• 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
P73458A
©2023 Pearson Education Ltd.
N:1/1/1/
*P73458A0116*
Answer ALL the questions. Write your answers in the spaces provided.
1 A student investigated two aqueous solutions, labelled P and Q.
DO NOT WRITE IN THIS AREA DO NOT WRITE IN THIS AREA DO NOT WRITE IN THIS AREA
Both solutions were green. Each solution contained one cation and one anion.
(a) Tests were carried out on solution P.
Complete the table.
Test Observation Inference
(i) A few drops of aqueous Chromium(III) ions (1)

sodium hydroxide were .............................................................. may be present in P
added to 5 cm3 of P
..............................................................
(ii) More sodium hydroxide Chromium(III) ions (1)

solution was added .............................................................. are confirmed to be
to the mixture from present in P
(a)‌(i) until there was no ..............................................................
further change
..............................................................
(iii) A few drops of dilute (1)

nitric acid were added
to 5 cm3 of a fresh
sample of P
A few drops of aqueous A white precipitate The formula of the
silver nitrate were formed anion likely to be
added to this acidified responsible for the
solution of P white precipitate is
..............................................................
(b) State why, in the silver nitrate test on P, the nitric acid was not needed in
this case. Justify your answer by considering the role of nitric acid in the
silver nitrate test.
(2)
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2
*P73458A0216* 
(c) The student carried out tests on Q and inferred that it was a solution of
iron(II) sulfate.
(i) The addition of dilute aqueous ammonia to a sample of solution Q produced

a green precipitate which changed colour on standing.
Explain why the colour change led the student to infer that Q contained
iron(II) ions.
(2)
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(ii) Describe a test, and its positive result, that the student could have carried out
to show the presence of sulfate ions.
(2)
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(d) Identify, by name or formula, a metal cation, other than chromium(III) and iron(II),
which could give a green colour in an aqueous solution.
(1)
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(Total for Question 1 = 10 marks)
3
 *P73458A0316* Turn over
2 Two organic compounds, X and Y, are colourless liquids.
Each compound contains only one functional group.
(a) A few drops of deionised water are added to a beaker containing X.
Misty fumes are formed.
A drop of concentrated ammonia on the tip of a glass rod is placed in the
misty fumes. White smoke is formed.
(i) Deduce the functional group in X.
Justify your answer by referring to the observations.
(3)
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(ii) State the precaution that you would take to minimise the risk of carrying out
this test on the misty fumes.
Assume gloves, safety goggles and laboratory coat are worn.
(1)
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(b) The 13C NMR spectrum of X has two peaks.

Draw the displayed formula of X.
(1)
4
*P73458A0416* 
(c) The mass spectrum of Y is shown.
100
80
60
Relative
intensity
40
20
0
10 15 20 25 30 35 40 45 50 55 60 65 70 75
m/z
(i) Bubbles are observed when aqueous sodium hydrogencarbonate is

added to Y.
Deduce the formula of the ion responsible for the peak at m / z = 45.
(1)
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(ii) Draw the structural formula of Y.

(1)
5
 *P73458A0516* Turn over
(d) Both X and Y can be used to produce esters.
(i) Name the compound that would react with both X and Y to form ethyl esters.
(1)
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(ii) A student prepared an ester using X and a suitable compound.

Explain why the student added aqueous sodium hydrogencarbonate to the
reaction mixture to allow the presence of an ester to be detected.
(2)
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(e) Both X and Y react with concentrated ammonia but form different products.
Identify these products, by name or formula.
(2)
Product with X
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Product with Y
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6
*P73458A0616* 
3 This question is about an experiment to investigate the kinetics of the reaction
between iodine and propanone with an acid catalyst.
The equation for the reaction is shown.
I2(aq) + CH3COCH3(aq) + H+(aq) → CH3COCH2I(aq) + 2H+(aq) + I –(aq)
To obtain the order of reaction with respect to iodine, the concentration of iodine in
the reaction mixture was determined at various times.
Procedure
Step 1 Mix 25 cm3 of 1.0 mol dm−3 sulfuric acid with
25 cm3 of 1.0 mol dm−3 propanone in a beaker.
Step 2 Start a clock as 50 cm3 of 0.020 mol dm−3 iodine solution is added to
the beaker. Mix the reactants thoroughly.
Step 3 Tip a spatula measure of sodium hydrogencarbonate into a
conical flask. After 3 minutes, pipette a 10.0 cm3 sample of the
reaction mixture into the conical flask and mix thoroughly.
Step 4 Titrate the iodine in the sample with
0.010 mol dm−3 sodium thiosulfate solution using a suitable indicator.
Record the titre.
Step 5 Repeat Steps 3 and 4 every 3 minutes to obtain four more titres.
(a) State why the sulfuric acid and propanone concentrations are both much larger
than the iodine concentration.
(1)
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(b) State why sodium hydrogencarbonate is used in Step 3.

(1)
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(c) Name the indicator that would be used for the titration in Step 4, stating the
colour change that would be seen at the end‑point of the reaction.
(2)
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7
 *P73458A0716* Turn over
(d) Titration results from the experiment are shown.
Time / minutes 3 6 9 12 15
Titre / cm3 16.05 15.30 14.50 13.70 12.95
(i) Plot a graph of titre against time.

(3)
8
*P73458A0816* 
(ii) State why the volume of thiosulfate may be used for plotting the graph rather
than the concentration of iodine.
(1)
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(iii) State the order of reaction with respect to iodine.

Justify your answer by referring to your graph.
(1)
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9
 *P73458A0916* Turn over
(e) Further experiments were carried out to determine the reaction orders with
respect to propanone and sulfuric acid.
(i) A graph of the concentration of propanone against time is shown.
0.20
0.15
Concentration
of propanone
/ mol dm–3
0.10
0.05
0
0 5 10 15 20 25 30
Time / s
10
*P73458A01016* 
The reaction is first order with respect to propanone.
Determine two half‑lives for this reaction.
You must show your working on the graph.

(2)
First half‑life
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Second half‑life
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(ii) A graph of the reaction rate against the concentration of sulfuric acid
is shown.
Rate
Concentration of acid
Deduce the rate equation for the overall reaction of iodine and propanone
with an acid catalyst.
Use your answer from (d)(iii) and information from (e)(i) and the graph
in (e)(ii).
(1)
11
 *P73458A01116* Turn over
4 A group of students prepared methyl 3‑nitrobenzoate by the nitration of
methyl benzoate.
CH3 CH3
O O O O
C C
+ HNO3 + H2O
NO2
Procedure
Step 1 Measure 9 cm3 of concentrated sulfuric acid into a small, dry conical flask.
Label the flask A and place it in an ice bath.
Step 2 Add 4.0 cm3 of methyl benzoate to flask A.
Gently swirl the flask.
Step 3 Mix 3 cm3 of concentrated nitric acid and 3 cm3 of
concentrated sulfuric acid in a test tube to form the nitrating mixture.
Place this test tube in the ice bath.
Step 4 Place a thermometer in flask A. Add the nitrating mixture very slowly to
flask A using a dropping pipette.
Take care to ensure that the temperature of the flask contents
does not rise above 15 °C.
Step 5 Remove flask A from the ice bath and allow it to stand at room temperature
for about 10 minutes.
Pour the reaction mixture into a small beaker containing crushed ice.
Stir the contents of the beaker with a glass rod.
Step 6 Allow the ice to melt. Separate the solid methyl 3‑nitrobenzoate by
suction filtration. Wash the solid with a small amount of
deionised water and then with a little ice‑cold ethanol.
Step 7 Recrystallise the methyl 3‑nitrobenzoate using ethanol as the solvent.
Step 8 Determine the melting temperature of the purified crystals of
methyl 3‑nitrobenzoate.
(a) An ice bath is a mixture of ice and water in a beaker.

Suggest an advantage of using an ice bath in Steps 1 and 3 rather than a beaker
containing only ice cubes. Justify your answer.
(1)
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12
*P73458A01216* 
(b) Side products form if the temperature rises above 15 °C in Step 4.
Give the structure of one side product that may form.
(1)
(c) One student drew the suction filtration apparatus in Step 6 as shown.
base of Buchner funnel
flask
Identify the three ways in which this diagram is incorrect.

You may assume that the apparatus is suitably clamped.
(3)
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13
 *P73458A01316* Turn over
(d) Describe the stages in the recrystallisation of methyl 3‑nitrobenzoate in Step 7,
stating which stages are required to remove the insoluble and soluble impurities.
Only outline details of the method are required.
(4)
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(e) The crystals must be dried before the melting temperature can be determined.
Methyl 3‑nitrobenzoate cannot be dried by the addition of a solid drying agent
such as anhydrous calcium chloride.
(i) Suggest why the addition of a solid drying agent is not suitable to dry
methyl 3‑nitrobenzoate.
(1)
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(ii) State how the crystals of methyl 3‑nitrobenzoate could be dried.

(1)
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14
*P73458A01416* 
(f ) The mass of dry methyl 3‑nitrobenzoate crystals prepared by one of the students
was 3.05 g.
Calculate the percentage yield by mass of methyl 3‑nitrobenzoate using the

data shown.
Compound Molar mass / g mol−1 Density / g cm−3
methyl benzoate 136 1.08
methyl 3‑nitrobenzoate 181
(3)
(g) The melting temperature range of methyl 3‑nitrobenzoate is given in a data book
as 78–80 °C.
Suggest a melting temperature range for a sample of the
methyl 3‑nitrobenzoate before recrystallisation. Justify your answer.
(2)
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TOTAL FOR PAPER = 50 MARKS
15
 *P73458A01516*

*P73458A01616*
16

Time 1 hour 20 minutes
Paper
reference WCH16/01
Chemistry
 


Instructions
• Use black ink or ball‑point pen.
• Fill in theis boxes
If pencil used for diagrams/sketches/graphs it must be dark (HB or B).
• centre number andat candidate
the top of this page with your name,
number.
• Answer all questions.
• – there may questions
Answer the in the spaces provided
be more space than you need.
Information
• The total mark for this paper is 50.
• The marks for each question are shown in brackets
Advice
• Show all your working in calculations and include units where appropriate.
• Try to answer every question.
• your answers if you have time at the end.
Check
Turn over
*P71889A0116*
P71889A
J:1/1/1/1/1/
1 Solution A and solution B are aqueous solutions.

The compound in each solution contains one cation and one anion.
The cations are different but the anions are the same.
Both solutions are green.
(a) Give the formulae of three cations which could be responsible for the
green colour.
(2)
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(b) A student added dilute aqueous sodium hydroxide, drop by drop, to samples of
each solution.
Initially a green precipitate formed in both solutions.
More aqueous sodium hydroxide was added until the sodium hydroxide was
present in excess.
The precipitate produced from solution A was insoluble and turned brown
on standing.
The precipitate produced from solution B dissolved to give a
dark green solution C.
(i) Give the formula of the green precipitate from solution A.

(1)
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(ii) Give the formula of the species responsible for the dark green colour in
solution C.
(1)
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(c) The student added hydrogen peroxide solution to C and warmed the mixture,
which turned yellow. The yellow solution was boiled to remove excess
hydrogen peroxide, cooled and then pure ethanoic acid was added, drop by drop.
The yellow solution gradually turned orange.
(i) State the type of reaction involved when the dark green solution
turned yellow.
(1)
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(ii) Identify, by name or formula, the ion responsible for the final orange colour of
the solution.
(1)
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2
*P71889A0216* 
(iii) Pure ethanoic acid is corrosive.
Identify the appropriate control measure to reduce the risk associated with
this hazard.
Assume the student carried out the addition in a fume cupboard, wearing
safety glasses and a lab coat.
(1)
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(iv) Describe the corrosive hazard label present on a bottle containing

pure ethanoic acid. You may use a diagram in your answer.
(2)
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3
 *P71889A0316* Turn over
(d) The student attempted to identify the anion present in the green solution A.
The student added dilute nitric acid and a few drops of aqueous silver nitrate to
about 2 cm3 of solution A.
A pale precipitate formed, which the student thought might be white or
cream coloured.
(i) Identify, by name or formula, two anions which might give this precipitate.
(1)
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(ii) The precipitate formed in (d)(i) was separated from the mixture and
aqueous ammonia was added.
Describe how this test allows the student to distinguish between the
two anions.
(2)
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(iii) Explain why, with solution A, the precipitate must be separated before adding
aqueous ammonia.
(2)
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4
*P71889A0416* 
2 The reaction between the tertiary halogenoalkane 2‑chloro‑2‑methylpropane and
hydroxide ions to form 2‑methylpropan‑2‑ol is shown.
(CH3)3CCl + OH– → (CH3)3COH + Cl–
The progress of the reaction can be followed by titrating portions of the

reaction mixture with a solution of hydrochloric acid of known concentration.
An experiment to determine the order of the reaction was carried out.
Procedure
Step 1 A flask containing 250 cm3 of an ethanolic solution of
2‑chloro‑2‑methylpropane, with a concentration 0.100 mol dm–3, was placed in
a water bath at 25 °C.
A similar flask, containing 250 cm3 of aqueous sodium hydroxide, with a
concentration 0.100 mol dm–3, was placed in the same water bath.
The temperature of each solution was allowed to reach 25 °C.
Step 2 Seven conical flasks were prepared, each containing about 50 cm3
of propanone.
Step 3 The reaction was started by mixing the two solutions from the water bath in a
large flask. The flask was returned to the water bath.
A timer was started as the solutions were mixed.
Step 4 At intervals, 25.0 cm3 samples of the reaction mixture were transferred to a
conical flask containing propanone. The time was noted.
Step 5 Each sample was immediately titrated with a solution of hydrochloric acid, of
concentration 0.0500 mol dm–3, using methyl orange as the indicator.
(a) (i) Give the expected colour change at the end‑point.

(1)
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(ii) Explain the effect on the volume of hydrochloric acid required if the titration
was not carried out immediately after Step 4.
(2)
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5
 *P71889A0516* Turn over
(iii) Explain how the use of aqueous ethanol in the reaction mixture allows the
reaction in Step 3 to proceed at a relatively fast rate.
A description of the forces involved is not required.
(2)
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(b) An experiment was carried out using this procedure. The results are shown.
Time / s 50 320 750 1200 2050 3180 4020
Volume of HCl / cm3 24.5 22.0 18.5 15.5 11.0 7.0 5.0
(i) Plot a graph of the data using the axes given.

(2)
Volume of
HCl / cm3
Time / s
6
*P71889A0616* 
(ii) Determine two successive half‑lives for the reaction.
You must show your working on the graph.
(2)
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(iii) State the order of this reaction. Justify your answer.

(1)
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7
 *P71889A0716* Turn over
3 Moss in lawns can be treated with ‘lawn sand’, a mixture that contains sand and a
double salt, ammonium iron(II) sulfate, (NH4)2Fe(SO4)2·6H2O.
The percentage by mass of Fe2+ in the mixture can be found by titration with a
solution of potassium manganate(VII) of known concentration.
Procedure
4.50 g of lawn sand was accurately weighed in a 250 cm3 conical flask.
The sample was shaken with 50 cm3 of dilute sulfuric acid (an excess).
The resulting mixture was titrated with potassium manganate(VII) solution of
concentration 0.0200 mol dm–3.
The titration volume was 40.35 cm3.
(a) (i) State what would happen in the titration if the mixture was not acidified.
(1)
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(ii) Neither hydrochloric acid nor nitric acid can be used to acidify the
titration mixture.
For each acid give a reason why it cannot be used.

(2)
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8
*P71889A0816* 
(b) The ionic half‑equations for the reactions of the iron(II) ions and the
manganate(VII) ions are shown.
Fe2+ → Fe3+ + e–
MnO4– + 8H+ + 5e– → Mn2+ + 4H2O
Calculate the percentage by mass of Fe2+ in the sample of lawn sand.

(4)
9
 *P71889A0916* Turn over
(c) The titration is carried out using the apparatus shown.
burette containing
potassium manganate(VII)
conical flask containing

lawn sand and dilute sulfuric acid
At the end‑point, the solution changes to a permanent pale pink.

To repeat the experiment, the burette is refilled with potassium manganate(VII)
and the procedure carried out again.
Give three ways in which a titration is carried out to give the most accurate
possible burette reading.
Assume that the equipment is the same, the burette is clamped in a vertical
position and that the titration volumes are read at eye level from the bottom of
the meniscus.
(3)
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10
*P71889A01016* 
BLANK PAGE
11
 *P71889A01116* Turn over
4 The compound 2‑ethanoylaminobenzoic acid can be prepared by the reaction of
2‑aminobenzoic acid and ethanoyl chloride.
O O
C heat under C
OH reflux OH
+ CH3COCl + HCl
NH2 NHCOCH3
2-aminobenzoic acid ethanoyl 2‑ethanoylaminobenzoic acid

chloride
Procedure
Step 1 Add 5.00 g of 2‑aminobenzoic acid and a few anti‑bumping granules to a
dry 100 cm3 pear‑shaped flask and fit a reflux condenser.
Step 2 Add 10 cm3 of ethanoyl chloride (an excess) by pouring it slowly down
the condenser.
Step 3 Gradually bring the mixture to boil and heat under reflux for 15 minutes.
Step 4 Allow the mixture to cool and slowly add 10 cm3 of water down
the condenser.
Step 5 Heat the solution slowly until boiling.
Step 6 Allow the solution to cool to room temperature.
Step 7 Collect the crystals of 2‑ethanoylaminobenzoic acid by filtration under
reduced pressure.
Step 8 Recrystallise the impure product from a mixture containing equal volumes of
ethanoic acid and water.
(a) Give two reasons why it is often necessary to heat a reaction under reflux as in
Step 3.
(2)
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12
*P71889A01216* 
(b) Explain why, in Step 4, water is added slowly to the cooled solution.
(2)
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(c) Draw a labelled diagram of the apparatus used for filtration

under reduced pressure in Step 7.
(3)
13
 *P71889A01316* Turn over
(d) The melting temperature may be used to confirm the identity of the crystals.
(i) Draw a labelled diagram of the apparatus you would use to measure the
melting temperature.
(2)
(ii) State how this melting temperature determination would show that a
pure sample of 2‑ethanoylaminobenzoic acid had been prepared.
(2)
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14
*P71889A01416* 
(e) Show by calculation that, in the preparation, 10 cm3 of ethanoyl chloride is an
excess compared to 5.00 g of 2‑aminobenzoic acid.
Data
Molar mass / g mol–1 CH3COCl = 78.5 C6H4(NH2)COOH = 137
Density / g cm–3 CH3COCl = 1.1
(2)
(f ) A student carried out the preparation using the amounts of reagents given in (e)
and obtained a yield of 56.7 % of 2‑ethanoylaminobenzoic acid.
Calculate the mass of 2‑ethanoylaminobenzoic acid obtained.
(3)
15
 *P71889A01516*
16
*P71889A01616* 

Paper
reference WCH16/01
Chemistry
 


Instructions
• centrethe
Fill in boxes at the top of this page with your name,
number and candidate number.
• Answer the questions in the spaces provided
Information
Advice
• Check your answers if you have time at the end.
Turn over
*P71944A0120*
P71944A
B:1/1/1/
1 (a) Compound X is a solid that contains a cobalt cation and one type of anion.
A small amount of X is added to deionised water and the mixture stirred until the
solid dissolves.
Tests are carried out on separate samples of the solution of X.
Complete the table.
(i) Note the A pink solution The formula of the complex (1)
appearance ion formed is
............................................................. . . . . . . . . . . . . . . . . . . .
(ii) Add acidified A white precipitate forms The formula of the anion in (1)
barium chloride X is
solution
............................................................. . . . . . . . . . . . . . . . . . . .
(iii) Add concentrated The formula of the complex (1)

hydrochloric acid . . . . . . . . . ....................................................................... ion formed is [CoCl4]2–
. . . . . . . . . .......................................................................
. . . . . . . . . .......................................................................
(iv) Add a small A blue precipitate forms The type of reaction (1)
amount of that takes place with the
dilute aqueous complex ion during this
ammonia precipitation is
............................................................. . . . . . . . . . . . . . . . . . . .
(v) Add excess The formula of the complex (3)

dilute aqueous . . . . . . . . . . ...................................................................... ion formed is
ammonia to
the precipitate . . . . . . . . . . ...................................................................... ............................................................. . . . . . . . . . . . . . . . . . . .
formed in (iv),
until no further . . . . . . . . . . ......................................................................
change is seen
. . . . . . . . . . ......................................................................
2
*P71944A0220* 
(b) Another cobalt salt, CoCl2.xH2O(s), decomposes when heated.
CoCl2.xH2O(s) → CoCl2(s) + xH2O(g)
Devise an outline procedure to determine the mass of water produced from a

sample of the hydrated salt in this reaction.
You do not need to show how x can be calculated from the mass of
water produced.
(4)
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................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
3
 *P71944A0320* Turn over
2 A plant fertiliser contains a mixture of sand and ammonium sulfate, (NH4)2SO4 .
The percentage by mass of ammonium sulfate in the fertiliser is determined by the
procedure shown.
Procedure
.75 g of the plant fertiliser is added to a conical flask containing 20.0 cm3 of
Step 1 5
sodium hydroxide solution with a concentration of 1.00 mol dm–3.
Ammonia is formed in the reaction.
(NH4)2SO4 (aq) + 2NaOH(aq) → 2NH3(g) + Na2SO4 (aq) + 2H2O(l)
Step 2 T he flask is heated for several minutes, to ensure that all the ammonia formed
is boiled off.
Step 3 The solution containing excess sodium hydroxide is separated from the sand.
Step 4 T he aqueous solution containing the excess sodium hydroxide is then made
up to 250.0 cm3 using deionised water.
5.0 cm3 samples of solution containing sodium hydroxide from Step 4 are
Step 5 2
titrated with hydrochloric acid of concentration = 0.0500 mol dm–3.
(a) Describe how all the solution containing excess sodium hydroxide is separated
from the sand in Step 3.
(2)
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(b) Describe how to make the 250.0 cm3 of sodium hydroxide solution in Step 4.
(2)
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................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
4
*P71944A0420* 
(c) The mean titre was 12.75 cm3.
Calculate the percentage by mass of ammonium sulfate, (NH4)2SO4 , in the sample
of plant fertiliser.
[Relative formula mass of (NH4)2SO4 = 132.1]
(5)
5
 *P71944A0520* Turn over
(d) A student carrying out the experiment did not heat the sample for long enough
in Step 2 to boil off all the ammonia.
(i) Explain the effect, if any, on the titre value and hence on the calculated
percentage of ammonium sulfate in the fertiliser.
(3)
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(ii) State how the student could have confirmed that all the ammonia was boiled
off in Step 2.
(1)
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6
*P71944A0620* 
3 The ester ethyl butanoate is found in mangoes.
O
ethyl butanoate
Ethyl butanoate can be synthesised from butanoic acid.

Procedure
dd 5 cm3 of ethanol and 10 cm3 of butanoic acid to a round‑bottomed flask
Step 1 A
containing anti‑bumping granules. Add 1 cm3 of concentrated sulfuric acid
drop by drop to the flask.
Step 2 H
eat the mixture under reflux for 60 minutes. Allow the reaction mixture to
cool before transferring it to a separating funnel.
Step 3 Add 15 cm3 of cold water to the separating funnel and shake the mixture to
wash the product. Remove the lower aqueous layer from the funnel.
ash the organic layer that remains in the separating funnel with 10 cm3 of
Step 4 W
aqueous sodium hydrogencarbonate solution, NaHCO3(aq).
Step 5 R
emove the aqueous layer from the funnel. Transfer the organic layer to a dry
conical flask. Add a drying agent and leave for 10 minutes. Then add more
drying agent if required. Remove the drying agent by filtration.
Step 6 Purify the dry organic liquid.
(a) Calculate which reactant is in excess in this synthesis.
Compound Molar mass / g mol–1 Density / g cm–3
ethanol 46.0 0.79
butanoic acid 88.0 0.96
(2)
7
 *P71944A0720* Turn over
(b) Explain why it is important from time to time in Step 4 either to invert the
separating funnel and open the tap, or to remove its stopper.
Include an equation to justify your answer. State symbols are not required.
(2)
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(c) A student set up a separating funnel in Step 5 as shown and opened the tap to
remove the lower layer.
Explain what happens.
Assume that the funnel is supported by suitable clamps.
stopper
organic layer
aqueous layer
tap

(2)
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8
*P71944A0820* 
(d) Drying agents are used to remove traces of water from an organic liquid.
(i) Identify, by name or formula, a suitable drying agent for use in Step 5.
(1)
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(ii) State how a student would decide whether or not more drying agent was
needed in Step 5.
(1)
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(iii) Name the technique used to obtain a pure sample of the dry organic liquid
in Step 6.
(1)
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9
 *P71944A0920* Turn over
(e) The high resolution proton NMR spectrum of ethyl butanoate is shown.
4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5

Chemical shift, δ / ppm
1
H nuclear magnetic resonance chemical shifts relative to tetramethylsilane (TMS)
10
*P71944A01020* 
(i) Explain the peaks in the NMR spectrum between 2.2 and 2.4 ppm.
CH3CH2CH2C OCH2CH3
ethyl butanoate
(2)
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................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(ii) Predict how the high resolution proton NMR spectrum of ethyl propanoate
will differ from that of ethyl butanoate in terms of the number of peaks and
their splitting patterns.
CH3CH2C OCH2CH3
ethyl propanoate
(3)
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................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
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................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
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................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
11
 *P71944A01120* Turn over
BLANK PAGE
12
*P71944A01220* 
4 Ethyl butanoate reacts with water.
CH3CH2CH2COOCH2CH3 + H2O → CH3CH2CH2COOH + CH3CH2OH
A student investigated the kinetics of this reaction.

Procedure
Step 1 50 cm3 of ethyl butanoate was heated under reflux with a very large excess
of water.
Step 2 After 30 minutes a sample of known volume was removed from the reaction
mixture and placed in a conical flask.
Step 3 This sample was titrated using aqueous sodium hydroxide solution.
Step 4 Further samples were removed from the refluxing mixture at 30‑minute
intervals. Each sample was titrated until the titres of three consecutive
samples were the same.
(a) Name the apparatus which is most suitable to remove the samples from the
reaction mixture.
(1)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ........................................................................................................................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
13
 *P71944A01320* Turn over
(b) A graph of the results obtained by the student is shown.
The student plotted Vfinal – Vt on the y‑axis against time on the x‑axis.
Vfinal is the volume of the titre at 4.5 hours.
Vt is the volume of the titre at time t.
50
40
30
Vfinal – Vt
/ cm3
20
10
0
0 1 2 3 4 5
Time / hours
(i) Give a reason why Vfinal – Vt is plotted on the y‑axis of the graph, rather than
the concentration of sodium hydroxide solution for each titre.
(1)
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14
*P71944A01420* 
(ii) Explain how the data collected indicates first order kinetics.
Show your working on the graph.
(2)
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(iii) The student concluded that the reaction is first order overall.
Explain whether or not this statement is valid.
(2)
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(iv) Calculate the rate of the reaction at a time of 2 hours.

Include units with your answer.
Show your working on the graph.
(4)
15
 *P71944A01520* Turn over
(c) The student suggested placing ice in the conical flask before carrying out
each titration.
Explain whether or not this suggestion would improve the validity of the
data collected.
(2)
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*P71944A01620* 
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 *P71944A01720*
BLANK PAGE
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*P71944A01820* 
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 *P71944A01920*
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*P71944A02020* 

Paper
reference WCH16/01
Chemistry
 


Instructions
• centrethe
Information
Advice
Turn over
*P71874A0116*
P71874A
Q:1/1/1/1/1/
1 A student investigates two aqueous solutions, each containing a salt.

Each salt has one cation and one anion.
Solution A is blue. Solution B is orange.
Observation when aqueous Observation when dilute nitric acid and

Solution
sodium hydroxide is added aqueous silver nitrate are added
blue precipitate insoluble in excess
A white precipitate in a blue solution
sodium hydroxide
solution changes from orange to yellow
B gas evolved on warming which turns red precipitate
damp red litmus paper blue
(a) (i) Identify, by name or formula, the salt in A.

(2)
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(ii) The white precipitate is separated from the solution.

Give a test on the precipitate and its positive result to confirm the identity of
the anion in A.
(2)
Test
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Result
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(b) (i) Identify, by name or formula, the gas given off when B is warmed with
aqueous sodium hydroxide.
(1)
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(ii) Give the formulae of the ions of the salt in B.

(2)
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2
*P71874A0216* 
2 A student is asked to identify three colourless liquids labelled C, D and E.
The compounds are all non‑cyclic isomers with the formula C5H10O.
(a) (i) The student carries out three tests on separate samples of each compound.
Complete Table 1 to show the observations that the student makes.
(3)
Observations on addition of reagents
2,4‑dinitro Fehling’s or
I2(aq) and NaOH(aq)
Sample phenylhydrazine Benedict's solution Functional group
and warm
(Brady’s reagent) and warm
C orange precipitate R‑COCH3
pale yellow precipitate

D R‑CH(OH)CH3
antiseptic smell
E orange precipitate R‑CHO
Table 1
(ii) Identify, by name or formula, the pale yellow precipitate that forms when
iodine and sodium hydroxide are added to a sample of D.
(1)
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3
 *P71874A0316* Turn over
(b) (i) The orange precipitates produced on the addition of Brady’s reagent to
samples of C and E are called derivatives.
The melting temperatures of derivatives are used to confirm the identity
of compounds.
Solids are recrystallised so that their melting temperatures may be
determined accurately.
Describe in outline the procedure for the recrystallisation of a solid.
(4)
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4
*P71874A0416* 
(ii) The melting temperatures of the derivatives of the reaction of Brady’s reagent
with some aldehydes and ketones are shown.
Carbonyl compound Melting temperature of the derivative / °C
3‑methylbutanal 123
2‑ethylbutanal 134
pentan‑2‑one 144
cyclopentanone 146
pentan‑3‑one 156
Table 2
The melting temperature of the recrystallised derivative of sample C is found

to be 138–140 °C.
Suggest the identity of compound C.
Justify your choice, using the information at the start of the question and the
data in Tables 1 and 2.
(2)
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5
 *P71874A0516* Turn over
(c) The high resolution proton NMR spectrum of E is shown.
P Q
11 10 9 8 7 6 5 4 3 2 1 0
δ / ppm
The relative numbers of protons responsible for the singlet peaks shown are P = 1
and Q = 9.
Use this information and the results of the tests in (a) to draw the displayed
formula of E, labelling the proton environments.
(2)
6
*P71874A0616* 
3 Brass is an alloy of copper. The percentage by mass of copper in a sample of brass can
be determined by a three-stage process.
Stage 1 O
xidation of the copper to copper(II) ions with excess
concentrated nitric acid.
Stage 2 Reduction of the copper(II) ions to copper(I) ions with excess iodide ions.
Stage 3 T itration of the iodine produced in Stage 2 against a standard solution of
sodium thiosulfate.
(a) In Stage 1, 2.53 g of brass is carefully warmed with 25 cm3 concentrated nitric acid
in a 250 cm3 beaker.
The equation for the oxidation of copper metal by nitric acid is shown.
Cu(s) + 4H+(aq) + 2NO3–(aq) → Cu2+(aq) + 2NO2(g) + 2H2O(l )
(i) State two hazards in this experiment, giving the precautions you would take
to minimise the risk associated with each hazard.
Assume safety spectacles and a laboratory coat are worn.
(2)
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(ii) State what would be seen during the reaction.

(2)
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7
 *P71874A0716* Turn over
(iii) Excess nitric acid must be neutralised before the iodide ions are added
in Stage 2.
Sodium carbonate solution is slowly added to the cooled solution.
The solution is neutralised when a faint precipitate appears.
Suggest why the solution is cooled before the addition of the
sodium carbonate solution.
(1)
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(iv) Ethanoic acid solution is added, drop by drop, to the neutralised mixture until
the precipitate redissolves.
Describe how the solution in the beaker should then be made into 250.0 cm3
of a homogeneous solution before Stage 2.
(3)
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................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
8
*P71874A0816* 
(b) In Stage 2, 25.0 cm3 portions of the solution from Stage 1 are transferred into
conical flasks.
10 cm3 of a solution of potassium iodide is added to each flask and the mixtures
are swirled. Copper(I) iodide is precipitated.
The redox equation for the reaction between copper(II) ions and iodide ions
is shown.
2Cu2+(aq) + 4I–(aq) → 2CuI(s) + I2(aq)
The standard electrode potentials for the half‑equations are
Reduction Cu2+ + e–  Cu+ E d = +0.15 V
Oxidation I2 + 2e–  2I– E d = +0.54 V
(i) Use the electrode potential data to explain why the redox reaction might not
be expected to be feasible.
(2)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ........................................................................................................................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ........................................................................................................................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ........................................................................................................................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(ii) Explain why the redox reaction does, in fact, take place.
(2)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ........................................................................................................................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ........................................................................................................................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ........................................................................................................................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ........................................................................................................................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ........................................................................................................................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
9
 *P71874A0916* Turn over
(c) The procedure in Stage 3 is shown:
• the iodine produced in each flask from Stage 2 is titrated with 0.095 mol dm–3
sodium thiosulfate solution until the iodine colour is pale yellow
• a few drops of starch indicator are added
• sodium thiosulfate is added drop by drop with swirling until the end‑point
is reached
• the titration is repeated until two concordant titres are obtained.
(i) Give a possible reason why the starch indicator is added when the iodine
colour is pale yellow rather than at the start of the titration.
(1)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(ii) Give the colour change at the end‑point of the reaction.

(1)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
10
*P71874A01016* 
(iii) The results of the titration are shown.
Titration number 1 2 3
Final burette reading / cm3 27.05 28.65 27.45
Initial burette reading / cm3 0.00 2.00 1.00
Titre / cm3 27.05 26.65
Complete the table and calculate the mean titre of the concordant results.
(1)
(iv) The redox equation for the reaction between copper(II) ions and iodide ions
is shown.
2Cu2+(aq) + 4I–(aq) → 2CuI(s) + I2(aq)
The reaction of sodium thiosulfate solution with iodine is shown.
2S2O32–(aq) + I2(aq) → S4O62–(aq) + 2I–(aq)
Calculate the percentage by mass of copper in the 2.53 g of brass.

[Ar Cu = 63.5]
(3)
11
 *P71874A01116* Turn over
(v) Nitric acid reacts with iodide ions to form iodine.
In another experiment the nitric acid was not neutralised before the start
of Stage 2.
Explain the effect on the value obtained for the percentage of copper in
the sample.
(2)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
12
*P71874A01216* 
4 Limonene is a liquid hydrocarbon which has a boiling temperature of 176 °C and a
density of 0.851 g cm3.
It can be obtained from orange peel using steam distillation.
The distillation apparatus is shown.
vent to sink
water
water + orange peel
HEAT HEAT
(a) (i) Label the diagram to show the direction of the water flow in the condenser.
(1)
(ii) Give a reason for using steam distillation to extract limonene.

(1)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
13
 *P71874A01316* Turn over
(iii) The distillate may be collected in a pear‑shaped flask.
Complete a labelled diagram showing the distillate.
You should show clearly the limonene layer.
(1)
(b) Limonene exists as optical isomers.
(i) Identify the chiral carbon on the diagram.

(1)
(ii) The limonene extracted from orange peel is D‑limonene.

State how the presence of a single optical isomer could be confirmed, naming
the apparatus used. No experimental details are required.
(2)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
14
*P71874A01416* 
(iii) A student obtained 1.20 cm3 of limonene.
Calculate the amount, in moles, of limonene produced.
(3)
(c) Limonene reacts with acidified potassium manganate(VII).

(i) Give the colour change for this reaction.
(1)
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(ii) Draw the structure of the organic product which might be expected when
excess acidified potassium manganate(VII) reacts with limonene.
(1)
15
 *P71874A01516*
BLANK PAGE
16
*P71874A01616* 

Paper
reference WCH16/01
Chemistry
 


Instructions
• centrethe
Information
Advice
Turn over
*P70957A0120*
P70957A
Q:1/1/1/
1 A flowchart of a series of reactions of chromium and some of its compounds

is shown.
Cr(s)
dilute
HCl(aq)
blue solution A
stand in air
dilute
NH3(aq)
green solution grey-green precipitate B
excess NaOH(aq)
dark green solution
warm with reagent C
H2SO4(aq)
yellow solution solution E
Ba(NO3)2(aq) warm with C2H5OH(l)
yellow precipitate D solution F
2
*P70957A0220* 
(a) Give the formula of a complex ion of chromium present in solution A.
(1)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(b) Give the formula of precipitate B.

(1)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(c) Identify reagent C, by name or formula.

(1)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(d) Suggest the identity, by name or formula, of precipitate D.

(1)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(e) State the colour of solution E.

(1)
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(f ) State the colour of solution F.

(1)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
3
 *P70957A0320* Turn over
BLANK PAGE
4
*P70957A0420* 
2 This question is about the identification of three organic compounds, X, Y and Z.
A molecule of each compound has only one type of functional group.
Each compound contains six carbon atoms and two oxygen atoms.
In the mass spectrum of X, the molecular ion peak is at m / z = 114.
(a) State the molecular formula of X.
(1)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ........................................................................................................................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(b) Three chemical tests are carried out on X.

Test 1 W
hen Brady’s reagent (2,4‑dinitrophenylhydrazine solution) is added to X,
an orange precipitate is observed.
Test 2 When X is heated with an acidified solution of potassium dichromate(VI),
no change is observed.
Test 3 When X is added to an alkaline solution of iodine, the formation of a
pale yellow precipitate is observed.
Explain what can be deduced about the functional group present in X, by
considering the results of each of these tests.
(3)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ........................................................................................................................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ........................................................................................................................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ........................................................................................................................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ........................................................................................................................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ........................................................................................................................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ........................................................................................................................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ........................................................................................................................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ........................................................................................................................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ........................................................................................................................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
5
 *P70957A0520* Turn over
(c) The high resolution proton NMR spectrum of X contains only two singlets with
relative peak areas of 3 : 2.
Draw the structure of X, identifying the two proton environments.
(2)
6
*P70957A0620* 
(d) The molecular formula of Y is C6H12O2 .
(i) When aqueous sodium carbonate is added to Y, effervescence is observed.
Identify, by name or formula, the functional group present in Y.
(1)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(ii) The 13C NMR spectrum of Y contains four peaks.

Give two possible structures for Y.
(2)
Structure 1 Structure 2
(iii) Explain how the low resolution proton NMR spectrum of Y would confirm
which of your structures in (d)(ii) is correct.
Chemical shifts are not required.
(2)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
7
 *P70957A0720* Turn over
(e) The molecular formula of Z is C6H12O2 .
The infrared spectrum of Z is shown.
100
Transmittance / %
50
0
4000 3000 2000 1500 1000 500
–1
Wavenumber / cm
Group Wavenumber range / cm–1
C H stretching vibrations
Alkane 2962–2853
Alkene 3095–3010
Aldehyde 2900–2820 and 2775–2700
O H stretching vibrations
Alcohols 3750–3200
Carboxylic acids 3300–2500
C O stretching vibrations
Aldehydes 1740–1720
Ketones 1720–1700
Carboxylic acids 1725–1700
Esters 1750–1735
8
*P70957A0820* 
(i) Z has a fruity smell.
Deduce the identity of the functional group present in Z, using all the
information given.
Include any relevant wavenumber ranges in your answer.
(2)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(ii) The high resolution proton NMR spectrum of Z contains four peaks
(J, K, L and M). Peak J has the highest chemical shift, showing that this proton
environment is close to an electronegative atom.
The splitting pattern of the peaks is shown.
Peak J K L M
Splitting pattern septet quartet doublet triplet
Draw the displayed structure of Z, labelling the proton environment

responsible for each of the peaks J, K, L and M.
(3)
9
 *P70957A0920* Turn over
3 A student investigated the kinetics of the reaction between bromide ions, Br –, and
bromate(V) ions, BrO3–, in aqueous acid.
5Br –(aq) + BrO3–(aq) + 6H+(aq) → 3Br2(aq) + 3H2O(l)
To determine the rate equation for the reaction, the student varied the concentration
of bromide ions, bromate(V) ions and acid in turn.
The effect of the concentration of bromide ions was investigated first.
Procedure
Step 1 Add 10.0 cm3 of 0.0050 mol dm–3 potassium bromate(V),
15.0 cm3 of acidified methyl orange indicator solution and
5.0 cm3 of 0.00010 mol dm–3 aqueous phenol to a beaker labelled P.
Step 2 Prepare the contents of beaker Q for Run 1 as specified in the table.
Step 3 Pour the contents of beaker Q into beaker P and start a timer.
Pour the contents of beaker P back into beaker Q and place beaker Q on a
white tile.
Step 4 Stop the timer as soon as the mixture turns colourless.
Record the time, along with the temperature of the solution.
Step 5 Repeat Steps 1 to 4 for the remaining runs.
Contents of beaker Q
Run Volume of 0.01 mol dm–3 KBr / cm3 Volume of H2O / cm3
1 10.0 0
2 8.0 2.0
3 6.0 4.0
4 5.0 5.0
5 4.0 6.0
6 3.0 7.0
10
*P70957A01020* 
(a) Give one reason why the contents of beaker P are poured back into beaker Q
in Step 3.
(1)
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................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(b) Methyl orange indicator is bleached colourless by bromine.

Under the experimental conditions, the reciprocal of the time taken for the
methyl orange to be bleached (1/t) is proportional to the initial rate.
(i) Explain why phenol is added to the reaction mixture.
(2)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(ii) Give the colour of the reaction mixture before it turns colourless.
(1)
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(iii) Give the reason why the temperature is measured in Step 4.

(1)
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................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
11
 *P70957A01120* Turn over
(c) The student’s results are shown.
Volume of KBr / cm3 10.0 8.0 6.0 5.0 4.0 3.0
Time, t / s 23 24 32 39 48 64
(1/t) / s–1 0.043 0.042 0.031 0.026
Temperature / °C 18 22 22 22 22 22
(i) Complete the table by calculating the remaining values of 1/t.

(1)
(ii) Plot a graph of 1/t against the volume of KBr.

Include a line of best fit.
(3)
0
0
12
*P70957A01220* 
(iii) State why the volume of KBr is proportional to the concentration of
bromide ions in the reaction mixture.
(1)
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................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(iv) State the order of reaction with respect to bromide ions, using your graph.
(1)
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(d) After investigating the effect on the rate of the concentration of bromate(V) ions
and the concentration of hydrogen ions, the student obtained the graphs shown.
1/t 1/t
[BrO3– ] [H+]2
Deduce the rate equation for the reaction, using these data and your
answer to (c)(iv).
(1)
13
 *P70957A01320* Turn over
4 This question is about the preparation of phenylamine by the reduction
of nitrobenzene.
NO2 NH2
+ 6[H] → + 2H2O
nitrobenzene phenylamine
Outline procedure
Step 1 Add 2.1 cm3 of nitrobenzene, 5 g of granulated tin and 10 cm3 of
concentrated hydrochloric acid to a round‑bottomed flask.
Step 2 Add a few anti‑bumping granules to the flask and heat the contents under
reflux for 15 minutes. Leave to cool.
Step 3 Dissolve 7.5 g of sodium hydroxide in 10 cm3 of distilled water and add to the
flask. An initial precipitate forms before redissolving.
Step 4 Add 15 cm3 of distilled water to the flask and steam distil the contents,
collecting the cloudy distillate in a conical flask.
Step 5 Add 3 g of powdered sodium chloride to the distillate and swirl to dissolve,
before transferring the contents to a separating funnel.
Add 8 cm3 of ether to the funnel and shake, occasionally relieving the
pressure. Allow the layers to separate.
Step 6 Discard the aqueous layer before transferring the ether layer to a clean flask
containing a few pellets of potassium hydroxide.
Step 7 Decant the contents of the flask from Step 6 into a pear‑shaped flask and
distil off all the ether.
Step 8 Distil the remaining contents of the pear‑shaped flask, collecting the fraction
boiling between 180 °C and 185 °C.
Some data relating to the organic chemicals involved in the preparation are shown.
Chemical Hazard Mr Density / g cm–3 Boiling temperature / °C
Toxic by inhalation
Nitrobenzene 123.0 1.20 211
and skin absorption
Toxic by inhalation
Phenylamine 93.0 1.03 184
and skin absorption
Ether Highly flammable 74.0 0.71 35
14
*P70957A01420* 
(a) Give two reasons why gloves should be worn in Step 1.
(2)
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................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(b) (i) State the role of tin in the preparation.

(1)
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................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(ii) Suggest, by name or formula, the identity of the initial precipitate formed
in Step 3.
(1)
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................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(c) State why the distillate in Step 4 is cloudy.

(1)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(d) Suggest why sodium chloride is added to the distillate in Step 5.

(1)
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................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
15
 *P70957A01520* Turn over
(e) (i) Draw a labelled diagram of the separating funnel at the end of Step 5.
(2)
(ii) State how you would relieve the pressure in the separating funnel in Step 5.
(1)
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................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(f ) Suggest one reason for adding pellets of potassium hydroxide in Step 6.

(1)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
16
*P70957A01620* 
(g) State how the mixture would be heated to distil off the ether in Step 7.
Justify your answer.
(2)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(h) Calculate the mass of phenylamine formed in this preparation.

The limiting reagent is nitrobenzene and the overall yield by mass is 43 %.
Refer to all the information at the start of the question.
(4)

17
 *P70957A01720*
BLANK PAGE
18
*P70957A01820* 
BLANK PAGE
19
 *P70957A01920*
20
*P70957A02020* 
Pearson Edexcel Centre Number Candidate Number

International
Advanced Level

Paper
reference WCH16/01
Chemistry

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
Advice
• Good luck with your examination.
Turn over
*P64628A0116*
P64628A
1/1/1/1/1/1
1 This question is about compounds containing the ammonium ion, NH+4 .
(a) Ammonium vanadate(V), NH4VO3 , is a white solid.
(i) When excess dilute sulfuric acid is added to an aqueous solution of NH4VO3 ,
the VO−3 ion is converted into the VO+2 ion.
Write the ionic equation for the conversion of VO−3 to VO+2 on the addition of
dilute sulfuric acid. State symbols are not required.
(1)
(ii) State the colour of an acidified solution of ammonium vanadate(V).

(1)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(iii) A student added zinc metal to an acidified solution of ammonium vanadate(V).

The zinc reduced the vanadium in a series of reactions.
The student suggested that the sequence of colours observed could be
explained by the presence of the vanadium species shown in the table.
Sequence of starting green blue green violet

colours observed colour
Suggested
VO+2 V3+ VO2+ V3+ V2+
vanadium species
Explain whether or not the student is correct.

Refer to oxidation states of vanadium and account for each colour in the sequence.
(2)
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................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
2
*P64628A0216*
(iv) When the mixture obtained at the end of the sequence in (a)(iii) is filtered,
the filtrate changes colour from violet to green on standing. No further
changes occur.
Suggest an explanation for these observations.
(2)
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................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(b) Ammonium tetrachlorocuprate(II) dihydrate, (NH4)2CuCl4.2H2O, is a blue-green solid.

When ammonium tetrachlorocuprate(II) dihydrate is dissolved in water,
a blue-green solution T is formed.
(i) Suggest the formulae of two complex ions present in solution T.
(2)
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................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(ii) State how the colour of solution T would change on the addition of excess
concentrated hydrochloric acid.
(1)
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................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(iii) Describe what would be observed on the addition of aqueous

sodium hydroxide to solution T.
(1)
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................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(iv) When the mixture from (b)(iii) is warmed, a gas is evolved.

Give a test to identify the gas stating the positive result of the test.
(2)
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................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
3
*P64628A0316* Turn over
(c) A white solid with a slight vinegar-like smell contains ammonium ions, NH+4 , and
an anion represented by Y− .
The smell of vinegar intensifies on the addition of a few drops of concentrated
sulfuric acid to an aqueous solution of NH4Y .
On subsequent addition of a few drops of ethanol and heating the mixture, the
smell of vinegar is replaced by a sweet and fruity smell.
Explain how all this information can be used to identify the anion Y−.
(3)
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................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
4
*P64628A0416*
2 This question concerns the laboratory preparation of
tetraamminecopper(II) sulfate-1-water, Cu(NH3)4SO4.H2O.
Procedure
Step 1 Weigh between 2.1 g and 2.3 g of hydrated copper(II) sulfate, CuSO4.5H2O, in a
boiling tube. Add 8 cm3 of distilled water and place the boiling tube in a
hot water bath. Stir the mixture until the crystals have dissolved.
Step 2 Working in a fume cupboard, slowly pour 5 cm3 of concentrated aqueous ammonia
into the boiling tube. Stir until a clear solution is obtained.
Step 3 Measure 12 cm3 of ethanol into a 100 cm3 conical flask and add the contents of
the boiling tube from Step 2. Stopper the flask and swirl the contents before
placing the flask in an ice bath. Allow the mixture to stand until crystals of
Cu(NH3)4SO4.H2O have formed.
Step 4 Filter the crystals obtained in Step 3 under reduced pressure, using a
Buchner funnel and flask.
Step 5 Pour 5 cm3 of cold ethanol over the crystals in the funnel.
Step 6 Using a spatula, transfer the crystals to a filter paper on a watch glass. Press a
second piece of filter paper on the crystals, to dry them as much as possible.
Step 7 Transfer the crystals to a dry, pre-weighed sample bottle and reweigh.
(a) Give a reason why a measuring cylinder is more suitable than a graduated pipette
for measuring the distilled water in Step 1.
(1)
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(b) Give the colour of the solution at the end of Step 2.

(1)
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(c) Give the reason why Step 2 should be carried out in a fume cupboard.
(1)
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................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ........................................................................................................................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
5
(d) Give the reason why the addition of ethanol in Step 3 results in the precipitation
of crystals of Cu(NH3)4SO4.H2O.
(1)
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................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(e) Draw a labelled diagram of the apparatus used to filter the crystals under
reduced pressure in Step 4.
(3)
(f ) (i) State the purpose of the ethanol in Step 5.

(1)
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................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(ii) Give a reason why the ethanol is cold.

(1)
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................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
6
*P64628A0616*
(g) Starting with 2.17 g of CuSO4 5H2O and using excess ammonia, a student obtained
2.54 g of product.
(i) Calculate the apparent percentage yield of Cu(NH3)4SO4.H2O.
Give your answer to an appropriate number of significant figures.
(3)
(ii) Suggest a reason why the apparent percentage yield in this preparation is
often greater than 100 %.
(1)
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................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
7
3 This question is about the identification of six organic compounds.
O
O
OH
OH
O
A B
O
O
O
C D
O O
OH
HO
O
O F
E
(a) From A, B, C, D, E and F, identify the compound with

(i) the fewest peaks in its carbon-13 NMR spectrum.
(1)
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(ii) the most peaks in its low resolution proton NMR spectrum.
(1)
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(iii) three peaks with relative peak area 3:2:3 in its low resolution
proton NMR spectrum.
(1)
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(iv) one triplet and one quartet as the only peaks in its high resolution
proton NMR spectrum.
(1)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
8
*P64628A0816*
(b) For each of the following pairs, give one chemical test, not including indicators,
that could be used to distinguish the compounds.
Identify the reagents and give the results of each test.
(i) A and B
O
O
OH
OH
O
A B

(2)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(ii) C and D
O
O
O
C D
(2)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
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9
(c) Liquids boil at the temperature at which their vapour pressure is equal to
atmospheric pressure.
The apparatus shown below was used to determine the boiling temperature
of compound A, which is a liquid at room temperature and pressure and has a
boiling temperature in the range 120 °C to 180 °C.
thermometer
rubber band micro test tube
capillary tube
compound A
Thiele tube
mineral oil
Bunsen burner
Procedure
Step 1 Place a capillary tube, sealed at one end and with the open end facing down,
into 0.5 cm3 of compound A in a micro test tube. Attach the micro test tube to
a thermometer with a rubber band.
Step 2 Clamp the micro test tube and thermometer in the mineral oil, making sure
neither test tube nor thermometer bulb is in contact with the glass walls of
the Thiele tube.
Step 3 Move a small Bunsen flame back and forth along the lower part of the
side-arm of the Thiele tube. An initial stream of bubbles will come from the
open end of the capillary tube.
Step 4 Continue heating until a rapid and continuous stream of bubbles comes
from the capillary tube. Stop heating and record the temperature as soon as
compound A is drawn up into the capillary tube.
10
*P64628A01016*
(i) State what causes the initial stream of bubbles from the capillary tube in Step 3.
(1)
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(ii) Suggest why the side-arm of the Thiele tube is heated, rather than point X on
the diagram.
(1)
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(iii) Suggest why mineral oil, and not water, is used in the Thiele tube when
determining the boiling temperature of compound A.
(1)
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(iv) Suggest why the results obtained when using this apparatus on different days
may not be the same, even when no mistakes are made in carrying out
the experiment.
(1)
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11
(d) One of the compounds A, B, C, D, E or F was analysed.
To determine its empirical formula, 1.57 g of the compound was burned
completely and the combustion products passed through the apparatus shown.
solid N
solid M
Solid M absorbed water and increased in mass by 1.28 g.

Solid N absorbed carbon dioxide and increased in mass by 3.14 g.
(i) Identify, by name or formula, suitable substances for solids M and N.
(2)
Solid M . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ....................................................................................................
Solid N . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ...................................................................................................
12
*P64628A01216*
(ii) Calculate the empirical formula of the compound, using the data given.
You must show your working.
(4)
13
(iii) The mass spectrum of the compound is shown.
100
80
60
Relative
intensity
40
20
0
0 10 20 30 40 50 60 70 80 90
m/z
Deduce the relative molecular mass of the compound, using the mass spectrum.
(1)
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(iv) Deduce the molecular formula of the compound, using your answers to
(d)(ii) and (d)(iii).
(1)
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14
*P64628A01416*
(v) Determine the identity of the compound, using your answer to (d)(iv) and the
fragmentation pattern of the mass spectrum.
Justify your answer.
(2)
O
O
OH
OH
O
A B
O
O
O
C D
O O
OH
HO
O
O F
E
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15
*P64628A01516*
16
*P64628A01616*

International
Advanced Level
Thursday 21 January 2021

Afternoon (Time: 1 hour 20 minutes) Paper Reference WCH16/01
Chemistry
Unit 6: Practical Skills in Chemistry II

Scientific calculator
Instructions
• Use black ink or ball-point pen.
• centrethe
Information
Advice
Turn over
*P67820A0116*
P67820A
1/1/1/1/1
1 A student carries out some tests on four aqueous solutions A, B, C and D.
One of the solutions is aqueous barium chloride, BaCl2(aq).
(a) The student is asked to add A to samples of B, C and D in separate test tubes,
a small amount at a time, until there is no further change.
The container of solution A has a hazard label.
(i) Identify the hazard indicated by this label.

(1)
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(ii) Describe how you would add small amounts of A until there is
no further change. Name the apparatus you would use.
(2)
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2
*P67820A0216*
(b) (i) B is a blue solution. When A is added to B, the mixture first turns green and
then gradually turns yellow.
Give the formula of the cation in B.
(1)
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(ii) When A is added to C, vigorous effervescence occurs and the gas produced
turns limewater cloudy.
Identify, by name or formula, the gas produced.
(1)
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(iii) Suggest the identity, by name or formula, of the anion in C.

(1)
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(iv) Identify A by name or formula. Justify your answer.

(2)
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(v) When A is added to D no change is seen.

A small amount of this mixture is added to B and a white precipitate forms.
Suggest what can be deduced about solutions B and D.
(2)
Solution B
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
Solution D
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
*P67820A0316*
3
Turn over
(vi) A concentrated solution of ammonia is added to B.
Initially a pale blue precipitate forms. When more ammonia is added,
the precipitate dissolves forming a dark blue solution F.
Identify, by name or formula, the pale blue precipitate and the species
responsible for the dark blue colour in F.
(2)
(vii) A solution of the sodium salt of EDTA, Na4EDTA, is added to a sample of

solution F. The solution turns pale blue.
Write an equation for the reaction.
State symbols are not required.
(2)
4
*P67820A0416*
BLANK PAGE
*P67820A0516*
5
Turn over
2 Students were told to determine the concentration of a solution of
potassium chlorate(V), KClO3 . Two methods were used: precipitation and titration.
Method 1 – Precipitation
Step 1 Bubble excess sulfur dioxide, SO2 , into 100 cm3 of the
potassium chlorate(V) solution.
Step 2 Boil the resulting mixture to remove excess SO2 and then add silver nitrate
solution until no more silver chloride precipitate forms.
Step 3 Filter, dry and weigh the precipitate.
The equation for the reaction in Step 1 is shown.
ClO–3(aq) + 3SO2(g) + 3H2O(l) → Cl–(aq) + 6H+(aq) + 3SO2–
4 (aq)
(a) Identify the main hazard in Step 1, giving a safety precaution that will
reduce the risk.
Assume that safety spectacles and a laboratory coat were used.
(2)
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(b) The reaction in Step 2 produced 0.430 g of a white precipitate of

silver chloride, AgCl.
Calculate the concentration of KClO3 in the solution, in mol dm–3,
found using Method 1.
(2)
6
*P67820A0616*
(c) A student who used Method 1 obtained a value that was significantly larger than
the actual concentration of the solution.
Explain one possible source of experimental error which might lead to this result.
(2)
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................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
Method 2 – Titration
Step 1 Mix a sample of potassium chlorate(V) solution with an acidified solution
containing iron(II) sulfate, FeSO4
Step 2 Remove the chloride ions produced in Step 1.
Step 3 Determine the concentration of excess iron(II) ions by titrating the whole
of the solution with a standard solution of potassium manganate(VII).
The equation for the reaction in Step 1 is shown.
ClO–3(aq) + 6Fe2+(aq) + 6H+(aq) → Cl–(aq) + 6Fe3+(aq) + 3H2O(l)
(d) Give the colour change observed in Step 1.
(1)
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*P67820A0716*
7
Turn over
(e) Describe how to carry out the titration in Step 3. You should identify suitable
apparatus and any additional chemicals required.
(5)
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................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
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................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
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................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
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................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
8
*P67820A0816*
(f ) In Method 2, 50.0 cm3 of potassium chlorate(V) was mixed with 150 cm3 of
0.0750 mol dm–3 of iron(II) sulfate. The iron (II) sulfate was in excess.
The whole of this solution required 9.25 cm3 of 0.050 mol dm–3 of
potassium manganate(VII) to completely react.
The equations for the reactions are
ClO–3(aq) + 6Fe2+(aq) + 6H+(aq) → Cl–(aq) + 6Fe3+(aq) + 3H2O(l)
MnO–4(aq) + 5Fe2+(aq) + 8H+(aq) → Mn2+(aq) + 5Fe3+(aq) + 4H2O(l)
Calculate the concentration, in mol dm–3, of the potassium chlorate(V) solution.
(6)
*P67820A0916*
9
Turn over
(g) Explain the change, if any, to the value calculated in (f ) if the chloride ions were
not removed before the reaction in Step 3 of Method 2.
(2)
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................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
10
*P67820A01016*
3 Azo dyes, such as Organol Brown, can be made from benzene, C6H6 , using the
reaction scheme shown.
Due to the toxicity of benzene, the first step is never carried out in a
school laboratory.
NO2 NH2
benzene nitrobenzene phenylamine
OH
Cl– + N
N N
N
organol brown benzenediazonium

chloride
(a) In the preparation of nitrobenzene, benzene is added slowly to a mixture of

concentrated nitric and sulfuric acids.
The mixture is warmed at 55°C under reflux for 45 minutes. The reaction mixture
is stirred continuously.
(i) State why a reflux condenser is needed when the mixture is warmed.
(1)
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................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
*P67820A01116*
11
Turn over
(ii) Draw a diagram of the apparatus used to warm under reflux
in this experiment.
(3)
(iii) Suggest why the reaction mixture is stirred continuously.

(2)
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12
*P67820A01216*
(b) The excess acid is removed from the reaction mixture. The layer containing
nitrobenzene is separated and dried before being purified by distillation.
Identify a suitable drying agent.
(1)
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(c) Nitrobenzene is then reduced to phenylamine, C6H5NH2 .

Phenylamine reacts with nitrous acid at a temperature between 0°C and 10°C to
form a diazonium compound.
(i) Nitrous acid is formed in the reaction mixture using sodium nitrite
and hydrochloric acid.
State why nitrous acid is generated in the reaction mixture instead of being
obtained from a chemical supplier.
(1)
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................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
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(ii) Explain why the temperature of the reaction between phenylamine and
nitrous acid must be neither lower than 0°C nor higher than 10°C.
(2)
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................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
*P67820A01316*
13
Turn over
(d) Reaction of the diazonium compound with an alkaline solution of
naphthalene-1-ol produces the solid azo dye, Organol Brown.
The solid is purified by recrystallisation.
Procedure
Step 1 The impure Organol Brown is dissolved in a
minimum volume of hot solvent.
Step 2 The solution is filtered hot through a preheated funnel.
Step 3 The solution is cooled and filtered using a Buchner funnel.
Step 4 The solid is rinsed with a small amount of ice-cold solvent.
Step 5 The solid is dried in a desiccator.
(i) State why a minimum volume of hot solvent is used in Step 1.
(1)
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................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(ii) Explain why a preheated funnel is used in Step 2.

(1)
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(iii) Give a reason for each of the two filtrations in Steps 2 and 3.
(2)
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................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(iv) Give a possible reason why it is preferable to dry the solid in a desiccator
rather than in an oven in Step 5.
(1)
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................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
14
*P67820A01416*
(e) The melting temperature of the recrystallised Organol Brown is measured to
check its purity.
State what you would observe if the sample was pure.
(1)
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................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
*P67820A01516*
15
16
*P67820A01616*

International
Advanced Level
Wednesday 17 June 2020

Morning (Time: 1 hour 20 minutes) Paper Reference WCH16/01
Chemistry
Unit 6: Practical Skills in Chemistry II
Candidates must have: Scientific calculator Total Marks

Ruler
Instructions
• centrethe
• Answer
Answer all questions.
• – there may
the questions in the spaces provided
be more space than you need.
Information
• There is a Periodic Table on the back cover of this paper.
Advice
Turn over
*P64622A0116*
P64622A
1/1/1/1/1
Answer ALL the questions.
Write your answers in the spaces provided.
DO NOT WRITE IN THIS AREA

1 Compound A is a green solid containing one cation and one anion.
A sample of compound A was dissolved in distilled water, forming a green solution.
Aqueous sodium hydroxide was added to the solution of A until there was no further change.
A pale blue precipitate B and a yellow solution C were formed.
(a) The pale blue precipitate B was separated and tested.
(i) B dissolved in excess ammonia to form a deep blue solution containing a
complex ion D.
Identify, by name or formula, B and D.
(2)
Precipitate B .. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
Complex ion D . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .

(ii) When another portion of B was heated gently, the solid turned black.
Suggest the name or formula of the black solid.
(1)
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(iii) Excess concentrated hydrochloric acid was added to a further portion of B and
the mixture warmed.
The precipitate dissolved to form a different yellow solution E.
Identify, by name or formula, the complex ion responsible for the yellow
colour in E.
(1)
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2
*P64622A0216*
(b) The yellow solution C was tested.
5 cm3 of dilute sulfuric acid was added to the same volume of C, and the mixture
turned orange.
1 cm3 of ethanol was added to the orange mixture which was heated gently. The
mixture turned green.
(i) Identify, by name or formula, the ions responsible for the colours observed.
(3)
Observation Ions
yellow colour of
solution C
orange colour on adding

dilute sulfuric acid to C
green colour of the

mixture after heating

with ethanol
(ii) Suggest the name or formula of the organic product formed in the green mixture.
(1)
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(c) Give the name or formula of compound A.

(1)
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(d) Give a possible reason why compound A is green.

(1)
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3
2 This question is about three organic compounds P, Q and R.
These compounds are isomers with the molecular formula C4H8O2.

(a) Compound P is a colourless liquid with a sweet fruity smell.
When a sample of P was heated with sodium hydroxide, a volatile product was
formed which had a molecular ion peak in its mass spectrum at m / z = 46.
The mass spectrum of P has a strong peak at m / z = 43.
Deduce the structure of P. Justify your answer using all this information.
(4)
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................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(b) (i) When sodium hydrogencarbonate solution is added to separate samples of Q

and R, effervescence occurs and a gas is evolved which turns limewater milky.
Deduce the two possible structures of Q and R.
Justify your answer using all this information.

(2)
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................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
4
*P64622A0416*
(ii) A simplified high resolution proton NMR spectrum of Q is shown.
The relative peak areas are given above each set of peaks.
1
TMS
1
12.0 10.0 8.0 6.0 4.0 2.0 0.0

Chemical shift (δ) / ppm

Deduce the structure of Q. Fully justify your answer by referring to the number of
peaks, the relative peak areas and the splitting patterns in the proton NMR spectrum.
(4)
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................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
5
*P64622A0616*
BLANK PAGE
6
3 A group of students carried out an experiment to determine the rate equation for the
reaction between bromide and bromate(V) ions in acid conditions.
The equation for this reaction is

BrO−3 (aq) + 5Br−(aq) + 6H+(aq) → 3Br2(aq) + 3H2O(l)
Procedure (to determine the order of reaction with respect to bromate(V) ions)
Step 1 Measure 10.0 cm3 of aqueous phenol solution into a boiling tube and
add five drops of methyl red indicator. The mixture turns yellow (the alkaline
colour of methyl red).
Step 2 Add 5.0 cm3 of aqueous potassium bromide and 10.0 cm3 of dilute sulfuric acid
to the boiling tube. The mixture turns red (the acid colour of methyl red).
Step 3 Measure 15.0 cm3 of aqueous potassium bromate(V) into a second boiling tube.
Step 4 Mix the contents of the two boiling tubes and start a timer.
Step 5 Record the time (t) when the colour of the methyl red is bleached from red to
colourless by excess bromine.
Step 6 Repeat the experiment using different volumes of aqueous potassium bromate(V),
adding distilled water so that the total volume of the reacting solution is
always 40.0 cm3.
(a) Two of the hazard warning signs for phenol are

State the most important hazard associated with phenol in this experiment and
the precaution you would take to reduce the risk, apart from wearing safety
goggles and a laboratory coat.
(1)
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7
(b) Explain the purpose of the phenol in this experiment.
(2)

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(c) Suggest a way of making the disappearance of the methyl red colour easier to see.
(1)
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................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(d) A student’s results are shown.

Volumes added to 10 cm3 of phenol / cm3 time (t) 1
Run t
BrO−3 (aq) Br−(aq) H2SO4(aq) H2O(l) /s / s−1
1 15.0 5.0 10.0 0.0 40 0.025

2 12.0 5.0 10.0 3.0 51 0.020
3 10.0 5.0 10.0 5.0 62 0.016
4 8.0 5.0 10.0 7.0 74 0.014
5 6.0 5.0 10.0 9.0 100 0.010
6 4.0 5.0 10.0 11.0 154 0.0065
(i) State why the total volume of the mixture is kept constant.
(1)

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8
*P64622A0816*
(ii) Plot a graph of reciprocal time (1/t) against volume of bromate(V) solution.
(3)

9
(iii) State the order of reaction with respect to bromate(V) ions. Justify your answer.
(1)

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(iv) Reciprocal time (1/t) is used as a measure of rate in this experiment.

Suggest the assumption on which this depends. Refer in your answer to the
shape of a typical graph of reactant concentration against time.
(1)

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................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
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................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(v) Another student accidentally measured 8.5 cm3 of potassium bromate(V)

rather than 8.0 cm3 in Run 4.
Explain whether or not this portion of potassium bromate(V) should be discarded.
(2)
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................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .

................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
10
*P64622A01016*
(e) All the volume measurements in this experiment were made using a 50 cm3 burette.
(i) Give a reason why the potassium bromate(V) solution is first measured into a
separate boiling tube rather than directly into the reaction mixture.
(1)
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................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(ii) Give two reasons why Run 1 has the lowest uncertainty in the
volume measurements.
(2)
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................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(f ) State the changes that you would make to the procedure to obtain the data
needed to determine the overall rate equation for the reaction between bromide
and bromate(V) ions in acid conditions.
(2)
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................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
11
4 A group of students prepared aspirin from 2-hydroxybenzoic acid using ethanoic anhydride.
O OH O O OH

C C
H3C C
OH O CH3 O
O
C
+ H3C C + H3C C
O O OH
ethanoic
2-hydroxybenzoic acid anhydride aspirin
Data
Melting
Molar mass Density of liquid
Compound temperature
/ g mol−1 / g cm−3
/ °C
2-hydroxybenzoic acid 138.0 — 159
ethanoic anhydride 102.0 1.082 —

aspirin 180.0 — 136
Procedure
Step 1 Weigh 2.00 g of 2-hydroxybenzoic acid and put it in a pear-shaped flask.
Clamp the flask and suspend it in a water bath containing cold water.
Step 2 Add 5.0 cm3 of ethanoic anhydride to the 2-hydroxybenzoic acid.
Add five drops of concentrated sulfuric acid to the mixture in the flask.
Add anti-bumping granules and fix a reflux condenser on the flask.
Step 3 Warm the mixture by heating the water bath using a Bunsen burner.
Gently swirl the mixture until all the solid has dissolved.
Step 4 Continue warming the mixture for another 10 minutes.
Step 5 Remove the flask from the hot water bath and add 10 cm3 of crushed ice
and some distilled water. DO NOT WRITE IN THIS AREA

Step 6 Stand the flask in a beaker of iced water until no more aspirin
crystals form.
Step 7 Filter off the aspirin crystals using a Bϋchner funnel and suction apparatus.
Step 8 Wash the aspirin crystals with the minimum volume of iced water.
Step 9 Recrystallise the aspirin crystals using a mixture of ethanol and water.
12
*P64622A01216*
(a) Give a reason for placing the flask in cold water in Step 1.
(1)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(b) Suggest the purpose of the concentrated sulfuric acid added in Step 2.
(1)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(c) Show, by calculation, that the ethanoic anhydride is in excess in this preparation.
(3)
13
(d) One student drew a diagram of the apparatus used for reflux in Step 4.

water in
water out
anti-bumping
granules

heat

Identify the three errors in the student’s diagram.
Assume that the apparatus is clamped correctly.
(3)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .

................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(e) Suggest the purpose of adding crushed ice and distilled water in Step 5.
(1)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
14
*P64622A01416*
(f ) The filtration in Step 7 is carried out under reduced pressure.
State two advantages of this method compared with ordinary (gravity) filtration.
(2)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(g) Describe how the purity of the recrystallised aspirin could be tested. Experimental
details are not required.
(2)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
Total for Paper = 50 marks

15
*P64622A01516*
*P64622A01616*
16

Pearson Edexcel
International
Advanced Level
Thursday 7 November 2019

Morning (Time: 1 hour 15 minutes) Paper Reference WCH06/01
Chemistry
Advanced
Unit 6: Chemistry Laboratory Skills II
Instructions
• centre
Fill in the boxes at the top of this page with your name,
Information
Advice
• Checkallyouryouranswers
Show working in calculations and include units where appropriate.
• if you have time at the end.
Turn over
P58301A
1/1/1/1/
*P58301A0116*
1 A pale green crystalline solid A contains two cations and one anion.

(a) When A is warmed with aqueous sodium hydroxide, a gas is evolved that turns
damp red litmus paper blue.
(i) Identify, by name or formula, the gas evolved.
(1)
. . . . . . . . . . . . .................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............ ............................................................................................................................... . . . . . . . . . . . . . . . . . . . . . . .
(ii) Give the name or formula of the cation in A that is identified by this test.
(1)
. . . . . . . . . . . . .................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............ ............................................................................................................................... . . . . . . . . . . . . . . . . . . . . . . .
(b) A dissolves in distilled water to form a very pale green solution B.

B reacts with aqueous sodium hydroxide to form a green precipitate, which turns
into a brown solid C, on standing in air.

(i) Give the name or formula of the cation in B that is identified by this test.
(1)
. . . . . . . . . . . . .................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............ ............................................................................................................................... . . . . . . . . . . . . . . . . . . . . . . .
(ii) Identify, by name or formula, the brown solid C.

(1)
. . . . . . . . . . . . .................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............ ............................................................................................................................... . . . . . . . . . . . . . . . . . . . . . . .
(c) B gives a white precipitate when aqueous barium chloride acidified with dilute
hydrochloric acid is added.
Give the name or formula of the anion in B that is identified by this test.
(1)
. . . . . . . . . . . . .................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............ ............................................................................................................................... . . . . . . . . . . . . . . . . . . . . . . .
(d) Suggest the formula of solid A. Do not include any water of crystallisation.
(1)
. . . . . . . . . . . . .................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............ ............................................................................................................................... . . . . . . . . . . . . . . . . . . . . . . .
. . . . . . . . . . . . .................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ........... ............................................................................................................................... .. . . . . . . . . . . . . . . . . . . . . .
2
*P58301A0216*
(e) A sample of 0.025 mol of solid A with a mass of 9.80 g is heated gently to remove
the water of crystallisation and leave 0.025 mol of the anhydrous solid.
The mass of anhydrous solid is 7.10 g.

Calculate the number of moles of water of crystallisation combined with 1 mol of
the anhydrous solid.
(2)

3
2 W is a white solid with the molecular formula C9H8O2.
(a) A series of tests is carried out on W.

Complete the table.
(i) Ignite a sample of W Very smoky flame W could be an alkene
or ........................................................................... (1)
compound
(ii) Add a little W to bromine Yellow solution turns W contains the

water and shake the mixture into a colourless
solution ................................................................................... (1)
group
(iii) Heat W until it melts then Steamy fumes form W contains the

add
phosphorus(V) chloride ................................................................................... (1)
group
(iv) Heat W until it melts then Bubbles of W contains the

add solid carbon dioxide form
...................................................................................
(2)
. . .................................. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
group
. . .................................. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(b) Complete the table, which contains information about the mass spectrum of W.
Peak Inference
+
(i) A peak occurs at m / e = The peak is due to C6H5
(1)
. ................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(ii) A peak occurs at m / e = 103 The peak is due to an ion with the formula
(1)
..................................................................................
4
*P58301A0416*
(c) The low resolution proton nmr spectrum of W has four peaks each with
relative area 1 and two peaks each with relative area 2.
(i) State the number of proton environments in W.

(1)
. . . . . . . . . . . . .................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............ ............................................................................................................................... . . . . . . . . . . . . . . . . . . . . . . .
(ii) State what can be deduced from the relative peak areas.
(1)
. . . . . . . . . . . . .................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............ ............................................................................................................................... . . . . . . . . . . . . . . . . . . . . . . .
. . . . . . . . . . . . .................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ........... ............................................................................................................................... .. . . . . . . . . . . . . . . . . . . . . .
. . . . . . . . . . . . .................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ........... ............................................................................................................................... . . . . . . . . . . . . . . . . . . . . . . .
(d) W exists as two geometric isomers.

Use all the information in this question to deduce the structure of one of these isomers.
(2)
5
3 A student used two methods to determine the concentration of vanadium(III) ions
in an aqueous solution X.

(a) Method 1 used a titration procedure.
10.0 cm3 of X was titrated with 0.0400 mol dm–3 acidified potassium manganate(VII).
The equation for the reaction is
5V3+(aq) + 2MnO4–(aq) + 2H2O(l) o 5VO+2(aq) + 2Mn2+(aq) + 4H+(aq)

The results of four titrations are shown.
Titration Rough 1 2 3
Final burette
21.10 41.30 19.85 20.10
reading / cm3
Initial burette
0.50 21.10 0.25 0.00
reading / cm3

Titre / cm3 20.10
Titres used to
calculate mean
(i) Complete the table and calculate the mean titre.

Show which titres you have used in your calculation by putting a tick ( ) in
the appropriate boxes in the table.
(2)
Mean titre = ...................................................... . . . . . . . . . cm3
6
*P58301A0616*
(ii) Calculate the concentration, in mol dm−3, of V3+(aq) ions in solution X.
Give your answer to three significant figures.
(3)
(iii) Each burette reading was accurate to ±0.05 cm3.

Calculate the percentage uncertainty in the titre value for Titration 3.
(1)
7
(b) Method 2 used an electrochemical cell.
An electrochemical cell was made from the electrode systems represented by

these half-equations:
Zn2+(aq) + 2e− U Zn(s)

V 3+(aq) + e− U V2+(aq)
The Ecell value was measured using the apparatus shown.
Solution Y was made by mixing 50 cm3 of an aqueous solution of V 2+ ions with
50 cm3 of the same solution X as used in Method 1.
......................................................
.................................................. . . . .
. . . . . . . . . . ..................................... . . . . . . .

solution Y containing
. . . . . . . . . . ..................................... . . . . . . . V 2+(aq) and V3+(aq)
salt
bridge
(i) Complete the diagram by adding labels on the dotted lines provided.
Conditions are not required.
(4)
(ii) The salt bridge consisted of a strip of filter paper soaked in a saturated
solution of potassium nitrate.
Give a reason why potassium hydroxide solution should not be used for the
salt bridge.
(1)
. . . . . . . . . . . . .................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............ ............................................................................................................................... . . . . . . . . . . . . . . . . . . . . . . .
. . . . . . . . . . . . .................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............ ............................................................................................................................... . . . . . . . . . . . . . . . . . . . . . . .
. . . . . . . . . . . . .................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............ ............................................................................................................................... . . . . . . . . . . . . . . . . . . . . . . .
8
*P58301A0816*
(iii) In this cell, the zinc half-cell was at standard temperature and concentration.
When the cell reaction occurred, the zinc was oxidised and Ecell = +0.44 V.
Write the overall equation for the cell reaction.

(1)
(iv) The standard electrode potential, E , for the Zn2+(aq)|Zn(s) half-cell = −0.76 V.
The V 3+(aq)|V 2+(aq) half-cell was not at standard concentration in this experiment.
Calculate the electrode potential, E, for the V 3+(aq)|V 2+(aq) half-cell in this
experiment.
(1)
(v) The standard electrode potential, E , for the V3+(aq)|V2+(aq) half-cell = −0.26 V.
Solution Y was 1 mol dm–3 with respect to V2+(aq).
For the half-cell in this experiment, the electrode potential is given by
E = E + 0.059 log [V3+(aq)]

Use this, and your answer to (b)(iv), to calculate the concentration of V3+(aq) in
solution Y. You must show your working.
(2)
9
(c) The concentration of V3+(aq) obtained in (a)(ii) was approximately double that
obtained in (b)(v).

Explain why these two values were different.
(1)
. . . . . . . . . . . . .................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............ ............................................................................................................................... . . . . . . . . . . . . . . . . . . . . . . .
. . . . . . . . . . . . .................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ........... ............................................................................................................................... .. . . . . . . . . . . . . . . . . . . . . .
. . . . . . . . . . . . .................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ........... ............................................................................................................................... . . . . . . . . . . . . . . . . . . . . . . .
. . . . . . . . . . . . .................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ........... ............................................................................................................................... .. . . . . . . . . . . . . . . . . . . . . .

10
*P58301A01016*
4 This question is about the preparation of iodobenzene from phenylamine, and its purification.
The preparation occurs in two steps.
NH2 N2Cl
Step 1
phenylamine benzenediazonium
chloride
N2Cl I
Step 2
iodobenzene
Some data about phenylamine and iodobenzene are given in the table.
Molar mass Density Boiling temperature

Compound
/ g mol–1 / g cm−3 / °C
Phenylamine 93.0 1.02 184
Iodobenzene 203.9 1.83 188
(a) In Step 1 of the preparation, phenylamine is converted into benzenediazonium chloride.

Give the reagents and condition for Step 1.
(2)
. . . . . . . . . . . . .................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ........... ................................................................................................................................. . . . . . . . . . . . . . . . . . . . . .
. . . . . . . . . . . . .................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ........... ................................................................................................................................. . . . . . . . . . . . . . . . . . . . . .
. . . . . . . . . . . . .................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ........... ................................................................................................................................. . . . . . . . . . . . . . . . . . . . . .

. . . . . . . . . . . . .................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ........... ................................................................................................................................. . . . . . . . . . . . . . . . . . . . . .
11
(b) In Step 2 of the preparation, aqueous potassium iodide is added slowly to the
reaction mixture from Step 1.

The mixture is left to stand for 10 minutes and then it is heated for 20 minutes.
The iodobenzene formed is steam distilled from the mixture.
(i) Suggest a reason why the aqueous potassium iodide is added slowly.
(1)
. . . . . . . . . . . . .................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............ ............................................................................................................................... . . . . . . . . . . . . . . . . . . . . . . .
. . . . . . . . . . . . .................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............ ............................................................................................................................... . . . . . . . . . . . . . . . . . . . . . . .
(ii) The apparatus used for steam distillation is shown.

E
A B
anti- D
bumping
granules
HEAT HEAT
Complete the labelling of the diagram, A, B, C and D.

(3)
A . . . . . . ................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ................ ........................................................................................................................... . . . .. . . . . . . . . . . . . . . . . .

B . . . . . . .................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ................ ........................................................................................................................... . . . .. . . . . . . . . . . . . . . . . .
C . . . . . . ................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ................ ............................................................................................................................ . . .. . . . . . . . . . . . . . . . . .
D . . . . . . .................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .................. ........................................................................................................................... . . . .. . . . . . . . . . . . . . . . .
12
*P58301A01216*
(iii) State the purpose of the part of the apparatus labelled E.
(1)
. . . . . . . . . . . . .................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............ ............................................................................................................................... . . . . . . . . . . . . . . . . . . . . . . .
. . . . . . . . . . . . .................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ........... ............................................................................................................................... .. . . . . . . . . . . . . . . . . . . . . .
(iv) The distillate collected contains iodobenzene and water.

Describe how iodobenzene is obtained from the distillate.
[Refer to the data given at the start of Question 4]
(2)
. . . . . . . . . . . . .................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............ ............................................................................................................................... . . . . . . . . . . . . . . . . . . . . . . .
. . . . . . . . . . . . .................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ........... ............................................................................................................................... .. . . . . . . . . . . . . . . . . . . . . .
. . . . . . . . . . . . .................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ........... ............................................................................................................................... . . . . . . . . . . . . . . . . . . . . . . .
. . . . . . . . . . . . .................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ........... ............................................................................................................................... .. . . . . . . . . . . . . . . . . . . . . .

(v) The iodobenzene obtained from the distillate is a cloudy liquid.

Name a substance that should be added to make the liquid clear.
(1)
. . . . . . . . . . . . .................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............ ............................................................................................................................... . . . . . . . . . . . . . . . . . . . . . . .
. . . . . . . . . . . . .................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ........... ............................................................................................................................... .. . . . . . . . . . . . . . . . . . . . . .
(vi) The clear liquid is distilled to obtain pure iodobenzene.

Give a suitable temperature range for collecting the pure iodobenzene.
(1)
. . . . . . . . . . . . .................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............ ............................................................................................................................... . . . . . . . . . . . . . . . . . . . . . . .

13
(c) This preparation and purification process has an expected yield of 70%.
Calculate the volume of phenylamine needed to produce 25.0 cm3 of iodobenzene.

(4)

14
*P58301A01416*
BLANK PAGE
*P58301A01516*
15
*P58301A01616*
16

International
Advanced Level
Wednesday 15 May 2019

Afternoon (Time: 1 hour 15 minutes) Paper Reference WCH06/01
Chemistry
Advanced
Unit 6: Chemistry Laboratory Skills II
Instructions
• 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
Advice
• Checkallyouryouranswers
Show working in calculations and include units where appropriate.
• if you have time at the end.
Turn over
*P56132A0116*
P56132A
2/2/1/1/1/1/
1 This question is about five inorganic compounds (A, B, C, D and E).

(a) Compounds A and B contain s-block elements.
(i) In flame tests, A gave a yellow colour and B gave a yellow-red colour.
Identify the s-block metal ions in A and B.
(1)
The metal ion in A .. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
The metal ion in B .. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ........................................................................................................................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .

(ii) Give the colour of the precipitate formed when concentrated
sodium hydroxide solution is added to an aqueous solution of B.
(1)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(iii) Compound A is a carbonate.

Write an ionic equation for the reaction that takes place when
dilute hydrochloric acid is added to an aqueous solution of A.
Include state symbols.
(2)
(iv) Compound B is a halide.

Identify, by name or formula, a reagent that may be used to test for
halide ions in an aqueous solution of B.
(1)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . DO NOT WRITE IN THIS AREA
2
*P56132A0216*
(b) Compounds C, D and E are nitrates of d-block elements.
Aqueous sodium hydroxide is added, drop by drop, until in excess to separate
solutions of C, D and E.
(i) Compound C forms an off-white precipitate which darkens on standing in air.
Identify the precipitate, by name or formula, and explain why it darkens.
(2)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ........................................................................................................................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ........................................................................................................................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ........................................................................................................................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(ii) Compound D forms a white precipitate which dissolves in excess sodium hydroxide
to form a colourless solution containing a complex ion.
Write the formula of this complex ion.
(1)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ........................................................................................................................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(iii) Compound E forms a green precipitate which does not dissolve in excess
sodium hydroxide.
The precipitate turns brown on standing in air.
Identify, by name or formula, the compound E and the brown solid.
(2)
Compound E.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
Brown solid.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .

3
2 This question is about three organic compounds: X, Y and Z.
X, Y and Z have the same molecular formula, C6H12O.

The table shows the observations made in some chemical tests on X, Y and Z.
Observations with reagent

Iodine in
Acidified Brady’s
Sodium Bromine aqueous
Compound sodium reagent
metal water sodium
dichromate(VI) (2,4‑DNPH)
hydroxide
Orange Pale yellow
X No change No change No change
precipitate precipitate
Y Effervescence Decolourises Turns green No change No change
Z Effervescence No change No change No change No change
(a) Use information from the table to answer the following questions.
(i) State what can be deduced about X from the positive test results.

(2)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ........................................................................................................................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ........................................................................................................................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ........................................................................................................................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ........................................................................................................................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ........................................................................................................................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ........................................................................................................................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(ii) Name the functional groups present in Y.

(2)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ........................................................................................................................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ........................................................................................................................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . DO NOT WRITE IN THIS AREA
4
*P56132A0416*
(iii) Complete the equation for the reaction between Z and sodium metal.
(1)
C6H12O + Na →
(b) The high resolution proton nmr spectrum of compound X has only two peaks
which are singlets with relative peak areas of 1 : 3.
(i) State what can be deduced from the presence of only two peaks in the
nmr spectrum.
(1)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(ii) State what can be deduced from the fact that these peaks are singlets.
(1)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(iii) Use the nmr information, your answer to (a)(i) and the molecular formula to
deduce the structure of X.
(1)
5
(c) Compound Y is straight-chained and does not have geometric or optical isomers.
(i) State what can be deduced from the fact that Y does not exist as geometric isomers.

(1)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(ii) State what can be deduced from the fact that Y does not have optical isomers.
(1)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(iii) Use information about Y, your answer to (a)(ii) and the molecular formula to
deduce the structure of Y.
(1)

(d) (i) Deduce the type and classification of the functional group present in Z,
using observations from the table.
(1)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(ii) Compound Z contains a five-membered carbon ring.

Deduce the structure of Z using this information, your deduction in (d)(i) and
the molecular formula.
(1)
6
*P56132A0616*
3 This question is about the analysis of iron supplements used to prevent or treat
iron deficiency anaemia.
A student used the following procedure to analyse iron tablets containing iron in the
form of hydrated iron(II) sulfate, FeSO4.7H2O.
Procedure
Step 1 Grind up two iron tablets with a little dilute sulfuric acid using a pestle
and mortar.
Step 2 Transfer the resulting paste into a 100.0 cm3 volumetric flask. Rinse the
apparatus used with dilute sulfuric acid, transferring all washings to the
volumetric flask.
Step 3 Add sufficient dilute sulfuric acid to the volumetric flask to make up the
solution to exactly 100.0 cm3. Stopper the flask and invert it several times.
Step 4 Using a pipette, transfer 10.0 cm3 of the solution to a conical flask and
titrate it with 0.00500 mol dm−3 potassium manganate(VII) solution.
Step 5 Repeat Step 4 until concordant results are obtained.
The overall equation for the reaction occurring in the titration is
MnO4−(aq) + 8H+(aq) + 5Fe2+(aq) → Mn2+(aq) + 5Fe3+(aq) + 4H2O(l)
(a) (i) Give the reason why the titration in Step 4 does not require the addition of
an indicator.
(1)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(ii) Give the colour change at the end-point.

(1)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
7
(b) The student decided to take the burette readings from the top of the liquid level
rather than from the bottom of the meniscus.

Suggest the effect of this, if any, on the titre values. Justify your answer.
(2)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(c) Results of the titrations are given in the table.
Titration number 1 2 3 4

Burette reading (final) / cm3 10.85 21.40 31.60 42.40
Burette reading (initial) / cm3 0.00 10.85 21.40 32.10
Titre / cm3 10.85
(i) Complete the table and use the concordant values to calculate the mean titre.
(2)
8
*P56132A0816*
(ii) Use your mean titre and information from the procedure to calculate the mass
of hydrated iron(II) sulfate, FeSO4.7H2O, present in one iron tablet.
Give your answer to an appropriate number of significant figures.

(5)
(d) The uncertainties in the burette and pipette measurements are ±0.05 cm3 and
±0.06 cm3 respectively.
Calculate which of these pieces of apparatus gives the greater percentage
uncertainty in this experiment.

(2)
9
4 This question is about the laboratory preparation of 3‑methylbutyl ethanoate,
an ester used as a banana flavouring in foods.

O O
+  + H2O
OH HO O
ethanoic acid 3-methylbutan-1-ol 3-methylbutyl ethanoate
Procedure
Step 1 Add 7.5 cm3 of 3-methylbutan-1-ol, 10 cm3 of ethanoic acid and
2 cm3 of concentrated sulfuric acid to a round-bottom flask.
Step 2 Add a few anti-bumping granules and heat the mixture under reflux
for 35 minutes.
Step 3 Transfer the cooled reaction mixture to a separating funnel. Add 30 cm3
of distilled water and washings from the flask. Shake the mixture, allow to
separate and discard the aqueous layer.
Step 4 Wash the organic layer with 15 cm3 of sodium hydrogencarbonate solution,

releasing the build up of pressure. Discard the aqueous layer and repeat
until the aqueous layer is slightly alkaline.
Step 5 Transfer the organic layer to a boiling tube and dry with
anhydrous magnesium sulfate.
Step 6 Decant the organic layer into a clean round-bottom flask and distil.
Collect the fraction boiling between 140 °C and 144 °C in a pre-weighed test tube.
Data
Compound Molar mass / g mol−1 Density / g cm−3 Boiling temperature / °C

3-methylbutan-1-ol 88.0 0.81 131
ethanoic acid 60.0 1.05 118
3-methylbutyl ethanoate 130.0 0.88 142
10
*P56132A01016*
(a) State the purpose of the concentrated sulfuric acid and of the anti‑bumping
granules added to the round-bottom flask.
(2)
Concentrated sulfuric acid in Step 1 .. . ........................................................................................................................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ........................................................................................................................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
Anti-bumping granules in Step 2 .. . . . . . . . . . ........................................................................................................................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(b) Draw a labelled diagram of the apparatus used to heat the reaction mixture
under reflux in Step 2.
(2)
11
(c) Draw a diagram of the separating funnel in Step 3, clearly labelling the aqueous
and organic layers.
(2)

(d) Give the reason why the organic layer is washed with sodium hydrogencarbonate solution
in Step 4 and suggest how the alkalinity of the aqueous layer should be confirmed.
(2)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . DO NOT WRITE IN THIS AREA

................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
12
*P56132A01216*
(e) Explain why the distillate is not collected below 140 °C in Step 6.
(2)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
(f ) A student prepared 4.75 g of 3‑methylbutyl ethanoate starting with 7.5 cm3 of

3‑methylbutan‑1‑ol and excess ethanoic acid.
(i) Calculate the percentage yield of 3‑methylbutyl ethanoate.
(3)
(ii) Give the main reason why the yield is significantly less than 100%.
Do not consider errors in the experimental procedure or transfer losses.

(1)
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
13
*P56132A01316*
*P56132A01416*
BLANK PAGE
14
15
*P56132A01516*
BLANK PAGE
*P56132A01616*
16
*P54564A0116*
l
*P54564A0216*
*P54564A0316*
*P54564A0416*
*P54564A0516*
*P54564A0616*
*P54564A0716*
I I
I I
*P54564A0816*
*P54564A0916*
*P54564A01016*
*P54564A01116*
Step A Dissolve the impure solid in some hot methanol.
Step B Cool the solution in an ice-bath.
Step C Separate the crystals using suction filtration.
Step D Dry the crystals by mixing them with solid anhydrous
sodium sulfate in a stoppered boiling tube.
*P54564A01216*
*P54564A01316*
*P54564A01416*
*P54564A01516*
*P54564A01616*

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Please check the examination details below before entering your candidate information

Candidate surname Other names

Centre Number Candidate Number

Pearson Edexcel International Advanced Level

International Advanced Level

You must have: Total Marks

Test Observation Inference

(i) A few drops of aqueous Chromium(III) ions (1)

(ii) More sodium hydroxide Chromium(III) ions (1)

(iii) A few drops of dilute (1)

(i) The addition of dilute aqueous ammonia to a sample of solution Q produced

(Total for Question 1 = 10 marks)

(b) The 13C NMR spectrum of X has two peaks.

(i) Bubbles are observed when aqueous sodium hydrogencarbonate is

(ii) Draw the structural formula of Y.

(ii) A student prepared an ester using X and a suitable compound.

(Total for Question 2 = 12 marks)

The equation for the reaction is shown.

I2(aq) + CH3COCH3(aq) + H+(aq) → CH3COCH2I(aq) + 2H+(aq) + I –(aq)

(b) State why sodium hydrogencarbonate is used in Step 3.

Titre / cm3 16.05 15.30 14.50 13.70 12.95

(i) Plot a graph of titre against time.

(iii) State the order of reaction with respect to iodine.

You must show your working on the graph.

(Total for Question 3 = 12 marks)

(a) An ice bath is a mixture of ice and water in a beaker.

base of Buchner funnel

Identify the three ways in which this diagram is incorrect.

(ii) State how the crystals of methyl 3‑nitrobenzoate could be dried.

Calculate the percentage yield by mass of methyl 3‑nitrobenzoate using the

Compound Molar mass / g mol−1 Density / g cm−3

methyl benzoate 136 1.08

methyl 3‑nitrobenzoate 181

(Total for Question 4 = 16 marks)

TOTAL FOR PAPER = 50 MARKS

Centre Number Candidate Number

Pearson Edexcel International Advanced Level

International Advanced Level

You must have: Total Marks

1 Solution A and solution B are aqueous solutions.

(i) Give the formula of the green precipitate from solution A.

(iv) Describe the corrosive hazard label present on a bottle containing

(Total for Question 1 = 14 marks)

(CH3)3CCl + OH– → (CH3)3COH + Cl–

The progress of the reaction can be followed by titrating portions of the

(a) (i) Give the expected colour change at the end‑point.

Time / s 50 320 750 1200 2050 3180 4020

(i) Plot a graph of the data using the axes given.

(iii) State the order of this reaction. Justify your answer.

(Total for Question 2 = 10 marks)

For each acid give a reason why it cannot be used.

MnO4– + 8H+ + 5e– → Mn2+ + 4H2O

Calculate the percentage by mass of Fe2+ in the sample of lawn sand.

conical flask containing

At the end‑point, the solution changes to a permanent pale pink.

(Total for Question 3 = 10 marks)

2-aminobenzoic acid ethanoyl 2‑ethanoylaminobenzoic acid

(c) Draw a labelled diagram of the apparatus used for filtration

(Total for Question 4 = 16 marks)

TOTAL FOR PAPER = 50 MARKS

Centre Number Candidate Number

Pearson Edexcel International Advanced Level