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Pearson Edexcel Level 3 GCE

Tuesday 18 June 2024
Morning (Time: 1 hour 45 minutes) Paper
reference 9CH0/02
Chemistry  

Advanced
PAPER 2: Advanced Organic and Physical Chemistry

You must have: Total Marks

Scientific calculator, Data Booklet, ruler

Instructions
• Use black ink or ball‑point pen.
• IfFillpencil is used for diagrams/sketches/graphs it must be dark (HB or B).
• centre number
in the boxes at the top of this page with your name,
and candidate number.
• Answer all questions.
• Answer the questions in the spaces provided
– there may be more space than you need.

Information
• The total mark for this paper is 90.
• The marks for each question are shown in brackets
– use this as a guide as to how much time to spend on each question.
• toForstructure
the question marked with an asterisk (*), marks will be awarded for your ability
your answer logically, showing the points that you make are related or
follow on from each other where appropriate.
• A Periodic Table is printed on the back cover of this paper.

Advice
• Read each question carefully before you start to answer it.
• Show all your working in calculations and include units where appropriate.
• Check your answers if you have time at the end. Turn over

P76896A
©2024 Pearson Education Ltd.
F:1/1/1/1/
*P76896A0132*
 Answer ALL questions.

Some questions must be answered with a cross in a box . If you change your mind about an

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answer, put a line through the box and then mark your new answer with a cross .

1 This question is about organic compounds that contain a halogen atom or a

nitrogen atom.

(a) Equal amounts of four bromoalkanes were added to separate test tubes
containing 2 cm3 of a silver nitrate solution.
The mixtures were heated in a water bath.
Which bromoalkane would be the first to form a precipitate?
(1)
A 1‑bromobutane

B 2‑bromobutane

C 1‑bromo‑2‑methylpropane

D 2‑bromo‑2‑methylpropane

(b) Which pair of reactants will form an N‑substituted amide?

(1)
A CH3COCl and NH3

B CH3CH2OH and NH3

C CH3COCl and CH3NH2

D CH3CH2OH and CH3NH2

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*P76896A0232* 
 (c) Ammonia reacts with bromoethane as shown.

2NH3 + CH3CH2Br → NH4Br + CH3CH2NH2

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(i) Explain, by referring to the reaction mechanism, the roles of ammonia in the
formation of each of the products of this reaction.
(3)

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(ii) What conditions are needed for this reaction?

(1)

Method of heating Solvent

A heat in a sealed tube ethanol

B heat under reflux ethanol

C heat in a sealed tube water

D heat under reflux water

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 (d) The halogenoalkane, 1‑bromobutane, can be formed by the reaction of
butan‑1‑ol with sodium bromide and sulfuric acid.

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CH3CH2CH2CH2OH + NaBr + H2SO4 → CH3CH2CH2CH2Br + NaHSO4 + H2O

Calculate the atom economy, by mass, for the formation of 1‑bromobutane.

Give your answer to one decimal place.
[Ar values: H = 1.0 C = 12.0 O = 16.0 Na = 23.0 S = 32.1 Br = 79.9]
(2)

(Total for Question 1 = 8 marks)

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*P76896A0432* 
 2 This question is about Grignard reagents.
A Grignard reagent is formed by reacting bromoethane with magnesium
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under reflux.

CH3CH2Br + Mg → CH3CH2MgBr

(a) The most suitable solvent for this reaction is

(1)
A cyclohexane

B ether

C ethyl ethanoate

D hexane

(b) State the use of Grignard reagents in organic synthesis.

(1)

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(c) In their reactions, the Grignard reagent is best described as

(1)
A a carbocation

B an electrophile

C a nucleophile
D a radical

(d) Grignard reagents must be kept dry.

Predict the organic product that forms when CH3CH2MgBr reacts with water.
Justify your answer by considering the polarity of both CH3CH2MgBr and water.
(2)

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 (e) Which compound will form a tertiary alcohol when it reacts with a
Grignard reagent, followed by acid hydrolysis?
(1)

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A CO2

B HCHO

C CH3CHO

D CH3COCH3
(Total for Question 2 = 6 marks)

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*P76896A0632* 
 3 This question is about hydrogen peroxide, H2O2 .
(a) Draw a dot‑and‑cross diagram of a molecule of hydrogen peroxide.
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(1)

(b) Hydrogen peroxide decomposes to form water and oxygen.

2H2O2(aq) → 2H2O(l ) + O2(g)

Explain, using oxidation numbers, why the decomposition of hydrogen peroxide

is classified as a disproportionation reaction.
(3)

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 (c) The decomposition of hydrogen peroxide is catalysed by iodide ions, I–(aq).
The kinetics of this reaction were investigated using different concentrations of

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hydrogen peroxide and iodide ions.
The results are shown in the table.

Experiment [H2O2(aq)] / mol dm–3 [I–(aq)] / mol dm–3 Rate / mol dm–3 s–1

1 0.100 0.0500 8.90 × 10–7

2 0.400 0.0500 3.56 × 10–6

3 0.200 0.100 3.56 × 10–6

(i) Deduce the order of reaction with respect to hydrogen peroxide and to
iodide ions.
(2)

Order with respect to hydrogen peroxide ................................................................................................. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .

Order with respect to iodide ions ....................................................................................................................... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .

(ii) Write the rate equation for the reaction using your answer to (c)(i).
(1)

(iii) Calculate the rate constant, k, using data from Experiment 3.

Include units in your answer.
(2)

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*P76896A0832* 
 (d) The breakdown of hydrogen peroxide with iodide ions as a catalyst is the basis of
the demonstration ‘Elephant’s Toothpaste’.
The presence of a detergent results in a rapid eruption of foam as the oxygen gas
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is released.
(i) Describe the test and the positive result that confirms the gas produced
is oxygen.
(1)

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(ii) The foam produced often has a slight yellow / brown colour.
Explain what causes this colour, which is not caused by the detergent.
(2)

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 (e) The effect of temperature on the rate of the decomposition of hydrogen peroxide
without a catalyst was also investigated.
A graph of ln k against 1/temperature (1/T) was plotted.

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1/T / K–1
0.0030 0.0032 0.0034 0.0036
–6

–7

–8

ln k

–9

–10

–11

(i) Determine the gradient of the graph.

Include units in your answer. You must show your working on the graph.
(3)

10
*P76896A01032* 
 (ii) Calculate the activation energy, Ea , of the reaction, in kJ mol–1, using your
answer to (e)(i) and the Arrhenius equation shown.
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Ea 1
ln k = – × + constant
R T

[Gas constant (R) = 8.31 J mol–1 K–1 ]

(1)

(f ) Another way to write the Arrhenius equation is shown.

k = Ae–Ea /RT

The constant A is often called the collision factor as it is linked to the orientation
of the particles colliding in a reaction.
The decomposition of hydrogen peroxide is also catalysed by aluminium.
Calculate a value for A at 370 K, for the catalysed decomposition of
hydrogen peroxide with an activation energy, Ea , of 5.02 × 104 J mol–1 and a
numerical value for the rate constant of 1.60 × 10–3.
Units are not required.
(2)

(Total for Question 3 = 18 marks)

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*4 Discuss the role society, and chemists in particular, can play in order to contribute to
a more sustainable use of polymers.

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Your answer should consider
• the different ways of dealing with waste polymers
• how chemists can limit the problems caused by the disposal of polymers.
(6)

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(Total for Question 4 = 6 marks)

13
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5 This question is about cyclic compounds.

(a) The hydrocarbon cyclopentane is present in some fuels and is used in the

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manufacture of insulation for freezers.

cyclopentane

Cyclopentane can be synthesised by passing 2‑methylbutane over a hot

platinum catalyst.

Pt
+ H2
heat
2‑methylbutane cyclopentane

Name the type of reaction that takes place in this synthesis.

(1)

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(b) The energy density of a fuel is defined as the energy released per dm3 of the
liquid fuel burned.
A sample of cyclopentane with a mass of 30.0 g releases 1.41 MJ of energy.
Calculate the energy density of cyclopentane.
Include units in your answer.
[Density of cyclopentane = 0.751 g cm–3]
(2)

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*P76896A01432* 
 (c) Under appropriate conditions, cyclopentane reacts with bromine to
form bromocyclopentane.
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Br
+ Br2 + HBr

cyclopentane bromocyclopentane

(i) State the condition needed to initiate the reaction.

(1)

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(ii) Complete the table showing the steps of the mechanism of this reaction.
Curly arrows are not required.
(3)

Step Equation(s)

Initiation

1.
.
+ Br . + HBr

Propagation
2.

Br
Termination

(iii) Draw the structure of the organic product of an alternative termination step.
(1)

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 *P76896A01532* Turn over
 (d) Bromocyclopentane forms cyclopentene when heated under reflux with a
concentrated solution of potassium hydroxide in ethanol.

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Br
+ HBr

(i) Explain why the solvent ethanol is treated with anhydrous sodium sulfate
before use in this reaction.
(2)

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(ii) Give the name of the reaction shown in the equation.

(1)

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(iii) Predict the mechanism for the reaction by adding two curly arrows.
(1)

H
Br
+ Br– + H2O
: OH–
H H

(Total for Question 5 = 12 marks)

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*P76896A01632* 
 17
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*P76896A01732*
BLANK PAGE

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6 This question is about nuclear magnetic resonance (NMR) spectroscopy.

(a) Which part of the electromagnetic spectrum is used in NMR?

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(1)
A infrared

B radio waves

C ultraviolet

D X‑ray

(b) Explain why tetramethylsilane, TMS, is used in NMR spectroscopy.

(2)

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(c) A secondary amine, Q, has the molecular formula C6H15N.

The low resolution 1H NMR spectrum of Q has three peaks.

(i) State what is meant by the term ‘secondary amine’.

(1)

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(ii) Deduce the structure of Q.

(1)

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*P76896A01832* 
 (d) Two cyclic alcohols have the structures shown.

OH OH
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OH

OH
cyclohexane-1,2-diol cyclohexane-1,3-diol

Show that the 13C NMR spectra of these compounds can be used to distinguish
between the two alcohols, labelling the diagrams to justify your answer.
(2)

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(Total for Question 6 = 7 marks)

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 *P76896A01932* Turn over
7 This question is about polymers, an example of which is neoprene, a synthetic
rubber material.
It is formed by the polymerisation of chloroprene.

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Cl

chloroprene

(a) What is the IUPAC name of chloroprene?

(1)
A 3‑chlorobuta‑1,3‑diene

B 2‑chlorobuta‑2,4‑diene

C 3‑chlorobuta‑2,4‑diene

D 2‑chlorobuta‑1,3‑diene

(b) Calculate the volume, in cm3, occupied by 10.0 g of chloroprene in the

gaseous phase, at 80.0 °C and 205 kPa.
Give your answer to an appropriate number of significant figures.
[Gas constant (R) = 8.31 J mol–1 K–1 ]
(5)

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*P76896A02032* 
 (c) Chloroprene is formed by first adding chlorine, Cl2 , to Compound A and then
removing hydrogen chloride from the product of this reaction.
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Step 1 Cl Step 2 Cl
+ Cl2 + HCl

Compound A
Cl

(i) Explain how chlorine, Cl2 , can act as an electrophile in Step 1 even though a
chlorine molecule is symmetrical.
You may find it helpful to include a diagram.
(2)

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

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

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

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

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

(ii) Draw the mechanism for Step 1.

Include curly arrows, and any relevant lone pairs and dipoles.
(3)

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 (iii) Chloroprene polymerises to form neoprene as shown.

H Cl H  H Cl H

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n C C C C C C C C



H H H H H H n

Give the name of the type of reaction that occurs when

chloroprene polymerises.
(1)

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(d) Flexible and water‑resistant materials can be made by combining neoprene with
polyester fabric.
A polyester may be made by the reaction of benzene‑1,4‑dicarboxylic acid with
ethane‑1,2‑diol.

(i) Explain why ethane‑1,2‑diol is soluble in water.

A detailed description of the forces involved is not required.
(2)

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

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

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

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

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

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*P76896A02232* 
 (ii) The molar mass of a polyester is 8400 g mol–1.
Calculate the number of polymer molecules in 4.25 mg of this polyester.
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[Avogadro constant (L) = 6.02 × 1023 mol–1 ]

(2)

(iii) A student spilled a small amount of 0.40 mol dm–3 sodium hydroxide solution
onto a polyester laboratory coat. A hole formed in the laboratory coat as the
result of a chemical reaction.
What type of reaction occurred?
(1)
A dehydration

B hydrolysis

C neutralisation

D redox
(Total for Question 7 = 17 marks)

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8 This question is about amino acids and related compounds.
The structures of two amino acids are shown.

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CH2OH CH3

H2N C COOH H2N C COOH

H H
serine alanine

(a) Both amino acids contain a chiral carbon atom.

(i) State what is meant by the term ‘chiral carbon atom’.

(1)

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

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

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

(ii) Draw diagrams of the two stereoisomers of alanine, showing their

three‑dimensional shape.
(2)

(b) Draw the skeletal formulae of the two dipeptides that could form when serine
and alanine react.
(2)

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*P76896A02432* 
 (c) Serine exists as a zwitterion.
What is the formula of this zwitterion?
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(1)
CH2OH
+
A H3N C CO2–

CH2OH
+
B H3N C COOH

CH2OH

C H2N C CO2–

CH2O–
+
D H3N C COOH

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 (d) Alanine can be synthesised as shown.
O O

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H

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H H H H
C C C C
O C O
H3C CH3
HN O
C

CH3

Compound X

Step 1 C2H5O–Na+

 –
 O O

 H H H H 
 C C C C


:

C O

 H3C O CH3 
 O  + C2H5OH + Na+
 HN
C

 
 
 CH3 


Step 2 CH3Br

O O
H H CH3 H H
C C C C + Br–
O C O
H3C CH3
HN O
C

CH3

Compound Y

Step 3

CH3

H2N C COOH + CH3COOH + 2CH3CH2OH + CO2

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*P76896A02632* 
 (i) Sodium ethoxide, C2H5ONa, needed in Step 1, is formed by the reaction of
sodium with ethanol.
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Write the equation for this reaction.

State symbols are not required.
(1)

(ii) Name the two functional groups present in Compound Y.

(2)

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

(iii) Give the reagent needed and conditions required for Step 3.
(2)

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

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

(iv) Calculate the mass of Compound X required to make 15.0 g of alanine,

assuming the overall yield of the synthesis is 55 %.
(3)

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 (e) A mixture of amino acids can be separated using a technique called
paper electrophoresis. A simplified diagram is shown.

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The movement of the amino acid on the paper depends on any charge on the
amino acid, and this is determined by the pH of the buffer solution.

positive electrode negative electrode

strip of filter paper concentrated spot of
soaked in a buffer amino acid mixture
solution of pH = 9 containing amino acid Z

Amino acid Z has the structure shown.

CH2COOH

H2N C COOH

H
amino acid Z

Explain in which direction, if any, amino acid Z would move when a current flows
in the circuit with a buffer solution of pH = 9.
(2)

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

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

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

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

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

(Total for Question 8 = 16 marks)

TOTAL FOR PAPER = 90 MARKS

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*P76896A03132*
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