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Pearson Edexcel Centre Number Candidate Number

Level 3 GCE
Chemistry
Advanced
Paper 2: Advanced Organic and Physical Chemistry

Extra Assessment Materials for first teaching September 2015 Paper Reference
Time: 1 hour 45 minutes 9CH0/02
Candidates must have: Data Booklet Total Marks
Scientific calculator

Instructions
• Use black ink or black ball-point pen.
• centre
Fill in the boxes at the top of this page with your name,
number and candidate number.
• Answer allthequestions.
Answer
• – there may bequestions in the spaces provided
more space than you need.

Information
• The total mark for this paper is 90.
• – usemarks

T he for each question are shown in brackets
this as a guide as to how much time to spend on each question.
• Ftoorstructure
questions 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.
• Try to answer every question.
• Show allyouryouranswers
Check if you have time at the end.
• working in calculations and include units where appropriate.

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*s50404A0132*
S50404A
©2015 Pearson Education Ltd.

2/5/4/6/6/
 Answer ALL questions.

Write your answers in the spaces provided.

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Some questions must be answered with a cross in a box .
If you change your mind about an answer, put a line through the box
and then mark your new answer with a cross .

1 This question is about alkanes.

(a) How many structural isomers have the molecular formula C6H14?
(1)
A 3
B 4
C 5
D 6

(b) What is the systematic name for this alkane?

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(1)

A 1,1,1,2-tetramethylbutane
B 3-ethyl-2,2-dimethylbutane
C 2,2,3-trimethylpentane
D 3,4,4-trimethylpentane

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2
*S50404A0232*
 (c) The molar masses and boiling temperatures of ethanol and propane are given in
the table.
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Molar mass Boiling temperature

Compound
/ g mol−1 / oC
ethanol 46 78.5
propane 44 −42.2

Explain the difference in boiling temperature between ethanol and propane.

(3)

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(Total for Question 1 = 5 marks)

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*S50404A0332* Turn over
2 This question is about some of the reactions of alkanes.
(a) (i) One mole of dodecane, C12H26 , is cracked to form two moles of ethene, one

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mole of propene and one mole of another organic product.
Write the equation for this reaction. State symbols are not required.
(1)

(ii) Write the equation for the complete combustion of dodecane.

State symbols are not required.
(1)

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(iii) State a hazard to health arising from a named product of the incomplete
combustion of dodecane.
(1)

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4
*S50404A0432*
 (b) Methane reacts with iodine monochloride, ICl, to form many products. Two of
these products are iodomethane and hydrogen chloride.
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(i) State the essential condition for this reaction.

(1)

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(ii) The initiation step is

ICl → I∙ + Cl∙
Write the propagation steps to form iodomethane and hydrogen chloride.
(2)
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(iii) Which of the following is a possible termination step for this reaction?
(1)

A H∙ + H∙ → H2
B H∙ + Cl∙ → HCl
C CH3∙ + H∙ → CH4
D CH3∙ + Cl∙ → CH3Cl
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(Total for Question 2 = 7 marks)

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*S50404A0532* Turn over
3 This question is about organic halogen compounds.
(a) The skeletal formulae for four organic halogen compounds, P, Q, R and S, are

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shown in the table.

P Q

Br Br

R Br S Br

(i) Which of these halogen compounds are primary?

(1)
A P only
B R only

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C P and Q only
D R and S only

(ii) Which of these halogen compounds are isomers?

(1)
A P and R
B Q and R
C Q and S
D R and S

(iii) Which of these halogen compounds reacts with aqueous potassium hydroxide
to form a compound with molecular formula C6H10O?
(1)
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A P
B Q
C R
D S

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*S50404A0632*
 (b) (i) The rate of hydrolysis of halogenoalkanes increases as the temperature increases.
Explain why a small increase in temperature causes a large increase in the rate
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of reaction.
(2)

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(ii) Give a reason why 1-chlorobutane undergoes hydrolysis at a slower rate than
1-bromobutane at the same temperature.
(1)
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*S50404A0732* Turn over
 (c) Devise a reaction scheme to convert phenylbromomethane into phenylethanoic acid.

H H

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O
C C
Br C

H H
OH
phenylbromomethane phenylethanoic acid
Include the essential reagents, conditions and the structure of any intermediates.
(4)

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(Total for Question 3 = 10 marks)

8
*S50404A0832*
 *4 A straight-chain organic compound A (C5H12O) is oxidised by potassium dichromate(VI)
and dilute sulfuric acid to give a compound B (C5H10O) which gives a pale yellow precipitate
with iodine and alkali.
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Heating compound A with phosphoric acid gives a mixture of products, including

compound C (C5H10), which exists as E/Z isomers.
Identify compounds A, B and C and justify your answers.
(6)
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(Total for Question 4 = 6 marks)

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*S50404A0932* Turn over
5 This question is about alkenes and aldehydes.
The organic compound but-2-enal is used in the manufacture of sorbic acid, which is

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a food additive. The skeletal formula of trans-but-2-enal is
O

(a) Draw the skeletal formula of cis-but-2-enal.

(1)

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(b) Trans-but-2-enal reacts with hydrogen bromide to form a mixture of products.
One of these products is 3-bromobutanal, CH3CHBrCH2CHO.
(i) Write the mechanism of this reaction to form 3-bromobutanal.
Include relevant dipoles.
(4)

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*S50404A01032*
 (ii) What is the name and type of the mechanism of this reaction between
trans-but-2-enal and hydrogen bromide?
(1)
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A electrophilic addition
B electrophilic substitution
C nucleophilic addition
D nucleophilic substitution

(c) When bromine is added to trans-but-2-enal, the aldehyde group is oxidised and
the carbon-carbon double bond reacts. The product is 2,3-dibromobutanoic acid.
When trans-but-2-enal reacts with bromine mixed with a little sodium chloride,
a mixture of 2,3-dibromobutanoic acid and 2-bromo-3-chlorobutanoic acid is
produced. No 2,3-dichlorobutanoic acid is formed.
Use your answer in (b)(i) to explain these observations.
(2)
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 (d) Which of these is the repeat unit of the polymer formed from trans-but-2-enal?
(1)

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A
H CHO

C=C

CH3 H
B
H CHO

C C

CH3 H

C
H H CHO

C C=C

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H

D
H H CHO

C C C

H H H

(e) (i) The C=O and C=C bonds have the same electronic structure but their
reactions occur by different mechanisms.
Give a reason for this.
(1)

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

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*S50404A01232*
 (ii) Write the mechanism for the reaction between trans-but-2-enal and
hydrogen cyanide, in the presence of potassium cyanide, to form
CH3CH=CHCH(OH)CN.
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Include relevant dipoles and lone pairs.

(4)
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(iii) Which types of covalent bond are broken when trans-but-2-enal reacts with
hydrogen cyanide?
(1)

Bond(s) broken in Bonds(s) broken in

trans-but-2-enal hydrogen cyanide
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A π only σ only

B σ and π σ only

C π only σ and π

D σ and π π only

(Total for Question 5 = 15 marks)

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*S50404A01332* Turn over
6 This question is about ascorbic acid.
Ascorbic acid, vitamin C, is an essential nutrient found mainly in fruits and vegetables.

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OH

O Data
O OH
Molecular formula C6H8O6
Molar mass 176 g mol–1
Very soluble in water
HO OH

(a) Use asterisks (*) to identify on the structure the chiral carbon atoms in ascorbic acid.
(1)
(b) Explain why ascorbic acid is very soluble in water.
(3)

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 (c) Ascorbic acid is hydrolysed in acidic conditions.
Draw the structure of the organic product.
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(2)
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*S50404A01532* Turn over
 (d) The percentage of ascorbic acid in a vitamin C tablet is found as follows.
● The vitamin C tablet of mass 0.550 g is dissolved in distilled water in a beaker

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and then the solution and washings are added to a volumetric flask.
The volume is made up to 250.0 cm3 with distilled water. The solution is
mixed thoroughly.
● 25.0 cm3 of the solution is placed in a conical flask and acidified with dilute
sulfuric acid.
● About 1 g of solid potassium iodide, an excess, is dissolved in the mixture in
the conical flask.
● 1 cm3 of starch solution is added.
● The mixture is titrated with 4.00 × 10−3 mol dm−3 potassium iodate(V), KIO3 ,
until the appearance of a permanent blue-black colour.
● The titration is repeated twice more and the mean titre is 20.45 cm3.
The reactions taking place are:

Reaction 1 The iodate(V) ions react with iodide ions to form iodine.

IO−3 + 5I− + 6H+ → 3I2 + 3H2O

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Reaction 2 As soon as the iodine is formed, it is reduced to iodide ions by the ascorbic acid.

C6H8O6 + I2 → C6H6O6 + 2I− + 2H+

Reaction 3 When all the ascorbic acid has been used up, the iodine produced reacts with the
starch to give the blue-black colour.
Calculate the percentage of ascorbic acid in the vitamin C tablet to an appropriate
number of significant figures.
(5)

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(Total for Question 6 = 11 marks)

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 7 This question is about oxides of nitrogen.
(a) Nitrogen monoxide reacts with oxygen to form nitrogen dioxide.
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2NO(g) + O2(g) → 2NO2(g)

The following graph was produced from a series of experiments to determine the
rate equation for this reaction. In each experiment the concentration of oxygen
was the same.

Initial rate

[NO]2 / mol2 dm–6

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(i) Deduce the order of reaction with respect to nitrogen monoxide.

(1)

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(ii) A new series of readings was taken with the concentration of oxygen doubled.
The gradient of the line doubled.
State, with a reason, the order of reaction with respect to oxygen.
(1)

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(iii) Write the rate equation for the reaction and give the units for the rate constant.
(2)
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*S50404A01732* Turn over
 (b) The rate of the decomposition of dinitrogen pentoxide was studied at different
temperatures.

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2N2O5(g) → 2N2O4(g) + O2(g)
The rate constant, k, was determined at each temperature, T, measured in kelvin.
(i) A graph was plotted of ln k against 1/T, resulting in a straight line.
The gradient of the straight line was −1.24 × 104 K.
Calculate the activation energy for the reaction, giving your answer to an
appropriate number of significant figures.
The rate constant of a reaction, k, is related to the temperature, T, by the expression

Ea 1
In k = − × + a constant
R T

[Gas constant, R = 8.31 J mol−1 K−1]

(3)

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*S50404A01832*
 (ii) Explain, in terms of all oxidation numbers, why the decomposition of
dinitrogen pentoxide is a redox reaction.
(2)
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................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .

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(Total for Question 7 = 9 marks)

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 8 This question is about the identification of an unknown organic compound X.
(a) 2.73 g of compound X is completely burned in oxygen.
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Carbon dioxide and water are the only two products.

The masses of carbon dioxide and water formed are 5.89 g and 2.41 g respectively.

Show, by calculation, that these data are consistent with a formula of C5H10O2 for
compound X.
(4)
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(b) Compound X does not react with sodium carbonate, phosphorus(V) chloride or
Fehling’s solution.
What is the functional group present in compound X?
(1)
A alcohol
B aldehyde
C carboxylic acid
D ester

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 (c) The infrared spectrum of compound X is shown below.
100

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Transmittance (%)

50

0
4000 3000 2000 1500 1000 500
Wavenumber / cm–1

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There are 4 peaks in the 13C NMR spectrum.
The high resolution proton NMR spectrum of compound X consists of 3 peaks in
the ratio 1:3:6 and with splitting patterns septet (split into 7): singlet : doublet.
Compound X was formed from ethanoic acid and another organic compound.
Identify compound X and explain how the structure of the compound is
consistent with all of the data provided.
(6)

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

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

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

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

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

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

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

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

(Total for Question 8 = 11 marks)

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*S50404A02432*
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 9 This question is about benzenediazonium chloride.
Benzenediazonium chloride is made from benzene in 3 steps.
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NO2 NH2
Step 1 Step 2

sodium nitrite, NaNO2

Step 3 hydrochloric acid
5°C
N2Cl

benzenediazonium chloride
(a) (i) State the reagents required for Step 1 and the type and mechanism of the reaction.
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(2)

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

(ii) State the reagents and conditions for Step 2 and the type of reaction occurring.
(3)

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

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

(iii) Write the balanced equation for the reaction taking place in Step 3.
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State symbols are not required.

(1)

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*S50404A02532* Turn over
 (b) Benzenediazonium chloride is hydrolysed in solution.

C6H5N2Cl(aq) + H2O(l) → C6H5OH(aq) + N2(g) + HCl(aq)

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The kinetics of this reaction can be followed by measuring the volume of
nitrogen at regular time intervals until the reaction is complete. The results of an
experiment are shown in the table.

Time, t Volume of nitrogen (V∞ – Vt)

/ min / cm3 / cm3
0 0 60
4 20 40
8 32 28
12 41 19
16 47 13
20 52 8

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24 54 6

∞ 60 0

(i) Show that the maximum volume of nitrogen produced from 250 cm3 of a
0.01 mol dm−3 solution of benzenediazonium chloride is 60 cm3.
[The molar volume of gas at room temperature and pressure is 24 dm3 mol−1]
(2)

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*S50404A02632*
 (ii) The concentration of benzenediazonium chloride at any time, t, is proportional to
the maximum volume of nitrogen produced minus the volume of nitrogen collected
at time t.
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[C6H5N2Cl] ∝ (V∞ – Vt)

Plot a graph to calculate the initial rate of reaction. Include units in your
answer.
(5)
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Initial rate of reaction .. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .

*S50404A02732*
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 (iii) Use your graph to determine the order of reaction with respect to
benzenediazonium chloride.

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Justify your answer.
(3)

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

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

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

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

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

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

(Total for Question 9 = 16 marks)

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TOTAL FOR PAPER = 90 MARKS

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