Oxford Cambridge and RSA

A Level Chemistry A
H432/02 Synthesis and analytical techniques

Practice paper – Set 2

Time allowed: 2 hours 15 minutes
*PRACTICE2016*

You must have:

• the Data Sheet for Chemistry A
You may use:
• a scientific or graphical calculator
• a ruler (cm/mm)

First name

Last name

Centre Candidate
number number

INSTRUCTIONS
• Use black ink. You may use an HB pencil for graphs and diagrams.
• Complete the boxes above with your name, centre number and candidate number.
• Answer all the questions.
• Write your answer to each question in the space provided. If additional space is
required, use the lined page(s) at the end of this booklet. The question number(s) must
be clearly shown.
• Do not write in the barcodes.

INFORMATION
• The total mark for this paper is 100.
• The marks for each question are shown in brackets [ ].
• Quality of extended responses will be assessed in questions marked with an
asterisk (*).
• This document consists of 28 pages.

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SECTION A

You should spend a maximum of 20 minutes on this section.

Write your answer to each question in the box provided.

Answer all the questions.

1 Propane reacts with chlorine as shown below.

CH3CH2CH3 + Cl 2 CH3CH2CH2Cl + HCl

What is the mechanism of this reaction?

A Electrophilic addition

B Electrophilic substitution

C Radical substitution

D Nucleophilic substitution

Your answer [1]

2 A chemist reacts the following compound with hydrogen bromide, HBr.

CH3 CH3

C C

CH3 H

What is the name of the major product?

A 2-Bromo-3-methylbutane

B 2-Bromo-2-methylbutane

C 3-Bromo-3-methylbutane

D 3-Bromo-2-methylbutane

Your answer [1]

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3 The compound shown below reacts with a mixture of NaBr and H2SO4.

HO
OH

What is the relative molecular mass of the organic product?

A 138.9

B 155.9

C 201.8

D 235.8

Your answer [1]

4 What is the number of sigma bonds in a benzene molecule?

A 3

B 6

C 9

D 12

Your answer [1]

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5 What is the number of chiral centres in the molecule below?

OH

O
O OH

A 4

B 5

C 6

D 7

Your answer [1]

6 Which compound cannot be hydrolysed?

A CH3COOH

B CH3COCl

C CH3CONHCH3

D CH3COOCH3

Your answer [1]

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7 The compound shown below can be prepared from phenol.

OH

NH2

Which reagent(s) is/are required?

A Concentrated NH3

B Dilute NH3

C Dilute HNO3 and then concentrated HCl /Sn

D Dilute HNO3 and then NaBH4

Your answer [1]

8 The compound shown below reacts with hydrogen chloride gas at room temperature and pressure
to form a saturated compound.

What volume of hydrogen chloride reacts with 0.25 mol of the compound?

A 6 cm3

B 12 cm3

C 6 dm3

D 12 dm3

Your answer [1]

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9 What is the systematic name of the compound below?

A 2-Ethylpentan-4-one

B 4-Ethylpentan-2-one

C 3-Methylhexan-5-one

D 4-Methylhexan-2-one

Your answer [1]

10 A student plans the two-step synthesis below.

HOCH2CH=CHCH2OH intermediate HOOCCH2COCOOH

Which compound could be the student’s intermediate?

A HOOCCH=CHCOOH

B HOCH2CH2CHICOOH

C HOCH2CH2CH(OH)CH2OH

D HOCH2CH(OH)CH(OH)CH2OH

Your answer [1]

11 Which reagent could be used to distinguish between CH3CH2OH and C6H5OH?

A AgNO3(aq) in ethanol

B CH3COCl

C Na2CO3(aq)

D Bromine water

Your answer [1]

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12 How many peaks are observed in the 13C NMR spectrum of 1,3-dimethylbenzene?

A 3

B 4

C 5

D 6

Your answer [1]

13 CH3CH2Cl reacts with an excess of ethanolic NH3.

Which compound is the main organic product?

A CH3CH2NH2

B (CH3CH2)2NH

C (CH3CH2)3N

D (CH3CH2)4N+

Your answer [1]

14 Which bond angle(s) is/are present in a molecule of but-2-en-1-ol?

1 120°

2 109.5°

3 104.5°

A 1, 2 and 3

B Only 1 and 2

C Only 2 and 3

D Only 1

Your answer [1]

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15 Which term(s) best describe(s) the following molecule?

1 aromatic

2 unsaturated

3 alicyclic

A 1, 2 and 3

B Only 1 and 2

C Only 2 and 3

D Only 1

Your answer [1]

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BLANK PAGE

PLEASE DO NOT WRITE ON THIS PAGE

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SECTION B

Answer all the questions.

16 This question is about two different homologous series, the alcohols and the haloalkanes.

(a) (i) Define the term homologous series.

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...................................................................................................................................... [2]

(ii) What is the general formula of a member of the alcohols homologous series?

...................................................................................................................................... [1]

(b) The mass spectrum of alcohol A is shown below.

100 X

80

60
relative
intensity
40

20

0
10 20 30 40 50 60 70 80 90
m/z

Determine the structure of alcohol A and fragment ion X.

Explain your reasoning.

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(c) Haloalkanes are hydrolysed by aqueous sodium hydroxide.

(i) Outline the mechanism of the reaction of 1-bromobutane with aqueous sodium hydroxide.

Include curly arrows, relevant dipoles and the structure of the organic product.

[3]

(ii) Name the type of mechanism in (c)(i).

...................................................................................................................................... [1]

(iii) The organic product in (c)(i) can be formed faster using a different haloalkane than
1-bromobutane.

Identify this haloalkane.

Explain your answer.

Haloalkane ........................................................................................................................

Explanation .......................................................................................................................

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

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(d) The use of some haloalkanes, such as chlorotrifluoromethane, has been banned as they
form Cl • radicals which break down ozone.

(i) Construct an equation to show the formation of Cl • radicals from chlorotrifluoromethane.

...................................................................................................................................... [1]

(ii) Ozone is broken down by Cl • radicals in a two-step process.

Write the equations for the two steps and the overall equation for this process.

Step 1 ................................................................................................................................

Step 2 ................................................................................................................................

Overall equation ........................................................................................................... [3]

(iii) A research chemist found that 1.00 g of Cl • radicals can breakdown 135 kg of O3.

Calculate the number of O3 molecules removed by one Cl • radical.

Give your answer in standard form and to three significant figures.

number of O3 molecules = ......................................................... [3]

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(e)* Five compounds B–F have the boiling points shown below.

Compound Boiling point / °C

B –12
C 0
D 35
E 48
F 97

The structural formulae of compounds B–F are shown below in no particular order.

CH3CH2CH2CH3, CH3CH2CH2NH2, CH3CH2CH2OH, CH3CH(CH3)CH3, CH3CHCl CH3

Using this information, identify compounds B–F.

Explain your reasoning.

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17 This question is about α-amino acids.

(a) Serine, H2NCH(CH2OH)COOH, is a naturally occurring α-amino acid.

(i) Serine has two optical isomers.

Explain what is meant by the term optical isomers, and draw the two optical isomers of
serine.

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[3]

(ii) Serine can react with the α-amino acid glycine, H2NCH2COOH, to form three different
organic products, each with the molecular formula C5H10N2O4.

Draw the structures of the three organic products that can be formed by the reaction of
serine with glycine.

[3]

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(b) The general formula of an α-amino acid is RCH(NH2)COOH.

(i) Aspartic acid (R = CH2COOH) is reacted as shown in the flowchart below.

Draw the structures of aspartic acid and the missing organic products in the boxes.

HCl (aq)

aspartic acid

excess CH3OH/H2SO4

[4]

(ii) Compound G is an α-amino acid with a branched R group.

0.0300 mol of G has a mass of 3.51 g.

Determine the molar mass of α-amino acid G and suggest its structure.

[2]
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(c) A student hydrolyses a sample of protein and uses Thin-Layer Chromatography (TLC) to
analyse the mixture of amino acids produced.

The chromatogram obtained is shown in Fig. 17.1.

Table 17.1 shows the Rf values for different amino acids in the solvent used.

solvent front
Amino acid Rf value
Threonine 0.65
Valine 0.60
Histidine 0.53
Serine 0.45
Leucine 0.38

Table 17.1
baseline

Fig. 17.1

(i) Analyse the chromatogram to identify the amino acids.

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(ii) The student runs a second chromatogram on the sample using a more polar solvent.

Predict the effect, if any, on the Rf values of the amino acids. Explain your reasoning.

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(d) A student plans a two-stage synthesis of alanine from lactic acid, CH3CH(OH)COOH.

The synthesis first prepared compound H, as shown in the flowchart.

Draw the structure of compound H in the box and add the formulae of the reagents for each
stage on the dotted lines.

HO ....................................
OH

lactic acid
compound H

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

H 2N
OH

alanine
[3]

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18 This question is about medical compounds made from salicylic acid.

(a) Salicylic acid can be made from the reaction of phenol with carbon dioxide as shown below.

OH O– O– OH
COO– COOH
Stage 1 Stage 2 Stage 3
NaOH(aq) CO2 HCl (aq)
phenol salicylic acid

(i) Stage 2 takes place by electrophilic substitution and part of the mechanism is shown
below.

Complete the mechanism by showing relevant dipoles, curly arrows and the structure of
the intermediate.

O– O

intermediate

O– O
C
O–
+ H+

[3]

(ii) What type of reaction takes place during Stage 1 and Stage 3?

Explain your answer.

Type of reaction .................................................................................................................

Explanation ........................................................................................................................

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

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(iii) A chemist prepares 4.83 g of salicylic acid from phenol. The percentage yield of this
reaction is 45.0%.

Calculate the mass of phenol that the chemist uses.

Give your answer to three significant figures.

mass of phenol = ........................................................ g [3]

(b) Aspirin is an ester of salicylic acid.

Aspirin can be prepared by reacting salicylic acid with ethanoic anhydride, (CH3CO)2O.
One other organic compound also forms.

Draw skeletal formulae for the products of this reaction.

[2]

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(c) ‘Oil of wintergreen’ is used to relieve aching muscles and can be prepared by reacting salicylic
acid with methanol.

OH
COOH

salicylic acid

(i) Suggest the structure of oil of wintergreen and the conditions needed to prepare oil of
wintergreen from salicylic acid.

Structure

Conditions .................................................................................................................... [1]

(ii) After its preparation, oil of wintergreen can be purified by distillation.

Draw a labelled diagram showing how the apparatus is set up for distillation.

[2]

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19 This question is about the synthesis of a polymer.

(a) The flowchart below shows the synthesis of polymer I starting from benzene.

Draw the structures of the missing compounds in the boxes and add the missing reagents on
the dotted lines.

conditions..................................
benzene

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

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

repeat unit of polymer I

[6]

(b) Polymer I cannot be disposed of in landfill sites as it is not biodegradable.

Suggest one way of processing waste polymer I other than landfill and recycling.

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20 A student was provided with five compounds: an aldehyde, a ketone, a carboxylic acid and two
esters. The student decides to identify the type of compound by carrying out some chemical tests.

(a) Suggest chemical tests to identify the carboxylic acid and aldehyde.

For each test, include essential reagent(s), observation(s) and a balanced equation.

In your equations, use ‘R’ for the alkyl group.

(i) Test for carboxylic acid.

Reagent(s) ........................................................................................................................

Observation(s) ...................................................................................................................

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

Equation

[2]

(ii) Test for aldehyde.

Reagent(s) ........................................................................................................................

Observation(s) ...................................................................................................................

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

Equation

[2]

(b) Suggest a chemical test to distinguish the ketone from the two esters.

Reagent(s) ................................................................................................................................

Observation(s) ..........................................................................................................................

.............................................................................................................................................. [1]

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(c) The student wants to confirm that the other two compounds are esters. Unfortunately there is
no direct test for an ester group.

The esters are CH3COOC(CH3)3 and (CH3)3CCOOCH3.

The student plans the following:

• hydrolyse the two esters using aqueous sodium hydroxide.
• separate the hydrolysis products.
• carry out tests on the hydrolysis products.

(i) Write an equation for the hydrolysis of one of the two esters with aqueous sodium
hydroxide.

Show the structures for the organic compounds.

[2]

(ii) Suggest a chemical test on the hydrolysis products that would allow the two esters to be
identified.

Write an equation for one reaction that takes place.

Show the structures for the organic compounds.

Reagent(s) ........................................................................................................................

Observation(s) ...................................................................................................................

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

Equation

[2]

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(iii) The student thought that NMR spectroscopy could be used to identify the two esters
without the need to carry out chemical tests.

The esters are CH3COOC(CH3)3 and (CH3)3CCOOCH3.

Explain whether the student is correct for 13C and 1H NMR spectroscopy. Your answer
should also clearly state any differences between the spectra of the two esters.

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(d) The ketone and aldehyde provided to the student both contain five carbon atoms.

The 1H NMR spectrum of the aldehyde contains two singlet peaks only:
a large peak at δ = 1.2 ppm and smaller peak at δ = 9.6 ppm.

Suggest all possible structures for the ketone and identify the aldehyde.

Show all your reasoning.

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21* Compound J is an organic compound containing carbon, hydrogen and nitrogen only.

A chemist analyses compound J and the results are shown below:

Elemental analysis by mass:

C: 74.17%; H: 11.41%; N, 14.42%

Mass spectrum
Molecular ion peak at m/z = 97.0

Infrared spectrum
100

transmittance
(%) 50

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

1H NMR spectrum

3 2 1 0
chemical shift, δ/ppm

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Use the information provided to suggest a structure for compound J.

Show all of your reasoning.

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END OF QUESTION PAPER

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If additional space is required, you should use the following lined page(s). The question number(s)
must be clearly shown in the margin(s).

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