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F324

1.

All Questions

p1 to p95

Short sections of the molecular structures of two polymers are shown below.
H

polymer C
O

polymer D

(a)

(i)

Circle, on the diagrams above, the simplest repeat unit in each polymer.
[2]

(ii)

In the boxes below, draw the displayed formulae of the two monomers that
could be used to prepare polymer D.

[2]

Strode's College

(b)

Chemists have developed degradable polymers to reduce the quantity of plastic


waste being disposed of in landfill sites. Polymer D is more likely to be a
degradable polymer than polymer C.
Suggest two reasons why.
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[2]
[Total 6 marks]

Strode's College

2.

Amino acids can act as monomers in the formation of polypeptides and proteins. The
structures below show three amino acids, glycine, phenylalanine and proline.
H
H2N

C
H

H
COOH

H2N

H
COOH

CH2
C6H5

glycine

phenylalanine

HN

H2C

COOH
CH2

C
H2
proline

Glycine, phenylalanine and proline can react together to form a mixture of tripeptides.
(i)

Draw the structure of the tripeptide formed in the order glycine, phenylalanine
and proline.

[3]

(ii)

How many different tripetides could have been formed containing glycine,
phenylalanine and proline?
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[1]

Strode's College

(iii)

The mixture of tripeptides can be analysed by using gas chromatography,


coupled with mass spectrometry.
Summarise how each method contributes to the analysis.
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[3]
[Total 7 marks]

3.

Propanal, CH3CH2CHO, can be used in the synthesis of organic compounds.


CH3CH2CHO reacts with NaBH4 in a nucleophilic addition reaction. The nucleophile
can be represented as a hydride ion, H. A mechanism for the reaction is shown below.
H
+
H

NaBH4
step 1

C
H
H

(i)

O
CH3C H2

CH3CH2

C
H

step 2
H

organic product

Add 'curly arrows' to the mechanism to show how the intermediate reacts with the
water molecule in step 2.
[2]

Strode's College

(ii)

Draw the structure of the organic product in the box above.


[1]

(iii)

What is meant by the term nucleophile?


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[1]

(iv)

Describe, in words, exactly what is happening to the electron pairs and bonds in
step 1 of the mechanism above.
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[3]
[Total 7 marks]

4.

Benzene reacts with chlorine in the presence of a halogen carrier, such as AlCl3.
(a)

(i)

Write the equation for the reaction of benzene with chlorine.

[1]

(ii)

How does the halogen carrier allow the reaction to take place?
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[1]

Strode's College

(iii)

Outline a mechanism for this reaction.


Include curly arrows and relevant dipoles.

[4]

(iv)

State the name of this mechanism.


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[1]

(b)

In contrast to benzene, the reaction of an alkene with bromine does not need a
halogen carrier.
Compare the different reactivities of benzene and alkenes towards chlorine.
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[3]
[Total 10 marks]

Strode's College

5.

An unknown colourless liquid with molecular formula C4H8O was thought to be one of
butanal, but-3-en-1-ol, or butanone.
H
H

O
C

C
H

butanal

(a)

OH

H
H

but-3-en-1-ol

butanone

State a simple chemical test that would positively identify:


(i)

butanal only;
reagent .................................................................................................
observation ...........................................................................................
organic product .....................................................................................
[3]

(ii)

but-3-en-1-ol only.
reagent .................................................................................................
observation ...........................................................................................
type of reaction .....................................................................................
[3]

Strode's College

(b)

Butanal and butanone both react with 2,4-dinitrophenylhydrazine to produce


mixtures containing orange precipitates.
Outline how the mixtures containing these orange precipitates can be used to
distinguish between butanal and butanone.
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[3]
[Total 9 marks]

6.

Unknown compounds are often identified by n.m.r. spectroscopy.


Part of the n.m.r. spectrum of butanone is shown on the axes below.

absorption
of energy
B

10

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5
4
chemical shift/

(i)

State which part of the butanone molecule is responsible for peak A at = 2.1.
Explain your reasoning.
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[2]

(ii)

Explain why peak B is split into a quadruplet.


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[1]

(iii)

Predict the remainder of the n.m.r. spectrum of butanone by sketching it on the


axes above.
[2]

(iv)

Write the relative peak area above each of the peaks on the completed spectrum
of butanone.

[1]
[Total 6 marks]

Strode's College

7.

In this question, one mark is available for the quality of the use and organisation of
scientific terms.
In all living organisms a large variety of polypeptides and proteins are formed naturally
from -amino acids.
State the general formula of an -amino acid and use it to describe how amino acids
can be combined to give a variety of polypeptides and proteins.

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[6]
Quality of Written Communication [1]
[Total 7 marks]

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10

8.

The method below can be used to make phenylamine from nitrobenzene in the
laboratory.
3.69 g of nitrobenzene and 8 g of tin (an excess) were placed into a flask. The flask
was fitted with a reflux condenser. Concentrated hydrochloric acid was then added
dropwise to the flask.
The mixture was heated for 30 minutes to complete the reaction.
Once the mixture had cooled, concentrated sodium hydroxide solution was added until
the mixture was alkaline.
Purification gave a 72.1% yield of phenylamine.

(a)

Reaction of nitrobenzene with the tin and hydrochloric acid produces


phenylammonium chloride as the organic product.
(i)

Complete the equation for this reaction.

NO2

[H]

HCl

NH3 + Cl

phenylammonium chloride
[2]

(ii)

State what the symbol [H] in the equation represents.


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[1]

(b)

When the sodium hydroxide was added, the phenylammonium chloride was
converted to phenylamine.
Write an equation for this reaction.

[2]

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(c)

Calculate the mass of phenylamine that was produced from the 3.69 g of
nitrobenzene in this experiment. Give your answer to three significant figures.
Mr: nitrobenzene,123; phenylamine, 93.1

mass of phenylamine = . g
[4]
[Total 9 marks]

9.

Noradrenaline is produced naturally by nerve cells in the brain. Compound P is a


synthetic compound that has been widely used as an appetite suppressant. It is
thought to be effective because it is similar to noradrenaline.
OH

OH
HO

NH2
CH3

HO
noradrenaline

(a)

(i)

NH2

compound P

Suggest a reagent that could be used in a test to distinguish compound P


from noradrenaline.
...............................................................................................................
[1]

(ii)

Draw a ring round the functional group responsible for the positive result in
the test you have chosen.
[1]

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(iii)

State the expected observation for the positive result in the test you have
chosen.
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[1]

(b)

Both these compounds have stereoisomers due to the presence of chiral centres.
(i)

Identify the chiral centres in each molecule by labelling them clearly with
asterisks (*) on the structures above.
[2]

(ii)

State the type of stereoisomerism caused by the presence of chiral centres.


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

(iii)

Using noradrenaline as an example, explain how a chiral centre gives rise


to the stereoisomers. Illustrate your answer with a suitable diagram of the
stereoisomers.
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[3]

Strode's College

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(c)

Explain why a pharmaceutical company may produce an appetite suppressant


containing only one stereoisomer of compound P, rather than a mixture of the
stereoisomers.
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[3]
[Total 12 marks]

Strode's College

14

10.

In this question, one mark is available for the quality of spelling, punctuation and
grammar.
Describe with the aid of suitable diagrams the bonding and structure of a benzene
molecule.

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[6]
Quality of Written Communication [1]
[Total 7 marks]

Strode's College

15

11.

The demand for natural shampoos and detergents has led to the development of more
biodegradable detergents such as sorbitan monolaurate, which is made from plants.

OH
O

C11 H23

O
O

HO

OH
sorbitan monolaurate

(i)

Suggest a type of reaction that could break down sorbitan monolaurate when it is
washed into drains and rivers.
Explain your answer and state the type of organic products formed.
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[3]

(ii)

Suggest one other reason why detergents such as sorbitan monolaurate are
regarded as environmentally friendly.
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[1]
[Total 4 marks]

Strode's College

16

12.

The four amino acids shown below are found in proteins and enzymes.

H
H2 N

H
COOH

H2 N

H
COOH

(CH 2 ) 4 NH2

glycine

lysine

H2 N

COOH

CH2 SH
cysteine

H
H2 N

COOH

CH2CH2 COOH
glutamic acid
Write down the structural formula for a dipeptide formed from one molecule of glycine
and one of lysine.

[Total 2 marks]

13.

Chromatography is an important analytical technique used to separate mixtures into


their individual components.
(a)

Define the following terms used in chromatography.


Rf value ..........................................................................................................
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retention time .................................................................................................
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[2]

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(b)

Volatile organic compounds that enter soil via waste disposal sites affect the
quality of the soil.
A preliminary step in analysing soil quality involves separation of these volatile
components using gas/liquid chromatography.
(i)

What name is given to the process by which components in a mixture are


separated during gas/liquid chromatography?
...............................................................................................................
[1]

(ii)

What are the roles of the gas and liquid in gas/liquid chromatography?
role of gas .............................................................................................
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role of liquid ..........................................................................................
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[2]

(iii)

Draw a diagram of a gas/liquid chromatogram for a mixture containing two


components.

time
[1]

Strode's College

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(iv)

Explain how the gas/liquid chromatogram could be used to determine the


percentage composition of each component in the mixture.
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[3]
[Total 9 marks]

Strode's College

19

14.

In this question, one mark is available for the quality of use and organisation of
scientific terms.
The structural formulae of three isomers of C3H9NO are shown below.

CH3
H2N

CH2

CH2

CH2

OH

H2N

CH2

CH

CH3
OH

H2N

OH

CH3
Describe the similarities and differences you would expect to see when comparing
the

infra-red spectrum of each isomer

mass spectrum of each isomer.

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[5]
Quality of Written Communication [1]
[Total 6 marks]

Strode's College

20

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15.

Compound A, shown below, is an amino acid that is being used in the development of
a new anti-inflammatory drug.

H2N

CH3 H

O
C
OH

compound A

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22

(a)

(i)

Explain why this molecule is described as an amino acid.


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[1]

Strode's College

23

(ii)

State the general formula of an -amino acid.


Explain whether or not compound A fits this general formula.

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[2]

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24

(b)

Compound A exists as a zwitterion in aqueous solution.


(i)

Draw the structure of this zwitterion.

[1]

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25

(ii)

Show how the structure of the zwitterion would change if the solution was
acidified with dilute hydrochloric acid.

[1]

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(c)

The anti-inflammatory drug is made by combining compound A with compound


B, shown below. R represents a side chain.
H
R

O
C

OH

compound B

Show the structure of the anti-inflammatory drug formed from compound A and
compound B.

[2]
[Total 7 marks]

Strode's College

27

16.

The diagram below shows some reactions of phenol.


O Na+

OH
Br

Br

Br
OH

II

phenol
IV

III
OH

OH

NO2

N
N

(i)

On the diagram above, identify suitable reagents that could be used to carry out
reactions I, II and III.
[3]

(ii)

State a use for the compound formed in reaction IV.


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[1]

Strode's College

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(iii)

Outline how you could carry out reaction IV in the laboratory starting from phenol
and a suitable aromatic amine.
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[5]
[Total 9 marks]

Strode's College

29

17.

In this question, one mark is available for the quality of spelling, punctuation and
grammar.
Phenol reacts much more readily with bromine than benzene does.

Describe, with the aid of a diagram, the bonding in benzene.

Explain why electrophiles, such as bromine, react much more readily with phenol
than with benzene.

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[7]
Quality of Written Communication [1]
[Total 8 marks]

Strode's College

30

18.

Nylon is sometimes used for electrical insulation. However, if there is a risk of high
temperatures then a polymer such as Nomex, with a higher melting point, is used.
The repeat unit of Nomex is shown below.

(i)

C
N

Draw the structures of two monomers that could be used to form Nomex.

[2]

(ii)

Suggest a reason why the melting point of Nomex is higher than that of nylon.
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[1]
[Total 3 marks]

Strode's College

31

19.

But-2-enal, CH3CH=CHCHO, is a pale yellow, flammable liquid with an irritating odour.


But-2-enal exists as two stereoisomers.
Draw skeletal formulae to show the structure of the two stereoisomers of but-2-enal.

[Total 2 marks]

20.

But-2-enal, CH3CH=CHCHO, is a pale yellow, flammable liquid with an irritating odour.


(a)

(i)

Describe a simple chemical test that would show that but-2-enal is an


aldehyde.
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[2]

(ii)

Explain why this test gives a different result with aldehydes than it does
with ketones.
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[1]

Strode's College

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(b)

But-2-enal also reacts with sodium borohydride, NaBH4.


(i)

Identify the organic compound formed in this reaction.

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

(ii)

State the type of chemical reaction occurring.


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[1]

(c)

Precautions must be taken to prevent but-2-enal catching fire.


Construct a balanced equation for the complete combustion of but-2-enal,
C4H6O.

[1]
[Total 6 marks]

Strode's College

33

21.

(a)

The reaction of trichloroethanal with water is a nucleophilic addition reaction. It


can be catalysed by small amounts of hydroxide ions, OH.
Complete the diagram below to suggest a mechanism for this reaction. Show all
the relevant dipoles and curly arrows.
H
Cl
Cl

O
Cl

C
H

Cl

Cl

Cl

H
H
[5]

(b)

The recommended adult dose of chloral hydrate as a sedative is 250 mg, three
times a day.
Calculate the mass of trichloroethanal you would need to react with water to
make one weeks supply of chloral hydrate for an adult, assuming a 60% yield.
Mr: chloral hydrate, 165.5; trichloroethanal, 147.5

mass of trichloroethanal = g
[3]
[Total 8 marks]

Strode's College

34

22.

Chloral hydrate is broken down in the body after several hours. One reaction is
oxidation to trichloroethanoic acid.
Complete the equation for this reaction below.
Cl3CCH(OH)2

[O]

[Total 1 mark]

23.

An ester D with the formula, CH3CH2COOCH2CH(CH3)2, is used in rum flavouring.


(a)

Draw a displayed formula of ester D.

[2]

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(b)

Outline how you could obtain a sample of ester D, starting with a named
carboxylic acid and a named alcohol.
Include any essential reaction conditions and write an equation for the reaction.
You do not need to include any details of the separation or purification of the
ester.

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[6]

(c)

State a spectroscopic method that could be used to confirm that a sample of


ester D has a molecular mass of 130.
Explain how you would obtain the molecular mass of D from the spectrum.
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[2]
[Total 10 marks]

Strode's College

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24.

In this question, one mark is available for the quality of the use and organisation of
scientific terms.
Describe and explain the different ways that a high resolution n.m.r. spectrum can give
information about a molecule.
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[7]
Quality of Written Communication [1]
[Total 8 marks]

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25.

Linoleic acid, C17H31COOH, is an unsaturated fatty acid found in triglycerides from


sunflower oil.
(i)

Draw the structure of the triglyceride made from linoleic acid, C17H31COOH, and
propane-1,2,3-triol. Show clearly all the bonds in the ester groups.

[2]

(ii)

Deduce the number of carbon to carbon double bonds in a molecule of the


triglyceride.
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[1]
[Total 3 marks]

26.

Explain why triglycerides are soluble in non-polar solvents and not in water.
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[Total 3 marks]

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27.

Compound A is used to add the flavour of mushrooms to foods.


O
C

H3C
C
H

CH2
O

C
CH3
compound A

(a)

(i)

Apart from the benzene ring, name the two functional groups in
compound A.
.....................................................

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

(ii)

Draw the skeletal formula of compound A.

[1]

(iii)

Deduce the molecular formula of compound A.


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[1]

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(b)

Compound B is a stereoisomer of compound A.


Explain what is meant by the term stereoisomerism. Use compounds A and B to
illustrate your answer.
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[2]

(c)

If the food is cooked for a long time, naturally occurring acids catalyse the
hydrolysis of compound A.
Draw structures to show the two organic compounds formed by the acid
hydrolysis of compound A.

[2]

(d)

The hydrolysis of compound A can be monitored by sampling the mixture at


regular intervals, separating the components, and recording their infra-red
spectra.
(i)

State two absorptions that would be expected in the infra-red spectrum of


compound A, and identify the parts of the molecule responsible for each.
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[2]

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(ii)

Suggest a wavenumber range within the spectrum that could be used to


clearly distinguish compound A from the products formed by the hydrolysis
reaction.
Explain your answer.
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[2]
[Total 12 marks]

28.

Thua nao is a traditional sauce made in Northern Thailand by fermenting cooked


soybeans. Its unique flavour is due to a range of volatile compounds formed during the
fermentation.
One of these volatile compounds is 3-hydroxybutanone.

OH H

3-hydroxybutanone

(a)

State the meaning of the term volatile.


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[1]

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(b)

Several hydroxyketones with similar boiling points can be separated from the
fermentation mixture.
Describe a method, which does not involve spectroscopy, that could be used to
distinguish 3-hydroxybutanone from the other hydroxyketones.
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[4]
[Total 5 marks]

29.

Phenol reacts readily with dilute nitric acid at room temperature in a nitration reaction to
produce a mixture of products as shown below.
OH

OH
dilute HNO3

OH
NO2
and

room temp
NO2

(a)

Suggest the structure of another organic product that is likely to be formed in the
nitration of phenol.

[1]

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(b)

Assuming a yield by mass of 27% for 4-nitrophenol, calculate the mass of


4-nitrophenol that would be produced from 100 g of phenol. Show your working.
Give your answer to an appropriate number of significant figures.

mass of 4-nitrophenol = g
[4]

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(c)

In this question, one mark is available for the quality of spelling, punctuation and
grammar.
Compare the reagents and conditions for the nitration of phenol with those used
for the nitration of benzene.
State and explain the effect of the OH group on the reactivity of the benzene
ring in phenol.
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[7]
Quality of Written Communication [1]
[Total 13 marks]

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30.

4-Nitrophenol can be converted into a range of useful organic chemicals. Draw the
structures of the organic products formed in the following reactions.

NaOH(aq)

Br2(aq)

OH

NO2

Sn(s)
conc.
HCl(aq)

CH3COCl(I)

[Total 4 marks]

31.

The reducing agent, NaBH4, is used widely in organic chemistry. One example is for
the reduction of diphenylethanedione, C14H10O2, shown below.
O
C
C
O
diphenylethanedione

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(i)

Draw a displayed formula to show the structure of the organic product that would
be formed by reducing diphenylethanedione with excess NaBH4.

[1]

(ii)

Complete and balance the equation for this reaction, using [H] to represent the
reducing agent.
C14H10O2

[1]
[Total 2 marks]

32.

Diphenylethanedione is a pale yellow colour, which disappears when it is reduced.


The colour results from the arrangement of the delocalised -bond electrons.
Explain what is meant by the term delocalised -bond electrons.
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[Total 2 marks]

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33.

Coloured organic compounds also include azo dyes.


Describe how an azo dye can be made from phenylamine. Show the structure of the
azo dye and the organic intermediate in your answer.
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[Total 6 marks]

34.

The fibres used in carpets are made from synthetic or natural polymers such as
nylon-6,6, OrlonTM and wool.
(a)

Complete the table below.


OrlonTM

nylo-6,6

monomer(s)

HO

repeat unit of
the polymer

(CH2)4

H2N

(CH2)6

NH2

OH

CN

type of
polymerisation
[4]

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47

(b)

Nylon-6,6 can be made from its monomers in the laboratory in two stages as
shown below.
O
HO

O
(CH2)4

OH

stage 1
O
Cl

O
(CH2)4

Cl

H2N

(CH2)6

NH2

stage 2
nylon-6,6

(i)

State a suitable reagent to carry out stage 1.


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

(ii)

Deduce the inorganic product that is also formed in stage 2.


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

(c)

Industrially, nylon-6,6 is not manufactured by the method in (b). Instead, the two
monomers are mixed directly at room temperature to give a salt. This salt is then
heated to convert it to nylon-6.6.
Suggest the structures of the two ions present in this salt.

[2]

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(d)

Wool is a protein. It is a natural polymer made by the same type of polymerisation


as nylon-6,6.
A section of the polymer chain in a protein is shown below.

CH2

H2C

CH3

OH

(i)

How many monomer units does this section contain?


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

(ii)

Draw the structure of one of the monomer molecules that was used to form
this section.

[1]

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49

(iii)

State three ways in which the monomer units of a protein differ from those
of nylon-6,6.
...............................................................................................................
...............................................................................................................
...............................................................................................................
...............................................................................................................
...............................................................................................................
[3]
[Total 13 marks]

35.

(a)

In this question, one mark is available for the quality of use and organisation of
technical terms.
Bromine is used in organic chemistry to carry out a variety of electrophilic
reactions.
(i)

Strode's College

Describe and explain how a molecule of bromine acts as an electrophile.


Illustrate your answer with a diagram showing relevant dipoles and curly
arrows.

50

(ii)

Use your answer to (i) to explain why bromine reacts much more readily
with cyclohexene than it does with benzene.

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[7]
Quality of Written Communication [1]

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(b)

The compound iodine monobromide, IBr, also reacts with benzene in an


electrophilic reaction.
(i)

Which compound would be the main product of this reaction, iodobenzene


or bromobenzene? Explain your answer.
...............................................................................................................
...............................................................................................................
...............................................................................................................
...............................................................................................................
[2]

(ii)

Deduce an equation for the reaction of iodine monobromide with benzene.

[1]
[Total 11 marks]

36.

Glyceryl trihexanoate is a triglyceride that can be made from glycerol


(propane-1,2,3-triol) and hexanoic acid, C5H11COOH.
Draw the structure of glyceryl trihexanoate. Show every bond in the functional groups.

[Total 2 marks]

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52

37.

Compound G can be extracted from sugar-cane and is commonly used in rejuvenating


skin creams because it helps to remove some of the dead cells from the skin surface.
The molecular formula of G is C2O3H4 and the compound contains two different
functional groups containing oxygen atoms.
The infra-red and mass spectra of G are shown below.

absorption

4000

3000

2000
1500
wavenumber / cm 1

1000

500

100
80

relative
intensity

60
40
20
0
25

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50
m/e

75

53

(a)

After inspection of the mass spectrum of G, an analyst wrote the comment:


The molecular ion peak appears to be missing from the spectrum.
The base peak is due to a fragment ion with m / e = 31.
(i)

Explain what is meant by the following terms.


molecular ion peak ...............................................................................
...............................................................................................................
base peak .............................................................................................
...............................................................................................................
[2]

(ii)

Suggest why the molecular ion peak is missing from the spectrum.
...............................................................................................................
...............................................................................................................
[1]

(b)

The structure of compound G is shown below.


OH
H

C
H

O
C
OH

Show how the infra-red and mass spectra confirm this structure. In your answer,
you should suggest a possible structure for the ion that gives the base peak at
m / e = 31 in the mass spectrum.
........................................................................................................................
........................................................................................................................
........................................................................................................................
........................................................................................................................
........................................................................................................................
........................................................................................................................
[4]

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54

(c)

The structure of compound G is shown below.


OH
H

O
C
OH

Sketch the 1H n.m.r. spectrum of compound G and label the relative peak areas.
Label any peaks that would be lost from the spectrum on shaking with D2O.

energy
absorbed

12

11

10

chemical shift /
[4]
[Total 11 marks]

38.

Leucine (2-amino-4-methylpentanoic acid) is a naturally occurring -amino acid that is


often used in protein supplements.
Leucine has a structural formula of (CH3)2CHCH2CH(NH2)COOH.
(a)

(i)

State the general formula of an -amino acid.


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

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55

(ii)

Draw a displayed formula of leucine.

[1]

(b)

Leucine can exist as a zwitterion.


(i)

State what is meant by the term zwitterion.


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

(ii)

Explain with the aid of a diagram how the zwitterion is formed from the
functional groups in leucine.

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

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56

(c)

Leucine can be obtained from a source of protein such as meat.


(i)

State suitable reagents and conditions to break down a protein into amino
acids.
...............................................................................................................
...............................................................................................................
[2]

(ii)

State the type of reaction occurring.


...............................................................................................................
[1]
[Total 8 marks]

39.

One of the final stages in winemaking involves the fermentation of malic acid to lactic
acid.
An equation for the reaction is shown below.
O
C
HO

OH

O
C

H
OH

malic acid

OH

O
C

CO2

OH

lactic acid

Both acids contain a chiral centre.


(i)

Identify the chiral centre on the structure of malic acid above using an asterisk *.
[1]

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57

(ii)

Draw a diagram to show the 3-D arrangement of groups around the chiral centre
in malic acid.

[1]
[Total 2 marks]

40.

Lactic acid produces an n.m.r. spectrum in D2O with peaks at chemical shift values of
1.4 ppm and 4.3 ppm.
(i)

On the axes below, sketch the high resolution n.m.r. spectrum of lactic acid in
D2O.
Show any splitting patterns and state the relative areas of the two peaks.

absorption
of energy

12

11

10

7
6
5
4
chemical shift /

0
[4]

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58

(ii)

How many peaks would you expect if the n.m.r. spectrum of lactic acid was run in
an inert solvent rather than in D2O? Explain your answer.
........................................................................................................................
........................................................................................................................
[2]
[Total 6 marks]

41.

As a wine ages, some of the acids slowly react with ethanol in the wine to produce
esters.
(i)

Draw a displayed formula to show the structure of the ester formed when lactic
acid reacts with ethanol.

[1]

(ii)

Suggest what effect this process might have on the flavour of the wine. Explain
your reasoning.
........................................................................................................................
........................................................................................................................
[1]
[Total 2 marks]

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59

42.

Salicylic acid is used in the manufacture of aspirin tablets. In the UK around 3500
tonnes of salicylic acid are manufactured per year.
O

OH

C
HO

salicylic acid

Salicylic acid is manufactured from phenol in three stages.

(a)

Phenol is first converted to sodium phenoxide, C6H5ONa+.


(i)

State a reagent that could be used for this reaction.


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

(ii)

Write a balanced equation for this reaction.

[1]

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60

(b)

The phenoxide ion is then combined with carbon dioxide under high pressure to
form the salicylate ion.
O

CO2

OH

This reaction is an electrophilic substitution reaction, which occurs by the


incomplete mechanism shown below. Carbon dioxide acts as the electrophile.
H+
O
C

O
step 1

H
step 2

O
intermediate

(i)

Add partial charges + and to show the polarisation of the C=O bonds in
the carbon dioxide molecule above.
[1]

(ii)

Complete the mechanism by adding curly arrows to show the movement of


electron pairs in step 1 to give the intermediate shown.
[2]

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61

(iii)

Carbon dioxide is normally a very poor electrophile. However, this reaction


does occur because the benzene ring in the phenoxide ion is activated.
Explain how the benzene ring in the phenoxide ion is activated.
...............................................................................................................
...............................................................................................................
...............................................................................................................
...............................................................................................................
...............................................................................................................
...............................................................................................................
[3]

(c)

In the final stage of this process, the salicylate ion is acidified to give salicylic
acid.
Assuming an overall yield by mass of 45% for this three stage process, calculate
the mass of phenol that is needed to produce the annual UK output of
3500 tonnes of salicylic acid.
Mr of phenol = 94.0; 1 tonne = 106 g

mass of phenol = ....................... tonnes


[4]
[Total 12 marks]

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43.

A dye can be made from 4-methylphenylamine and 2,6-dimethylphenol, shown below.


OH
H3C
H3C

CH3

NH2

4-methylphenylamine

2,6-dimethylphenol

4-Methylphenylamine is dissolved in ice-cold hydrochloric acid and sodium nitrite is


added.
This mixture is then slowly added to an alkaline solution of the phenol to form the dye.

(i)

Identify the inorganic nitrogen-containing compound formed by the mixture of


hydrochloric acid and sodium nitrite.
........................................................................................................................
[1]

(ii)

Draw the structure of the organic compound formed in the ice-cold acidic mixture,
showing a displayed formula of the nitrogen-containing group.

[1]

(iii)

State the name of the type of organic compound drawn in (ii).


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

(iv)

Suggest why the mixture must be kept at a low temperature.


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

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(v)

Suggest the structure of the dye.

[2]
[Total 6 marks]

44.

In this question, one mark is available for the quality of use and organisation of
scientific terms.
4-Methylphenylamine can be manufactured from benzene in three stages.
NH2
stage 1

stage 2

stage 3

CH3
benzene

Strode's College

4-methylphenylamine

64

Describe how benzene could be converted by these three stages into


4-methylphenylamine.
Include the structures of the intermediate compounds A and B. State the reagents and
conditions. Give a balanced equation for each stage.
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[11]
Quality of Written Communication [1]
[Total 12 marks]

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45.

Chemists are currently developing renewable sources of organic chemicals to replace


diminishing crude oil reserves.
One process involves the conversion of plant material to 4-oxopentanoic acid. This can
then be converted to other useful organic compounds, including those shown below.
COOH

4-oxopentanoic acid
SOCl2

reagent C
COOH

OH

compound D

compound E

hot
Al2O3

C2H5OH
O

COOH
O
O

compound F
(polymer production)

(a)

compound G
(diesel fuel additive)

Complete the scheme by filling in the boxes to:


(i)

identify reagent C
[1]

(ii)

state the name of compound D


[1]

(iii)

draw the structure of compound E.


[1]

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66

(b)

Compound F can be used to form a polymer.


(i)

Draw a short section of this polymer showing at least three repeat units.

[1]

(ii)

Draw a circle round one repeat unit on your structure.


[1]

(c)

Compound G can be added to diesel fuel to reduce the amount of soot formed
when the fuel burns.
(i)

Deduce the molecular formula of compound G.


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

(ii)

Write a balanced equation for the complete combustion of compound G.

[2]

(iii)

Suggest how compound G reduces the amount of soot when the fuel burns.
...............................................................................................................
...............................................................................................................
[1]

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(d)

If compound G is accidentally spilt, it is broken down rapidly in the environment


by reactions such as alkaline hydrolysis.
(i)

State the reagents and conditions that would normally be used for alkaline
hydrolysis in the laboratory.
...............................................................................................................
...............................................................................................................
[2]

(ii)

Explain why compound G is able to be hydrolysed.


...............................................................................................................
...............................................................................................................
[1]
[Total 12 marks]

46.

Geraniol, C9H15CH2OH, is a naturally occurring compound that contributes to the smell


of roses. The skeletal formula of geraniol is shown below.
OH

geraniol

(a)

Name the two different functional groups in geraniol.


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

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(b)

Geraniol has stereoisomers due to one of the double bonds in the molecule.
(i)

What is meant the term stereoisomer?


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

(ii)

Name the type of stereoisomerism shown by geraniol.


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

(iii)

State how this type of stereoisomerism arises in organic molecules.


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

(iv)

Explain why one of the double bonds in geraniol does not give rise to
stereoisomerism.
...............................................................................................................
...............................................................................................................
...............................................................................................................
[1]
[Total 5 marks]

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47.
OH

geraniol
Mild oxidation of geraniol gives an aldehyde Y.
(i)

Draw the skeletal formula of aldehyde Y below.

aldehyde Y
[2]

(ii)

Complete the equation for the oxidation of geraniol to aldehyde Y.


C9H15CH2OH +

[O]

[2]
[Total 4 marks]

48.

Reaction of geraniol with ethanoic acid can be used to make ester Z, which is used in
chewing gum and desserts.
(i)

Suggest why esters are used in the manufacture of foods.


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

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70

(ii)

State the conditions needed to make ester Z from geraniol and ethanoic acid.
........................................................................................................................
........................................................................................................................
[2]

(iii)

Complete the equation for the formation of ester Z.


+

C9H15CH2OH

[3]
[Total 6 marks]

49.

The nitration of benzene is a very important industrial reaction.


(a)

Name two types of commercially important material whose manufacture involves


the nitration of benzene.
........................................................................................................................
........................................................................................................................
[2]

(b)

State the conditions required for the nitration of benzene using nitric acid and
sulphuric acid.
........................................................................................................................
........................................................................................................................
[2]

(c)

Write a balanced equation for the nitration of benzene.

[2]

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71

(d)

The mechanism for the reaction is given below.


Step 1: formation of the electrophile, NO2+, from HNO3 and H2SO4
HNO3

H2SO4

H2O

NO2+

HSO4

Steps 2 and 3: substitution of NO2+ into the benzene ring


+
NO2
H

NO2

NO2

step 2

+
H

step 3

+
intermediate

Step 4: protonation of the HSO4


H+
(i)

HSO4

Explain what a curly arrow

H2SO4

represents in this type of mechanism.

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

(ii)

State why the NO2+ is described as an electrophile in this mechanism.


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

(iii)

State why this mechanism is described as substitution.


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

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(iv)

How does the mechanism show that the sulphuric acid is acting as a
catalyst?
...............................................................................................................
...............................................................................................................
[1]

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(e)

In this question, one mark is available for the quality of spelling, punctuation and
grammar.
The benzene ring and the ring in the intermediate formed after step 2 have
different structures shown below. Both structures have -bonds.

+
benzene ring

ring in the intermediate

Deduce how many electrons are involved in the -bonding in each structure and
describe how their arrangements are different.
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[5]
Quality of Written Communication [1]
[Total 17 marks]

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50.

E110 is a yellow colouring agent that is commonly added to a variety of foods.


E110 contains an azo dye made from an amine and a phenol.
(a)

Describe how you would prepare a sample of an azo dye in the laboratory from
an amine, a phenol and any other necessary reagents.

Include in your answer

essential reagents and conditions for each stage

names of any functional groups formed during the process.


........................................................................................................................
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[7]

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(b)

The structure of E110 is shown below.


OH
N
SO3Na+

SO3Na+

(i)

E110

On the structure above, draw a circle around the functional group that
identifies this molecule as an azo dye.
[1]

(ii)

Deduce how many carbon and hydrogen atoms are in a molecule of E110.
..................... carbon atoms and ..................... hydrogen atoms.
[2]

(c)

The solubility of E110 in water can be improved by converting the phenolic OH


group into a charged O group.
Suggest a suitable reagent that will convert the OH group in E110 into an O
group.
........................................................................................................................
[1]

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(d)

In the boxes below, draw the structures of a phenol and an amine that could be
used to make E110 by the method in part (a).
Assume that the SO3Na+ groups do not change during the process.

phenol

amine
[2]
[Total 13 marks]

51.

Glutamic acid and glycine are both -amino acids that occur widely in living organisms.
Their structures are shown below.

H
H2N

H
COOH

H2N

CH2

COOH

CH2
COOH
glutamic acid

(a)

(i)

glycine

State the general formula for an -amino acid.


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

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77

(ii)

Explain how glutamic acid and glycine both fit the general formula given in
part (i)
...............................................................................................................
...............................................................................................................
...............................................................................................................
[2]

(b)

Amino acids react with both acids and alkalis.


Draw structures below to show how the glutamic acid molecule is changed in the
presence of excess acid and alkali.
H
H2N

COOH

CH2
excess
HCl(aq)

CH2

excess
NaOH(aq)

COOH
glutamic acid

[5]

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(c)

In this question, one mark is available for the quality of use and organisation of
scientific terms.
Glutamic acid exists as two optical isomers, but glycine does not.
Explain what structural feature causes optical isomerism in organic molecules.
Include appropriate diagrams and use these two amino acids to illustrate your
answer.
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[7]
Quality of Written Communication [1]
[Total 16 marks]

52.

Poly(phenylethene) is one of the most versatile and successful polymers.


The 3-D skeletal formula of a section of atactic poly(phenylethene) is shown in the
diagram below.

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79

(i)

State the type of polymerisation used to make poly(phenylethene).


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

(ii)

Draw a skeletal or displayed formula to show the monomer used to make


poly(phenylethene).

[1]

(iii)

Outline how the polymer is formed from the monomer molecules. (You do not
need to give any details of the catalyst or conditions involved.)

........................................................................................................................
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[2]
[Total 4 marks]

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53.

Forest fires release a large number of organic compounds into the atmosphere. These
include alcohols and carboxylic acids. An environmental chemist is trying to identify
one of these compounds in a sample of air.
The unknown compound X is thought to be a carboxylic acid with empirical formula
C2H3O2.
(a)

Mass spectrometry is used to help deduce the molecular formula of compound X.


(i)

Describe how the mass spectrum of compound X is used to determine its


relative molecular mass.
...............................................................................................................
...............................................................................................................
[2]

(ii)

The relative molecular mass of compound X is shown to be 118.


Explain how this relative molecular mass and the empirical formula are
used to deduce that the molecular formula of compound X is C4H6O4.
Show any working.
...............................................................................................................
...............................................................................................................
...............................................................................................................
...............................................................................................................
[2]

(b)

The two dicarboxylic acids with molecular formula C4H6O4 are shown below.

H
O
C
HO

OH

H O

C
OH

HO

OH

N.m.r. spectroscopy is used to deduce which of these is the unknown compound.


The environmental chemist obtains an n.m.r. spectrum of compound X and then
adds some D2O and obtains a second n.m.r. spectrum.

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81

(i)

What difference would you expect between these two n.m.r. spectra?
...............................................................................................................
...............................................................................................................
[1]

(ii)

Predict the number of peaks and any spin-spin splitting expected on the
n.m.r. spectrum of a solution in D2O of the other acid with formula C4H6O4.
Explain your reasoning.
(The two possible structures of compound X are shown again below.)
H
O
C
HO

OH

H O

C
OH

HO

OH

...............................................................................................................
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[3]
[Total: 8 marks]

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54.

Chromatography is a versatile technique that may be used to separate and identify


compounds.
(i)

Name a type of chromatography that is used to separate and identify dissolved


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

(ii)

State what quantitative value may be determined from the chromatogram to


identify the substances present in the solution.
........................................................................................................................
[1]

(iii)

Sketch a chromatogram to show how the value in (ii) is determined.

[1]
[Total 3 marks]

55.

(a)

Gas-liquid chromatography is used to separate and identify gases and liquids.


(i)

State what quantitative value is normally used to identify the components in


this type of chromatography.
...............................................................................................................
[1]

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83

(ii)

Sketch the chromatogram to show how the value in (i) is determined.

[1]

(b)

State the physical process on which the separation used in gas-liquid


chromatography depends.
........................................................................................................................
[1]
[Total 3 marks]

56.

Benzoic acid and phenylmethanol will react with each other in the presence of a
suitable catalyst.
(i)

State a suitable catalyst for this reaction.


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

(ii)

Draw the displayed formula of the organic product.

[2]
[Total 3 marks]

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84

57.

Cinnamaldehyde is the compound that gives cinnamon its distinctive flavour.

H
C

H
C

C
O

H
cinnamaldehyde

(a)

Draw the skeletal formula of cinnamaldehyde.

[1]

(b)

Cinnamaldehyde shows cis-trans isomerism.


(i)

Explain how cis-trans isomerism arises in cinnamaldehyde.


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

(ii)

State and explain whether cinnamaldehyde is a cis or a trans isomer.


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

Strode's College

85

(iii)

Draw a skeletal or displayed formula to show the structure of the other


cis-trans isomer of cinnamaldehyde.

[1]
[Total 5 marks]

58.

Cinnamaldehyde can be reduced using sodium borohydride, NaBH4.


(i)

State which functional group reacts with the sodium borohydride.


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

(ii)

Complete and balance the equation for this reaction.


C6H5CH=CHCHO

[H]

[1]
[Total 2 marks]

Strode's College

86

59.

In this question, one mark is available for spelling, punctuation and grammar.
Tollens reagent can be used to identify the aldehyde group in cinnamaldehyde.

Describe how you would make Tollens reagent and carry out this test in the
laboratory.

Explain what happens to both the Tollens reagent and the cinnamaldehyde in
this reaction. Identify the organic product.

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[7]
Quality of Written Communication. [1]
[Total 8 marks]

Strode's College

87

60.

Compound A is currently being tested as a possible anti-allergic drug.


O

OH
C
CH2

CH2

H
N
H

CH2

C
H

OH
C
O

compound A

Compound A can be hydrolysed to form three organic products.


(i)

Name a suitable reagent and conditions for the hydrolysis of compound A.


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[2]

(ii)

The three organic products all belong to the same class of compound. State the
general name for this class of organic compound.
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[1]

(iii)

Draw the structure of one of the organic products from the hydrolysis of A using
the reagent you have given in (a)(i) above.

[2]

Strode's College

88

(iv)

Explain what is meant by the term hydrolysis. Use this reaction to illustrate your
answer.
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[2]
[Total 7 marks]

61.

Compound A is currently being tested as a possible anti-allergic drug.


O

OH
C
CH2

CH2

H
N
H

CH2

C
H

OH
C
O

compound A

Compound A can exist as a number of stereoisomers, but only one of them is


pharmacologically active as the anti-allergic drug.

(i)

Explain what causes stereoisomerism in compounds such as A.


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[3]

Strode's College

89

(ii)

Explain why there are four different stereoisomers of compound A.


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[2]

(iii)

Suggest how a drug company could synthesise compound A so that the drug
contains only the pharmacologically active stereoisomer.
........................................................................................................................
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[1]

(iv)

Sometimes it is difficult to manufacture a drug containing only the one


pharmacologically active stereoisomer.
Describe two possible disadvantages of producing a drug containing a mixture of
several stereoisomers.
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[2]
[Total 8 marks]

62.

1,4-Diaminobenzene is used in the manufacture of a variety of materials including dyes


and polymers.

H2N

NH2

1,4-diaminobenzene

Strode's College

90

(a)

Explain what is meant by the term 1,4-diamino in the name of this compound.

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[2]

(b)

1,4-diaminobenzene can be manufactured from 1,4-dinitrobenzene.

O2N

NO2

H2N

1,4-dinitrobenzene

(i)

NH2

1,4-diaminobenzene

What type of reaction is this?


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[1]

(ii)

State reagents and conditions that could be used to carry out this reaction.
...............................................................................................................
...............................................................................................................
[2]

(iii)

Complete and balance the equation below for this reaction.

O2N

NO2 +

[H]

H2 N

NH2 +
[2]

Strode's College

91

(c)

1,4-Diaminobenzene is used to make permanent black dye for hair.


1,4-Diaminobenzene can irritate the skin because it is basic. Therefore, it is
sometimes neutralised with excess hydrochloric acid to give the salt.
(i)

Explain how the amino groups in a primary amine such as


1,4-diaminobenzene allow the molecule to act as a base.
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[2]

(ii)

Draw the structure of the salt formed in this reaction.

[2]

(iii)

State whether you would expect hexane-1,6-diamine to be a stronger or


weaker base than 1,4-diaminobenzene. Explain your reasoning.
NH2

H2N
hexane-1,6-diamine

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[3]
[Total 14 marks]

Strode's College

92

63.

Kevlar is a very tough polymer made from 1,4-diaminobenzene and


benzene-1,4-dicarboxylic acid.
(i)

State a use for Kevlar.


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

(ii)

Describe the polymerisation reaction that forms Kevlar. Include in your answer:

an explanation of the type of polymerisation involved

an equation for the reaction

a repeat unit to show the structure of Kevlar.

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[5]
[Total 6 marks]

Strode's College

93

64.

This question is about the use of spectrometry in helping to gain information about the
structure of organic molecules.
The major peaks in the mass spectra of two hydrocarbons A and B are shown below.
Compounds A and B have the same empirical formula.
compound A

relative
abundance

10

15

20

25 30
m/e

35

40

45

50

25

30

35 40
m/e

45

50

55

60

compound B

relative
abundance

10

(i)

15

20

Deduce the molecular formula of each compound.


Compound A
Compound B
[2]

Strode's College

94

(ii)

Draw the structural formula of compound A.

[1]

(iii)

Suggest the species responsible for the peak at m/e 41 in the spectrum of
compound B.
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[2]
[Total 5 marks]

Strode's College

95