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

H H H H H H

C C C C C C

H H H

polym er C

O O H H O O H H

C C O C C O C C O C C O

H H H H
polym er 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]
(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]
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 H H

H 2N C COOH H 2N C COOH HN C COOH

H CH2 H 2C CH2
C
C 6H 5 H2

glycine phenylalanine 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]
(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. 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 α-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]
4. 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 NH2

CH3
HO
noradrenaline com pound P

(a) (i) Suggest a reagent that could be used in a test to distinguish

compound P from noradrenaline.

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[1]

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

(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.

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 [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]

(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]
5. The four amino acids shown below are found in proteins and enzymes.
H H H

H2N C COOH H2N C COOH H2N C COOH

H (C H 2 ) 4 N H 2 CH 2 SH

glycine lysine cysteine

H2N C COOH

C H 2C H 2 C O O H

glutam ic acid

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

[Total 2 marks]

6. Compound A, shown below, is an amino acid that is being used in the

development of a new anti-inflammatory drug.
H H O

H 2N C C C

C H H OH
3

com pound A
(a) (i) Explain why this molecule is described as an amino acid.

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[1]

(ii) State the general formula of an -amino acid.

Explain whether or not compound A fits this general formula.

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[2]

(b) Compound A exists as a zwitterion in aqueous solution.

(i) Draw the structure of this zwitterion.

[1]
 (ii) Show how the structure of the zwitterion would change if the solution
was acidified with dilute hydrochloric acid.

[1]

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

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

R C C

H OH

com pound B

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

and compound B.

[2]
[Total 7 marks]
7. 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.

O O

C C
N N

H H
n

(i) 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]
8. 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]

9. 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.

nylo-6,6 OrlonTM
O O
monomer(s)
HO C (C H 2 ) 4 C OH

H 2N (C H 2 ) 6 NH2

repeat unit of H CN
the polymer
C C

H H

type of
polymerisatio
n
[4]
(b) Nylon-6,6 can be made from its monomers in the laboratory in two stages
as shown below.
O O

HO C (C H 2 ) 4 C OH

stage 1
O O

Cl C (C H 2 ) 4 C Cl H 2N (C H 2 ) 6 NH2

stage 2

nylon-6,6

(i) State a suitable reagent to carry out stage 1.

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[1]

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

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[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]
(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.

H O H 2C O H O H O

N C C N C C N C C N C C

H CH2 H H H H H 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]
 (iii) State three ways in which the monomer units of a protein differ from
those of nylon-6,6.

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[3]
[Total 13 marks]

10. Leucine (2-amino-4-methylpentanoic acid) is a naturally occurring α-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 α-amino acid.

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[1]

(ii) Draw a displayed formula of leucine.

[1]
(b) Leucine can exist as a zwitterion.

(i) State what is meant by the term zwitterion.

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[1]

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

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[2]

(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.

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[2]

(ii) State the type of reaction occurring.

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[1]
[Total 8 marks]
11. 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 H O H O H OH O

C C C C H C C C + CO2

H O H H O H H H OH

m a lic a c id la c tic a c id

Both acids contain a chiral centre.

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

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

[1]
[Total 2 marks]
12. 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

O
4-oxopentanoic acid
S O C l2
reagent C

COOH

OH

com pound D com pound E

hot
C 2H 5O H
A l2O 3
O

COOH
O

O
com pound F com pound G
(polym er production) (diesel fuel additive)

(a) 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]
(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.

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[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.

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[1]
 (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.

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[2]

(ii) Explain why compound G is able to be hydrolysed.

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[1]
[Total 12 marks]

13. Geraniol, C9H15CH2OH, is a naturally occurring compound that contributes to

the smell of roses. The skeletal formula of geraniol is shown below.
O H

geraniol

(a) Name the two different functional groups in geraniol.

....................................................... and ........................................................

[1]
(b) Geraniol has stereoisomers due to one of the double bonds in the
molecule.

(i) What is meant the term stereoisomer?

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[1]

(ii) Name the type of stereoisomerism shown by geraniol.

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[1]

(iii) State how this type of stereoisomerism arises in organic molecules.

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[1]

(iv) Explain why one of the double bonds in geraniol does not give rise to
stereoisomerism.

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[1]
[Total 5 marks]
14. Glutamic acid and glycine are both -amino acids that occur widely in living
organisms. Their structures are shown below.
H H

H 2N C COOH H 2N C COOH

CH2 H

CH2

COOH
glutam ic acid glycine

(a) (i) State the general formula for an -amino acid.

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[1]
 (ii) Explain how glutamic acid and glycine both fit the general formula
given in part (i)

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[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

H 2N C COOH

CH2
excess excess
H C l (aq) CH2 N aO H (aq)
COOH

glutam ic acid

[5]
(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]
15. 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.

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

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.
[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]

16. Cinnamaldehyde is the compound that gives cinnamon its distinctive flavour.
H H

C C
C O

cinnam aldehyde

(a) Draw the skeletal formula of cinnamaldehyde.

[1]

(b) Cinnamaldehyde shows cis-trans isomerism.

(i) Explain how cis-trans isomerism arises in cinnamaldehyde.

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[2]

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

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[1]

(iii) Draw a skeletal or displayed formula to show the structure of the

other cis-trans isomer of cinnamaldehyde.

[1]
[Total 5 marks]
17. Compound A is currently being tested as a possible anti-allergic drug.

O OH
C

CH2

H CH2 H CH2 H H OH

N C C N C C N C C

H H O H O H O

com pound 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]
 (iv) Explain what is meant by the term hydrolysis. Use this reaction to illustrate
your answer.

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[2]
[Total 7 marks]

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

O OH
C

CH2

H CH2 H CH2 H H OH

N C C N C C N C C

H H O H O H O

com pound 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]
 (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]

19. Kevlar is a very tough polymer made from 1,4-diaminobenzene and benzene-
1,4-dicarboxylic acid.
(i) State a use for Kevlar.

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[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]