(c) Suggest an environmental advantage of polymer Q over polymer P.

Repeating units of two polymers, P and Q, are shown in the figure below. Justify your answer.
1
Advantage .....................................................................................................

Justification ....................................................................................................

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

........................................................................................................................
(a) Draw the structure of the monomer used to form polymer P.
Name the type of polymerisation involved. ........................................................................................................................
Monomer ........................................................................................................................
(3)
(Total 7 marks)

Which compound can polymerise by reaction with itself?

2
A NH2CH2CH2NH2

B CH3CH2CONH2

Type of polymerisation .................................................................................... C HOOCCH2COOH

(2)
D NH2CH2COCl
(b) Draw the structures of two compounds that react together to form polymer Q.
(Total 1 mark)
Structure of compound 1

Structure of compound 2

(2)

Page 1 of 86 Page 2 of 86
 (a) The structures and common names of two amino acids are shown. (iii) Draw the section of a polymer made from a dicarboxylic acid and a diamine that is
3 isomeric with the section of polymer M shown.
(1)

(vi) Explain why polymer L is non-biodegradable.

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

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

...............................................................................................................
(1)
(i) Draw the structure of the zwitterion of proline. (Total 7 marks)

(1)

(ii) Draw the structure of the tripeptide formed when a proline molecule bonds to two
alanine molecules, one on each side.
(2)

(b) Sections of two polymers, L and M, are shown.

(i) Give the IUPAC name of a monomer that forms polymer L.

...............................................................................................................
(1)

(ii) Give the IUPAC name of the monomer that forms polymer M.

...............................................................................................................
(1)
Page 3 of 86 Page 4 of 86
 This question is about some isomers of C5H8O2 (ii) HOCH2CH2CH2CH2COCl can also react to form a polyester in a mechanism similar to
4 that in part (i).
(a) Compound H is a cyclic ester that can be prepared as shown.
Draw the repeating unit of the polyester and name the type of polymerisation
On the structure of H, two of the carbon atoms are labelled. involved.

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

...............................................................................................................
HOCH2CH2CH2CH2COCl + HCL
...............................................................................................................

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

H ...............................................................................................................
(2)
(i) Name and outline a mechanism for this reaction.
(b) State how you could distinguish between compounds J and K by a simple test-tube
Use Table C on the Data Sheet to give the 13C n.m.r. δ value for the carbon atom reaction.
labelled a and the δ value for the carbon atom labelled b.
State how you could distinguish between J and K by giving the number of peaks in the
............................................................................................................... 1
H n.m.r. spectrum of each compound.

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

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

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

............................................................................................................... J K

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

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

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

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

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

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

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

............................................................................................................... ........................................................................................................................
(5)
...............................................................................................................

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

...............................................................................................................
(7)

Page 5 of 86 Page 6 of 86
 (c) Draw the structure of each of the following isomers of C5H8O2 (b) A molecule of lactic acid contains an asymmetric carbon atom.
Label each structure you draw with the correct letter L, M, N, P or Q. The lactic acid in the body occurs as a single enantiomer.
A racemic mixture (racemate) of lactic acid can be formed in the following two-stage
L is methyl 2-methylpropenoate. synthesis.

M is an ester that shows E-Z stereoisomerism.

N is a carboxylic acid with a branched carbon chain and does not show stereoisomerism.

P is an optically active carboxylic acid.

(i) Name and outline a mechanism for Stage 1.
Q is a cyclic compound that contains a ketone group and has only two peaks in its 1H n.m.r.
spectrum. Name of mechanism ............................................................................

Mechanism

(5)
(Total 19 marks)

Lactic acid, CH3CH(OH)COOH, is formed in the human body during metabolism and exercise.
5 This acid is also formed by the fermentation of carbohydrates such as sucrose, C12H22O11. (5)

(a) (i) Give the IUPAC name for lactic acid. (ii) Give the meaning of the term racemic mixture (racemate).

............................................................................................................... ...............................................................................................................
(1)
...............................................................................................................
(ii) Write an equation for the formation of lactic acid from sucrose and water.
...............................................................................................................
............................................................................................................... (1)
(1)
(iii) Explain how you could distinguish between a racemic mixture (racemate) of lactic
acid and one of the enantiomers of lactic acid.

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

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

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

...............................................................................................................
(2)

(c) A mixture of lactic acid and its salt sodium lactate is used as an acidity regulator in some
foods. An acidity regulator makes sure that there is little variation in the pH of food.

(i) Write an equation for the reaction of lactic acid with sodium hydroxide.

...............................................................................................................
(1)

Page 7 of 86 Page 8 of 86
(ii) The acid dissociation constant Ka for lactic acid has the value 1.38 × 10−4 mol dm−3 at (d)
298 K.

Calculate the pH of an equimolar solution of lactic acid and sodium lactate.

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

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

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

...............................................................................................................
(2)

(iii) Suggest an alternative name for the term acidity regulator.

Explain how a mixture of lactic acid and sodium lactate can act as a regulator when
natural processes increase the acidity in some foods.
The cup shown is made from PLA, poly(lactic acid).
Name ................................................................................................... PLA is the condensation polymer formed from lactic acid.

Explanation ........................................................................................... The polymer is described as 100% biodegradable and 100% compostable.

............................................................................................................... Compostable material breaks down slowly in contact with the moist air in a garden bin. This
produces compost that can be used to improve soil.
...............................................................................................................
The manufacturers stress that PLA cups differ from traditional plastic cups that are neither
...............................................................................................................
biodegradable nor compostable.
(Extra space) ........................................................................................
(i) Draw a section of PLA that shows two repeating units.
...............................................................................................................
(3)

(2)

(ii) Name the type of condensation polymer in PLA.

...............................................................................................................
(1)

Page 9 of 86 Page 10 of 86
(iii) An intermediate in the production of PLA is a cyclic compound (C6H8O4) that is (a) The tripeptide shown is formed from the amino acids alanine, threonine and lysine.
formed from two PLA molecules.
6

Draw the structure of this cyclic compound.

(i) Draw a separate circle around each of the asymmetric carbon atoms in the tripeptide.
(1)

(1)
(ii) Draw the zwitterion of alanine.

(iv) Traditional non-biodegradable plastic cups can be made from poly(phenylethene),

commonly known as polystyrene.

Draw the repeating unit of poly(phenylethene).

(1)

(iii) Give the IUPAC name of threonine.

...............................................................................................................
(1)

(iv) Draw the species formed by lysine at low pH.

(1)

(v) The manufacturers of PLA claim that the material will break down to compost in just
12 weeks.
(1)
Suggest one reason why PLA in landfill may take longer than 12 weeks to break
down. (b) The repeating unit shown represents a polyester.
...............................................................................................................

...............................................................................................................
(1)
(Total 22 marks) (i) Name this type of polymer.

...............................................................................................................
(1)

(ii) Give the IUPAC name for the alcohol used to prepare this polyester.

...............................................................................................................
(1)

Page 11 of 86 Page 12 of 86
(c) The repeating unit shown represents a polyalkene co-polymer. This co-polymer is made Acyl chlorides and acid anhydrides are important compounds in organic synthesis.
from two different alkene monomers.
7
(a) Outline a mechanism for the reaction of CH3CH2COCl with CH3OH and name the organic
product formed.

Mechanism

(i) Name the type of polymerisation occurring in the formation of this co-polymer.

...............................................................................................................
(1)

(ii) Draw the structure of each alkene monomer.

Alkene monomer 1 Alkene monomer 2 Name of organic product ...............................................................................

(5)

(b) A polyester was produced by reacting a diol with a diacyl chloride. The repeating unit of the
polymer is shown below.

(2)

(d) One of the three compounds shown in parts (a), (b) and (c) cannot be broken down by
hydrolysis. (i) Name the diol used.

Write the letter (a), (b) or (c) to identify this compound and explain why hydrolysis of this ...............................................................................................................
(1)
compound does not occur.
(ii) Draw the displayed formula of the diacyl chloride used.
Compound ....................................................................................................

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

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

........................................................................................................................
(1)
(2)
(Total 11 marks)

Page 13 of 86 Page 14 of 86
 (iii) A shirt was made from this polyester. A student wearing the shirt accidentally (d) Complete the following equation for the reaction of one molecule of benzene-
splashed aqueous sodium hydroxide on a sleeve. Holes later appeared in the sleeve 1,2-dicarboxylic anhydride (phthalic anhydride) with one molecule of methanol by drawing
where the sodium hydroxide had been. the structural formula of the single product

Name the type of reaction that occurred between the polyester and the aqueous
sodium hydroxide. Explain why the aqueous sodium hydroxide reacted with the
polyester.

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

Explanation ........................................................................................... (1)

............................................................................................................... (e) The indicator phenolphthalein is synthesised by reacting phthalic anhydride with phenol as
shown in the following equation.
...............................................................................................................

...............................................................................................................
(3)

(c) (i) Complete the following equation for the preparation of aspirin using ethanoic
anhydride by writing the structural formula of the missing product.

......................
(1)
(i) Name the functional group ringed in the structure of phenolphthalein.
(ii) Suggest a name for the mechanism for the reaction in part (c)(i).
...............................................................................................................
...............................................................................................................
(1)
(1)
13
(iii) Give two industrial advantages, other than cost, of using ethanoic anhydride rather (ii) Deduce the number of peaks in the C n.m.r. spectrum of phenolphthalein.
than ethanoyl chloride in the production of aspirin.
...............................................................................................................
Advantage 1 .......................................................................................... (1)

(iii) One of the carbon atoms in the structure of phenolphthalein shown above is labelled
...............................................................................................................
with an asterisk (*).
............................................................................................................... Use Table 3 on the Data Sheet to suggest a range of δ values for the peak due to
this carbon atom in the 13C n.m.r. spectrum of phenolphthalein.
Advantage 2 ..........................................................................................
...............................................................................................................
............................................................................................................... (1)

...............................................................................................................
(2)

Page 15 of 86 Page 16 of 86
 (f) Phenolphthalein can be used as an indicator in some acid–alkali titrations. (b) The following structures are the repeating units of two different condensation polymers.
The pH range for phenolphthalein is 8.3 – 10.0
For each example, name the type of condensation polymer. Give a common name for a
(i) For each acid.alkali combination in the table below, put a tick ( ) in the box if polymer of this type.
phenolphthalein could be used as an indicator.

(i)
Tick
Acid Alkali
box ( )

sulfuric acid sodium hydroxide Type of condensation polymer .............................................................

Common name ....................................................................................

hydrochloric acid ammonia (2)

ethanoic acid potassium hydroxide

(ii)

nitric acid methylamine

(2)
Type of condensation polymer .............................................................
(ii) In a titration, nitric acid is added from a burette to a solution of sodium hydroxide
Common name ....................................................................................
containing a few drops of phenolphthalein indicator.
(2)
Give the colour change at the end-point.
(iii) Explain why the polymer in part (b)(ii) has a higher melting point than the polymer in
............................................................................................................... part (b)(i).
(1)
(Total 21 marks)
...............................................................................................................

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

...............................................................................................................
Common substances used in everyday life often contain organic compounds. (Extra space) ........................................................................................
8
(a) State an everyday use for each of the following compounds. ...............................................................................................................
(2)
– +
(i) CH3(CH2)17COO Na ...................................................................... (Total 9 marks)
(1)

(ii) CH3(CH2)19COOCH3 ..........................................................................

(1)

(iii) [C16H33N(CH3)3]+ Br– ..........................................................................

(1)

Page 17 of 86 Page 18 of 86
 The amide or peptide link is found in synthetic polyamides and also in naturally (b) (i) Name and outline a mechanism for the reaction of CH3CH2COCl with CH3NH2
9 occurring proteins.
Name of mechanism............................................................................
(a) (i) Draw the repeating unit of the polyamide formed by the reaction of propanedioic acid
with hexane-1,6-diamine. Mechanism

(2)

(ii) In terms of the intermolecular forces between the polymer chains, explain why
polyamides can be made into fibres suitable for use in sewing and weaving, whereas
polyalkenes usually produce fibres that are too weak for this purpose.

............................................................................................................. (5)

............................................................................................................. (ii) Give the name of the product containing an amide linkage that is formed in the
reaction in part (b) (i).
.............................................................................................................
.............................................................................................................
............................................................................................................. (1)

............................................................................................................. (c) The dipeptide shown below is formed from two different amino acids.

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

(Extra space) ......................................................................................

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

............................................................................................................. Draw the structure of the alternative dipeptide that could be formed by these two amino
(3) acids.

(1)

Page 19 of 86 Page 20 of 86
(d) The amino acids serine and aspartic acid are shown below. Items softened with plasticisers have become an essential part of our modern society.
10
Compound S, shown below, is commonly known as phthalic acid.

Esters of phthalic acid are called phthalates and are used as plasticisers to soften polymers such
as PVC, poly(chloroethene).

(i) Give the IUPAC name of serine.

.............................................................................................................
(1)

(ii) Draw the structure of the species formed when aspartic acid reacts with aqueous
sodium hydroxide. (a) Give the IUPAC name for phthalic acid.

......................................................................................................................
(1)

(b) Draw the displayed formula of the repeating unit of poly(chloroethene).

(1)

(iii) Draw the structure of the species formed when serine reacts with dilute hydrochloric
acid.

(1)

(c) The ester diethyl phthalate (DEP) is used in food packaging and in cosmetics.

(i) Complete the following equation showing the formation of DEP from phthalic
(1) anhydride.

(iv) Draw the structure of the species formed when serine reacts with an excess of
bromomethane.

(2)
(1)
(Total 16 marks) (ii) Deduce the number of peaks in the 13C n.m.r. spectrum of DEP.

.............................................................................................................
(1)

Page 21 of 86 Page 22 of 86
 (iii) One of the peaks in the 13C n.m.r. spectrum of DEP is at δ = 62 ppm. (ii) Suggest what needs to be done so that the public could feel confident that the
research discussed above is reliable.
Table 3 on the Data Sheet can be used to identify a type of carbon atom responsible
for this peak. .............................................................................................................

Draw a circle around one carbon atom of this type in the structure below. .............................................................................................................

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

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

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

(Extra space) .......................................................................................

(1)
.............................................................................................................
(d) The mass spectrum of DEP includes major peaks at m/z = 222 (the molecular ion) and at
m/z = 177 .............................................................................................................
(2)
Write an equation to show the fragmentation of the molecular ion to form the fragment that (Total 11 marks)
causes the peak at m/z = 177

(a) Name compound Y, HOCH2CH2COOH

11
......................................................................................................................
(1)

(b) Under suitable conditions, molecules of Y can react with each other to form a polymer.

(i) Draw a section of the polymer showing two repeating units.

......................................................................................................................
(2)

(e) Because of their many uses, phthalates have been tested for possible adverse effects to
humans and to the environment.

An organisation that represents the manufacturers of plasticisers asserts that experimental

evidence and research findings show that phthalates do not pose a risk to human health
because they biodegrade in a short time scale.

According to the organization’s research, phthalates do not represent a risk for humans or (1)
for the environment and they are biodegradable.
(ii) Name the type of polymerisation involved.
(i) Hydrolysis of DEP in an excess of water was found to follow first order kinetics.
.............................................................................................................
Write a rate equation for this hydrolysis reaction using DEP to represent the ester. (1)

.............................................................................................................
(1)

Page 23 of 86 Page 24 of 86
(c) When Y is heated, an elimination reaction occurs in which one molecule of Y loses one (e) The amino acid, glutamic acid, is shown below.
molecule of water. The organic product formed by this reaction has an absorption at
1637 cm–1 in its infrared spectrum.

(i) Identify the bond that causes the absorption at 1637 cm–1 in its infrared spectrum.

.............................................................................................................
(1) Draw the structure of the organic species formed when glutamic acid reacts with each of
the following.
(ii) Write the displayed formula for the organic product of this elimination reaction.
(i) an excess of sodium hydroxide

(1)
(1)
(ii) an excess of methanol in the presence of concentrated sulfuric acid
(iii) The organic product from part (ii) can also be polymerised.
Draw the repeating unit of the polymer formed from this organic product.

(1) (1)

(d) At room temperature, 2-aminobutanoic acid exists as a solid. (iii) ethanoyl chloride
Draw the structure of the species present in the solid form.

(1)

(1)

Page 25 of 86 Page 26 of 86
 (f) A tripeptide was heated with hydrochloric acid and a mixture of amino acids was formed. (ii) Name the type of mechanism in Reaction 1.
This mixture was separated by column chromatography.
Outline briefly why chromatography is able to separate a mixture of compounds. .............................................................................................................
Practical details are not required. (1)

...................................................................................................................... (iii) Give the full IUPAC name of compound B.

......................................................................................................................
......................................................................................................................
(b)
......................................................................................................................
.............................................................................................................
(1)
The infrared spectra shown below are those of the four compounds, A, B, C and D.
Using Table 1 on the Data Sheet, write the correct letter in the box next to each spectrum.

...................................................................................................................... (i)

......................................................................................................................
(3)
(Total 13 marks)

Haloalkanes are useful compounds in synthesis.

12 Consider the three reactions of the haloalkane A shown below.

(ii)

(iii)
(a) (i) Draw a branched-chain isomer of A that exists as optical isomers.

(1)

Page 27 of 86 Page 28 of 86
 (iv) (iii) Draw the structure of the secondary amine formed as a by-product in Reaction 3.

(1)

(e) D is a primary amine which has three peaks in its 13C n.m.r. spectrum.

(i) An isomer of D is also a primary amine and also has three peaks in its 13C n.m.r.
(4)
spectrum. Draw the structure of this isomer of D.
(c) Draw the repeating unit of the polymer formed by B and name the type of polymerisation
involved.

Repeating unit

(1)

(ii) Another isomer of D is a tertiary amine. Its 1H n.m.r. spectrum has three peaks. One
of the peaks is a doublet. Draw the structure of this isomer of D.

Type of polymerisation .................................................................................

(2)

(d) (i) Outline a mechanism for Reaction 3.

(1)
(Total 17 marks)

(4)

(ii) State the conditions used in Reaction 3 to form the maximum amount of the primary
amine, D.

.............................................................................................................
(1)

Page 29 of 86 Page 30 of 86
 Esters have many important commercial uses such as solvents and artificial flavourings in foods. (c) Name and outline a mechanism for the reaction of CH3COCl with CH3OH to form an ester.
13
Esters can be prepared in several ways including the reactions of alcohols with carboxylic acids,
acid anhydrides, acyl chlorides and other esters.

(a) Ethyl butanoate is used as a pineapple flavouring in sweets and cakes.

Write an equation for the preparation of ethyl butanoate from an acid and an alcohol.

Give a catalyst used for the reaction.

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

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

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

...................................................................................................................... (5)

...................................................................................................................... (d) The ester shown below occurs in vegetable oils. Write an equation to show the formation of
biodiesel from this ester.
......................................................................................................................
CH2OOCC17H31
...................................................................................................................... │
CHOOCC17H33
......................................................................................................................
│
(4)
CH23OOCC17H29
(b) Butyl ethanoate is used as a solvent in the pharmaceutical industry.
......................................................................................................................
Write an equation for the preparation of butyl ethanoate from an acid anhydride and an
alcohol. ......................................................................................................................

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

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

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

...................................................................................................................... ......................................................................................................................
(3)
......................................................................................................................

......................................................................................................................
(3)

Page 31 of 86 Page 32 of 86
 (e) Draw the repeating unit of the polyester Terylene that is made from benzene- (ii) Draw the displayed formula of the compound used as a standard in recording these
1,4-dicarboxylic acid and ethane-1,2-diol. spectra.

Although Terylene is biodegradeable, it is preferable to recycle objects made from Terylene.

Give one advantage and one disadvantage of recycling objects made from Terylene.

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

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

......................................................................................................................
(1)
......................................................................................................................
(b) Isomer X is prepared from nitrobenzene by reaction with a mixture of concentrated nitric
...................................................................................................................... acid and concentrated sulfuric acid.

...................................................................................................................... The two acids react to form an inorganic species that reacts with nitrobenzene to form X.

...................................................................................................................... (i) Give the formula of this inorganic species formed from the two acids and write an
equation to show its formation.
......................................................................................................................
(4) .............................................................................................................
(Total 19 marks)
.............................................................................................................

.............................................................................................................
(2)

Three isomers of C6H4(NO2)2 are shown below. (ii) Name and outline a mechanism for the reaction of this inorganic species with
14 nitrobenzene to form X.

(a) (i) Give the number of peaks in the 13C n.m.r. spectrum of each isomer.

.............................................................................................................
(4)
.............................................................................................................

.............................................................................................................
(3)

Page 33 of 86 Page 34 of 86
(c) Isomer Y is used in the production of the polymer Kevlar. (iii) Kevlar can be used as the inner lining of bicycle tyres. The rubber used for the outer
part of the tyre is made of polymerised alkenes.
Y is first reduced to the diamine shown below.
State the difference in the biodegradability of Kevlar compared to that of rubber made
of polymerised alkenes.

(i) Identify a suitable reagent or mixture of reagents for the reduction of Y to form this
diamine. Write an equation for this reaction using [H] to represent the reducing agent.
.............................................................................................................
.............................................................................................................
.............................................................................................................
.............................................................................................................
(2)
(ii) This diamine is then reacted with benzene-1, 4-dicarboxylic acid to form Kevlar.
Draw the repeating unit of Kevlar.
Use your knowledge of the bonding in these polymer molecules to explain this
difference.
.............................................................................................................
.............................................................................................................
.............................................................................................................
.............................................................................................................
.............................................................................................................
.............................................................................................................
(4)
(Total 18 marks)

Fibres are made from natural and from synthetic polymers. Both types of polymer have
15 advantages and disadvantages.

(a) Amino acids are the building blocks of naturally-occurring polymers called proteins.
(2)
Consider the following amino acid.

(i) Draw the structure of the amino acid species present in a solution at pH 12.

Page 35 of 86 Page 36 of 86
 (ii) Use your understanding of amino acid chemistry to deduce the structure of the (d) Two plastic objects were manufactured, one from the polyalkene represented by the
dipeptide formed from two molecules of this amino acid and illustrate your answer repeating unit in part (b)(i) and the other from the polyamide represented by the repeating
with a sketch showing the structure of the dipeptide. unit in part (c).

After use it was suggested that both objects be disposed of as landfill.

(i) Describe an experiment in which you could compare the biodegradability of these two
objects.

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

.............................................................................................................
(iii) Protein chains are often arranged in the shape of a helix. Name the type of
interaction that is responsible for holding the protein chain in this shape. .............................................................................................................

............................................................................................................. .............................................................................................................
(3)
.............................................................................................................
(b) Alkenes are the building blocks of synthetic addition polymers.
.............................................................................................................
Consider the hydrocarbon G, (CH3)2C=CHCH3, which can be polymerised.
.............................................................................................................
(i) Draw the repeating unit of the polymer. (3)

(ii) Describe an advantage or a disadvantage of a different method of disposal of such

objects compared with landfill.

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

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

.............................................................................................................
(ii) Draw the structure of an isomer of G which shows E-Z isomerism.
.............................................................................................................

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

.............................................................................................................
(iii) Draw the structure of an isomer of G which does not react with bromine water. (3)
(Total 14 marks)

(3)

(c) Draw the repeating unit of the polymer formed by the reaction between butanedioic acid
and hexane-1,6-diamine.

(2)
Page 37 of 86 Page 38 of 86
 (a) The repeating units of two polymers, P and Q, are shown below. (b) Draw the structures of the two dipeptides which can form when one of the amino acids
16 shown below reacts with the other.

Structure 1 Structure 2
(i) Draw the structure of the monomer used to form polymer P. Name the type of (2)
polymerisation involved.
(c) Propylamine, CH3CH2CH2NH2, can be formed either by nucleophilic substitution or by
Structure of monomer reduction.

(i) Draw the structure of a compound which can undergo nucleophilic substitution to
form propylamine.

Type of polymerisation .......................................................................

(ii) Draw the structure of the nitrile which can be reduced to form propylamine.
(ii) Draw the structures of two compounds which react together to form polymer Q.
Name these two compounds and name the type of polymerisation involved.

Structure of compound 1

(iii) State and explain which of the two routes to propylamine, by nucleophilic substitution
or by reduction, gives the less pure product. Draw the structure of a compound
formed as an impurity.
Name of compound 1 ......................................................................... Route giving the less pure product .....................................................
Structure of compound 2 Explanation .........................................................................................

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

Structure of an impurity
Name of compound 2 ........................................................................

Type of polymerisation .......................................................................

(iii) Identify a compound which, in aqueous solution, will break down polymer Q but not
polymer P. (5)
(Total 15 marks)
.............................................................................................................
(8)

Page 39 of 86 Page 40 of 86
 (a) The structure below shows the repeating unit of a polymer. Consider the reaction sequence shown below.
17 18

By considering the functional group formed during polymerisation, name this type of
polymer and the type of polymerisation involved in its formation.

Type of polymer ........................................................................................... (a) Name and outline a mechanism for the reaction in Step 1.

Type of polymerisation ................................................................................. Name of mechanism ....................................................................................

(2)
Mechanism
(b) Draw the structure of the species present in solid aminoethanoic acid, H2NCH2COOH

(1)

(c) Explain why the melting point of aminoethanoic acid is much higher than that of
hydroxyethanoic acid, HOCH2COOH

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

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

......................................................................................................................
(2)
(Total 5 marks)

(5)

Page 41 of 86 Page 42 of 86
(b) (i) Name compound Q formed in Step 2. (d) The amino acid R is shown below.

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

(ii) Two stereoisomers are formed by the dehydration of Q. Give the structures of these
two isomers and name the type of stereoisomerism shown.

Structures of isomers
(i) Draw the structure of the zwitterion formed by R.

(ii) Draw the structure of the major organic product formed when an excess of R is
reacted with bromomethane.

Type of stereoisomerism ..............................................................................

(4)

(c) An isomer of Q which has the structure shown below is polymerised to form the
biodegradeable polymer known as PHB.

(iii) Name the mechanism of the reaction which results in the formation of the product
given in part (ii).

.............................................................................................................
(3)
(i) Draw the repeating unit of the polymer PHB. (Total 14 marks)

(ii) Suggest a reason why the polymer is biodegradeable.

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

.............................................................................................................
(2)

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 This question is about the following reaction scheme which shows the preparation of polymer P. (b) When the dipeptide shown below is heated under acidic conditions, a single amino acid is
19 produced.

(i) Name this amino acid.

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

(ii) Draw the structure of the amino acid species present in the acidic solution.

Polymer P is formed in a two-step reaction from N. The first stage is a neutralisation reaction.
The volume, in cm3, of a 0.20 mol dm−3 solution of H2NCH2CH2NH2 required to neutralise 6.8 ×
10−3mol of the acid N is

A 17

B 34

C 68 (2)

D 136 (c) The repeating unit of a polyester is shown below.

(Total 1 mark)

(a) The compound H2C=CHCN is used in the formation of acrylic polymers.

20
(i) Draw the repeating unit of the polymer formed from this compound.
(i) Deduce the empirical formula of the repeating unit of this polyester.

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

(ii) Draw the structure of the acid which could be used in the preparation of this polyester
and give the name of this acid.

(ii) Name the type of polymerisation involved in the formation of this polymer.

.............................................................................................................
(2)

Structure ..............................................................................................

Name ...................................................................................................

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 (iii) Give one reason why the polyester is biodegradable. (ii) Give the repeating unit in the polyamide nylon 6,6.

.............................................................................................................
.............................................................................................................
(4) (b)
(Total 8 marks)
.............................................................................................................
(2)
Synthetic polyamides have structures similar to those found in proteins.
(i) Draw the structure of 2-aminopropanoic acid.

Terylene is made by reacting benzene-1,4-dicarboxylic acid and ethane-1,2-diol.

21
Terylene is

A an addition polymer.
(ii) Draw the organic product formed by the condensation of two molecules of
B a polyamide. 2-aminopropanoic acid.

C a polyester.

D a nylon.
(Total 1 mark)

(a) Compound C, H2N(CH2)4NH2, can be synthesised from ethene in three steps as shown
22 below.
(2)
Step 1 Step 2 Step 3
Ethene Compound Compound Compound (c) Compounds like H2N(CH2)6NH2 are also used to make ionic compounds such as X, shown
addition A substitution B C below.
reaction reaction C4H4N2 H2N(CH2)4NH2

Name compound C and draw a structure for each of compounds A and B.

State the reagent(s) required for each step and name the type of reaction involved in the
conversion of B into C.
(7)

(b) Draw the repeating unit of the polyamide formed when C reacts with hexanedioic acid.
Discuss the interactions between the chains of the polyamide. (i) X belongs to the same type of compound as (CH3)4N+Br–
(4)
Name this type of compound.
(c) Explain why polyamides are degraded by sodium hydroxide whereas polymers such as
.............................................................................................................
poly(ethene) are not.
(3)
(Total 14 marks)
(ii) State a reagent which could produce X from H2N(CH2)6NH2 and give a necessary
condition to ensure that X is the major product.
(a) Synthetic polyamides are produced by the reaction of dicarboxylic acids with compounds
23 such as H2N(CH2)6NH2 Reagent .............................................................................................

(i) Name the compound H2N(CH2)6NH2 Condition ............................................................................................

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

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(iii) Name the mechanism involved in this reaction to form X.

.............................................................................................................
(4)
(Total 8 marks)

Page 49 of 86