POLYMERISATION A2:

1. (b) The diacid L occurs naturally and is used as a food additive to enhance the acidic
flavour in some fruit drinks.
HO2CCH2CH2CO2H
L
When the diacyl chloride of L is reacted with HOCH2CH2OH, a polymer is formed.
(i) What type of polymerisation is occurring here?
.....................................................................

(ii) Write an equation showing the reaction between one mole of the diacyl chloride
of L and two moles of HOCH2CH2OH.

[3]

(c) The following formula represents a section of another polymer.

(i) What type of polymer is this?

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

(ii) Draw the structural formula of each of the monomers that make up this polymer.

[3]

2. Hydrophilic polymers find important uses in the manufacture of contact lenses

and wound dressings. Their chemical structures allow them to bond with water
molecules, which keeps them soft and flexible. Sections of two hydrophilic
polymers are shown below.

1
 J

(a) What type of polymerisation has produced

(i) polymer H? ...................................................
(ii) polymer J? .................................................... [2]

(b) What type of attractions might occur between these polymers and molecules of
water?
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . [1]

(c) Chains of polymer H can be ‘cross–linked’, i.e. joined together, by reaction with a
small bifunctional molecule.
(i) Which one of the following molecules would be most suitable for such
crosslinking?
(place a tick in one box only)

(ii) What type of bond would be formed during the cross–linking?

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

2
(d) (i) Suggest the reagents and conditions needed to hydrolyse polymer J into its
monomers.
.....................................................................

(ii) Draw the structural formulae of the two products of this hydrolysis reaction.
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . [3]

(e) The last compound in the list in (c)(i) above is 3–aminopropanoic acid. This can be
made from potassium chloroethanoate by the following 3–stage route.

(i) In the box above write the structure of the intermediate in this route.

(ii) Suggest reagents and conditions for

Stage II .....................................................................................................................
Stage III ................................................................................................................ [3]

3. (f) The formula of part of the chain of a synthetic polyamide is shown below.

(i) Identify the repeat unit of the polymer by drawing square brackets around it on
the above formula.

(ii) Draw the structures of the two monomers from which the polymer could be
made.

. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . [3]

3
4. Ethylbenzene is an important starting material for making polystyrene
(poly(phenylethene)).

(a) (i) State the conditions needed to carry out reaction I in the laboratory.
.....................................................................

(ii) State the reagent and conditions needed for reaction II.
.....................................................................

(iii) Draw the structure of the repeat unit of polystyrene.

(iv) There are several polymers that consist of phenylethene co-polymerised with
other monomers. The following formula shows part of the chain of one such co-
polymer.

Deduce the structural formula of the other monomer.

[5]

4
5. Each of the following structures is an 8-atom segment of the chain of a
commercial polymer.
For each structure,
• decide whether it is part of a condensation or an addition polymer, and
• draw the structural formulae of the monomer(s) from which the polymer is
made.

[8]
5
6. (a) The viscosity of engine oil can be improved by the addition of certain medium
chainlength polymers.
A portion of the chain of one such polymer is shown below.
–CH2CH(CH2CH2CH3)CH2CH(CH2CH2CH3)CH2–
On average, the molecules of the medium-chain polymer contain 40 carbon
atoms.
(i) Suggest the structure of the monomer.
.....................................................................

(ii) How many monomer units are incorporated into the average molecule of the
polymer?
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . [2]

7. (a) Spider silk is a natural polymer which has an exceptional strength for its weight.
Kevlar is a man-made polymer designed to have similar properties. It has a wide
variety of uses from sporting equipment to bullet-proof vests.

Kevlar

6
(i) In Kevlar, the polymer strands line up to form strong sheets with bonds between
the strands.
On the diagram above, draw part of a second polymer chain showing how bonds
could be formed between the chains.
(ii) Suggest what type of bonds these are.
.....................................................................

(iii) Draw two possible monomer molecules for making the polymer Kevlar.

[5]

(b) The transport of oil by sea has resulted in a number of oil spills in recent years. As
well as a waste of a valuable resource, these have caused major environmental
problems. Traditional sorbent materials absorb water and sink. Researchers have
developed new sorbent materials to help collect the spilled oil. The sorbent
consists of a material called ‘hydrophobic aerogels’. This is a network of
silicon(IV) oxide with some of the silicon atoms attached to fluorine-containing
groups.
—O—Si—CH2—CF3
The introduction of these fluorine-containing groups allows the oil to be
absorbed but not the water. Tests show that these materials can absorb more
than 200 times their mass of oil without sinking.
(i) Suggest what the word hydrophobic means.
.....................................................................

(ii) Suggest why the fluorine-containing groups allow oil to pass through but not
water molecules.
.....................................................................
.....................................................................

7
 .....................................................................

(iii) Suggest another important fluorine-containing polymer that repels water-

containing materials.
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . [4]

8. (a) Polyvinyl acetate, PVA, is a useful adhesive for gluing together articles made from
wood, paper or cardboard. The monomer of PVA is ethenyl ethanoate, B.

B
PVA is formed from B by the process of addition polymerisation.
(i) Draw a section of the PVA molecule containing at least 2 monomer molecules,
and identify clearly the repeat unit.

The ester B can be hydrolysed in the usual way, according to the following
equation.

(ii) Use this information to suggest a possible structure for C and draw it in the box
above.

When substance C is extracted from the product mixture, it is found that it does
not decolourise Br2(aq), but it does form a pale yellow precipitate with alkaline
aqueous iodine.

8
(iii) Suggest a structure for C that fits this new information.

(iv) Suggest a confirmatory test for the functional group in the structure you have
drawn in (iii). Your answer should include the reagent you would use and the
observation you would make.
.....................................................................
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . [6]

(b) The following diagram represents a section of another polymer.

(i) On the above formula draw brackets, [ ], around the atoms that make up the
repeat unit of this polymer.

(ii) Name the functional group in polymer D.

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

(iii) Suggest and draw the structure of the monomer, E, that could form this polymer.

(iv) What type of polymerisation is involved in making polymer D from its monomer?
.....................................................................

9
(v) What is the relationship between the repeat unit of polymer D and the repeat
unit of PVA?
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . [5]

(c) Monomer E exists as two stereoisomers. Heating either isomer with Al 2O3 gives a
mixture of two unsaturated carboxylic acids F and G, which are stereoisomers of
each other.
(i) Name the type of stereoisomerism shown by compound E.
.....................................................................

(ii) Suggest structures for F and G, and name the type of stereoisomerism they show.

Type of isomerism . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . [4]

9. In today’s world, many traditional materials have been replaced by different sorts
of polymers.
This includes rigid polymers such as those used in car bodies to replace steel and
flexible polymers like those used in textiles to replace cotton or wool.
(a) (i) To form a polymer, what is the minimum number of functional groups that the
monomer must possess?
.......................................................

(ii) Illustrate your answer to (i) with the structure of a possible monomer.

[2]

10
(b) State two differences between addition and condensation polymerisation.
(i) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
.....................................................................
(ii) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . [2]

(c) The polymer formed from the co-polymerisation of the two monomers shown is
known as Terylene.

benzene-1, 4-dicarboxylic acid ethane-1-2-diol

(i) The two monomers react by condensation polymerisation. What other molecule
is formed in this reaction?
.......................................................

(ii) Draw the structure of one repeat unit of Terylene.

(iii) What is the name given to polymers containing the same functional group as
Terylene?
....................................................... [4]

(d) The monomers ethene and but-1-ene can also co-polymerise to form a
polyalkene, but this does not produce a regular alternating structure like
Terylene. Explain why this is the case, drawing diagrams if you wish.
.....................................................................
.....................................................................

11
 .....................................................................
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . [2]

10. In today’s world we make use of a wide range of different polymers. These
polymers are often substitutes for traditional materials, but may have more
useful properties.
(a) Complete the table identifying one traditional material that has been replaced by
each polymer.
Traditional material Modern polymer and its use

PVC in packaging

Terylene in fabrics

polycarbonate bottle
[2]

(b) Throwing away articles made from polymers after use is a major environmental
concern for two main reasons. Identify each of these reasons and suggest a
strategy that has been adopted to try to overcome each of these.
Reasons : . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
.....................................................................
.....................................................................
Strategy 1 : . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
.....................................................................
Strategy 2 : . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . [3]

(c) One suggestion for the disposal of polymers is to use them as a fuel to provide
energy for small-scale power stations or district heating schemes.
Identify one polymer which would be unsuitable for this use, explaining the
reason behind this.

12
 Polymer ................................................
Reason . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
.....................................................................
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . [2]

(d) Polymers can be either thermoplastic or thermosetting.

Name a thermoplastic polymer. .........................................................
State which type of polymerisation produces thermoplastic polymers, explaining
your answer in terms of the structure of the polymer.
.....................................................................
.....................................................................
.....................................................................
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . [3]

11. Some of the most commonly used polymers are formed by the polymerisation of
ethene, C2H4.
The presence of side-chains affects the bulk properties of an addition polymer.
Unbranched polymers pack closer together than polymers with several side-
chains. Poly(ethene) exists in two different forms LDPE (low density poly(ethene))
which has lots of side-chains, and HDPE (high density poly(ethene)) in which
there are fewer and shorter side-chains.
(a) Explain with the aid of sketches why the presence of side-chains causes a
difference in density in poly(ethene).

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

13
(b) By reference to the type of bonding between the poly(ethene) chains, explain
why LDPE has a lower melting point that HDPE.
.....................................................................
.....................................................................
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . [2]

(c) Polymerisation can take place by two different methods depending on the
monomers involved. The two methods are addition and condensation.
Give two differences between the methods.
1. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
.....................................................................
2. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . [2]

(d) There has been a great deal of commercial interest in the development of
polymers that can conduct electricity and/or emit light. A length of one such
polymer is shown.

(i) Suggest how this polymer conducts electricity.

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

(ii) Suggest the molecular geometry required for this molecule to conduct. Explain
your answer.
.....................................................................
.....................................................................

(iii) What is the empirical formula of this polymer?

14
 . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . [4]
12. (c) The following diagram shows a section (not a repeat unit) of a polymer, G, that
can be made from the two monomers E and F.

(i) What type of polymerisation made this polymer?

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

(ii) Draw the structures of the two monomers E and F.

(iii) Suggest the conditions needed to make polymer G from E and F in the laboratory.
.....................................................................
.....................................................................
.....................................................................

(iv) One of the monomers, E or F, could be changed to make a more rigid polymer of
a similar chemical type to G.
Suggest which of your two monomers could be changed, and suggest a structure
for the new monomer.
Monomer to be changed (E or F) ...........................
Structural formula of the new monomer

15
 [6]
13. The increasing awareness of the diminishing supply of crude oil has resulted in a
number of initiatives to replace oil-based polymers with those derived from
natural products. One such polymer, ‘polylactide’ or PLA, is produced from corn
starch and has a range of applications.
(a) The raw material for the polymer, lactic acid (2-hydroxypropanoic acid), is formed
by the fermentation of corn starch using enzymes from bacteria.
(i) Calcium hydroxide is added to the fermentation tanks to prevent the production
of lactic acid from slowing down.
Why might high acidity reduce the effectiveness of the enzymes?
.....................................................................
.....................................................................

(ii) The structure of lactic acid is shown.

What type of reaction takes place in this polymerisation?

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

(b) Lactic acid exists in two stereoisomeric forms. Draw the other form in the box.

[1]

(c) One of the reasons PLA has attracted so much attention is that it is
biodegradeable. This does, however, restrict some potential uses. The simple
polymer has a melting point of around 175 °C, but softens between 60-80 °C.

16
 However, its thermoplastic properties enable it to have a range of uses in fibres
and in food packaging.
(i) Explain why PLA would not be a suitable packaging material for foods pickled in
vinegar.
.....................................................................
.....................................................................

(ii) PLA containers are not used for hot drinks. Suggest why.
.....................................................................
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . [2]

(d) Lactic acid can also be co-polymerised with glycolic acid.

Glycolic acid
(i) Draw a section of the co-polymer showing one repeat unit.

(ii) Suggest what type(s) of bonding will occur between chains of this co-polymer,
indicating the groups involved.
.....................................................................
.....................................................................
.....................................................................

(iii) Suggest one property in which the co-polymer differs from PLA.
.....................................................................
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . [5]

17
14. The physical properties of polymers depend on the average relative molecular
mass of the polymer chains and on the functional groups present in the
monomers.
The presence of side-chains in addition polymers can increase the spacing
between polymer chains in the bulk substance and hence reduce the overall
density.
In condensation polymers it is the nature of the side-chain that is often more
important since this can lead to cross-linking of the polymer chains forming a
three-dimensional structure.
(a) For each of the following polymers, give the structure of the monomer(s) and
state the type of reaction used to produce the polymer.

Polymer A
Monomer(s)

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

Polymer B
Monomer(s)

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

Polymer C

18
 Monomer(s)

Type of reaction .................................................................................... [5]

(b) Look at the structures of the three polymers and answer the following questions.
(i) Suggest why the density of B is lower than that of A.
.....................................................................
.....................................................................

(ii) Which polymer will have the weakest forces between chains, and what is the
nature of these forces?
.....................................................................
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . [2]

15. In recent years there has been a lot of interest in polymers in the form of gels
that absorb aqueous materials. One of the largest uses of these polymers is in
disposable nappies (diapers). The gel which is used in this case is a polymer of
propenoic acid.

Propenoic acid
(a) (i) Draw a section of the polymer of propenoic acid showing two repeat units.

(ii) By what type of chemical reaction is this polymer formed?

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

19
(iii) By what type of bonding is water held on the polymer?
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . [3]

(b) For some disposable nappies (diapers), the monomer is a mixture of propenoic
acid and sodium propenoate. The properties of the polymer are influenced by the
proportion of sodium salt in the monomer mixture.
(i) Suggest and explain how the difference in the structure of this polymer
compared to one formed only from propenoic acid might affect the water
absorbing properties of the polymer.
.....................................................................
.....................................................................
.....................................................................

(ii) Suggest a property the polymer should have in order to be used in disposable
products.
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . [3]

(c) A variation on the gel used for disposable nappies (diapers) containing more
sodium propenoate has been used to treat soils contaminated by heavy metals
such as lead (Pb2+) and cadmium (Cd2+). Suggest why the gel is effective.
.....................................................................
.....................................................................
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . [2]

(d) Another variation on this type of polymer is used in hair gels. In these, the
polymer chains are cross-linked by a compound known as pentaerythritol.

pentaerythritol

20
(i) By what type of chemical reaction are the cross-links in this polymer formed?
.....................................................................

(ii) It is important that the gel should be easily washed out of hair. What is it about
the structure of the polymer that allows this to happen?
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . [2]

16. In recent years there has been considerable interest in a range of polymers
known as ‘hydrogels’. These polymers are hydrophilic and can absorb large
quantities of water.
(a) The diagram shows part of the structure of a hydrogel.

The hydrogel is formed from chains of one polymer which are cross-linked using
another molecule.

21
(i) Draw the structure of the monomer used in the polymer chains.

(ii) State the type of polymerisation used to form these chains.

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

(iii) Draw the structure of the molecule used to cross-link the polymer chains.

(iv) During the cross-linking, a small molecule is formed as a by-product. Identify this
molecule.
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . [5]

(b) Once a hydrogel has absorbed water, it can be dried and re-used many times.
Explain why this is possible, referring to the structure on the opposite page.
.....................................................................
.....................................................................
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . [2]

(c) Not every available side chain in the polymer is cross-linked, and the amount of
cross-linking affects the properties of the hydrogel.
(i) The amount of cross-linking has little effect on the ability of the gel to absorb
water. Suggest why this is the case.
.....................................................................
.....................................................................
.....................................................................

22
(ii) Suggest one property of the hydrogel that will change if more cross-linking takes
place. Explain how the increased cross-linking brings about this change.
.....................................................................
.....................................................................
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . [3]

17. Super-absorbent polymers have the ability to absorb 200-300 times their own
mass of water.
They are classified as hydrogels and they are widely used in personal disposable
hygiene products such as babies’ nappies (diapers).
These polymers are commonly made by the polymerisation of compound K mixed
with sodium hydroxide in the presence of an initiator.

K
(a) (i) Explain what is meant by the term polymerisation.
.....................................................................
.....................................................................

(ii) What type of polymerisation is involved in the formation of hydrogels?

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

(iii) Describe the changes in chemical bonding that occur during the polymerisation of
K.
.....................................................................
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . [3]

(b) Acrylic acid is the common name for compound K.

Suggest the systematic (chemical) name of K.
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . [1]
23
(c) (i) Draw the structure of at least two repeat units of the polymer formed by the
above method from acrylic acid, K, when mixed with NaOH.

(ii) The C–C–C bond angle in compound K changes when the polymer is formed.
State and explain how the C–C–C bond angle differs between a molecule of K and
the polymer.
Angle changes from ............................................ to .................................................
Explanation. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . [4]

(d) (i) Draw a detailed diagram of a portion of the polymer you have drawn in (c)(i) to
explain how it can absorb a large volume of water.

(ii) A student added 0.10 g of the polymer to 10 cm 3 of aqueous copper(II) sulfate

solution.
Predict, with a reason, what you expect to observe.
.....................................................................
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . [4]

(e) Compound L, CH2=CHCONH2, can also be polymerised to form a super-absorbent

polymer.
(i) Name the two functional groups in compound L.
.....................................................................
.....................................................................

24
 Compound K can be converted into compound L by the following two-step route.

(ii) Suggest a reagent for step 1.

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

(iii) What other product is formed in step 2?

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

(iv) State the reagents and conditions necessary to re-form K from L.

. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . [5]

18. Polymers consist of monomers joined by either addition or condensation

reactions.
(a) Name an example of a synthetic addition polymer and a synthetic condensation
polymer.
Addition polymer . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
Condensation polymer . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . [2]

(b) Addition polymers are long-term pollutants in the environment but condensation
polymers are often biodegradable.
(i) What type of reaction occurs when condensation polymers biodegrade?
.....................................................................

(ii) Identify two functional groups that could undergo this type of reaction.
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . [2]

(c) Petroleum is a non-renewable resource from which a wide range of useful

polymers is currently produced. Current polymer research is looking at renewable
plant material as a potential source of monomers.
Two monomers obtained from plants are shown.

25
 CH3CH(OH)COOH HOCH2COOH
Draw the displayed formula of the repeat unit of a polymer using both
monomers.

[2]

(d) Monomers obtained from plant sources do not usually form addition polymers.
Suggest why this is.
.....................................................................
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . [1]

(e) The diagrams show sections of two polymers Y and Z.

(i) What would be the main force between the chains in each polymer?
Y.................................................................................................................................
Z.................................................................................................................................

(ii) Which is likely to be the more hydrophilic of these two polymers? Explain your
answer.
.....................................................................
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . [3]

19. (a) Polymers can be formed by addition or condensation polymerisation.

26
 Complete the table.
Polymer method of polymerisation
Nylon

PVC (polychloroethene)

Terylene
[1]

(b) Nomex is a polymeric material with excellent flame-resistant properties.

It contains a polymer made from the two monomers shown below.

Draw the structure of the polymer showing two repeat units. The linkages
between monomer units should be shown fully displayed.

[2]

20. (b) 1,3-dimethylbenzene is also a starting material for the synthesis of the polymer
Nomex, used in fireproof protective clothing worn by fire fighters, military pilots
and racing car drivers. The polymer is made from 1,3-dimethylbenzene and 1,3-
dinitrobenzene by the following route.

27
(i) Draw the structure of one repeat unit of Nomex in the box above. [1]

(ii) What type of polymer is Nomex?

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

(iii) Suggest the by-product formed during step 3.

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

(iv) Suggest reagents and conditions for step 2.

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

(v) Suggest how and why the properties of the polymer might change if some of the
diamine monomer were replaced with 1,3,5-triaminobenzene.

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

28
21. Polymers consist of monomers joined either by addition or condensation
reactions.
(a) Complete the table by placing a tick (✓) in the correct column to indicate the
type of reaction that would polymerise each of the monomers.
Monomer Addition Condensation Both

[3]

(b) Poly(ethene) bags pollute the environment for a long time because they are non-
biodegradable. Suggest why.
.....................................................................
.....................................................................
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . [2]

(c) There has been considerable research into making biodegradable plastic bags.
The repeat unit for one of the polymers used, polylactic acid (PLA), is shown.

29
(i) Draw the structure of the monomer for PLA.

[1]

(ii) Suggest why PLA breaks down more easily in the environment than poly(ethene).
.....................................................................
.....................................................................
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . [1]

(d) The table shows the melting points of three polymers.

Polymer Melting point / °C

Polyethene 137

Polychloroethene (PVC) 212

Nylon 6,6 265

Explain the differences in melting point of these three polymers in terms of the
intermolecular forces between the chains.
.....................................................................
.....................................................................
.....................................................................
.....................................................................
.....................................................................
.....................................................................
.....................................................................
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . [3]

30
22.(a) (i) Name an example of a synthetic polyester and a synthetic polyamide.
Polyester . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
Polyamide . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . [1]

(ii) Polyesters and polyamides are formed by condensation reactions.

Name a molecule which is commonly eliminated in such reactions.
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . [1]

(b) (i) The table shows the repeat units of a number of polymers. Place a tick ( ✓)
against the ones which are biodegradable.
Polymer Repeat unit Biodegradable

[2]

31
(ii) Draw the structures of two monomers used to form polymer B.

[2]

23. (f) (i) Under certain conditions, ethane-1,2-diamine reacts with ethanedioic acid,
HO2CCO2H, to form the polymer Z.
Draw the structure of this polymer, Z, showing two repeat units.

[2]

(ii) Name the type of reaction occurring during this polymerisation.

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

(iii) Polymer Z is an example of a biodegradable polymer.

Name a polymer that is non-biodegradable.
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . [1]

24. (d) (i) State what you would observe when an excess of aqueous bromine is
added to a solution of K.

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

(ii) K can be polymerised.

32
Draw the structure of the polymer showing two repeat units. The linkage
between the monomer units should be fully displayed.

[2]

33
 POLYMERISATION A2 MARK SCHEME:
1. (b) Condensation (1)

(ii) ClCOCH2CH2COCl + 2HOCH2CH2OH → (1)

HOCH2CH2OCOCH2CH2CO2CH2CH2OH (+ H2O) (1) [3]

(c) (i) Polyamide or nylon (allow condensation) [NOT peptide or protein] (1)

(ii) (or dichloride) NH2(CH2)4NH2 (1) + (1) [3]

[Total: 6]

2. (a) (i) Addition (polymerisation) (1)

(ii) Condensation (polymerisation) (1) [2]

(b) Hydrogen bonding (1)

(c) (i) HO2CCH2CH2CO2H (1)

(ii) Ester (accept “covalent”) (1) [2]

(d) (i) Heat with H3O+ or heat with OH–(aq) (1)

(ii) H2N–CH2–CH(OH)–CH2–NH2 or H3N+–CH2–CH(OH)–CH2–NH3+ (1)

34
HO2C–CH(OH)–CH(OH)–CO2H or –O2C–CH(OH)–CH(OH)–CO2– (1)

(Allow bonus mark if the acid/base forms are consistent with the reagent used for the
hydrolysis) (1)

[4 max 3]

(e) (i) NC–CH2–CO2– K+ (1)

(ii) II: H2 + Ni or Na in ethanol [allow LiAlH4] (1)

III: dilute HCl or H2SO4 or H+(aq) (1) [3]

[Total: 11]

3. (i) e.g.

(1)

(ii)

(1)
(1) [3]

4. (a) Light or heat [aq or AlCl3 negates] (1)

(ii) NaOH/KOH/alkali/OH– (1)

In alcohol/ethanol + heat [aq negates] (1)

(iii) [–CH2CH(C6H5)–] [C–C not needed, but C=C is wrong] (1)

(iv) CH2=CHCN [C=C is needed here] (1) [5]

35
5.

⇑ ⇑
(2) (6)
(2 correct: (1)) (6 correct: (5)) etc
(2 correct: (1))
(C=C bonds not needed, but penalise –(1) if C–C drawn instead of C=C)
(If more than 7 formulae drawn, then penalise –(1) for each formula in excess of
7) [8]
[Total: 8]

6. (a) (i) CH2=CH–CH2CH2CH3 accept C3H7 on RHS (1)

(ii) 8 (1) [2]

7. (a) Correct diagram showing at least one monomer unit, and at least one N-H and
C=O.
i.e. –NH-C6H2-NH-CO– or –CO-C6H4-CO-NH–
(No mark for this, but apply a penalty of –[1] if candidate’s diagram does NOT
show these points correctly)
One H-bond between N-H of original chain and C=O group of new chain (1)
One H-bond between C=O of original chain and N-H group of new chain (1)

(ii) Hydrogen bonds or H-bonds (in words; can be written on diagram)

36
 (Ignore ref to v d W) (1)

(iii)

(1)

(1) [5]

(b) (i) Water-hating/fearing/repelling/resistant or can’t form bonds with water

(molecules) (1)
[NOT insoluble or does not dissolve in water, also NOT “non-polar”]

(ii) Fluorine-containing groups form van der Waals bonds (with the oil molecules)...
(1)
…but cannot form hydrogen bonds (with the water molecules) (1)

(iii) Teflon/PTFE (1) [4]

[Total: 9]

8. (a) (i) (allow displayed, structural or skeletal formula)

37
 Chain (1)
Repeat unit (1)

(ii) C should be CH2=CHOH (or skeletal formula) (1)

(iii) C is CH3CH=O (or skeletal formula) (1)

(iv) E.g. add (2,4-)DNPH or DNP or Brady’s reagent ecf (1)
Orange or red ppt forms (NOT yellow) ecf (1)
(Or could use Fehling’s or Tollens’, or H + Cr2O7 : orange to green, or H + MnO4–:
+ 2– +

purple to colourless) [6]

(b) (i) (allow displayed, structural or skeletal formula)

D
Correct repeat unit bracketed (any 3 atoms in chain) (1)

(ii) Ester (1)

(iii) E is CH3CH2CH(OH)CO2H (or skeletal structure etc.)(2-hydroxybutanoic acid) (1)

Allow ecf here from the formula of the repeat unit shown in (b)(i)

(iv) Condensation (polymerisation) (1)

(v) They have the same “molecular” formula or C 4H6O2 (do NOT allow empirical
formula) or same no. and type of atoms or same functional group or both are
esters or they are isomers (1) [5]

(c) (i) Optical isomerism (or chiral) (1)

(ii)

38
 (letters may be reversed)(allow ecf from E, also allow ecf for G from F) (1) + (1)
Cis-trans or geometrical isomerism (1) [4]
[Total: 15]

9. (a) (i) One (1)

(ii) Any alkene (or allow a cyclic amide, as in caprolactam) (1) [2]

(b) Any TWO from: addition needs unsaturated/double bonds/alkene

Condensation eliminates a small molecule
Condensation needs a molecule other than a hydrocarbon
Empirical formula of addition polymer is the same as that of its monomer
Condensation needs two different functional groups
(NOT – “condensation needs two different monomers”) 2 × (1)

(c) (i) Water (1)

(ii)

Correct ‘ester’ bond (1)

‘Sticks’ to rest of molecule (1)
Note : candidates need only show ‘brackets’ if more than one repeat unit shown

(iii) Polyesters (1) [4]

(d) Monomers in Terylene have to alternate in order to condense out water (1)
Alkenes can link in any order (and still form a polyalkene) (or diagram showing
this) (1) [2]
[Total: 10]

39
10. (a)

Traditional material Modern polymer used

Paper/cardboard/wood/leaves
hessian/hemp/jute PVC in packaging
steel/aluminium

Cotton/wool/linen Terylene in fabrics

Glass/china/porcelain/earthenware
Polycarbonate bottle
metal/leather
3 → 2 marks, 2 → 1 mark
[2]

(b) Reasons: Plastics/polymers pollute the environment for a long time do not
decompose/ biodegrade quickly (1)
They are mainly produced from oil (1)
Produce toxic gases on burning (1)
[max two]
Strategy 1: Recycle polymer waste / use renewable resources (1)
Strategy 2: Develop biodegradable polymers (1)
[max 3]

(c) PVC (1)

Combustion would produce HCl / dioxins as a pollutant (1)
Or
Nylon/ Acrylic (1)
Combustion would produce HCN (1) [2]

(d) (i) Polythene (or other addition polymer) (1)

(ii) Addition polymerisation (1)

The polymer chains don’t have strong bonds between them – easy to melt (1) [3]
Could be answered with a suitable diagram
[Total: 10]

11.
40
 LDPE HDPE minimum of 2 chains suitable sketches (1)
(The close packing of unbranched side chains means)
LDPE more space between the chains/polymers or HDPE less empty space
between the chains (1) [2]

(b) van der Waals’ (VDW) forces (1)

are weaker (1) [2]

(c)
Addition OR Condensation

Requires C=C/double bond does not need C=C/double bond

Uses the same functional group needs two different functional groups
Same general (empirical) formula as
different formula
monomer
No loss of small molecule/H2O/HCl small molecule /H2O/HCl is formed
Any two differences (1) [2]

(d) (i) (Through its long chain of) delocalised electrons/mobile electrons (1)
Free electrons is not sufficient

(ii) Planar (1)

the π bonds/p-orbitals overlap (with each other) (1)

(iii) C 8 H6
C 4 H3 (2)
[5 max 4]
[Total: 10]

12. (c) Condensation (1)

41
(ii) (in parts (ii) and (iii), allow structural formulae instead of skeletal) (1) + (1)
or NaO

E F
(N.B. letters E and F may be reversed.)

(iii) Make acyl chloride from F (if not already there) (1)
Add that to a solution of E in NaOH(aq) (1)

(iv) F (or E, i.e. the alphatic di-acid) should be changed to something less flexible, e.g.

(Any size ring with n < 6; any orientation) (but not HO2C(CH2)3CO2H or longer)
(Ignore side chains: length of chain is the important feature)
Or allow a tri-carboxylic acid (or triphenol), i.e. one that will allow cross linking
(1) [6]
[Total: 16]

13. (a) (i) It could denature the enzyme or

Alter the 3D structure/tertiary structure/shape of active site. (1)

(ii) Condensation (1) [2]

(b)

(1)

(c) (i) (Acid present would) hydrolyse the ester (linkage) (1)

42
(ii) (Hot water would) soften (the container) (1) [2]

(d) (i)

Ester linkage shown (1)

Rest of repeat unit correct (ONE) (1)

(ii) Van der Waals’ from CH3/methyl group (1)

Permanent dipole-dipole from ester group (1)

(iii) Accept any sensible physical property suggestion e.g. different melting point or
different density or different solubility. (1) [5]
[Total: 10]

14. (a) A monomers: H2N–(CH2)6–NH2 and HO2C–(CH2)4–CO2H or ClCO(CH2)4COCl (1)

Condensation or nucleophilic substitution or addition-elimination (1)
B monomer: H2C=CHCH3 (1)
Addition (NOT additional) (1)
C monomer: H2N–(CH2)5–CO2H or H2N–(CH2)5–COCl or (1)
Condensation (1)
[max 5]

(b) (i) Need a statement from both columns for [1] mark.
(a) (b)
More compact packing in A Stronger (inter-chain) forces in A
Chains closer in A Hydrogen bonding in A
Chains further apart in B Weaker (inter-chain) or van der Waals'
forces in B
B contains side-chain/branched chains
(1)

43
(ii) Polymer B – van der Waals’/London (dispersion)
forces/induced-instantaneous/induced dipoles
NOT just 'dipole' (1) [2]
[TOTAL: 7]
15. (a) (i)

(1)

(ii) Addition (1)

(iii) Hydrogen bonding (1) [3]

(b) (i) More / increase water absorbing properties (allow attracts water more) (1)
More polar (ity) /more hydrophilic / has ionic side-chains (as well as hydrophilic
ones) (1)

(ii) It should be biodegradable/decompose [1] [3]

(c) Idea of ion exchange / replacement of Na+ for Cd2+/Pb2+ (1)

(The metal ions) will be attracted to the carboxylate ions (1) [2]

(d) (i) Condensation ([1))

(ii) OH/alcohol groups

So highly soluble / able to form hydrogen bonds (1) [2]
[Total: 10]

16. (a) (i) CH2 = CH–CO2H or CH2 = CH–CO2R or CH2 = CH–COCl (2)

(ii) Addition (polymerisation) (1)

(iii) C(CH2OH)4 (1)

(iv) Water (1) [5]

44
(b) (Water is bonded to the polymer by) hydrogen bonding (1)
hydrogen bonds are weak or easily broken (1) [2]

(c) (i) Cross-linking causes no reduction in the number of –OH groups

Or cross-linking molecules also have –OH groups (1)

(ii) Property e.g. becomes harder / more rigid / less flexible / stronger / higher
melting point. (1)
Because the chains are more strongly / tightly held (1) [3]
[Total: 10]

17. (a) (i) Many monomers form a polymer (1)

(ii) Addition (1)

(iii) C=C/double/π bond is broken and new C-C single bonds are formed
Or double bond breaks and forms single bonds with other monomers (1) [3]

(b) Propenoic acid (1)

(c) (i)

Carbon chain and CO2H (1)

At least one sodium salt (1)

(ii) 120° to 109(.5)° (1)

Due to the change from a trigonal/sp2 carbon to a tetrahedral/sp3 carbon (1) [4]

(d) (i)

45
 Any four:
Hydrogen bond labelled
Water H-bonded to O through H atom
δ+/δ– shown on each end of a H-bond
Lone pair shown on O- or C=O or H2O on a correct H-bond
Na+ shown as coordinated to a water molecule )3)

(ii) Solution became paler and Cu(2+) swapped with Na(+)

Or darker in colour and polymer absorbs water (1) [4]

(e) (i) Alkene(1), amide(1) (2)

(ii) NH3 (1)

(iii) H2 O (1)

(iv) HCl (aq)/H3O+ and heat/reflux (not warm) (1) [5]

Or OH– (aq), heat and acidify
[Total: 17]

18. (a) (i) Any addition polymer (e.g. polyethene, polypropene, polystyrene, PVC,
PTFE, PVA, Teflon) (1)

(ii) Any condensation polymer (e.g. polyamide, polyester, nylon, Terylene, PET, PLA,
Kevlar, Nomex) (1) [2]

(b) Hydrolysis or nucleophilic substitution (1)

Ester and amide / peptide or –CO2– and –CONH– (1) [2]

(c)

46
 Correct ester linkage (1)
CH3 side chain on only one monomer unit (1) [2]

(d) Plant materials do not generally contain unsaturated hydrocarbons / alkenes /

C=C (1)

(e) (i) Y van der Waals’ forces (1)

Z hydrogen bonding (1)

(ii) Z, because it can form hydrogen bonds with water or it contains polar CO and NH
groups (1) [3]
[Total: 10]

19. (a) Nylon, Terylene – condensation; PVC – addition – all three correct (1)

(b) Correct fully displayed formula of –CO–NH– unit correct polymer structure (1)
Correct polymer structure (1) [2]

20. (a) (i)

(1)

47
(ii) Polyamide or condensation (1)

(iii) H2O / water (1)

(iv) Sn / Fe + HCl + conc / aq / heat/warm (1)

(v) Harder or more dense or stronger or higher m.pt or tougher or more rigid due to
cross-linking or more H-bonding between the chains (1) [5]

21. (a) (3)

Monomer Addition Condensation Both

(b) Polythene is non-polar or its bonds are non-polar (2)

So not (easily) hydrolysed

(c) (i) (1)

48
 (Allow displayed, skeletal, part-skeletal, structural etc.)

(ii) The ester (or –COO–) linkage / bond is hydrolysed or reacts with water (1)

(d) Polythene has (weak) van der Waals’ (or id–id) forces (3)
PVC has stronger van der Waals’ forces or additional dipole forces
Nylon has (strong) hydrogen bonding
[Total: 10]

22. (a) (i) Polyester : Terylene / polylactic acid (PLA) / (1)

Polyamide : nylon / Kevlar / Nomex

(ii) Water or hydrochloric acid / hydrogen chloride (1)

(b) (i) (2)

Polymer Biodegradable
A Yes
B Yes
C No
D Yes

(ii) (2)

49
 [Total: 6]

23. (f)(i) Amide bond, displayed or –CONH– (1)

Rest of the molecule with continuation bonds (1) [2]

(ii) Condensation / addition – elimination (1)

(iii) Any named polyalkene / eg polyethene, PVC (1)

Allow Bakelite or Kevlar (1) [2]

24. (d) (i) No change / colour remains orange (1)

(ii)

Amide bond displayed (1)

Two repeat units (1) [2]
[Total: 03]

50