ORGANIC WS 9 - POLYMERS

11

1(d) Kevlar is a low weight, high strength polyamide used as a reinforcement in car tyres,
aircraft wings and in bullet-proof vests. A portion of its chain is shown below.
NH
(i)

NHCO

CONH

NH

What type of polymerisation produces Kevlar?

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

(ii)

Draw the structural formulae of the monomers from which Kevlar is made.

(iii)

Suggest a reason why Kevlar is much stronger than most other polyamides.
...................................................................................................................................

(iv)

What reaction conditions are needed to break the amide bonds in Kevlar?
...................................................................................................................................
[4]
[Total: 11]

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11

(b) The diacid L occurs naturally and is used as a food additive to enhance the acidic
flavour in some fruit drinks.

For
Examiners
Use

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.
CO
(i)

CONHCH2CH2CH2CH2NH

What type of polymer is this?

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

(ii)

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

[3]
[Total : 10]

9701/04/M/J/03

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10

35

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.
OH

OH

CH

OH

CH
C
H2

OH

CH
C
H2

CH
C
H2

C
H2

H
O

OH
H
N

H2
C

CH
C

CH

OH

N
H

H2
C
CH

N
H

OH
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)
HOCH2CH2OH
H2NCH2CH2NH2
HOCH2CH2CO2H
HO2CCH2CH2CO2H
H2NCH2CH2CO2H
(ii) What type of bond would be formed during the cross-linking?
..................................................................................................................................
[2]
UCLES 2005

BILAL HAMEED

9701/04/O/N/05

For
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11
(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.

ClCH2CO2 K+

stage II

KCN

H2NCH2CH2CO2 K+
stage III

H2NCH2CH2CO2H
(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]
[Total: 11]

UCLES 2005

BILAL HAMEED

9701/04/O/N/05

For
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13
13

77

Eachof
ofthe
thefollowing
following structures
structures is
is an
an 8-atom
8-atom segment
Each
segment of
of the
the chain
chain of
of aa commercial
commercialpolymer.
polymer.

For
For
Examiners
Examiners
Use
Use

For each structure,

For each structure,

decide whether it is part of a condensation or an addition polymer, and

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.
draw the structural formulae of the monomer(s) from which the polymer is made.
addition or
addition or
condensation?
condensation?

polymer
polymer
O
O

formulae of monomers
formulae of monomers

O
O
CH2
CH2

C
C

H
H
N
N

CH2
CH2

N
NH
H

C
C
N
N
H
H

C
C
O
O

O
O

O
O
CH2
CH2

C
C
CH
CH

C
C

CH2
CH2
CH
CH

O
O

CH2
CH2

O
O

CH3
CH3

CH3
CH3

CH3
CH3

CONH2
CONH2

CH
CH

CH
CH
CH2
CH2

UCLES 2008

UCLES 2008

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CONH2
CONH2
CH
CH

CH2
CH2

CH
CH
CH2
CH2

CH2
CH2

9701/04/M/J/08

9701/04/M/J/08

[8]
[8]
[Total: 8]
[Total: 8]
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55

Kevlar is a tough polyamide used in bullet-proof vests and high-specification bicycle tyres.
It can be manufactured by the following process.
H 3C

CH3

HO2C

CO2H

II

ClOC

COCl
C

H 2N

NH2
D

Kevlar

(a) (i)

(ii)

Suggest reagents and conditions for

reaction I,

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

reaction II.

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

Draw the structural formula of one repeat unit of Kevlar in the box above.
[4]

(b) The di-acid chloride C reacts with a variety of reagents. Suggest the structural formulae
of the products of the reaction of C with
(i)

CH3NH2,

(ii)

HOCH2CH2OH.

[3]

UCLES 2009

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9701/41/O/N/09

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13
(c) The diamine D also reacts with a variety of reagents. Suggest the structural formulae of
the products of the reaction of D with
(i)

HCl (aq),

(ii)

Br2(aq).

For
Examiners
Use

[3]
(d) 4-aminobenzoic acid, E, is a useful intermediate for making dyes.

HO2C

NH2

III

HO2C

N N
Cl -

IV

HO2C

N=N

OH

a dye

E
Suggest reagents and conditions for

reaction III, .....................................................................................................................

reaction IV. .....................................................................................................................

[4]
(e) 4-aminobenzoic acid, E, forms a zwitterion.
(i)

What is meant by the term zwitterion?

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

(ii)

Draw the structural formula of the zwitterion formed from 4-aminobenzoic acid.

[2]
[Total: 16]
UCLES 2009

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9701/41/O/N/09

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10

66

Acyl chlorides are useful intermediates in organic syntheses.

(a) (i)

State a suitable reagent for converting carboxylic acids into acyl chlorides.
..................................................................................................................................

(ii)

Construct an equation for the reaction between ethanoic acid, CH3CO2H, and the
reagent you have stated in (i).
..................................................................................................................................
[2]

(b) (i)

In the boxes provided draw the structures of the compounds formed when benzoyl
chloride undergoes the following reactions.

COC
C2H5OH

NH3

II

A
(ii)

(iii)

Name the functional group in

compound A ..................................................................

compound B ................................................................. .

What type of reaction is reaction II?

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

UCLES 2010

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9701/41/M/J/10

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11
(c) (i)

Suggest suitable acyl chlorides to use in the following reaction. Draw their structures
in the boxes provided.
O
+

H2N

HN

NH2

For
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NH
E

OH

O
O

+
D

O
OH

O
F

O
n

Compound E dissolves in, but does not react with, cold water.
(ii)

Suggest the major type of intermolecular interaction that occurs between E and
water.
..................................................................................................................................

(iii)

A solution of the diamine H2NCH2CH2NH2 in water has pH = 11 but a solution of E

in water has pH = 7. Suggest why this is the case.
..................................................................................................................................
..................................................................................................................................

(iv)

What type of polymer is compound F?

..................................................................................................................................
[5]
[Total: 12]

UCLES 2010

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9701/41/M/J/10

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10
10

(a) Describe and explain how the acidities of CHCl CO H and CH Cl CO H compare to each
5 (a) Describe and explain how the acidities of CHCl2 2CO2 2H and CH22Cl CO22H compare to each
other, and to the acidity of ethanoic acid.
other, and to the acidity of ethanoic acid.
...........................................................................................................................................
...........................................................................................................................................
...........................................................................................................................................
...........................................................................................................................................
...........................................................................................................................................
...........................................................................................................................................
...........................................................................................................................................
...........................................................................................................................................
...........................................................................................................................................
...........................................................................................................................................
[3]
[3]
each
following
pairsofofcompounds,
compounds,suggest
suggestone
one chemical
chemical test (reagents
(b) (b)
ForFor
each
of of
thethe
following
pairs
(reagents and
and
conditions)
that
would
distinguishbetween
betweenthem.
them.
conditions)
that
would
distinguish
State
observations
you
would
makewith
witheach
eachcompound,
compound,writing
writing none
none if appropriate.
State
thethe
observations
you
would
make
appropriate.

rstrst
compound
compound

2
NHNH
2

second
test
observation with
with observation
observation with
second
test
observation
with
compound (reagents
(reagentsand
andconditions)
conditions) rst
rstcompound
compound second
second compound
compound
compound

2
NHNH
2

CH3CH2COCl CH3COCH2Cl
CH3CH2COCl CH3COCH2Cl

CH3COCH3
CH3CH2CHO
CH3COCH3
CH3CH2CHO

[7]
[7]

UCLES 2012

UCLES 2012

BILAL HAMEED

9701/42/M/J/12

9701/42/M/J/12

For
For
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Use

11
(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.
O
E + F

O
O

For
Examiners
Use

O
polymer G

(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

[6]
[Total: 16]

UCLES 2012

BILAL HAMEED

9701/42/M/J/12

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