Resourse Booklet

for seminar presented by

Y.T. Liu
Y.T. Wang
X. Zhang

Specimen Question
(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.
O

CH3

O
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.
O

CH3

+ H2 O

O
B

CH3

OH + C(C2 H4 O)

(ii) Use this information to suggest a possible structure for C.

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

O
O

O
O

D
(i) On the above formula draw brackets, [ ], around the atoms that make up the repeat
unit of the 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?
(v) What is the relationship between the repeat unit of polymer D and the repeat unit
of PVA?
[5]
1

(c) Monomer E exists as two stereoisomers. Heating either isomer with Al2 O3 gives a mixture
of two unsaturated carboxylic acids F and G, which are stereoisomers of each other.
Al O

3
E 2
F+G

(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.
[4]
[Total:15]

Write your answers here

(a) (i)

(b) (i)

O
O

(ii)

(ii)
(iii)

(iii)

(iv)

(iv)
(v)
(c) (i)
(ii)
STOP! Do not turn over unless you are told to do so.

O
O

Mark Scheme
Accept all forms of structual formulae.
OCOCH3

OCOCH3

(a) (i)

[1]
repeat unit

[1]

(ii) C should be CH2 CHOH

(iii) C is CH3 CHO

[1]
[1]

(iv) e.g. add (2,4-)DNPH or DNP or Bradys reagent

orange or red ppt forms (NOT yellow)
(or could use Fehlings or Tollens,
or H+ + Cr2 O2
7 : orange to green,
+

or H + MnO4 : purple to colourless)

(b) (i) Any 3 atoms in a chain

ecf [1]
ecf [1]

[1]

(ii) Ester

[1]

(iii) E is CH3 CH2 CH(OH)CO2 H (2-hydroxybutanoic acid)

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

[1]

(iv) Condensation(polymerisation)

[1]

(v) they have the same molecular formula or C4 H6 O2 (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]
(c) (i) optical isomers (or chiral)

[1]

(ii) F is
CO2 H
[1]
G is

CO2 H
[1]
F and G may be reversed. Allow ecf from E, also allow ecf for G from F
cis-trans or geometrical isomerism

[1]

Discussion
Suppose that we do not wish to synthesise the following:
O

O
O

O
O

Instead, we want to produce

O
O

O
O

O
O

But this can be difficult. Why?

Summary
Addition Polymerisation
1. Requires unsaturated bonds. nC2 H4

2. Addition polymers are difficult to dispose due to non-biodegradability and harmful combustion products

Condensation Polymerisation
Molecules containing different functional groups capable of reacting with each other required.
Ester/amide bond are usually formed, eliminating a small molecule such as H2 O or HCl.
COOH
O

HO CH2 CH2 OH +

O CH2 CH2 O C

O
C O

+ H2O

COOH
T erylene

Factors affecting properties of polymers

1. Type of polymerisation. Hydrogen bonds are usually associated with condensation polymers.
2. Length. The longer polymer chains, the stronger VDW forces, less likely to break.
3. Types of side-chains. This determines the intermolecular forces present.
4. Side chains. Unbranched chains tend to pack closer together so stronger interaction
between adjacent polymer chains, makes it less flexible, but higher melting point.
Example.Fibroin (in dragline silk). M r=20000-30000. 42% glycine + 25% alanine + 33% other
seven amino acids. The elasticity of spider silk comes from regions rich in glycine. In these
regions, a sequence of 5 amino acids is repeated. After each sequence a 180 turn occurs to
produce a spiral. The structure is held by numerous hydrogen bonds to give its mechanical
strength.

Uses of Polymers
1. Coating gold nano-cages for drug delivery(PEG)
2. Synthetic rubber(Neoprene).
3. Variety of uses of Nylon, e.g. ropes, clothing.
4. Bullet-proof vests(Kevlar).