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 30 QUIZRR

POLYMERS

1.1 Pol yme r s

The word ÂpolymerÊ is coined from two Greek words : poly means many and mer means unit or
part. The term polymer is defined as very large molecules having high molecular mass. These are
also referred to as macromolecules

1.2 Mono mer s

The repeating structural units are derived from some simple and reactive molecules known as
monomers. They are linked to each other by covalent bonds.

1.3 Pol yme r i sa ti on

This process of formation of polymers from respective monomers is called polymerisation.

Examples :

Polymerisation
nCH2 = CH2 n·CH2 · CH2 · ·CH2 · CH2 ·n
Ethene Repeating unit Polythene polymer

H H O O
Polymerisation
nNH 2 (CH2) 6 NH2 + nHOOC (CH2) 4 COOH · N · (CH2)6 · N · C · (CH2)4 · C ·
n
Hexamethylene Adipic acid Nylon 6.6
diamine

C la
lass s i f i ca
catt i on O f Po
Poll y me
merr s

There are several ways of classification of polymers based on some special considerations. The
following are some of the common classifications of polymers:
(I) Classification based upon source
Under this type of classification, there are three sub categories.
1. Na tura l p olymers
These polymers are found in plants and animals. Examples are proteins, cellulose, starch,
resins and rubber.
2. Semi-synthetic polymers
Cellulose derivatives as cellulose acetate (rayon) and cellulose nitrate, etc. are the usual
examples of this sub category.
3. Synthetic polymers
A variety of synthetic polymers as plastic (polythene), synthetic fibres (nylon 6,6) and
synthetic rubbers (Buna - S) are examples of manmade polymers extensively used in daily
life as well as in industry.

POLYMERS
 QUIZRR 31

(II) Classification based upon structure

There are three different types based on the structure of the polymers.
(i) Linea r polymers
These polymers consist of long and straight chains. The examples are high density polythene,
polyvinyl chloride, etc. These are represented as :

(ii) Branched cha in polymers

These polymers contain linear chains having some branches, e.g., low density polythene.
These are depicted as follows :

Examples are glycogen, low density polyethylene, etc.

(iii) Cross linked or Network polymers

These are usually formed from bi-functional and tri-functional monomers and contain strong
covalent bonds between various linear polymer chains, e.g. bakelite, melamine, etc. These
polymers are depicted as follows :

(III) Classification based upon synthesis

(i) Addition polymers :
monomer molecules possessing double or triple bonds, e.g., the formation of polythene from
ethene and polypropene from propene. However, the addition polymers formed by the
polymerisation of a single monomeric species are known as homopolymers, e.g., polythene.

POLYMERS
32 QUIZRR

nCH 2  CH 2   (CH 2  CH2 ) n ă Homopolymer

Ethene Polythene

The polymers made by addition polymerisation from two different monomers are termed as
copolymers, e.g., Buna-S, Buna-N, etc.

C6H5
|
nCH 2  CH  CH  CH 2  n C 6H 5CH  CH 2   (CH 2  CH  CH  CH 2 ăCH 2 ă C H)ăn
1, 3-Butadiene Styrene Butadiene-styrene copolymer
(Buna-S)

(ii) Condensation polymers

The condensation polymers are formed by repeated condensation reaction between two
different bi-functional or tri-functional monomeric units. In these polymerisation reactions,
the elimination of small molecules such as water, alcohol, hydrogen chloride, etc. take place.
The examples are terylene (dacron), nylon 6,6, nylon 6, etc. For example, nylon 6,6 is
formed by the condensation of hexamethylene diamine with adipic acid.

C6 H5
|
n CH2  CH  CH  CH2  n C6 H5 CH  CH2   (CH2  CH  CH  CH2 ăCH2 ă C H) ăn
1, 3-Butadiene Styrene Butadiene-styrene copolymer
(Buna-S)

(IV) Classification based on inter-molecular forces (secondary forces)

1. Elastomers
Elastomers are polymers in which the polymer chains are held by weakest intermolecular
forces. These forces permit the polymers to be stretched. A few cross links are introduced
between the chains to help the polymer retract to its original position after the force is
released.
Example : Vulcanized rubber
2. Fibers
These polymers possess high tensile strength and high modulus, because of strong
intermolecular forces like hydrogen bonding which operate in polyamides. These strong
forces also lead to close packing of chains and thus impart crystalline nature. As a result
these polymers show sharp melting points. These polymers are used for making fibers.
Examples : Nylon and terylene

POLYMERS
 QUIZRR 33

3. Thermoplastics
In thermoplastics, the intermolecular forces are intermediate between elastomers and fibers
and the polymer chain has no cross-links.
Thus thermoplastics can be moulded on heating. These polymers have no cross-linking
between chains.
Examples : Polyethylene, polystyrene etc.
4. Thermosetting polymers
Polymers which become hard on heating are called thermo setting polymers. Thermo setting
polymers can be heated only once when it permanently sets into a solid, which cannot be
remelted by heating.
Thermosetting polymers made from relatively low molecular mass semi-fluid polymers which
when heated in a mould forms an insoluble hard mass which is infusible. This is due to
extensive crosslinks between the different polymer chains forming three dimensional network
of bonds.
Example : Bakelite and melamine

Polymerization, the joining together of many small molecules to form very large molecules. The
simple compounds from which polymers are made are called monomers.
Polymers are formed in two general ways.
(a) In chain-reaction polymerization, there is a series of reactions each of which consumes
a reactive particle and produces another, similar particle; each individual reaction thus
depends upon the previous one. The reactive particles can be free radicals, cations, or
anions. A typical example is the polymerization of ethylene. Here the chain-carrying particles
are free radicals, each of which adds to a monomer molecule to form a new, bigger free
radical.

2 2 CH CH
Rad. +CH2  CH2  Rad CH 2CH2 .  RadCH2CH 2CH 2CH 2 .  etc.

(b) In step reaction polymerization, there is a series of reactions each of which is essentially
independent of the preceding one; a plymer is formed simply because the monomer happens
to undergo reaction at more than one functional group. A diol, for example, reacts with a
dicarboxylic acid to form an ester; but each moiety of the simple ester still contains a group
that can react to generate another ester linkage and hence a larger molecule, which itself
can react further, and so on.

O O

HO +
OH
HO OH
ethylene glycol terephthalic acid

POLYMERS
 34 QUIZRR

OH

O O

O OH

HOCH2CH 2OH

OH

OH
O O

O O
OH
p- C6 H4(COOH)2
O O

O O
HO O

O O

F R EE R
RAA DI
DICC AL V
VII NY
NYLL P O LY
LYMM E R IZ
IZAATION

CH2 CH2 CH2 CH2

nCH2 initiator
CH CH CH CH
vinyl monomer G
G G G G

or ·CH2ăCH·
n
G
polymer

at the doubly bonded carbons · the vinyl groups · and is called vinyl polymerization. A wide
variety of unsaturated monomers may be used, to yield polymers with different pendant groups
(G) attached to the polymer backbone. For example :

POLYMERS
 QUIZRR 35

CH2 CH2 CH2

H2 C
CH CH CH
Cl
vinyl chloride
Cl Cl Cl
Poly (vinyl chloride) (PVC)

CH2 CH2 CH2

H2 C
CH CH CH
CN
acrylonitrile
CN CN CN
Polyacrylonitrile (Orion)

CH2 CH2 CH2

H2 C CH
Styrene
CH CH CH

C 6H 5 C6 H5 C6H5 C6 H5
Polystyrene

CH3 CH3 CH3 CH3

H2C CH2 CH2 CH2
C C C
O
O COOCH3 COOCH 3 COOCH3
Poly(methyl methacrylate)
CH3 (Plexiglas, Lucite)
Methyl methacrylate

Polymerzation involves addition of free radicals to the double bond of the monomer: addition, first,
of the free radicals generated from the initiator, and then of the growing polymer molecule. This
is, of course, an example of chain-reaction polymerization.

1. Peroxide Rad
2. Rad. + H2 C CH
Rad CH2 CHĆ
Chain · initiating steps
G
G

CH2 · CH Ć

3. Rad CH2 CHĆ+ H2C CH Rad CH2 · HC Chain propagating steps

G G G

then steps like (3) repeated, until finally :

POLYMERS
36 QUIZRR
4. 2Rad(CH2CH)n CH2CHĆ

G G
combination

Rad(CH 2CH) n CH 2CH · CHCH 2(CHCH 2) n Rad

G G G G

or Chain terminating steps

5. 2Rad(CH2CH)n CH2CHĆ

G G
disproportionation

Rad(CH2CH)n CH2 CH2 + Rad(CH 2CH) n CH = CH

G G G G

In each step the consumption of a free radical is accompanied by the formation of a new, bigger
free radical. Eventually, the reaction chain is terminated by steps that consume but do not form
free radicals; combination or disproportionation of two free radicals.
Copolymerization: Polymerization of a single monomeric compound to form a homopolymer is
known as homopolymerization. Evidently such a polymer is made up of identical units. In contrast,
a copolymer results when two different kinds of monomers are polymerized together to give a
product containing both the monomers. Such as process, known as copolymerization, is of great
industrial importance as it enables us to get a polymer possessing desired properties. To a certain
extent we can control the composition of a copolymer by varying the proportions of the monomer
in the polymerizing mixture. However, the composition of the polymer depends not only on the
relative concentrations of the two monomers, but also on the relative reactivities of the monomers
toward free radical addition. In other words, a more reactive monomer has greater chance of being
incorporated into a copolymer. As the reactivity of a carbon-carbon double bond toward free
radical addition is affected by the stability of the new free radical being formed, the more stable
free radicals will preferentially be produced.
Copolymerization of styrene with methyl methacrylate to produce polystyrene (co-methyl
methacrylate) (A) is an industrially important process.

CH 3
CH3 CH2 CH2
CH C
H2 C CH + H2C C
C 6H 5
C O O O
C 6H 5
H3C · O
CH3
n
(A)

POLYMERS
 QUIZRR 37

Saran Wrap (B) is another copolymer formed by the copolymerization of vinylidene and chlorides.

Cl Cl
H2 C C + H2 C CH
CH2 ă C · CH2
Cl Cl
Cl CH ·
n
Cl
(B)

I O NI
NICC P
POO LY
LYMM E R IZ
IZAA T I O N: L I VI
VINN G PO
POLL Y M ER
ERSS

Chain-reaction polymerization can proceed with ions instead of free radicals as the chain-carrying
particles : either cations or anions, depending on the kind of initiator that is used.
Cationic Polymerization

+
Y H2C CH Y : H 2C · CH
An acid
G A carbocation G
G

CH2 · CH
+ +
Y : H2C · CH H2C CH Y : H 2C · HC etc.
A carbocation G
G G

Anionic polymerization

ă
Z: H2 C CH Z : H 3C · CH:
A base
G G
A carbanion

CH2 · CH:
ă ă
Z : H 2C · CH: H2 C CH Z : H2C · HC etc.
G
G G
A carbanion

Cationic Polymerization is initiated by acids. Isobutylene, for example, undergoes cationic

polymerization to a tacky material used in adhesives. Copolymerization with a little isoprene gives

POLYMERS
38 QUIZRR
butyl rubber, used to make automobile inner tubes and tire liners. A variety of acids can be used:
sulfuric acid; AlCl 3 or BF 3 plus a trace of water.

CH3 CH3
CH3 CH 3 CH 3
H+ H2 C H 2C H2C H 3C · C · CH 2 · C · CH 2
CH3 CH 3 CH 3
CH3 CH3

Anionic polymerization, as we might expect, is initiated by bases: Li +, NH 2 , for example, or

organometallic compounds like n-butyllithium. For example :

CH2 CH 2
ă +
NH ă2 K+ + H2C CH H2N CH2 = CHPh H 2N CH CH K etc.

Ph Ph Ph
Styrene K+ HCă
Ph

H 3C
CH3 ă +
O C Li
n ă BuLi + H 2C H3C etc.
O O năBu
O
CH3
methyl methacrylate

Active metals like Na or Li can be used: here the initiation becomes a little more complicated, as
in the polymerization of styrene by the action of sodium metal and naphthalene. A sodium atom
transfers an electron (1) to naphthalene to form a radical-anion:
+ ă
1. Na + naphthalene Na naphthalene .
Naphthalene radicalăanion

naphthalene. + HC
ă
2. CH2 naphthalene + CH CH2 .

Ph Ph
styrene radicalăanion Formed by
oneăelectron transfer

ă
CH CH2 Ph
ă
3. 2 HC CH2 . Ph CH2 CH
ă

Ph A dianion

POLYMERS
 QUIZRR 39

The radical-anion then donates the electron to styrene (2) to form the styrene radical-anion. Like
many other free radicals, these dimerize (3). The resulting dianion is the true initiator, and begins
to grow at both ends :

ă
CH CH2 Ph
Ph CH2 CH
ă
CH2=CHPh

Ph Ph
ă
CH CH CH CH2 CH2 CH2 Ph
Ph CH2 CH 2 CH 2 CH CH CH
ă

Anionic polymerization is not limited to the vinyl kind, involving addition to carbon-carbon double
bonds. Ethylene oxide, for example, is converted by a small amount of base into a high molecular
weight polyether.

O
ă ă
CH3O + H3C O
O

ă
O O O
ă H3 C O
H3 C O +
O

So m e i mp
mpoo r ta
tann t po
poll ym
ymeers

(a) Polythene :
There are two types of polythene as given below:
(i) Low density polythene :
Ć It is obtained by the polymerisation of ethene under high pressure of 1000 to 2000
atmoshpheres at a temperature of 350 K to 570 K in the presence of traces of dioxygen
or a peroxide initiator (catalyst).
Ć The low density polythene (LDP) obtained through the free radical addition and H-atom
obstraction has highly branched structure.
Ć Low density polythene is chemically inert and tough but flexible and a poor conductor
of electricity.
High density polythene : It is formed when addition polymerisation of ethene takes place
in a hydrocarbon solvent in the presence of a catalyst such as triethylaluminium and
titanium tetrachloride (Ziegler-Natta catalyst) at a temperature of 333 K to 343 K and under
a pressure of 6-7 atmospheres.
POLYMERS
40 QUIZRR
Ć High density polythene (HDP) thus produced, consists of linear of Ziegler-Natta catalyst.
molecules and has a high density due to close packing.
Ć It is also chemically inert and more tougher and harder.
(b) Polyacrylonitrile :
Ć The addition polymerisation of acrylonitrile in presence of a Acrylic fibres leads to the
formation of polyacrylonitrile.
Ć It has resistance to stains, chemicals, insects and fungi.
Ć Polyacrylonitrile is used as a substitute for wool in making commercial fibres as orlon or
acrilan

CN
Polymerisation
n CH2 CHCN Peroxide catalyst · CH2 · CH ·
n
Acrylonitrile Polyacrylonitrile

(c) Natural Rubber : Natural rubber is an addition polymer of isoprene (2-methyl-1,3-

butadiene). Rubber has an average chain length of 5000 monomer units of isoprene.
The rubber in which the arrangement of carbon chain is trans with respect to the double
bond is known as Gutta Percha and this is the natural rubber obtained from bark of
various trees. Natural rubber is sticky material. This disadvantage is removed by
ÂVULCANISATIONÊ which involves addition of sulphur to rubber and heating the mixture,
sulphur forms short chains of sulphur atoms that link hydrocarbon (isoprene) units together.

CH3 CH3

CH · C CH · CH2 · CH · C CH · CH2

S S

CH · C CH · CH2 · CH2 · C CH · CH · CH

CH3 CH3

When tension is applied the chains can strengthen out but they cannot slip over each other
because of sulphur bridges. Thus rubber can be stretched only to a certain extent and
hydrocarbon chains have the tendency to regain their shape when tension is removed.
Vulcanised rubber is thus stronger and less sticky than the natural rubber.
(d) Synthetic rubber : (Polychloroprene or Neoprene) it is obtained by free radical polymerisation
of chloroprene
Cl Cl

nCH2 C · CH CH2 (· CH 2 · C CH · CH2 ·) n

Neoprene

POLYMERS
 QUIZRR 41

it is a thermoplastic and need not to be vulcanised. It is a good general purpose rubber and
superior to natural rubber as it is resistant to the reaction of air, heat, light chemicals,
alkalis and acids below 50% strength. It is used for making transmission belts, printing rolls
and flexible tubing employed for conveyence of oil and petrol.

(e) Buna rubbers : Butadiene polymerises in the presence of sodium to give a rubber substitute
viz. Buna. It is of two types :
(i) Buna - N or GRA: it is synthetic rubber obtained by copolymerisation of one part of acryl
nitrile and two parts of butadiene.

nCH2 CH · CH CH2 + nCH2 CH · CH2 · CH CH · CH2 · CH2 · CH

CN BUNAăN CN n

It is more rigid, responds less to heat and very resistant to swelling action of petrol, oils
and other organic solvents.
(ii) Buna -S or GRS (General purpose Styrene rubber): It is a copolymer of three moles of
butadiene and one mole of styrene and is an elastomer. It is obtained as a result of free
radical copolymerisation of its monomers.

nC6H5CH CH2 + nCH2 CH · CH CH2 [ăCH 2·CH CH·CH 2·CH·CH 2·] n

C6H5
BUNAăS

It is generally compounded with carbon black and vulcanised with sulphur. It is extremely
resistant to wear and tear and finds use in manufacture of tyres and other mechanical
rubber goods.
(e) Teflon : It is polymer of tetrafluroethylene (F2 C=CF2 ) which on polymerization gives telfon.
(NH4)2S2O8 870 · 1020K
nCF 2 CF 2 (· CF 2 · CF 2 ·) n
It is thermoplastic polymer with a high softening point (600K). It is very tough and difficult
to work. It is ipert to most chemicals except fluorine and molten alkali metals. It withstands
high temperatures. Its electrical properties make it an ideal insulating material for high
frequency installation.

Ex
Exaa m pl
plee 1

Which of the following is an elastomer?

(1) Vulcanized rubber (2) Dacron (3) Polystyrene
Solution :
Vulcanized rubber is an elastomer.

POLYMERS
 42 QUIZRR
NYLO N

Nylon is used as a general name for all synthetic fibres forming polyamides, i.e., having a protein
like structure. A number is usually suffixed with the name ÂnylonÊ which refers to the number of
carbon atoms present in the monomers.

N Y L O N –6
–666

(read as nylon six, six)

It is obtained by the condensation polymerisation of hexamethylenediamine (a diamine with six
carbon atoms) and adipic acid (a dibasic acid having 6 carbon atoms).

nHOOC(CH 2) 4COOH + nH 2N(CH 2) 6NH 2 280Ĉ C · OC(CH2 )4CONH(CH2 )6 NH ·

n
Adipic acid Hexamethylene High pressure Nylonă66
diamine ă(n ă1)H2 O

NYON–6 10

(read as nylon six, ten)

It is obtained by condensation polymerisation of hexamethylenediamine (six carbon atoms) and
sebacic acid (a dibasic acid with 10 carbon atoms).
Nylon fibres are stronger than natural fibres and so are used in making cords and ropes. The
fibres are elastic, light, very strong and flexible. They have drip dry property and retain creases.
It is inert towards chemicals and biological agents. It can be blended with wool. Nylon fibres are
used in making garments, carpets, fabrics, tyre cords, ropes, etc.

N YL
YLOO N –6 ((P
P e r l on L
L))

A polyamide closely related to nylon is known as perlon L (Germany) or Nylonă6 (USA). It is

prepared by prolonged heating of caprolactum at 260ă270ĈC. It is formed by self condensation of
a large number of molecules of amino caproic acid. Since, caprolactum is more easily available,
it is used for polymerization, which is carried out in the presence of H2O that first hydrolyses the
lactam to amino acid. Subsequently, the amino group of the amino acid can react with the lactam
and the process goes on and onto form the polyamide polymer.
Carpolactam is obtained by Beckmann rearrangement of cyclohexanone oxime.

OH O NOH

[O] [O] NH 2OH

Cyclohexane Cyclohexanol Cyclohexanone Cyclohexanone

oxime

POLYMERS
 QUIZRR 43

NOH
O
H2SO 4
Beckmann
O 260 ă 270Ĉ C
· C ·(CH2)5 · NH ·
rearrangement H 2O
NH Nylonă6

Caprolactam (Six carbon atoms in the

repeating units)

N Y L O N – 2 – N Y L O N–
N–66

It is an alternating polyamide copolymer of glycine and amino caproic acid and is biodegradable.

Ex
Exaa m pl
plee 2

Nylonă66 is obtained by condensation polymerization of

(a) Adipic acid and hexamethylene diamine
(b) Phenol and formaldehyde
(c) Terephthalic acid and ethylene glycol
(d) Sebacic acid and hexamethylene diamine
Solution :
(a) Adipic acid and hexamethylene diamine on condensation will generate Nylonă66

Ex
Exaa m pl
plee 3

Which of the following type of forces are present in Nylonă66?

(a) Van der WaalÊs forces of attraction
(b) Hydrogen bonding
(c) Threeădimensional network of bonds
(d) None of these
Solution :
(b) Hydrogen bonds are present in Nylonă66.

PO LY ETHY LEN E

Polyethylene is of two types:

(a) Low Density Poly Ethylene (LDPE) : It is manufactured by heating ethylene at 200ĈC
under a pressure of 1500 atmoshperes and in the presence of traces of oxygen. This
polymerisation is a free radical polymerisation.

200Ĉ C
nCH2 CH2 · CH 2 · CH 2 ·n
1500 atmosphere

The polyethylene produced has a molecular mass of about 20,000 and has a branched
structure. Due to this, polyethylene has a low density (0.92) and low melting point (110ĈC).

POLYMERS
 44 QUIZRR
That is why polyethylene prepared by free radical polymerisation is called low density
polyethylene. It is a transparent polymer of moderate and as insulation for electrical wires
and cables.

(b) High Density Poly Ethylene (HDPE) : It is prepared by the use of ZieglarăNatta catalyst
at 160Ĉ under pressure of 6 to 7 atmoshphere.
The polymer is linear chain, hence it has high density (0.97) and has high melting point
(130ĈC). That is why it is called high density polyethylene. It is a translucent polymer. It
has greater tough ness, hardness and tensile strength than low density polyethylene. It is
used in the manufacture of containers (buckets, tubes), house wares, bottles and toys.

M E L A M I N E – F O R M A L D E HY
HYDDE RESIN

This resin is formed by condensation polymerisation of melamine and formaldehyde.

H2N N NH2 H 2N N NHCH 2OH ·H2 N N NH·CH2 ·

+ HCHO
N N N N Polymerisation N N

NH 2 NH2 NH2
n
(Intermediate) Melamineăformaldehyde polymer

It is a quite hard polymer and is used widely for making plastic crockery under the name
melamine. The articles made from this polymer do not break even when dropped from considerable
height.

BAKELI TE

Phenolăformaldehyde resins are obtained by the reaction of phenol and formaldehyde in the
presence of either an acid or a basic catalyst. The reaction starts with the initial formation of ortho
and paraăhydroxymethyl phenol derivatives, which further react with phenol to form compounds
where rings are joined to each other with ăCH2 groups. The reaction involves the formation of
methylene bridges in ortho, para or both ortho and para positions. Linear or crossălinked materials
are obtained depending on the conditions of the reaction.

OH OH OH
CH2 OH
+ ă
H or OH +
+ HCHO

(Intermediate)
CH2OH
Oăand păhydroxymethyl phenol

POLYMERS
 QUIZRR 45

OH OH OH
CH2OH Polymerisation
CH2
n

Linear polymer n
Novolac

OH OH OH OH OH
CH2 OH
Polymerisation
CH2 CH 2 CH2 CH2·
n +n

CH2OH CH2 CH2

·CH2 CH 2 CH2 CH2·

OH OH OH
Crossălinked polymer (Bakelite)

PO LY E STER S

Dacron is a common polyester, prepared using ethylene glycol and terephthalic acid. The reaction
is carried out at 140Ĉ to 180Ĉ C in the presence of zinc acetate and Sb2 O3 as catalyst.

nHOCH2 CH2OH + nHO2 C CO 2H · OCH2CH2 · C C·

Dacron
O O n

TABLE OF POLYMERS
S.N. Name of Polymer Structure Monomer Uses
1. Polythene An insulator,
· CH 2 · CH 2 · CH2 CH 2 anticorrosive,
n packing material,
household and
laboratory wares.
2. Polysyrene · CH · CH 2 · HC CH2 An insulator ,
wrapping material,
C 6H 5
C6H 5 n manufacture of
toys and household
articles.
POLYMERS
 46 QUIZRR
3. Polyvinylchloride (PVC) Cl In manufacture of
CH2 CHCl raincoats, hand
· CH2 · CH2 ·
n bags, vinyl
flooring and
leather clothes.
4. Polytetrafluoro ethylene CF2 CF2 As lubricant,
· CF2 · CF2 ·
(PTFE) or Telflon n insulator and
making cooking
wares.
5. Polymethyl metha CH3 CH3 As subsitute of
acrylate (PMMA) or glass and making
· CH2 · C · H 2C CCOOCH 3
Plexi glass decorative
COOCH 3 n materials.

6. Polyacrylonitrile CN In making
(Orlon)(PAN) CH2 CHCN sy nthetic fibr es
· CH2 · CH ·
n and synthetic wool.

7. Styrene butadiene (a) H2 C CH · CH CH2 In making

rubber (SBR or (b) HC CH2 automobile tyres
BuNa-S) CH and footwear.
6 5

8. Nitrile rubber (Buna-N) (a) H2 C CH · CH CH2 In making oil

(b) HC CH 2 seals, manufacture
of hoses and tank
CN
linings.
9. Neoprene As insul ator,
· CH 2 · C CH · CH2 · H2C C · CH CH2
making conveyor
Cl Cl belts and printing
rollers.
10. Polyethyl acrylate In making films,
· CH2 · CH · CH2 CH · COOC 2H5
house pipes and
COOC2 H5 n finishing fabrics.

11. Terylene (Dacron) For making fibres,

(a) HOOC COOH
safety belts, tyre
cords, tents etc.
(b) HO · CH2 · CH2 · OH

POLYMERS
 QUIZRR 47

12. Glyptal (a) HOOC COOH As binding

· OCH2 .CH2OOC COO·
material in
n preparation of
mixed plastics and
(b) HO · CH 2 · CH 2 · OH paints.

O H
13. Nylon 6 N O In making fibres,
C plastics, tyre cords
· NH · (CH 2) 5 · C · n
and ropes.

14. Nylon 66 (·NH(CH2)6NHCO(CH2)4CO·)n (a) HOOC · (CH2)4 · COOH In making

(b) H2 N · (CH2 )6 · NH2 brushes, synthetic
fibres, parachutes,
ropes and carpets.

15. Bakelite OH OH (a) HCHO For making gears,

(b) C 6H 5OH protective coating
CH2 CH2·
and electrical
fittings.

CH3 CH3 n

16. Urea formaldehyde (a) HCHO For making un-

(· NH · CO · NH · CH 3 ·) n (b) NH2CONH2
resin breakable cups
and laminated
sheets.

17. Melamine (a) H 2N N NH2 In making plastic

· NH · NH N NH · CH2 ·
formaldehyde crockery,
resin N N unbreakable cups
N N
and plates.
NH2
NH2 n
(b) HCHO

18. Poly--hydroxy OH As packaging

butyrate-co- - · O · CH · CH 2 · CO · orthopaedic
(a) H 3C · CH · CH 2 · COOH
hydroxy valerate devices and in
R O OH
(PHBV) n controlled drug
R CH 3, C 2H 5
(b) H 3C · CH 2 · CH · CH 2· COOH release.

POLYMERS
 48 QUIZRR
Ex a m pl
plee 4

A polymeric substance, tetrafluoroethylene, can be represented by the formula (C2 F4) where
x is a large number. The material was prepared by polymerizing C 2F 4 in the presence of a
sulphur bearing catalyst that served as a nucleus upon which the polymer grew. The final
product was found to contain 0.012% S. What is the value of x if each polymeric molecule
contains 2 sulphur atoms? Assume that the catalyst contributes a negligible amount to the
total mass of polymer.
Solution :
Final product contain 0.012% S
If contains two S atoms

Molecular weight ï 0.012

  2  32
100

Weight of monomer, i.e. C2F4 is 100

 100 ï x = 5.33 ï 105
 x = 5.33 ï 10 3

Ex
Exaa m pl
plee 5

A
nCF 2 = CF2 
  
heat, high pressure
 (ăCF ă CF ă) Teflon
2 2 n

Solution :
A = (NH 4)2S2O 8

Ex
Exaa m pl
plee 6

Oxidation NH2OH H2 SO4  

A B C D E
H2O

Identify A to E.

O NOH H
Solution :
O
N
Oxidation NH2 OH H2 SO4

Caprolactam

O H2O4

· NH · (CH2 )5 · C · H2N · (CH2)5 · COOH

Nylon ă 6 Amino caproic acid

POLYMERS
 QUIZRR 49

Ex a m pl
plee 7

nCH 2 CH
K2S2O8
C CH2 B

Cl

Solution :

· CH2 · C CH · CH2 ·
B
Cl n
neoprene

Ex
Exaa m pl
plee 8

(a) Show how an aldohexose can be used to syntheisze 2-ketohexose. (b) Since glucose is
converted to fructose by this method, what can you say about the configurations of C3 , C4
and C5 in the sugars.
Solution :
(a) CHO CH N.NHC6 H5
2C 6H 5CHO
(CHOH)4 + 3C6 H5 NH.NH2 C N.NHC6H5
ăC 6H 5NH 2 ă2C6H 5CH = NNHC6H 5
ăH2O
CH2OH ăNH3
(CHOH) 3
Aldohexase
CH2OH
Osazone

H·C O CH2OH

C O C O
Zn/CH3COOH
(CHOH)3 (CHOH)3

CH2OH CH2OH
Osazone 2ăketohexose

Here aldohexose reacts with one molecule of phenylhyrazine which condenses with the
aldehyde group to give phenylhydrazone. When warmed with excess of phenyl hydrazine,
the secondary alcoholic group adjacent to the aldehyde group is oxidized by another molecule
of phenylhydrazine, to a ketonic group. With this ketonic group, the third molecule of
phenylhydrazine condenses to give osazone. The phenylhydrazinyl group is transferred
from osazone to C6H5 CHO giving C 6H 5CH = N.NHC 6H5 and a dicarbonyl compound called
an osone. The more reactive aldehyde group of the osone is reduced, not the less reactive
keto group and it gives the 2-ketohexose.

POLYMERS
 50 QUIZRR
(b) The configurations of these carbons which are unchanged in the reactions, must be identical
in order to get the same osazone.

Ex a m pl
plee 9

Compound (A) C5 H10O 5, give a tetra-acetate with Ac2O and oxidation of (A) with Br2 ăH2O
gives an acid, C5H10 O6. Reduction of (A) with HI and red phosphorous gives 2-methylbutane.
What is structure of (A)?
Solution :
The formation of tetraacetate indicates presence of 4 OH groups and oxidation with bromine
water indicates presence of CHO group. Reduction with red phosphorous and HI indicates presence
of one carbon in the side chain. Thus, the structure of (A) would be
CHO

CHOH

HO · CH2 · C · OH

CH2OH

Ex
Exaa m pl
plee 10

Compound (A) C5 H10 O4, is oxidised by Br2 ăH2O to the acid, C 5 H10 O5, which readily forms a
lactone. (A) forms a triacetate with Ac2O and an osazone with PhNHNH 2. (A) is oxidised by
HIO 4, only one molecule of which is consumed. What is the structure of (A) ?
Solution :
(A) contains three hydroxyl groups and an aldehyde group. Formation of a lactone shows that one
hydroxyl group is in the  ă or -position with respect to the carboxyl group. Since (A) contains
four oxygen atoms and these have been accounted for as three hydroxyl groups and an aldehyde
group, the formation of an osazone shows the presence of the group ăCH(OH)CHO. Since only
one molecule of periodic acid is consumed, (A) contains only one set of adjacent oxidisable groups.
This must therefore be the CH(OH)CHO group and so the other CHOH groups must be ÂseparatedÊ
from each other and from the CHOH of CH(OH)CHO. Also, the absence of four hydroxyl groups
in a five-carbon chain suggests (A) is a deoxy-compound. this Âdeoxy-carbon atomÊ is therefore the
one that ÂseparatesÊ all the three CHOH groups. (A) structure which fits all the facts is

Ex
Exaa m pl
plee 12

(a) Supply structures of H through K. Given :

NH2 OH/base Ac2 O/NaOAc ăHOAC NaOMe/MeOH

An aldohexose H I J K

POLYMERS
 QUIZRR 51

(b) Explain the last step (c). What is net structural change (d) Name this overall method.
(e) Discuss the possibility of epimer formation.
Solution :
(a) H is an oxime HOCH2 (CHOH)4CH = NOH; I is the completely acetylated oxime,
AcOCH2 (CHOAc)4CH = NOAc that loses 1 mole of HOAc to form J, AcOCH 2(CHOAc)4CN; K
is an aldopentose, HOCH2(CHOH) 2CHO.
(b) The acetates undergo transesterification to give methyl acetate freeing all the sugar OHÊs. This
is followed by reversal of HCN addition.
(c) There is loss of one C from the carbon chain.
(d) Wohl degradation
(e) The -CHOH becomes the ăCH = O without any configurational changes of the other chiral
carbons. Thus no epimers are formed.

POLYMERS
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