Condensation Polymerization

Condensation polymerization is a process whereby monomers join together to form polymers with the
elimination of small molecules (e.g H2O, HCl, NH3…).
Hence, during a condensation polymerization, there is more than one product formed: one is the polymer
while the other one is the small eliminated molecule.

Synthetic condensation polymers Natural condensation polymers

Nylon Fats
Terylene Proteins

There are 2 main groups of condensation polymers: polypeptides and polyesters

Nylon
Nylon is made from two types of monomers: a dicarboxylic acid (a dioic acid) and a diamine. The two
monomers combine to form a polymer. A molecule of water is formed from each pair of monomers.

A dicarboxylic acid means that there are 2 COOH group in the monomer and a diamine means that there are
2 NH2 group in the monomer. The monomers are represented using different shapes like shaded boxes/white
boxes/other shapes/R1 and R2/… to represent the whole monomer without actually drawing it.

Above is an example of a dicarboxylic acid monomer for nylon. It is a long molecule but only the first and last
carbon matters as it is where the COOH is. So, for the ease of drawing the structures, we only draw the first
and last carbons while everything in the middle is replaced by a shape or something else. The same applies
for the diamine but we will use a different shape to differentiate between the one from the dicarboxylic acid
and the diamine.

Nylon is strong but light and can be stretched without breaking. Today, we use nylon as:
- a replacement in the manufacture of garments to replace silk
- make tents and parachutes
- fishing lines
- rugs and carpets
Formation of nylon

Repeat unit

The linkage in nylon is called an amide linkage (CONH) hence making nylon a polyamide. It is also referred to
as a peptide bond in biology. Care also has to be taken when drawing. Make sure the carbon and nitrogen
are correctly bonded to the right monomer because in nylon it will alternatively reverse itself:
……CONH..….NHCO…….CONH…….NHCO……

Terylene
Terylene is also made from two types of monomers: a dicarboxylic acid (dioic acid) and a dialcohol (diol). The
two monomers combine to form a polymer. A water molecule is eliminated from each pair of monomers.

Today, we use terylene in fabrics as it’s strong, resists stretching, shrinking and doesn’t crumple when
washed.
Formation of Terylene

Repeat unit
n

The linkage between the monomers in terylene is called an ester linkage (COO). Therefore, we can call this
polymer a polyester. Care also has to be taken when drawing. Make sure the carbon and oxygen are correctly
bonded to the right monomer because in terylene it will alternatively reverse itself:

……COO……OOC……COO……OOC…..

Uses of these synthetic fibres for clothing

Today, synthetic fibres, such as nylon and polyester, are used to make most clothing instead of natural fibres
like cotton. Unlike cotton, synthetic fibres are hard wearing, do not rot, are not eaten by insects and keep
their shapes in humid conditions.
However, they are less comfortable than cotton as they do not allow perspiration to evaporate from the
body. Hence, most clothing is made of a mixture of both cotton and synthetic fibres so that good features
of both materials are included.

Problems associated with plastics

- Plastics are non-biodegradable – they cannot be decomposed by bacteria. Therefore, many plastic
wastes will pollute the Earth.
- Plastics produce toxic gas (such as HCl, Cl 2, HCN, CO) when burnt and this contributes to acid rain and
health problems.
- Plastics produce carbon dioxide when burnt – increases global warming.
- Plastics that require CFC during production may contribute to the depletion of the ozone layer when
the CFC is allowed to escape.
Natural Macromolecules (polymers)

Carbohydrates (polysaccharides)

Carbohydrates contain Carbon, Hydrogen and Oxygen. General formula is Cn(H2O)n. The simplest
carbohydrate is C 6H12O6 (glucose). Glucose polymerize each other to form starch.

This is the structure of glucose and like previously done, we

will replace all the complex structure by a simple one. We will
only keep 2 OH functional groups as they take part in the
reaction.

Starch (complex carbohydrates) can also be broken down back into glucose (simple sugar) by heating with
an acid. This is hydrolysis. This is why in biology, we can do a test for non-reducing sugars by adding HCl and
heating with benedict’s reagent.

Proteins

Proteins have similar linkage to that of a nylon only that their monomers are amino acids joined together.
Amino acids are substances having both the COOH and the NH2 functional groups. proteins are formed by
condensation polymerisation and can be called polyamides as they have the amide linkage.

Proteins can also be broken down into amino acids by heating with an acid (H2SO4 or HCl). This adds water
molecule back into the polymer (hydrolysis).
 Repeat unit
n

In proteins, because there is only one type of monomer, there’s no alternate boxes with different shadings
and the amide linkage is not alternatively reversed.

……CONH……CONH……CONH……CONH……

Fats

Fats have similar linkage to that of a terylene (ester linkage) only that their monomers consist of glycerol
and fatty acids; different from terylene.
Fats can also be broken down to sodium salts of fatty acids and glycerol by heating it with an acid or alkali.
This is hydrolysis.

Congratulations, you’ve reached the end of Chemistry 5070. Pat yourselves

on the back 😊😊