ESTERS

General formula of Esters

1.The general formula of esters is , where = 1, 2, 3 ... and = 1, 2,

3 ... The values of and in both the alkyl groups may be the same or different.

2.Esters are formed by the reaction between carboxylic acids and alcohols.
Hence, the general formula of esters is obtained by combining the
general formula of carboxylic acids and alcohols.

O
||

O
||
3.The general formula of esters can also be represented as RCOOR’ , where R and R’
represents the same or different alkyl groups.

The Functional Group of Esters

1.The functional group of esters is the carboxylate group, -COO- .

O
| | || |
–C – C – C – O – C –
| | |

2.The molecular formula of esters can be written as . The molecular

formula of carboxylic acid can be written as . This means esters
and carboxylic acids that have the same number of carbon atoms are
known as isomers.
 Naming Esters
Esters are named in the same manner as salts : two-word names are used.
First part of the name is taken from the alkyl group of the alcohol.
For example:
(a) methanol → methyl
(b) ethanol → ethyl
Second part of the name is taken by the changing –oic on the name of the carboxylic acid to –oate.
For example :
(a) methanoic acid → methanoate
(b) ethanoic acid → ethanoate

Esterification
1.A reversible reaction between an alcohol and a carboxylic acid causes loss of water and the formation of an
ester.
Alcohol + Carboxylic Acid Ester + Water

R'OH + RCOOH RCOOR' + H2O

2.Esters are named as derivatives of the carboxylic acid from which they are formed. The esterification
reactions are generally easily reversible by addition of water. The reverse reaction is called the hydrolysis
of the ester and proceeds in the presence of aqueous base. For example, condensation of ethanoic acid with
methanol will produce methyl ethanoate.

Methyl ethanoate
CH3OH + CH3COOH CH3COOCH3 + H2O

methanol  + ethanoic acid methyl ethanoate + water

 3.The esterification process will proceed more nearly to completion if a substance
which removes water without reacting with the acid or the alcohol is
added to the reaction, such as sulfuric acid.   For example, the reaction
between ethanoic acid and ethanol produces the ester ethyl ethanoate.

Ethyl ethanoate

CH3COOH + CH3CH2OH H2SO4 CH3COOCH2CH3 + H2O

ethanoic acid + ethanol H2SO4 ethyl ethanoate + water

*The concentrated sulphuric acid, H2SO4 removes water from the products and is a dehydrating agent.

Preparation of Ester
1.In the laboratory, ester can be produced by condensation reaction.
For example, ethyl ethanoate can be produced by the condensation
reaction of ethanol and ethanoic acid.

C2H5OH + CH3COOH CH3COOC2H5 + H2O

ethanoic acid + ethanol ethyl ethanoate + water

Esterification Process :
Physical properties of esters
Esters are neutral compound with a sweet fruity smell.
Insoluble in water but soluble in organic solvents such as benzene.

Low boiling point.

Colourless liquid.

Less dense than water.

Non-conductor of electricity.

Natural sources of Esters

Exist in flowers and fruits. For example : Pentyl ethanoate found in bananas and octy ethanoate in lime.
Vegetable oils such as coconut oil, olive oil and palm oil.
Animal fats are esters with large molecules.
Beeswax and the wax found on leaves are a mixture of esters.

Uses of Esters in Everyday Life

Used to make perfumes, cosmetics and artificial food flavourings.
Used as solvents for organic compounds such as pentyl ethanoate used to remove nail varnish in nail
polish remover.
Aspirin as an analgesic (pain reliever) for headaches.
Used to make synthetic polymers such as Terylene for making clothing fabrics.