Esterification

Defination:
The chemical reaction that takes place during the formation of the ester is
called esterification

OR
 
Esterification is the process of combining an organic acid (RCOOH) with
an alcohol (ROH) to form an ester (RCOOR) and water; or a chemical
reaction resulting in the formation of at least one ester product. Ester is
obtained by an esterification reaction of an alcohol and a carboxylic
acid
Agents:
(1) Organic acid (RCOOH)

(2) Alcohol (ROH)

Esterification reaction:
When primary alcohol is treated with a carboxylic acid in the presence of sulphuric acid a
compound is formed. This compound has a sweet smell. The compound obtained is
called ester. The chemical reaction occurring in the formation of the ester is known as an
esterification reaction.
 Esterification Mechanism

Step 1: Cation formation

Step 2: Delocalized carbocation:

 Carboxyl oxygen gets protonated to give delocalized carbocation
making the carbocation a better electrophile.

Step 3: Transfer of proton:

 A proton is transferred to one of the hydroxyl groups to form a
good leaving group
Step 4: Formation of the pi bond:
 The hydroxy group’s alcohol oxygen atom
donates a pair of electrons to a carbon atom
which makes a π bond by eliminating water. The
concentration of water is less than methanol,
therefore, it is not a feasible nucleophile to
reverse the reaction.

Step 5: Ester formation:

 In the final step ester is formed
 Ethyl acetate
Definition:
It is the organic compound with the formula CH3COOCH2CH3.This
colorless liquid has a characteristic sweet smell (similar to pear drops) and
is used in glues, nail polish removers, and in the decaffeination process of
tea and coffee. Ethyl acetate is the ester of ethanol and acetic acid; it is
manufactured on a large scale for use as a solvent.
Reagents:
 Ethanol
 Acetic acid
 Sulphuric acid
Preparation:
 Ethyl acetate is traditionally synthesised from by heating ethanol with
ethanoic acid in the presence of a catalytic amount of a strong acid such
as sulphuric acid (the "Fischer" method).

CH3COOH + CH3CH2OH  ↔  CH3COOCH2CH3 + H2O

        

 The equilibrium lies slightly on the ester side; yields can be improved by
removing water as an azeotropic mixture with benzene (or a drying agent
like molecular sieves) or by the use of excess alcohol (application of le
Chatelier's principle).
 Other routes include the reaction of acetyl chloride(ethanoyl chloride)
with ethanol.
Uses of ethyl acetate:

 Artificial fruit essences and aroma enhancer

 artificial flavours for confectionery, ice cream and cakes
 solvent in many applications (including decaffeinating tea and coffee) for
varnishes and paints (nail varnish remover); manufacture of printing inks and
perfumes, etc.