ESTERS (RCOOR)

Prepared by Dr Eslam Roshdy

 ESTERS SYNTHESIS
• Esters are produced when carboxylic acids ,acid
chloride or acid anhydride are heated with alcohols or
phenols in the presence of an acid catalyst. The
catalyst is usually concentrated sulphuric acid.
ESTERS SYNTHESIS
 Ester results from reaction of
acids with alcohols or phenols

Examples
ESTERS
Ethyl acetate(apple like odour)
CH3COOC2H5

Ethyl formate(apple like

odour) HCOOC2H5
 Benzyl acetate (Jasmine like odour)

Methyl salicylate (winter green like odour)

ESTERS
Ethyl benzoate (odourless)
Salicylic acid esters
 GENERAL REACTIONS

• 1-Hydrolysis
All esters are hydrolyzed by aqueous sodium
hydroxide solution under reflux to obtain the free
alcohol and the sodium salt of the acid that can
be acidified to get the free acid .
HYDROLYSIS OF ASPIRIN
HYDROLYSIS OF METHYL SALICYLATE
2-AMIDE FORMATION :
 ACID CHLORIDES(RCOCL)&
ANHYDRIDES ( RCO)2O

• ACID CHLORIDES
Acetyl chloride CH3COCl

Benzoyl chloride

Acetic anhydride
 GENERAL REACTIONS FOR ACID
CHLORIDE AND ACID ANHYDRIDE

• 1-Hydrolysis :
• Acid chlorides hydrolyzed by water or (more rapidly) by alkalis to
the corresponding carboxylic acid or salt.
2-ESTER FORMATION
3-CONDENSATION WITH ANILINES:
• Acid chlorides, and some anhydrides, condense with aniline
to give anilides
 4-HYDROXAMIC ACID FORMATION
• Acid chlorides and anhydrides give hydroxamic acids with
hydroxylamine
 5- DISTINCTION BETWEEN ACID
CHLORIDE &ACID ANHYDRIDE :

Acid chloride + HNO3+AgNO3 White ppt (AgCL)

Acid anhydride +HNO3+AgNO3 No ppt