2. Conversion into functional derivatives

 

 

          2290_Chemical compound 24.JPG

 

(a) Conversion into acid chlorides

 

                 

 

 

           417_Chemical compound 25.JPG

 

Examples:

 

 

         20_Chemical compound 26.JPG

 
 

 

 

Illustration 16:

 

Benzoyl chloride is prepared from benzoic acid by

 
 

(A) Cl2,                         (B) SO2Cl2

 

(C) SOCl2                          (D) Cl2, H2O

 

 

 

Solution:

 

 

(C)

 

 

 

(b) Conversion into esters

 

 

 

Conversion into Esters (Esterification):

 

 

 

Carboxylic acid on reacting with alcohols in presence of dehydrating agent (H2SO4 or dry HCl gas) gives esters. The reaction is known as esterification.

 

 

 

 

 

 

             1104_Chemical compound 27.JPG

 

This reaction is reversible and the same catalyst, hydrogen ion, that catalyzes the forward reaction, esterification, necessarily catalyzes the reverse reaction hydrolysis.

 

 

The equilibrium is particularly unfavourable when phenols (ArOH) are used instead of alcohol; yet if water is removed during the reaction, phenolic esters [RCOOAr] are obtained in high yield.

 

 

The presence of bulky group near the site of reaction, whether in alcohol or in the acid, slows down esterification (as well as its reverse, hydrolysis).

 

 

Reactivity CH3OH > 1° > 2° > 3°

 

 

In esterification HCOOH > CH3COOH > RCH2COOH > R2CHCOOH > R3CCOOH

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