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(ii) Carboxylic acid anhydrides

 

Carboxylic acid anhydrides can be used to prepare esters and amides.

 
      O         O                      O                 O
     ||        ||                      ||                ||
R – C – O – C – R ———→ R – C – OR' + R – C – OH
                                                      NH3 ↓ excess
                                                            O                O
                                                           ||                ||
                                                      R – C – NH2 + R – C – O NH4+
 

 

 

Anhydrides can be hydrolysed to get back acids.

 
      O        O                            O
     ||        ||          H2O           ||
R – C – O – C – R ————→ 2R – C – OH
 

 

 

Illustration 25:

 

 

 

 

 

1933_Chemical compound 44.JPG

The compound (X) is

 

(A) CH3COOH                   (B) BrCH2 – COOH

 

(C) (CH3CO)2O                 (D) CHO – COOH

 

 

 

Solution:

 

 

(C)

 

 

 

Exercise 10:

 

 

         1781_Chemical compound 45.JPG

 

 

(iii) Esters

 

 

Ester hydrolysis

 

 

Acid catalysed esterification is an essentially reversible reaction. If you follow the backward course of reactions of esterification it gives you the mechanism for ester hydrolysis.

      O                            O
     ||            H2O          ||
R – C – OR' ————→ R – C – OH + R'OH


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