Base hydrolysis of esters

Specific acid and base Hydrolysis of esters Ri COOR. + H.O = Ri COOH + R.OH... 

Spontaneous and metal-ion catalyzed base hydrolysis of esters, amides, etc. ... 

Base hydrolysis of fats with sodium or potassium hydroxide liberates glycerol and the salt of the carboxylic acid(s). This reaction was the basis of soap making the salt, or mixture of salts, is a soap with characteristic detergent properties. The relationship of ester hydrolysis to soap-making remains, in that base hydrolysis of esters is still commonly referred to as saponification. 

Base hydrolysis of amides also requires quite vigorous conditions, but mechanistically it is exactly equivalent to base hydrolysis of esters. After nucleophilic attack of hydroxide on to the carbonyl, the tetrahedral anionic intermediate is able to lose either an amide anion (care with nomenclature here, the amide anion is quite different from the amide molecule) or hydroxide. Although loss of hydroxide is preferred, since the amide anion is a stronger base than hydroxide, this would merely reverse the reaction. 

The reaction progresses because the amide anion, once a small amount is released, abstracts a proton from the carboxylic acid product. Again, we have an analogy with the last step in the base hydrolysis of esters, and the ionization becomes an essentially... 

Table 16 Rate Constants for the Base Hydrolysis of Ester, Amide and Peptide Bonds in Various Cobalt(III) Complexes (25 °C, / = 1.0 M)a...

Table 7.6 Rate constants for the base hydrolysis of ester, amide and peptide bonds in various cobalt(III) complexes (25°C, 1 = 1.0 M)...

Draw the condensed structural formulas for the products from acid and base hydrolysis of esters. 

Chapter 14, Carboxylic Acids, Esters, Amines, and Amides, discusses the functional groups and naming of carboxylic acids, esters, amines, and amides. Chemical reactions include esterification, amidation, and acid and base hydrolysis of esters and amides. 

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