CARBOXYLIC ACIDS AND THEIR DERIVATIVES
Amides from Carboxylic Acids and Ammonium Carboxylates
Carboxylic acids react with aqueous ammonia to form ammonium salts:
Because of the low reactivity of the carboxylate ion toward nucleophilic addition–elimination, further reaction does not usually take place in aqueous solution. However, if we evaporate the water and subsequently heat the dry salt, dehydration produces an amide:
This is generally a poor method for preparing amides. A much better method is to convert the acid to an acyl chloride and then treat the acyl chloride with ammonia or an amine.
Amides are of great importance in biochemistry. The linkages that join individual amino acids together to form proteins are primarily amide linkages. As a consequence, much research has been done to find convenient and mild ways for amide synthesis. Dialkylcarbodiimides (R-N=C=N-R), such as diisopropylcarbodiimide and dicyclohexylcarbodiimide (DCC), are especially useful reagents for amide synthesis. Dialkylcarbodiimides promote amide formation by reacting with the carboxyl group of an acid and activating it toward nucleophilic addition–elimination.
A MECHANISM FOR THE REACTION
DCC-Promoted Amide Synthesis
The intermediate in this synthesis does not need to be isolated, and both steps take place at room temperature. Amides are produced in very high yield.
Next Topic:- Hydrolysis of Amides