Amides are the least reactive of the carboxylic acid derivatives.  As an example of their low reactivity, it is often required to heat amides in strong aqueous acids or basic solutions to hydrolyze.


Take Note

Naming Amides:

Amides are named by replacing "is acid" or "oic acid" of the corresponding acid with "amide".

If there are other groups on the N, preceded the group with an "N".  Use Di, tri, tetra etc for multiple groups of the same type.


Hydrolysis of Amides

Much like esters, amides can be hydrolyzed to carboxylic acids.  Amides produce amines as by-products in the hydrolysis.

Base Catalyzed Hydrolysis

Heating an amide in aqueous NaOH will result in the slow hydrolysis of the amide.  recall that amides are the least reactive of the carboxylic acid derivatives so they require heating.

The mechanism for the first step is analogous to that for saponification of an ester.  The first step results in the carboxylate and is acidified in the second step to produce the carboxylic acid.


Acid Catalyzed Hydrolysis

Amides will also undergo acidic hydrolysis when heated in the presence of aqueous acid.  Under these conditions, the amine by-product becomes protonated.


Reduction of Amides

The reduction of amides with LiALH4 is slightly different for amides.  With amides the carbonyl oxygen is completely removed, producing an amine.