Question

Why are amides weaker bases than amines?

Answer 1

We need to know that the amide also known as carboxamide is an organic compound having the general formula, RCONR′R″. Here, R, ${R^{'}}$ and ${R^{''}}$ are the hydrogen atoms or organic groups. In formamide, the carbonyl group is linked with hydrogen and the amino group. The formamide is a derivative of formic acid. And the amine is an organic compound which contains a basic nitrogen atom having a lone pair of electrons.

Complete answer:

As we know that the amides have weaker bases than amines. Because, relative to amines, the amides are weak electron donors. Hence, the mixture of amide and water does not have the properties of acid and base which are easily visible. The elimination of electrons present in the amine by using the carbonyl group explains the relative loss of its basicity.

The amine contains a basic nitrogen atom having a lone pair of electrons. Hence, the lone pair of electrons of amines are more available for accepting the proton to act as a base. The carbonyl group present in the amide is strongly electronegative. And it has more ability to attract the electrons towards it. And it involves resonance. Hence, amide is less basic than amine.

Note:

We need to remember that the amides have weaker bases than amines. The amides contain the carbonyl group in their structure which is attached with the nitrogen atom but the amine does not have. The degree of basicity is less than that of amines. Because, the amide is very weak for protonation. In amine, the nitrogen is attached with the hydrogen and these are in three types. Which is, primary amine, secondary amine and tertiary amine.