Comparing the basicity of alkylamines to amides

With an alkyl amine the lone pair electron is localized on the nitrogen. However, the lone pair electron on an amide are delocalized between the nitrogen and the oxygen through resonance. This makes amides much less basic compared to alkylamines.

In fact,when and amide is reacted with an acid, the protonation occurs at the carbonyl oxygen and not the nitrogen. This is because the cation resulting from oxygen protonation is resonance stabilized. The cation resulting for the protonation of nitrogen is not resonance stabilized.