Amides such as acetamide

are much weaker bases than amines, such as ethylamine (CH3CH2NH2).
(a) Use resonance forms to show why the nonbonding electrons on the nitrogen atom of the amide are very weakly basic.
(b) Strong acid is required to protonate the amide. Predict where acetamide will undergo protonation, and use resonance forms to show why the site you have chosen is more basic.

Transcribed Image Text:

CH C-NH,)