Question
Why is an amide more acidic than an amine?
Solution
Amides are less basic than amine because unlike amines the lone pair of nitrogen in amide is not always available with nitrogen due to the following resonating structures:
In structure (II), a positive charge is developed on nitrogen because of which it can liberate a proton and shows acidic character.
2CH3CONH2 + HgO → (CH3CONH)2 + HgO
