Question

Why are Amides more acidic than Amines?

Answer 1

Amines:

1. Amine is a chemical substance generated from Ammonia$\left(N{H}_3\right)$ hence termed Ammonia derivatives.
2. They are functional groups or organic Nitrogen compounds that contain a Nitrogen atom with a lone pair.

Amides:

Amides are functional groups in which a carbonyl carbon atom is linked to a Nitrogen atom, as well as a Hydrogen or Carbon atom, by a single bond.

Nature:

1. Amides are less basic or more acidic than amines.
2. It is because the nitrogen in amines contains a lone pair of electrons that takes protons.
3. But, in amides, the amide group and carbonyl groups are bound together due to the strong electronegativity of oxygen, making it either less basic or more acidic.
4. Also, amides prefer to stabilize negative charge, any element that increases the stability of a molecule's conjugate base will raise its acidity hence, the acidity is high in them.
5. Basicity increases with an increased negative charge.