Question

Why is aniline soluble in aqueous hcl whereas acetanilide is not?

Answer 1

Answer:

Explanation:

aniline, the nitrogen atom donates its lone pair to the acid and by forming a salt (ionic compound), it dissolves in water(aqueous HCl). Whereas in acetanilide the nitrogen lone pair is in resonance with the carbonyl group. That's why acetanilide is not soluble in aqueous HCl.

Answer 2

Acetanilide is not soluble in aqueous HCl because it undergoes resonance with the carbonyl group.

• Aniline is a base. Here the lone pair on the N atom is free for donation and undergoes an acid-base reaction with aqueous HCl and form a salt. Thus aniline is soluble in aqueous HCl.
• The N lone pair of Acetanilide undergoes resonance with the carbonyl group and is no longer available for donation. That's why acetanilide is insoluble in aqueous HCl.