Question

Hoffmann bromamide degradation of benzamide gives product A, which upon heating with $CHC{l}_3$ and $NaOH$ gives product B. The structures of A and B are:

• A.
• B.
• C.
• D.

Answer 1

The correct option is D

When an amide is treated with bromine in an aqueous or ethanolic solution of sodium hydroxide, degradation of amide takes place leading to the formation of primary amine. This reaction involving degradation of amide and is popularly known as Hoffmann bromamide degradation reaction. The primary amine thus formed contains one carbon less than the number of carbon atoms in that amide.

Hoffmann bromamide degradation of benzamide gives aniline.

Reaction of a primary amine with chloroform and a base will give isocyanides. This reaction is called Carbylamine reaction.
Thus, (A) upon heating with $CHC{l}_3$ and NaOH gives phenyl isocyanide (B).

Hence, option (b) is the correct answer.