Question

Which of the following will not give Hofmann-Bromamide reaction ?

• A.
• B.
• C.
• D.

Answer 1

The correct option is D

Hoffmann developed a method for preparation of primary amines by treating an amide with bromine in an aqueous or ethanolic solution of sodium hydroxide. In this degradation reaction, migration of an alkyl or aryl group takes place form place from carbonyl carbon of the amide to the nitrogen atom. The amine so formed contains one carbon less than that present in the amide.

(A) In this molecule, the amide is primary because the nitrogen has two hydrogen atoms. So it will give Hoffmann Bromamide reaction.

(B) In this molecule, the amide is primary because the nitrogen has two hydrogen atoms. So it will give Hoffmann Bromamide reaction.

(C) In this molecule, the amide is primary because the nitrogen has one hydrogen atom and one bromine atom and it is an intermediate in the Hoffmann bromamide reaction. So it will give Hoffmann Bromamide reaction.

(D) In a molecule, the amide is secondary because the nitrogen atom has only one hydrogen atom so it will not give Hoffmann bromamide reaction.