Q60 / 180 · COMEDK 2024 (Evening Shift) · Chemistry
Identify the final product formed when Benzamide undergoes the following reactions:
- ABenzoic acid
- BAniline
- CAcetophenone
- Correct answerDAcetanilide
Solution
The reaction of benzamide with $Br_{2} / KOH$ is the Hofmann bromamide degradation reaction. This reaction converts a primary amide into a primary amine with one less carbon atom. Thus, benzamide ($C_{6}H_{5}CONH_{2}$) reacts to form aniline ($C_{6}H_{5}NH_{2}$), which is the product [X].
The subsequent reaction of aniline with acetic anhydride ($(CH_{3}CO)_{2}O$) in the presence of pyridine is an acetylation reaction. The amino group of aniline undergoes nucleophilic substitution with the acetic anhydride to form N-phenylacetamide, commonly known as acetanilide ($C_{6}H_{5}NHCOCH_{3}$), which is the final product [Y].
Answer: Acetanilide
The subsequent reaction of aniline with acetic anhydride ($(CH_{3}CO)_{2}O$) in the presence of pyridine is an acetylation reaction. The amino group of aniline undergoes nucleophilic substitution with the acetic anhydride to form N-phenylacetamide, commonly known as acetanilide ($C_{6}H_{5}NHCOCH_{3}$), which is the final product [Y].
Answer: Acetanilide
Hence, the correct answer is option: 'D'.