Question

When acetamide is treated with $B{r}_2$ and caustic soda, the product formed is

• A. $N$ -bromamide
• B. bromoacetic acid
• C. methanamine
• D. ethanamine

Answer 1

Answer: (C)

Amides react with bromine and caustic soda to give their corresponding primary amines. Thus, acetamide gives methanamine. This reaction is known as Hofmann’s bromamide degradation reaction.

$\underset{\text{acetamide}}{H_{3}C-\stackrel{\underset{||}{O}}{C}-N{H}_2}+B{r}_2+4KOH\stackrel{343\mathrm{K}}{\to }$

$2KBr+K_{2}C{O}_3+\underset{\text{methanamine}}{H_{3}C-N{H}_2}+2H_{2}O$