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Q. In a set of reactions propionic acid yielded a compound $D$.
$CH_3CH_2COOH\xrightarrow{SOCL_2} B\xrightarrow{NH_3}C\xrightarrow [Br_2]{KOH} D$
The structure of $D$ would be

AIPMTAIPMT 2006Aldehydes Ketones and Carboxylic Acids

Solution:

For the reaction,
image
Hence, it is also called Hofmann bromamide degradation reaction.
Hence, compound ' $D$ ' is $CH _{3}- CH _{2}- NH _{2}$.
Hofmann bromamide reaction degrade the one $C$ in amine product from amide.