JEE Main · 2013 · 07 Apr 2013 · Offline · Aldehydes Ketones and Carboxylic Acids

An organic compound

A

upon reacting with

NH_{3}

gives

B

. On heating

B

gives

C

C

in presence of KOH reacts with

Br_{2}

to give

CH_{3} CH_{2} NH_{2}

. A is

Answer: (C)

Solution

The final amine

CH X_{3} CH X_{2} NH X_{2}

has one carbon fewer than the amide it came from, the signature of the Hofmann bromamide degradation, in which

C

treated with

Br X_{2}

and

KOH

loses a carbon to give the amine. Stepping back,

C

must be the amide

CH X_{3} CH X_{2} CONH X_{2}

, formed by heating the ammonium salt

B

CH X_{3} CH X_{2} COONH X_{4}

, which in turn came from

A

reacting with ammonia. So

A

is propionic acid,

CH X_{3} CH X_{2} COOH

JEE Main · 2013 · 07 Apr 2013 · Offline · Single correct option