An organic compound A upon reacting with NH 3 gives B. On heating, B gives C. C in presence of KOH reacts…

An organic compound A upon reacting with NH3 gives B. On heating, B gives C. C in presence of KOH reacts with Br2 to give CH3CH2NH2. A is :
  1. CH 3 CH 2 COOH
  2. CH 3 COOH
  3. CH 3 CH 2 CH 2 COOH

Solution

Ammonia reacts with carboxylic acid to form ammonium carboxylate (B). Which on heating form amide (C). Amide on reaction with bromine and KOH undergo Hoffmann Bromamide reaction to form amine with one carbon less.

CH3CH2CO||OH+NH3(A)CH3CH2CO||O(B)NH4CH3CH2CO||O(B)NH4ΔCH3CH2CO||NH2(C)CH3CH2CO||NH2(C)(Hoffmann bromamide degradation)Br2/KOHCH3CH2NH2

Asked in: JEE Main 2013 (07 Apr)

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