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JEE Main2013ChemistryCarboxylic Acid DerivativesActual

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 :

Options

  1. ACH 3 CH 2 COOH
  2. BCH 3 COOH
  3. CCH 3 CH 2 CH 2 COOH

Correct answer

B. CH 3 COOH

Step-by-step 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. CH 3 − CH 2 − C O | | − OH + NH 3 ( A ) → CH 3 CH 2 − C O | | − O ⊖ ( B ) N ⊕ H 4 CH 3 CH 2 − C O | | − O ⊖ ( B ) N ⊕ H 4 → Δ CH 3 CH 2 − C O | | − NH 2 ( C ) CH 3 CH 2 − C O | | − NH 2 ( C ) →

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