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JEE Main 20137 April
Exam
JEE Main
Year
2013
Date
7 April
Subject
Chemistry
Chapter
Carboxylic Acid Derivatives

JEE Main 2013 · 7 April · Chemistry · Carboxylic Acid Derivatives

An organic compound A upon reacting with NH _ 3 gives B. On...

An organic compound A upon reacting with NH3{NH}_{3} gives B. On heating, B gives C. C in presence of KOH reacts with Br2 to give CH3CH2NH2. A is :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

Options

  1. ALet S = \ x ∈ (- (π)/(2), (π)/(2)): 9 ^ 1 - ^ 2 x + 9 ^ ^ 2 x = 10\ and β = ∑ _ x ∈ S ^ 2 ((x)/(3)) , then (1)/(6) ( β
  2. BCH3CH2COOH{\text{CH}}_{3} {\text{CH}}_{2} \text{COOH}
  3. CCH3COOH{\text{CH}}_{3} \text{COOH}
  4. DCH3CH2CH2COOH{\text{CH}}_{3} {\text{CH}}_{2} {\text{CH}}_{2} \text{COOH}

Correct answer

B. CH3CH2COOH{\text{CH}}_{3} {\text{CH}}_{2} \text{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.

CH3−CH2−CO∣∣−OH+NH3(A)\begin{array}{ll}{CH}_{3} - {CH}_{2} - C\mathop{O}_{| |} - OH + {NH}_{3} \\ ( A )\end{array}\overset{}{\to}CH3CH2−CO∣∣−O⊖(B)\begin{array}{ll}{CH}_{3}{CH}_{2} - C\mathop{O}_{| |} - {O}^{⊖} \\ ( B )\end{array}\overset{⊕}{N}{H}_{4}CH3CH2−CO∣∣−O⊖(B)\begin{array}{ll}{CH}_{3}{CH}_{2} - C\mathop{O}_{| |} - {O}^{⊖} \\ ( B )\end{array}\overset{⊕}{N}{H}_{4}\overset{\Delta}{\to}CH3CH2−CO∣∣−NH2(C)\begin{array}{ll}{CH}_{3}{CH}_{2} - C\mathop{O}_{| |} - {NH}_{2} \\ ( C )\end{array}CH3CH2−CO∣∣−NH2(C)\begin{array}{ll}{CH}_{3}{CH}_{2} - C\mathop{O}_{| |} - {NH}_{2} \\ ( C )\end{array}\mathop{\to}_{( Hoffmannbromamidedegradation )}^{{Br}_{2} / KOH}{CH}_{3}{CH}_{2} - {NH}_{2}$

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