JEE Advanced · 2013 · 02 Jun 2013 · Paper 2 · Aldehydes Ketones and Carboxylic Acids

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After completion of the reactions (I and II), the organic compound(s) in the reaction mixtures is(are)

Reaction I:

Reaction II:

(A)Reaction I : $P$ and Reaction II : $P$
(B)Reaction I : $U$ , acetone and Reaction II : $Q$ , acetone
(C)Reaction I : $T, U$ , acetone and Reaction II : $P$ ✓ Correct
(D)Reaction I : $R$ , acetone and Reaction II : $S$ , acetone

Answer: (C)

Solution

Reaction I involves

CH_{3} C O C H_{2} B r

with

NaOH

. The base abstracts the acidic α-hydrogen, and the enolate can undergo elimination to form acetone, or react further. The products are sodium acetate (

T

CHBr_{3}

(

U

), and acetone.

Reaction II involves

CH_{3} C O C H_{2} B r

with

CH_{3} C O O N a

. This leads to nucleophilic substitution forming

CH_{3} C O C H_{2} O C O C H_{3}

(

P

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JEE Advanced · 2013 · 02 Jun 2013 · Paper 2 · Aldehydes Ketones and Carboxylic Acids

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