JEE Main · 2023 · 12 Apr 2023 · Shift 1 · Aldehydes Ketones and Carboxylic Acids

The major product ' P ' formed in the following sequence of reactions is
'P' (Major Product)

(A)(see structure)
(B)(see structure)
(C)(see structure)
(D)(see structure)
✓ Correct

Answer: (D)

Solution

The substrate is

(E)

4

-phenylbut-

3

-enoic acid,

C X_{6} H X_{5} CH = CHCH X_{2} COOH

. Thionyl chloride converts the carboxylic acid into the acyl chloride, which the amine

R - NH X_{2}

then turns into the secondary amide

C X_{6} H X_{5} CH = CHCH X_{2} CONHR

. Lithium aluminium hydride reduces an amide carbonyl all the way to a methylene group, giving an amine, and it does not touch the carbon-carbon double bond, which is conjugated only with the aromatic ring. After the acidic work-up the major product P is the

(E)

-unsaturated amine

C X_{6} H X_{5} CH = CHCH X_{2} CH X_{2} NHR

JEE Main · 2023 · 12 Apr 2023 · Shift 1 · Single correct option

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JEE Main · 2023 · 12 Apr 2023 · Shift 1 · Aldehydes Ketones and Carboxylic Acids

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