JEE Main · 2023 · 29 Jan 2023 · Shift 1 · Aldehydes Ketones and Carboxylic Acids

The major product 'P' for the following sequence of reactions is:
(see reaction scheme)

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

Answer: (C)

Solution

The substrate carries two different carbonyl groups: a ketone on the phenyl side and a primary amide at the far end. Zinc amalgam with hydrochloric acid is Clemmensen's reagent, which reduces the ketone carbonyl to a methylene group but leaves the amide untouched, giving

Ph - C H_{2} C H_{2} C H_{2} - CON H_{2}

. Lithium aluminium hydride then reduces the amide to a primary amine,

- CON H_{2} \to - C H_{2} N H_{2}

, and aqueous work-up sets the free base free. The major product P is 4-phenylbutan-1-amine,

Ph (C H_{2})_{4} N H_{2}

JEE Main · 2023 · 29 Jan 2023 · Shift 1 · Single correct option

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JEE Main · 2023 · 29 Jan 2023 · Shift 1 · Aldehydes Ketones and Carboxylic Acids

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