$\ce{CH3-CH2-CN} \xrightarrow[\text{Ether}]{\ce{CH3MgBr}} \ce{A} \xrightarrow{\ce{H3O+}} \ce{B} \xrightarrow[\text{HCl}]{\ce{Zn-Hg}} \ce{C}$ The correct structure of C is

JEE Main · 2022 · 25 Jul 2022 · Shift 2 · Aldehydes Ketones and Carboxylic Acids

CH X_{3} - CH X_{2} - CN CH X_{3} MgBr Ether A H X_{3} O X^{+} B Zn - Hg HCl C

The correct structure of C is

(A) $CH X_{3} - CH X_{2} - CH X_{2} - CH X_{3}$ ✓ Correct
(B)(see structure)
(C)(see structure)
(D) $CH X_{3} - CH X_{2} - CH = CH X_{2}$

Answer: (A)

Solution

Grignard reagent (

CH X_{3} MgBr

) reacts with nitrile to form a ketone after hydrolysis.

CH X_{3} CH X_{2} CN

CH X_{3} MgBr

→

CH X_{3} CH X_{2} C (= O) CH X_{3}

(B, a ketone). Clemmensen reduction (

Zn - Hg / HCl

) reduces the ketone to an alkane:

CH X_{3} CH X_{2} C (= O) CH X_{3}

→

CH X_{3} CH X_{2} CH X_{2} CH X_{3}

(butane). Answer: (A).

JEE Main · 2022 · 25 Jul 2022 · Shift 2 · Single correct option

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