'A' $(\ce{C8H6Cl2O}) \xrightarrow{\ce{NH3}} \ce{C8H8ClNO} \xrightarrow[\ce{NaOH}]{\ce{Br2}}$ Consider the above reaction, the compound 'A' is:

JEE Main · 2022 · 29 Jul 2022 · Shift 1 · Aldehydes Ketones and Carboxylic Acids

'A'

(C X_{8} H X_{6} Cl X_{2} O) NH X_{3} C X_{8} H X_{8} ClNO Br X_{2} NaOH

Consider the above reaction, the compound 'A' is:

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

Answer: (C)

Solution

The reaction sequence is a Hofmann bromamide degradation. Compound A with molecular formula

C X_{8} H X_{6} Cl X_{2} O

is an acyl chloride. Treatment with

NH X_{3}

converts it to an amide (

C X_{8} H X_{8} ClNO

). The Hofmann degradation with

Br X_{2} / NaOH

removes one carbon as

CO X_{2}

, yielding an amine. The structure must be 4-chloro-3-methylbenzoyl chloride to match the molecular formula and reaction pathway.

JEE Main · 2022 · 29 Jul 2022 · Shift 1 · Single correct option

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