A compound X (C7H7Cl) is boiled with aqueous NaOH, acidified with dilute HNO3 and treated with AgNO3: no precipitate forms. Oxidation of X with hot alkaline KMnO4 followed by acidification gives 4-chlorobenzoic acid. X is

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JEE Advanced levelSingle correct optionDifficulty 3 of 3si048

A compound X ( $C X_{7} H X_{7} Cl$ ) is boiled with aqueous NaOH, acidified with dilute $HNO X_{3}$ and treated with $AgNO X_{3}$ : no precipitate forms. Oxidation of X with hot alkaline $KMnO X_{4}$ followed by acidification gives 4-chlorobenzoic acid. X is

A3-chlorotoluene
B4-chlorotoluene
Cbenzyl chloride
D2-chlorotoluene

Answer: B

AgCl

means the chlorine is bonded to the ring (aryl halide), not to a benzylic carbon, which excludes benzyl chloride. Side-chain oxidation of the methyl group to

COOH

giving the 4-chloro acid places the groups para. X is 4-chlorotoluene.

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A compound X (CX7​HX7​Cl) is boiled with aqueous NaOH, acidified with dilute HNOX3​ and treated with AgNOX3​: no precipitate forms. Oxidation of X with hot alkaline KMnOX4​ followed by acidification gives 4-chlorobenzoic acid. X is

Answer: B

More questions on Distinguishing tests for functional groups

A compound X ( $C X_{7} H X_{7} Cl$ ) is boiled with aqueous NaOH, acidified with dilute $HNO X_{3}$ and treated with $AgNO X_{3}$ : no precipitate forms. Oxidation of X with hot alkaline $KMnO X_{4}$ followed by acidification gives 4-chlorobenzoic acid. X is