Q.

An aromatic compound C7H6Cl2(A), gives AgCl on boiling with alcoholic AgNO3 solution and yields C7H7OCl on treatment with sodium hydroxide. (A) on oxidation gives monochlorobenzoic acid. The compound (A) is 

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a

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b

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c

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d

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answer is A.

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Detailed Solution

Concept:

1. The compound A has the molecular formula C7H6Cl2, which suggests it is an aromatic compound with two chlorine atoms attached to the benzene ring.

2. When A is boiled with alcoholic AgNO3, it produces AgCl. This indicates that A contains a chlorine atom attached to a benzylic carbon (–CH2Cl).

3. Treatment with NaOH gives C7H7OCl. This suggests that the benzylic chloride group (–CH2Cl) is converted to a benzylic alcohol group (–CH2OH).

4. On oxidation, A forms monochlorobenzoic acid. This indicates that the benzylic carbon (CH2) is oxidized to a carboxylic acid group (–COOH).

Reaction Steps:

C7H6Cl2 (A) → Alcoholic AgNO3 → AgCl + Intermediate

C7H6Cl2 (A) + NaOH → C7H7OCl

C7H6Cl2 (A) + Oxidizing agent → Monochlorobenzoic acid

Identification:

The structure of A must contain one benzene ring, one benzylic chloride group (–CH2Cl), and one additional chlorine atom directly attached to the benzene ring. The correct structure of A is benzyl chloride with a chlorine atom attached to the benzene ring.

The compound A is option a.

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