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  4. Which chloro derivative of benzene, would undergo hydrolysis most readily with aqueous KOH?

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Q. Which chloro derivative of benzene, would undergo hydrolysis most readily with aqueous KOH?

JIPMERJIPMER 1998

Solution:

Hydrolysis of an halide is nucleophilic substitution reaction, which is possible in aryl halides only when some powerful electron withdrawing groups (like $ --N{{O}_{2}}, $ $ --COOH $ etc.) are attached to especially o- and p-positions. Thus 2, 4, 6-trinitrochloro benzene will undergo hydrolysis (aq. KOH) most readily as it has $ 3-{{e}^{-}} $ -withdrawing groups.