Question

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

• A.
• B.
• C.
• D.

Answer 1

Answer: (D)

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.