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Question 68 of 72

Q.Ethylidene chloride on treatment with aqueous KOH gives :

(a) formaldehyde
(b) acetaldehyde
(c) glyoxal
(d) ethylene glycol
Puducherry TnboardTamil Nadu HSC First Year (DGE) Board 2025MCQ· 1mImportance★★★★★
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CH3-CHCl2 (ethylidene chloride, a gem-dihalide) hydrolyses with aqueous KOH to give acetaldehyde (CH3CHO), because the intermediate gem-diol is unstable and loses water to form a carbonyl group.

Ethylidene chloride is 1,1-dichloroethane, CH3-CHCl2 — both chlorines sit on the SAME carbon (a geminal dihalide), unlike ethylene dichloride (CH2Cl-CH2Cl), which has one chlorine on each carbon.

When a gem-dihalide is treated with aqueous KOH, nucleophilic substitution (OH- replacing Cl-, twice) first gives a geminal diol:

CH3-CHCl2 + 2KOH -> CH3-CH(OH)2 + 2KCl

A carbon bearing two -OH groups on the same carbon (a gem-diol) is unstable and spontaneously eliminates a molecule of water to form a carbonyl (C=O) group:

CH3-CH(OH)2 -> CH3-CHO + H2O

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