Q.Ethylidene chloride on treatment with aqueous KOH gives :
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Start your 14-day free trial to unlock the full solution →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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