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Choose the Best Answer · Q21

Q.Ethylidene chloride on treatment with aqueous KOH gives a) acetaldehyde b) ethylene glycol c) formaldehyde d) glyoxal

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Step 1. Ethylidene chloride, CH3-CHCl2, is a gem-dihalide (both chlorines on the same carbon).

Step 2. Hydrolysis of a gem-dihalide with aqueous KOH first replaces both chlorines with -OH groups, giving an unstable geminal diol, CH3-CH(OH)2.

Step 3. A geminal diol (two -OH on the same carbon) is inherently unstable and immediately loses a molecule of water, collapsing to the corresponding carbonyl compound -- here, since the diol carbon also bears one H, it collapses to an aldehyde, acetaldehyde (CH3CHO), …

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