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Choose the Best Answer · Q12

Q.Which of the following reagents is helpful to differentiate ethylene dichloride and ethylidene chloride? a) Zn/methanol b) KOH/ethanol c) aqueous KOH d) ZnCl₂/Con.HCl

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Step 1. Ethylene dichloride (a vic-dihalide, ClCH2-CH2Cl) and ethylidene chloride (a gem-dihalide, CH3-CHCl2) both undergo dehalogenation with Zn/methanol to give the SAME product, ethylene, and both undergo dehydrohalogenation with alcoholic KOH to give the SAME product, acetylene -- neither reagent can tell them apart.

Step 2. With aqueous KOH, however, the two dihalides behave differently: the vic-dihalide hydrolyses directly to a stable glycol (ethylene glycol), while the gem-dihalide hydrolyses to an unstable geminal diol that collapses to an aldehyde (acetaldehyde). …

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