Monday, January 15, 2018

organic chemistry - Halogenation of alcohols in the presence of ZnCl2


I know that OHX is usually a bad leaving group, but why does the following reaction occur via SN1 in presence of anhydrous ZnClX2?


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Answer



You are right, OHX is a bad leaving group. But the HCl in the reaction mixture protonates it. Thus, the bad leaving group OHX is converted to the good leaving group HX2O. Anhydrous ZnClX2 might additionally facilitate the reaction by acting as a Lewis acid and it binds the expelled water thus preventing the back reaction.


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