Monday, January 15, 2018

organic chemistry - Halogenation of alcohols in the presence of ZnCl2


I know that $\ce{OH-}$ is usually a bad leaving group, but why does the following reaction occur via SN1 in presence of anhydrous $\ce{ZnCl2}$?


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Answer



You are right, $\ce{OH-}$ is a bad leaving group. But the $\ce{HCl}$ in the reaction mixture protonates it. Thus, the bad leaving group $\ce{OH-}$ is converted to the good leaving group $\ce{H2O}$. Anhydrous $\ce{ZnCl2}$ might additionally facilitate the reaction by acting as a Lewis acid and it binds the expelled water thus preventing the back reaction.


enter image description here


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