Haloalkanes and Haloarenes

Question

Out of C6H5CH2Cl and C6H5CHCIC6H5 which is more easily hydrolysed by aqueous KOH. 

Answer

Hydrolysis by aqueous KOH proceed through the formation of carbocation. If carbocation is stable, then the compound is easily hydrolyzed by aqueous KOH. In the given compounds benzyl chloride forms  primary carbocation, while chlorodiphenylmethane forms secondary carbocation, which is more stable than primary carbocation, hence C6H5CHClC6H5 is more easily hydrolysed by aqueous KOH.

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