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Why can arylhalide not be prepared by reaction of phenol with HCl in the presence of ZnCl2.
In case of alkyl halide, formation of carbo-cation takes place, which ultimatly reacts with HCl to give an alkyl halide.
However, for arylhalide to react with HCl in the presence of ZnCl2, formation of phenyl carbocation should takes place, which is not possible as it is an highly unstable structure and never exists in free state. Hence, we cannot use HCl and ZnCl2 to prepare arylhalide.
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