Why can aryl halides not be prepared by the reaction of phenol with $HCl$ in the presence of $ZnCl_{2}$?
In phenol,the lone pair of electrons on the oxygen atom is involved in resonance with the benzene ring.
This gives the $C-O$ bond a partial double bond character.
Due to this partial double bond character,the $C-O$ bond is much stronger and shorter than a pure single bond,making it difficult to break.
Therefore,the nucleophilic substitution reaction required to replace the $-OH$ group with a $-Cl$ atom cannot occur easily under these conditions.
This gives the $C-O$ bond a partial double bond character.
Due to this partial double bond character,the $C-O$ bond is much stronger and shorter than a pure single bond,making it difficult to break.
Therefore,the nucleophilic substitution reaction required to replace the $-OH$ group with a $-Cl$ atom cannot occur easily under these conditions.
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