Benzyl chloride undergoes nucleophilic substitution much more easily than chlorobenzene
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Explanation:
In chlorobenzene,Cl atom remains directly attached to benzene ring.
As a result,the lone pair of electrons on Cl are in conjugation with benzene ring.There is resonance,owing to which there is large stability due to formation of phenyl cation.sp3 carbon gets converted to sp2.So,it can't take part in nucleophilic substitution reaction.
In benzyl chloride,CH2Cl group is attached to the benzene ring,no resonance takes place,and no phenyl cation is formed.So,it easily undergoes nucleophilic substitution reaction.
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