Answer to Question #100879 in Organic Chemistry for Surbhi

Question

which is more reactive towards electrophillic substitution reaction and why?
a)C6H5OH(Phenol)
b)C6H5CH2OH

Answer 1

When the substituents like -OH have an unshared pair of electrons, the resonance effect is stronger than the inductive effect which make these substituents stronger activators, since this resonance effect direct the electron toward the ring.

The reason the benzyl alcohol is less reactive than phenol has to do with the pi electrons on the oxygen. In the phenol molecule, the extra electrons can contribute to the aromatic pi system, but in benzyl alcohol they can't because they are next to a sp3 carbon which doesn't allow any overlap