Question
Draw resonating structures for phenol showing the correct position of positive and negative charges and then account for the following:
(i) The ring of phenol is more easily oxidised than that of benzene.
(ii) Phenol is nitrated more easily than benzene.
Solution
The resonating structures for phenol are:
(i) The OH group is strongly activating group and increases the electron density on benzene and making the ring of phenol very electron rich. As a result, it can readily donate electrons to an oxidising agents.
(ii) Nitration of phenol is an electrophilic substitution reaction. OH group increases the electron density on benzene ring making it more electron rich. As a result, NO2+ ion can easily attack on the ring of phenol.
(i) The OH group is strongly activating group and increases the electron density on benzene and making the ring of phenol very electron rich. As a result, it can readily donate electrons to an oxidising agents.
(ii) Nitration of phenol is an electrophilic substitution reaction. OH group increases the electron density on benzene ring making it more electron rich. As a result, NO2+ ion can easily attack on the ring of phenol.
