Why does phenol readily undergo electrophilic substitution but benzene does not without the aid of a catalyst?

Benzene's delocalised π system of electrons makes it not quite electron rich enough for the reaction to take place. The lone pair from the -OH group in phenol adds enough electron density into the ring so that it becomes more susceptible to electrophilic attacks, hence resulting in a reaction.

Answered by Frederick B. Chemistry tutor

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