Why is phenol more easily nitrated than Benzene?

This is due to the -OH phenol functional group, which makes nitrating the molecule easier. Benzene has a delocalised pi-system above and below the plane of the molecule. The result of this is that: it is attacked by electrophiles in an electrophilic substitution reaction. Phenol also has this, but the -OH group has an oxygen atom with 2 lone pairs. One of these lone pairs are partially donated/delocalised into Benzene's pi-system, which increases the electron density across the molecule. This makes Phenol more susceptible to attack from electrophiles than Benzene and hence is more easily nitrated!

Answered by George W. Chemistry tutor

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