Benzene Chemistry part 3

Phenols
Phenol is a benzene ring with an OH group attached:

students often get confused with phenyl and phenol. Phenyl means that you have a substituted
benzene, usually with an alkyl group. Phenol means that you have an OH group.

Reactivity

Phenols are useful as they make the benzene ring more reactive to electrophiles, meaning milder
conditions can be used.

The increased reactivity is due to the lone pair of electrons on the oxygen being delocalised into the
benzene ring increasing the electron density, and hence its reactivity towards electrophiles.

the reactivity of phenol is more like an alkene than benzene

Sometimes they will compare the reactivity of phenol to benzene and an alkene. Phenol reacts similarly
to an alkene as it will react at room temperature.

But phenol still does electrophilic substitution.

remember that alkenes do not have delocalised electrons but phenol and benzene do.

Phenol will react with bromine water at room temperature. 2,4,6-tribromophenol is produced (a white
precipitate):
 the phenol/activated ring stuff is very common in exam questions. Note that NH2 or alkyl groups will
also activate the ring.

Reaction with base

Phenol is slightly acidic. Alcohols are usually not acidic but the presence of the benzene ring stabilises the
negative charge on the O making phenol acidic.

Phenol can react with NaOH (and Na). But it is not acidic enough to react with Na 2CO3, which is a much
weaker base.

Product formed when phenol reacts with NaOH.