Benzene Substitution

Benzene undergoes substitution of hydrogen with another atom/atom group Nitration of

Benzene Benzene + nitric acid (sulfuric acid catalyst at 50°) creates nitrobenzene and water.

Halogenation of Benzene
Halogens do not react with benzene unless a halogen carrier is present e.g. AlCl3
Bromination of Benzene Room temperature in the presence of a halogen carrier on
hydrogen on benzene is replaced with Br Electrophilic substitution

Benzene and Nitric Acid

Bromine and nitric acid react more readily with phenol than benzene Increased reactivity
due to lone pair of electrons from Oh being donated to pi-system increasing the electron
density. This means phenol attracts electrophiles more.

Phenol
Phenol Organic chemical containing OH bonded directly to benzene ring Phenol as a Weak
Acid Less soluble in water than alcohol due to non-polar benzene ring Phenol partially
dissociates in water forming phenoxide ion and a proton Phenols and carboxylic acids react
with strong bases Phenol can’t react with sodium carbonate Phenol and Sodium Hydroxide
Phenol + sodium hydroxide -> sodium phenoxide salt + water Electrophilic substitution of
Phenol Bromination

Phenol + bromine water -> 2,4,6- tribromophenol (precipitate) Decolourised bromine water
and forms white precipitate

Activation – aromatic ring reacts more readily with electrophiles Deactivation – aromatic
ring reacts less readily with electrophiles