Two Types of Benzene Substituents

Electron donating groups (EDG)/Activators with lone

pairs (e.g. -OMe, -NH2) on the atoms adjacent to
the system activate the aromatic ring by increasing
the electron density on the ring through a resonance
donating effect.
o Make benzene ring more nucleophilic by pushing
electrons toward the ring
Electron withdrawing groups/Deactivators (EWG)
with p bonds to electronegative atoms (e.g. -C=O,
-NO2) adjacent to the system deactivate the
aromatic ring by decreasing the electron density on
the ring through a resonance withdrawing effect.
o Make benzene ring less nucleophilic

Methyl Benzene
Methylbenzene (Toulene) is an example of a
substituted aromatic compound.
Methylbenzene is an activated or more reactive
compared to benzene.
Methyl group is an activated group/EDG that increases
the rate of reaction.

 Methyl group is an ortho/para director- it directs the

incoming groups to ortho and para positions.

As the temperature increases, you get increasing

proportions of the 4- isomer and less of the 2- isomer
because the 4-position is more stable due to less steric
clash between the methyl group.

Nitrobenzene
Deactivator less reactive than benzene
Meta-director
Reaction with Tin in concentrated HCL: Preparing Phenylam
ine
The mixture is heated under reflux in a boiling water
bath for about half an hour.
Under the acidic conditions, rather than getting
phenylamine directly, you instead get phenylammonium
ions formed
The lone pair on the nitrogen in the phenylamine picks
up a hydrogen ion from the acid.