Electrophilic aromatic substitution reaction of Benzene

Halogenation: Chlorination of Benzene

Mechanism
STEP 1: Formation of the Electrophile.
Reaction between chlorine (a Lewis base) and FeCl3 (a Lewis acid) gives an ion pair
containing a chloronium ion (an electrophile):

STEP 2: Attack of electrophile

Reaction of a nucleophile and an electrophile to form a new covalent bond.

STEP 3: Removal of proton

Take a proton away, Proton transfer from the cation intermediate to FeCl4 forms HCl,
regenerates the Lewis acid catalyst, and gives chlorobenzene
 Nitration:

The electrophile in the nitration of benzene is the +NO2 (the nitronium ion),
which is formed by protonation of HNO3 by H2SO4

Mechanism:
STEP 1: Formation of the Electrophile. {+NO2 (the nitronium ion)}
STEP 2: Addition of Electrophile

STEP 3: Loss of Proton

 Sulfonation
Benzene can be converted into benzenesulfonic by reacting it with fuming sulfuric acid which is
prepared by adding sulfur trioxide (SO3). The electrophile in this reaction is the sulfonium ion
(+SO3H) that forms when concentrated sulfuric acid reacts with SO3.

STEP 1: Formation of the Electrophile {Sulfonium ion (+SO3H)}

STEP 2: Addition of Electrophile

STEP 3: Loss of Proton