Toluene reacts with a halogen in the presence of iron (III) chloride giving ortho and para halo compounds. The reaction is

1.  Electrophilic elimination reaction

2.  Electrophilic substitution reaction

3.  Free radical addition reaction

4.  Nucleophilic substitution reaction


Toluene reacts with a Cl2 in the presence of lewis acid Ferric chloride which facilitates Cl+ electrophile generation. The formed Cl+ electrophile will give aromatic electrophilic substitution reaction to form ortho and para chloro compounds. The systematic mechanism of this chlorination will be shown below.

In this mechanism, electrophile Cl* prefer to attack at elecronically rich position of aromatic ring and replaces H+, Hence mechanism will Aromatic electrophilic substitution.