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.