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