The reaction of toluene with $$Cl_2$$ in presence of $$FeCl_3$$ gives predominantly

Chlorination of an aromatic compound can follow two different pathways, depending on the reaction conditions:

1. Radical (side-chain) chlorination: $$Cl_2$$ in the presence of heat, light, or peroxides produces benzyl chloride, benzal chloride, etc.
2. Electrophilic (ring) chlorination: $$Cl_2$$ in the presence of a Lewis-acid catalyst such as $$FeCl_3$$ produces chlorinated aromatic rings.

In this question the reagent system is $$Cl_2/FeCl_3$$, so the reaction proceeds through the electrophilic aromatic substitution (EAS) mechanism.
The methyl group in toluene is:

  • Electron-donating through hyperconjugation and +I effect.
  • Activating and ortho/para-directing in EAS.

Therefore the incoming electrophile $$Cl^+$$ attacks predominantly at the ortho and para positions of the benzene ring relative to the $$CH_3$$ group.

Hence the major products are $$o$$-chlorotoluene and $$p$$-chlorotoluene.

Option C which is: $$o-$$ and $$p-$$chlorotoluene