Identify the reaction conditions

Toluene is reacting with $Cl_2$ in the presence of $FeCl_3$.

• $FeCl_3$ acts as a Lewis acid catalyst.
• This condition is characteristic of electrophilic aromatic substitution (ring chlorination), not side-chain chlorination.

Nature of the substituent already present on benzene

In toluene, the substituent is $-CH_3$.

• The methyl group is electron-donating due to hyperconjugation and inductive effect.
• Therefore, it activates the benzene ring.
• It is an ortho/para-directing group.

Effect on chlorination

Since the methyl group directs incoming electrophile to the ortho and para positions, chlorination occurs mainly at these positions:

$\text{Toluene} \xrightarrow[ ]{Cl_2/FeCl_3} \text{o-chlorotoluene} + \text{p-chlorotoluene}$

The para product is often favored somewhat due to less steric hindrance, but both ortho and para are the predominant products.

Check the options

• A: benzoyl chloride — incorrect; this would require formation of an acyl chloride, not possible here.
• B: benzyl chloride — incorrect under $Cl_2/FeCl_3$; benzyl chloride forms in side-chain radical chlorination using light or heat, not $FeCl_3$.
• C: o-and p-chlorotoluene — correct.
• D: m-chlorotoluene — incorrect because $-CH_3$ is not meta-directing.

Final answer

The predominant products are ortho- and para-chlorotoluene.