The reaction of toluene with chlorine in the presence of iron and in the

absence of light produces:-

1. 

2. 

3. 

4. Mixture of 2 and 3

The reaction of toluene with chlorine in the presence of Fe catalyst that is carried out without light, so the aromatic elctrophilic substitution occurs in the benzene ring in ortho and para position to -CH3 group then product is the mixture of (b) and (c) ie.,

o-chlorotoluene and p-chlorotoluene.