Predict the product of the reaction between toluene and bromine in presence of iron. Draw arrow-pushing mechanism for the major products.

anything would be appreciated because I have no idea how to start this!

Structures of products have been given below

Explanation:

It is an example of bromination reaction of toluene in presence of a catalyst e. g. Fe Methyl group in toluene is o/p-directing group. Therefore Br adds onto ortho and para position to methyl group in toluene. Reaction goes through electrophilic aromatic substitution. Here Br replaces one H atom from benzene ring. Here ortho product appears as a major one due to the fact that inductive effect of methyl substituent operates majorly at ortho position. reaction mechanism and structures of products have been shown below.