Predict the product of the reaction between toluene and bromine in presence of iron. draw arrow-pushing mechanism for the major products.
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Structures of products have been given below

Explanation:

It is an example of bromination reaction of toluene in presence of a catalyst e.g. FeMethyl 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.