Question

Draw the structure of the major monohalo product for each of the following reactions:

Hint:

The reaction of an alkylbenzene with HBr typically results in benzylic substitution, where the alkyl group is replaced by a bromine atom.

Answer 1

The reaction of toluene (methylbenzene) with HBr leads to the alkyl group (methyl) being substituted with a bromine atom at the benzylic position, forming 1-bromo-2-methylbenzene as the major product. 
The structure of the product is: \[ \text{C}_6\text{H}_4\text{CH}_3\text{Br} \]