Side chain reactions

The C-H bonds of the methyl group in toluene are benzylic, therefore they are weaker than C-H bonds in simpler alkanes. Reflecting this weakness, the methyl group in toluene undergoes a variety of free radical reactions. For example, when heated with ''N''-bromosuccinimide (NBS) in the presence of AIBN, toluene converts to benzyl bromide.