Question

Toluene reacts with bromine in the presence of the light to give benzyl bromide, while in presence of FeBr₃ it gives p-bromotoluene. Give explanation for the above observations.

Answer 1

This reaction is based upon free radical substitution concept, i.e, it is completed in form of free radical mechanism.

So, in presence of sunlight the substitution takes place from side chain while in presence of FeBr₃ substitution takes place from benzene nucleus.