Toluene on reaction with N-Bromosuccinimide gives

Phenyl bromomethane

The correct answer is option 1. Phenyl bromomethane.

N-bromosuccinimide is a white crystalline solid and is structurally represented as follows:

Due to the presence of a partial positive charge on bromine, NBS acts as a good electrophile and has a tendency to give two major reactions i.e., allylic or benzylic bromination (most common) and bromohydrin formation.

In the reaction of toluene with NBS, allylic bromination takes place as per the following reaction mechanism:

Step-1: NBS reacts with trace amounts of hydrogen bromide in order to form low concentration of bromine when suspended in carbon tetrachloride. The reaction takes place as follows:

Step-2: Bromine molecule in the presence of light breaks into its respective radicals and the reaction takes place as follows:

Step-3: One of the bromine radicals removes the allylic hydrogen from the molecule and a radical intermediate is formed which is resonance stabilized along with the removal of hydrogen bromide. The reaction takes place as follows:

Step-4: The radical intermediate formed in the previous step reacts with the other bromine radicals to give the final product. The reaction proceeds as follows:

Hence, on reaction of toluene with N-bromosuccinimide, the formation of phenyl bromomethane takes place.