In toluene, there is no electrophilic center. So by the addition of chlorine oxidation occurs and the free radical substitution reaction takes place. Only chlorine can give chlorine as a free radical in the presence of light. It is just like a photochemical reaction.
Treatment of toluene with chlorine in presence of sunlight
Benzyl chloride is prepared industrially by the gas phase photochemical reaction of toluene and chlorine. This reaction yields by a free radical mechanism connecting the free chlorine intermediate. The side product is hydrochloric acid. In toluene, no electrophilic center oxidation happens by controlled free radical reaction using Cl2.
in presence of high.