Benzene and Alkyl Benzene - Result Question 44

44. Toluene reacts with bromine in the presence of the light to give benzyl bromide, while in presence of $\mathrm{FeBr}_3$ it gives $p$-bromotoluene. Give explanation for the above observation.

(1996)

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Solution:

In presence of light, free radical reaction takes place at $-\mathrm{CH}_3$ group while in presence of $\mathrm{FeBr}_3$, electrophilic substitution occur in the ring.

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