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)

Show Answer

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.

<img src=“https://temp-public-img-folder.s3.amazonaws.com/sathee.prutor.images/sathee_image/snip_images_8DjoqlfCiWsD4c-lxmWaCU9Dy4hmrJziwXzVc03f5vI_original_fullsize_png.jpg"width="400"/>