Ethylbenzene reacts with bromine in the presence of light (side-chain radical bromination). The major monobromo product is

A(1-bromoethyl)benzene
B1-bromo-2-ethylbenzene
C1-bromo-4-ethylbenzene
D(2-bromoethyl)benzene

Answer: A

Radical bromine attacks the C-H bond whose cleavage gives the most stable radical. Removal of a benzylic hydrogen gives a radical stabilised by the ring, and bromination is very selective. The product is (1-bromoethyl)benzene. Ring bromination needs a Lewis acid and an ionic path.

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