Question

The reaction of `C_6H_5CH=CHCH_3` with HBr produces
A. `C_6H_5CH_2CH_2CH_2Br`
B.
C. `C_6H_5undersetunderset"Br"|CHCH_2CH_3`
D. `C_6H_5CH_2undersetunderset"Br"|CH_2CH_3`

Answer 1

Correct Answer - C
Addition of `H^+` preferentially occurs on `C_2` rather than `C_1` since it generates a carbocation which is stabilized by resonance over the benzene ring.
`C_6H_5-overset1CH=overset2CHCH_3overset(H^+)to underset"(Stabilized by resonance over the benzene ring)"(C_6H_5-overset+CH-CH_2CH_3) overset(Br^-)to underset"1-Bromo-1-phenylpropane"(C_6H_5-undersetunderset(Br)|CH-CH_2CH_3)`