The reaction of C6H5CH=CHCH3 with HBr produces
- C6H5CH2CH2CH2Br
- [figure]
- C6H5 Br |CHCH2CH3
- C6H5CH2 Br |CHCH3
Answer
(3) C6H5 Br |CHCH2CH3
Solution
Addition of HBr is electrophilic and goes through the more stable carbocation.
H adds to the carbon next to CH3 ⇒ C6H5 CH-CH2CH3, a benzylic carbocation stabilised by resonance with the benzene ring (more stable than C6H5CH2 CHCH3).
Br then attacks the benzylic carbon
⇒ product C6H5 Br |CHCH2CH3 (1-bromo-1-phenylpropane)
Answer: (3)