The light-initiated reaction of 2,3-dimethylbut-2-ene with N-bromosuccinimide (NBS) gives two products:

(a) Give a mechanism for this reaction, showing how the two products arise as a consequence of the resonance-stabilized intermediate.
(b) The bromination of cyclohexene using NBS gives only one major product, as shown on page 227. Explain why there is no second product from an allylic shift.

Transcribed Image Text:

CH CH H,C CH2 Br H,C NBS, hv с с C-C CH H C CH3 CH CH H,C 2.3-dimethylbut-2-ene