Solved: The light-initiated reaction of 2,3-dimethylbut-2-ene with N-bromosuccinimide
Chapter 0, Problem 6-9(choose chapter or problem)
The light-initiated reaction of 2,3-dimethylbut-2-ene with N-bromosuccinimide (NBS) gives two products: H3C CH3 C C H3C CH3 2,3-dimethylbut-2-ene H3C CH2 C C H3C CH3 + Br Br C CH3 CH3 CH2 C CH3 NBS, h (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.
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