When Br2 is added to buta-1,3-diene at -15 °C, the product mixture contains 60% of product A and 40% of product B. When the same reaction takes place at 60 °C, the product ratio is 10% A and 90% B.
(a) Propose structures for products A and B. (Hint: In many cases, an allylic carbocation is more stable than a bromonium ion.)
(b) Propose a mechanism to account for formation of both A and B.
(c) Show why A predominates at 15 °C, but B predominates at 60 °C.
(d) If you had a solution of pure A, and its temperature were raised to 60 °C, what would you expect to happen? Propose a mechanism to support your prediction.
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