When Br2 is added to buta-1,3-diene at -15 C, the product mixture contains 60% of

Chapter 15, Problem PROBLEM 15-8

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When \(Br_2\) is added to buta-1,3-diene at -\(15^{\circ}C\), the product mixture contains 60% of product A and 40% of product B. When the same reaction takes place at \(60^{\circ}C\), 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 -\(15^{\circ}C\) and B predominates at \(60^{\circ}C\).

(d) If you had a solution of pure A, and its temperature were raised to \(60^{\circ}C\), what would you expect to happen? Propose a mechanism to support your prediction.

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