Organic Chemistry (9th Edition)
Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Chapter 15.6, Problem 15.8P

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.

  1. a. Propose structures for products A and B. (Hint: In many cases, an allylic carbocation is more stable than a bromonium ion.)
  2. b. Propose a mechanism to account for formation of both A and B.
  3. c. Show why A predominates at −15 °C and B predominates at 60 °C.
  4. 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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Organic Chemistry (9th Edition)

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