When Br2 is added to buta-1,3-diene at -15 °C, the product mixture contains 60% ofproduct A and 40% of product B. When the same reaction takes place at 60 °C, theproduct ratio is 10% A and 90% B.Show why A predominates at -15 °C and B predominates at 60 °C.

When Br2 is added to buta-1,3-diene at -15 °C, the product mixture contains 60% ofproduct A and 40% of product B. When the same reaction takes place at 60 °C, theproduct ratio is 10% A and 90% B.Show why A predominates at -15 °C and B predominates at 60 °C.

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter9: Nucleophilic Substitution And Β-elimination

Section9.7: Experimental Evidence For E1 And E2 Mechanisms

Problem 9.7P

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Question

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.
Show why A predominates at -15 °C and B predominates at 60 °C.

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When Br2 is added to buta-1,3-diene at -15 °C, the product mixture contains 60% ofproduct A and 40% of product B. When the same reaction takes place at 60 °C, theproduct ratio is 10% A and 90% B.If you had a solution of pure A, and its temperature were raised to 60 °C, what wouldyou expect to happen? Propose a mechanism to support your prediction.
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