Explain the following observation. When 3-methylbutan-2-ol is treated with HBr, a single alkyl bromide is isolated, resulting from a 1,2-shift. When 2-methylpropan-1-ol is treated with HBr, no rearrangement occurs to form an alkyl bromide.

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
Chapter11: Ethers, Epoxides, And Sulfides
Section: Chapter Questions
Problem 11.27P
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Explain the following observation. When 3-methylbutan-2-ol is treated with HBr, a single alkyl bromide is isolated, resulting from a 1,2-shift. When 2-methylpropan-1-ol is treated with HBr, no rearrangement occurs to form an alkyl bromide.

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