This is a tale about Algernon the Organic Chemist. In his laboratory one night, Algernon attempted to prepare an alcohol, 3-methyl-2- butanol (shown below) by the acid-catalyzed hydration of 3-methyl-1- butene. Well, guess what? His reaction made an alcohol in high yield, but it was NOT the alcohol he was trying to make. What alcohol did he make instead? [ HINT: Mechanistically, a carbocation is formed. When a carbocation is especially unstable, what will it always try to do first? ] он H* H,ö: 3-methyl-2-butanol он OH III HQ IV OH

This is a tale about Algernon the Organic Chemist. In his laboratory one night, Algernon attempted to prepare an alcohol, 3-methyl-2- butanol (shown below) by the acid-catalyzed hydration of 3-methyl-1- butene. Well, guess what? His reaction made an alcohol in high yield, but it was NOT the alcohol he was trying to make. What alcohol did he make instead? [ HINT: Mechanistically, a carbocation is formed. When a carbocation is especially unstable, what will it always try to do first? ] он H* H,ö: 3-methyl-2-butanol он OH III HQ IV OH

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

Chapter24: Catalytic Carbon-carbon Bond Formation

Section: Chapter Questions

Problem 24.8P

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