13. Alcohols and Carbonyl Compounds
Oxidizing Agent
4:15 minutes
Problem 11-66 (c)
Textbook Question
Textbook QuestionUnder normal circumstances, tertiary alcohols are not oxidized.
However, when the tertiary alcohol is allylic, it can undergo
a migration of the double bond (called an allylic shift)
and subsequent oxidation of the alcohol. A particularly effective
reagent for this reaction is Bobbitt’s reagent, similar to TEMPO
used in many oxidations.
(M. Shibuya et al., J. Org. Chem., 2008, 73, 4750.)
<IMAGE of reaction>
Show the expected product when each of these 3° allylic
alcohols is oxidized by Bobbitt’s reagent
(c) <IMAGE>
(d) <IMAGE>
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