(a) Tetramethyloxirane is too hindered to undergo nucleophilic substitution by the
Chapter 14, Problem 14-52(choose chapter or problem)
(a) Tetramethyloxirane is too hindered to undergo nucleophilic substitution by the hindered alkoxide, potassium tert-butoxide. Instead, the product is the allylic alcohol shown. Propose a mechanism to explain this reaction. What type of mechanism does it follow?
(b) Under mild acid catalysis, 1,1-diphenyloxirane undergoes a smooth conversion to diphenylethanal (diphenylacetaldehyde). Propose a mechanism for this reaction. (Hint: Think Pinacol.)
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