Tetramethyloxirane is too hindered to undergo nucleophilic substitution by the hindered alkoxide, potassium tert butoxide. Instead, the

Question:

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?

ОН CH2 H,C CH3 (CH3)3C-O K+ H,C- (CH3)3С —ОН CH3 tetramethyloxirane H;C CH3 CH3