Tetramethyloxirane is too hindered to undergo nucleophilic

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?

Equation Transcription:

Text Transcription:

H_{3}C

CH_{3}

H_{3}C

CH_{3}

(CH_{3})_{3}C-O- K^+

(CH_{3})_{3}C-OH

H_{3}C

OH

CH_{3}

CH_{2}

CH_{3}

CH_{3}