The S N 2 reaction between a Grignard reagent and an epoxide works reasonably well when the

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The SN2 reaction between a Grignard reagent and an epoxide works reasonably well when the epoxide is ethylene oxide. However, when the epoxide is substituted with groups that provide steric hindrance, a competing reaction can dominate, in which an allylic alcohol is produced. Propose a mechanism for this transformation and use the principles discussed in Section 8.13 to justify why the allylic alcohol would be the major product in this case below.

но он 1) EtMgBr 2) H20 Et Major product Minor product

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Organic Chemistry

ISBN: 978-0470917800

1st edition

Authors: David R. Klein

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