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13.70 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 7.9 (substitution vs. elimination) to justify why the allylic alcohol would be the major product in this case below. OH НО 1) EtMgBr T ye. Et 2) H₂O* Major product Minor product

13.70 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 7.9 (substitution vs. elimination) to justify why the allylic alcohol would be the major product in this case below. OH НО 1) EtMgBr T ye. Et 2) H₂O* Major product Minor product

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Chemistry
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ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
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13-70 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 7.9 (substitution vs. elimination) to justify why the allylic alcohol would be the major product in this case below. OH HO 1) EtMgBr 2) H₂O+ Et Major product Minor product A, a cytotoxic marine natural product. Draw the structures of 13.71 The following sequence of reactions was employed during synthetic studies on reidispongiolide compounds A, B, C, and D. Ph 1) CH₂=CHMgBr A 1) NaH 2) CH₂1 B cat. OsO4 NMO C+D Phi 2) H,O* Ph
Transcribed Image Text:13-70 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 7.9 (substitution vs. elimination) to justify why the allylic alcohol would be the major product in this case below. OH HO 1) EtMgBr 2) H₂O+ Et Major product Minor product A, a cytotoxic marine natural product. Draw the structures of 13.71 The following sequence of reactions was employed during synthetic studies on reidispongiolide compounds A, B, C, and D. Ph 1) CH₂=CHMgBr A 1) NaH 2) CH₂1 B cat. OsO4 NMO C+D Phi 2) H,O* Ph
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