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

Chemistry

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Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

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Concept explainers

Organomagnesium compounds

The interaction of alkyl halide with Mg metal in a suitable ether solvent is the common method for the synthesis of the Grignard reagent.

Hydrolysis Grignard Reactions and Reduction

Organomagnesium halides are Grignard reagents. Francois Auguste Victor Grignard, a French chemist who received the Nobel Prize in Chemistry in 1912, created these highly useful reagents.

Question

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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