8 Organocuprates predominantly react to give 1,4-addition products with a,B-unsatu- rated carbonyl species, while Grignard reagents often add to the carbonyl, in a process referred to as 1,2-addition. To increase the yield of 1,4-addition products, Cul is added to convert an easily prepared Grignard reagent into a organocuprate reagent in situ (during the reaction). Predict the major product and stereochemistry of the following reaction, assuming that the more stable chair product predominates. MgBr Cul, THF, -30 C 2. Equilibration to more stable chair product in base

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8 Organocuprates predominantly react to give 1,4-addition products with a,B-unsatu-
rated carbonyl species, while Grignard reagents often add to the carbonyl, in a process
referred to as 1,2-addition. To increase the yield of 1,4-addition products, Cul is added
to convert an easily prepared Grignard reagent into a organocuprate reagent in situ
(during the reaction). Predict the major product and stereochemistry of the following
reaction, assuming that the more stable chair product predominates.
MgBr
Cul, THF, -30 C
2. Equilibration to
more stable chair
product in base
Transcribed Image Text:8 Organocuprates predominantly react to give 1,4-addition products with a,B-unsatu- rated carbonyl species, while Grignard reagents often add to the carbonyl, in a process referred to as 1,2-addition. To increase the yield of 1,4-addition products, Cul is added to convert an easily prepared Grignard reagent into a organocuprate reagent in situ (during the reaction). Predict the major product and stereochemistry of the following reaction, assuming that the more stable chair product predominates. MgBr Cul, THF, -30 C 2. Equilibration to more stable chair product in base
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