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
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
Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter11: Ethers, Epoxides, And Sulfides
Section: Chapter Questions
Problem 11.18P
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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](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F714f200d-bc54-45fd-bba6-52e5c2579cce%2F2a2df111-4366-48e9-a486-159fecbea6c5%2Fpw06d7.jpeg&w=3840&q=75)
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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