Consider the sequence of reactions below. In this sequence of reactions, an unsaturated ketone is treated with a Gilman reagent, followed by treatment with an aqueous base. The base allows a rapid equilibration to take place, producing the more stable stereoisomer of the product. 1. Et,CuLi 2. Equilibration with base For this process: show both stereoisomeric products, explain which is more stable, and explain why aqueous base allows equilibration between the stereoisomers.

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
Chapter16: Aldehydes And Ketones
Section: Chapter Questions
Problem 16.42P: When cis-2-decalone is dissolved in ether containing a trace of HCl, an equilibrium is established...
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Consider the sequence of reactions below. In this sequence of reactions, an
unsaturated ketone is treated with a Gilman reagent, followed by treatment
with an aqueous base. The base allows a rapid equilibration to take place,
producing the more stable stereoisomer of the product.
1. Et,CuLi
2. Equilibration
with base
For this process: show both stereoisomeric products, explain which is more
stable, and explain why aqueous base allows equilibration between the
stereoisomers.
Transcribed Image Text:Consider the sequence of reactions below. In this sequence of reactions, an unsaturated ketone is treated with a Gilman reagent, followed by treatment with an aqueous base. The base allows a rapid equilibration to take place, producing the more stable stereoisomer of the product. 1. Et,CuLi 2. Equilibration with base For this process: show both stereoisomeric products, explain which is more stable, and explain why aqueous base allows equilibration between the stereoisomers.
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