Following are two diastereomers of 3-bromo-4-ethyl-2,3,5-trimethylhexane. On treatment with sodium ethoxide in ethanol, each gives 3-ethyl-2,4,5-trimethyl-3- hexene as the major product. One diastereomer gives the E alkene, and the other gives the Z alkene. Which diastereomer gives the E alkene? Br Me H Br Me H iPr Et iPr b Et iPr iPr a

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
Chapter9: Nucleophilic Substitution And Β-elimination
Section: Chapter Questions
Problem 9.39P: Following are diastereomers (A) and (B) of 3-bromo-3,4-dimethylhexane. On treatment with sodium...
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Following are two diastereomers of 3-bromo-4-ethyl-2,3,5-trimethylhexane. On treatment with sodium ethoxide in ethanol, each gives 3-ethyl-2,4,5-trimethyl-3-
hexene as the major product. One diastereomer gives the E alkene, and the other gives the Z alkene. Which diastereomer gives the E alkene?
Br
Me
H
Br
Me
iPr
Et
Et
iPr
iP"
iPr
b
Transcribed Image Text:Following are two diastereomers of 3-bromo-4-ethyl-2,3,5-trimethylhexane. On treatment with sodium ethoxide in ethanol, each gives 3-ethyl-2,4,5-trimethyl-3- hexene as the major product. One diastereomer gives the E alkene, and the other gives the Z alkene. Which diastereomer gives the E alkene? Br Me H Br Me iPr Et Et iPr iP" iPr b
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