Following are diastereomers (A) and (B) of 3-bromo-3,4-dimethylhexane. On treat- ment with sodium ethoxide in ethanol, each gives 3,4-dimethyl-3-hexene as the major product. One diastereomer gives the E alkene, and the other gives the Z alkene. Which diastereomer gives which alkene? Account for the stereoselectivity of each B-elimination. H C-C Mẹ Me Br H Ме Br C-C Me Et Et Et Et (A) (В)

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
Chapter6: Reactions Of Alkenes
Section: Chapter Questions
Problem 6.46P
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Following are diastereomers (A) and (B) of 3-bromo-3,4-dimethylhexane. On treat-
ment with sodium ethoxide in ethanol, each gives 3,4-dimethyl-3-hexene as the major
product. One diastereomer gives the E alkene, and the other gives the Z alkene. Which
diastereomer gives which alkene? Account for the stereoselectivity of each B-elimination.
H
C-C
Mẹ
Me
Br
H
Ме
Br
C-C
Me
Et
Et
Et
Et
(A)
(В)
Transcribed Image Text:Following are diastereomers (A) and (B) of 3-bromo-3,4-dimethylhexane. On treat- ment with sodium ethoxide in ethanol, each gives 3,4-dimethyl-3-hexene as the major product. One diastereomer gives the E alkene, and the other gives the Z alkene. Which diastereomer gives which alkene? Account for the stereoselectivity of each B-elimination. H C-C Mẹ Me Br H Ме Br C-C Me Et Et Et Et (A) (В)
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