9.39. Following are diastereomers (A) and (B) of 3-bromo-3,4-dimethylhexane. On treatment 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 8-elimination. Me н Ме Br C-C Me Br H C-C Me Et Et Et Et (A) (B)

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9.39. Following are diastereomers (A) and (B) of 3-bromo-3,4-dimethylhexane. On treatment 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 3-elimination.
Me
Me
H
Br
Me
Br
Me
Et
Et
Et
Et
(A)
(В)
Transcribed Image Text:9.39. Following are diastereomers (A) and (B) of 3-bromo-3,4-dimethylhexane. On treatment 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 3-elimination. Me Me H Br Me Br Me Et Et Et Et (A) (В)
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