When 2-bromo-3-phenylbutane is treated with sodium methoxide, two alkenes result (by E2 elimination). The Zaitsevproduct predominates.(a) Draw the reaction, showing the major and minor products.(b) When one pure stereoisomer of 2-bromo-3-phenylbutane reacts, one pure stereoisomer of the major product results.For example, when (2R,3R)-2-bromo-3-phenylbutane reacts, the product is the stereoisomer with the methyl groups cis.Use your models to draw a Newman projection of the transition state to show why this stereospecificity is observed.(c) Use a Newman projection of the transition state to predict the major product of elimination of (2S,3R)-2-bromo-3-phenylbutane.(d) Predict the major product from elimination of (2S,3S)-2-bromo-3-phenylbutane. This prediction can be made withoutdrawing any structures, by considering the results in part (b)
When 2-bromo-3-phenylbutane is treated with sodium methoxide, two
product predominates.
(a) Draw the reaction, showing the major and minor products.
(b) When one pure stereoisomer of 2-bromo-3-phenylbutane reacts, one pure stereoisomer of the major product results.
For example, when (2R,3R)-2-bromo-3-phenylbutane reacts, the product is the stereoisomer with the methyl groups cis.
Use your models to draw a Newman projection of the transition state to show why this stereospecificity is observed.
(c) Use a Newman projection of the transition state to predict the major product of elimination of (2S,3R)-2-bromo-3-
phenylbutane.
(d) Predict the major product from elimination of (2S,3S)-2-bromo-3-phenylbutane. This prediction can be made without
drawing any structures, by considering the results in part (b)
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