(S)-1-Bromo-1,2-diphenylethane reacts with a strong base to produce cis-stilbene and trans-stilbene: a) This reaction is stereo-selective, and...

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(S)-1-Bromo-1,2-diphenylethane reacts with a strong base to produce cis-stilbene and trans-stilbene:

Br NaOEt trans-Stilbene cis-Stilbene (major product)

a) This reaction is stereo-selective, and the major product is trans-stilbene. Explain why the trans-isomer is the predominant product. To do so, draw the Newman projections that lead to formation of each product and compare their stability.

b) When (R)-1-bromo-1,2-diphenylethane is used as the starting substrate, the stereo-chemical outcome does not change. That is, trans-stilbene is still the major product. Explain.

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Organic Chemistry

ISBN: 978-0470917800

1st edition

Authors: David R. Klein

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