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Solution: The stereoselectivity of elimination of 5-bromononane on tre...

Question

The stereoselectivity of elimination of 5-bromononane on treatment with potassium ethoxide was described in Section 5.14. Draw Newman projections of 5-bromononane showing the conformations that lead to cis -4-nonene and trans -4-nonene, respectively. Identify the proton that is lost in each case, and suggest a mechanistic explanation for the observed stereoselectivity.