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the elimination of 5-bromononane on treatment with potassium ethoxide is stereos

ID: 850591 • Letter: T

Question

the elimination of 5-bromononane on treatment with potassium ethoxide is stereoselective. Select the correct Newman projections of 5-bromononane showing the conformations that lead to cis-4-nonene an trans-4-nonene, respectively. Identify the proton that is lost in each case by selecting the Newman projections that have this hydrogen colored blue. Suggest a mechanistic explanation for the oberserved stereoselectivity.

leads to cis-4-nonene:

the elimination of 5-bromononane on treatment with potassium ethoxide is stereoselective. Select the correct Newman projections of 5-bromononane showing the conformations that lead to cis-4-nonene an trans-4-nonene, respectively. Identify the proton that is lost in each case by selecting the Newman projections that have this hydrogen colored blue. Suggest a mechanistic explanation for the oberserved stereoselectivity. leads to cis-4-nonene:

Explanation / Answer

Compound B is the structure that leads to Cis-nonene as major product because in this case the Leaving group i.e Br and the electrophile i.e H is not anti-periplanar to each other