Question

Draw the major organic product(s) formed when (3R,4S)-3-bromo-4-methylhexane is treated with NaOCH2CH3 in HOCH2CH3 and heated....

Draw the major organic product(s) formed when (3R,4S)-3-bromo-4-methylhexane is treated with NaOCH2CH3 in HOCH2CH3 and heated.

I know the answer is a cis alkene but I dont understand why its cis!

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Answer #1

The elimination requires antiperiplanar arrangement as shown in the following figure.

The H atom and the Br atom (that are removed ) must be opposite to each other. This gives rise to cis alkene. The C-H and C-Br bonds are coplanar with 180 degrees between them. In this conformation, the σ bonds that are being broken are positioned in the correct alignment to become the π bond.  

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