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Suppose in the reaction preparation of Diphenylacetylene you start with cis-stilbene instead of trans-stilbene, would you...

Suppose in the reaction preparation of Diphenylacetylene you start with cis-stilbene instead of trans-stilbene, would you expect the MP of the stilbene dibromide produced be the same as the one obtained from trans stilbene? Why and why not?

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Answer #1

The melting point of stilbene dibromide obtained through both sources (cis and trans stilbene) will be different. This is because both stilbene dibromide products are not the same. Stilbene dibromide obtained from cis stilbene is a racemic mixture (equall amount of two enantiomers), whereas stilbene dibromide obtained from trans stilbene is a meso compound. Hene, the relation between products obtained from both sources are diastereomer and they will have different chemical and physical properties.

This is because of addition of bromine across the double bond is anti.

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