Diphenylacetylene can be synthesized by the double dehydrohalogenation of
Chapter 9, Problem 9.36(choose chapter or problem)
Diphenylacetylene can be synthesized by the double dehydrohalogenation of 1,2-dibromo1,2-diphenylethene. The sequence starting from (E)-1,2-diphenylethene consists of bromination to give the dibromide, followed by dehydrohalogenation to give a vinylic bromide, then a second dehydrohalogenation to give diphenylacetylene. C6H5 C6H5 C6H5 C6H5 Br Br S Br2 R KOH ethanol meso-1,2-Dibromo1,2-diphenylethane (E)-1,2-Diphenylethene C14H11Br KOH 190C Diphenylacetylene C C Vinylic bromide (a) What is the structure, including stereochemistry, of the vinylic bromide? (b) If the sequence starts with (Z)-1,2-dibromo-1,2-diphenylethene, what is (are) the structure(s) of the intermediate dibromide(s)? What is the structure of the vinylic bromide?
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