Bromination of Z -Stilbene

Apply the procedure given for bromination of (E)-stilbene to study this reaction with (Z)-stilbene. Develop a protocol whereby you could demonstrate the stereochemical outcome of the dibromide(s) produced. Consult with your instructor before undertaking any experimental procedures. 

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Elimination of Alternate Non-Terminal Alkyl Halides, p. 343 Elimination of Stereoisomeric Alcohols, p. 355 NEW Analysis of Bromohexanes, p. 370 NEW Bromination of (Z)-Stilbene, p. 380... 

Pyridine bromide is a useful reagent for halogenation of alkenes and ketones, but both pyridine and bromine are noxious reagents, and the solid pyridinium perbromide complex is dangerous to handle. Poly(vinylpyridine perbromide) (21) quantitatively produces a-bromo ketones from cyclohexanone and propiophenone and is easy to handle. Bromination of (Z)-stilbene and ( )- and (Z)-1-phenylpropene gave 98-100% anti addition, as in equation (2), while bromine in solution yielded dibromophenylpropanes with 25-92% anti addition, depending upon the solvent. 

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