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Lab 6 - Bromination of Stilbene_10

Lab 6 - Bromination of Stilbene_10 -...

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The Bromination of Stilbene Adapted from Doxsee, K. M. & Hutchinson, J. E., “A Greener Bromination of Stilbene,”  Green Organic  Chemistry 2004 , pp 125-128. Key Concepts/Definitions Electrophilic Addition to Alkenes  – a reaction where pi electrons attack an electrophile, forming a  cationic species, followed by nucleophilic attach to form an uncharged product. There are many examples  in organic chemistry including hydroxylation, epoxidation, halogenation, to mention a few. Chiral(ality) Centers  – an atom where all of the groups attached to it are different; in carbon compounds a  chiral center would have 4 different groups attached to a central carbon. Chirality centers are characterized  as having a non-superimposable mirror image. Meso compounds   – compounds that have chiral centers, but which have a mirror plane in the molecule. In this experiment, we will take advantage of the  in situ  generation of bromine, through the oxidation of  hydrobromic acid with hydrogen peroxide, to effect the bromination of ( E )-stilbene to 1,2-dibromo-1,2- diphenylethane (dibromostilbene). Although the requisite reagents – hydrobromic acid and hydrogen peroxide – 
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