diphenylacetylenefromstilbene-091026224601-phpapp01

diphenylacetylenefromstilbene-091026224601-phpapp01 -...

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Diphenylacetylene Diphenylacetylene from from Stilbene Stilbene
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Overview Overview Dibromide Dibromide Alkyne Alkyne Alkene Alkene Addition Elimination X 2 Ph H Br H Br CC H H Br 2 - OH
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Electrophilic Addition ¾ The most common applications of alkene halogenation are chlorination and bromination , which are electrophilic addition reactions. ¾ General mechanism of electrophilic addition: C=C E + Nu - Nu - E Nu Carbocation intermediate E
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Bromination Bromination of Alkenes of Alkenes ± Bromonium ion intermediate formation ± Anti-addition of nucleophilic Br ± Pyridinium tribromide (PyH + Br 3 ) is used as a source for bromine. Br a b b a Bromonium Ion Br --- Br δ + δ − Minor Shifts in Electron Density
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Bromination Bromination of of trans - - Stilbene Stilbene 1R, 2S 1S, 2R Meso Meso Compounds: Identical Compounds: Identical rotate An internal plane of symmetry CC H H Br Br N H 3 - Ph H H - a b a b H H H H H H
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Elimination of Elimination of Dibromide Dibromide H Br H Br Ph OH H Br Diphenylacetylene E2 E2
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diphenylacetylenefromstilbene-091026224601-phpapp01 -...

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