Ch_322a_7.011

Ch_322a_7.011 - Alkenes by Debromination of Vicinal...

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Alkenes by Debromination of Vicinal Dibromides Vicinal dibromides are debrominated to produce alkenes by: C Br Br C NaI acetone C=C or (2) Reaction with zinc dust in acetic acid or ethanol. C Br Br C Zn (dust) acetic acid or ethanol C=C C-C X X geminal dihalide Geminal dihalides have the halogens on the same carbon. Vicinal dihalides have halogen atoms on adjacent carbons. C-C X X vicinal dihalide
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Debromination by Sodium Iodide in Acetone: An E2 Reaction Two equivalents of NaI are needed: C Br Br C + 2NaI C=C + I 2 + 2NaBr Mechanism I: : : - + C C Br Br E2 Iodide ion acts as a nucleophile and attacks bromine atom initiating an elimination reaction. C=C + I Br + Br
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This note was uploaded on 07/22/2009 for the course CHEM 322AL taught by Professor Jung during the Summer '07 term at USC.

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Ch_322a_7.011 - Alkenes by Debromination of Vicinal...

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