Chem 243a - Alkenes by Elimination

Chem 243a - Alkenes by Elimination - 11A: Alkenes by...

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11A: Alkenes by Elimination Antonio Alarcon Chem 243a 11/10/07 I. Abstract In this lab, both the dehydration of 2-butanol and the dehydrohalogenation of 2-bromobutane were performed. The dehydration of 2-butanol yielded the following: trans -2-butene 50%, cis -2-butene 30%, 1-butene 20%. The dehydrohalogenation of 2-bromobutane yielded the following: trans -2-butene 50%, 1-butene 30%, cis -2-butene 20%.
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II. Introduction Throughout this semester, numerous mechanisms of organic synthesis have been encountered. However, the ones encountered thus far have been limited to that of reduction of alkynes or the addition of alkenes. In this lab students worked in pairs to prepare alkenes by the means of elimination, one running the base-catalyzed dehydrohalogenation of 2-bromobutane, the other running the acid-catalyzed dehydration of 2-butanol (Padias, 85-86). E1) Within the above reaction scheme, one notices that there are four key components; pronation, formation of a carbocation, formation of a “good” leaving group, and depronation. Here one sees a classic example of an electrophile and a nucleophile, 2-butanol being the nucleophile. In this case, one
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Chem 243a - Alkenes by Elimination - 11A: Alkenes by...

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