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ELECTROPHILIC ADDITION TO ALKENES MECHANISM - formation of carbocation, followed by attack of carbocation by nucleophile - hydroxylation, hydrogenation, halogenation, oxidative cleavage, hydration, epoxidation, cyclopropanation, halohydrin formation - Markovnikov product (nucleophile added to the more highly substituted carbon) nuc : = nucleophile E + = electrophile Steps: 1. Pi electrons attack an electrophile, forming a carbocation on the most stable C 2. A nucleophile then attacks the carbocation to form the product There are many different kinds of such addition, including: - Hydroxylation - Hydration - Hydrogenation - Epoxidation - Halogenation
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Unformatted text preview: - Cyclopropanation-Oxidative Cleavage - Halohydrin Formation Clearly, there are numerous kinds of products that can be formed as a result of this mechanism. Orientation of Addition : Electrophilic Addition adds to give the Markovnikov Product , with the nucleophile added to the more highly substituted carbon . This is because the carbocation intermediate is significantly stabilized by alkyl substituents. Example of electophilic addition to alkenes: First, formation of the carbocation on the most highly substituted carbon Followed by attack of chloride on the carbocation to give the addition product...
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This note was uploaded on 03/21/2008 for the course CHEM 261 taught by Professor Austell during the Spring '08 term at UNC.

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