ELECTROPHILIC ADDITION TO ALKENES MECHANISM

ELECTROPHILIC ADDITION TO ALKENES MECHANISM - -...

Info iconThis preview shows page 1. Sign up to view the full content.

View Full Document Right Arrow Icon
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
Background image of page 1
This is the end of the preview. Sign up to access the rest of the document.

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...
View Full Document

This note was uploaded on 03/21/2008 for the course CHEM 261 taught by Professor Austell during the Spring '08 term at UNC.

Ask a homework question - tutors are online