Lecture 10 - Cation Intermediates – Alkenes: Formation, Addition, and Stability

author: J. Michael McBride, Department of Chemistry, Yale University
recorded by: Yale University
published: Aug. 19, 2014,   recorded: February 2011,   views: 1455
released under terms of: Creative Commons Attribution No Derivatives (CC-BY-ND)

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Bridged pentavalent carbon structures can be intermediates or transition states of cation rearrangement during SN1 reactions, and short-lived ion pairs explain net stereochemical inversion. The different perspectives of preparative organic chemists and mechanistic organic chemists on reaction yields are illustrated by a study designed to demonstrate that molecular rotation can be rate-limiting in viscous solvents. "Electrophilic" addition to alkenes is the reverse of E2 or E1 reaction, and its mechanisms can be studied by analogous techniques. The NIST Webbook provides thermochemical data to help understand the relative stability of isomeric alkenes.

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