Lecture 7 - Nucleophilic Substitution Tools - Stereochemistry, Rate Law, Substrate, Nucleophile, Leaving Group

author: J. Michael McBride, Department of Chemistry, Yale University
recorded by: Yale University
published: Aug. 19, 2014,   recorded: February 2011,   views: 1710
released under terms of: Creative Commons Attribution No Derivatives (CC-BY-ND)
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Description

SN2 substitution provides an example of establishing the mechanism of a chemical reaction by disproving all the alternatives. Five general pathways are envisioned (two-step involving either pentavalent or trivalent carbon intermediates, and one-step). They can be discriminated by applying a variety of experimental tools including stereochemistry (Walden inversion), rate law (second order and pseudo first order), and the variation of rate constant with changes in the substrate (steric hindrance and ring strain), and with changes in nucleophile or leaving group. Classic experiments by Kenyon and Phillips and by Bartlett and Knox established the nature of Walden inversion.

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