Lecture 17 - Reaction Analogies and Carbonyl Reactivity

author: J. Michael McBride, Department of Chemistry, Yale University
recorded by: Yale University
published: June 10, 2010,   recorded: October 2008,   views: 2757
released under terms of: Creative Commons Attribution No Derivatives (CC-BY-ND)
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Description

Continuing the examination of molecular orbital theory as a predictor of chemical reactivity, this lecture focuses on the close analogy among seemingly disparate organic chemistry reactions: acid-base, SN2 substitution, and E2 elimination. All these reactions involve breaking existing bonds where LUMOs have antibonding nodes while new bonds are being formed. The three-stage oxidation of ammonia by elemental chlorine is analyzed in the same terms. The analysis is extended to the reactivity of the carbonyl group and predicts the trajectory for attack by a high HOMO. This predicted trajectory was validated experimentally by Bürgi and Dunitz, who compared numerous crystal structures determined by X-ray diffraction.

Problem sets/Reading assignment:

Reading assignments, problem sets, PowerPoint presentations, and other resources for this lecture can be accessed from Professor McBride's on-campus course website, which was developed for his Fall 2008 students. Please see Resources section below.

Resources:

Professor McBride's web resources for CHEM 125 (Fall 2008)

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