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Introductory Organic Chemistry - Lecture 17

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Lecture 17 - Reaction Analogies and Carbonyl Reactivity

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.

Prof. J. Michael McBride
CHEM 125: Freshman Organic Chemistry, Fall 2008
(Yale University: Open Yale)
Date accessed: 2009-11-11
License: Creative Commons BY-NC-SA

Lecture Material

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Supplementary lecture material is listed below.

1. LUMO Analogies
2. Where should R2C=O be attacked?



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