Open Yale CoursesCHEM 125: Freshman Organic ChemistryLecture 17 - Reaction Analogies and Carbonyl Reactivity<< previous session| next session >>Overview:Continuing the examination of molecular orbital theory as a predictor of chemical reactivity, this lecturefocuses on the close analogy among seemingly disparate organic chemistry reactions: acid-base, SN2substitution, and E2 elimination. All these reactions involve breaking existing bonds where LUMOs haveantibonding nodes while new bonds are being formed. The three-stage oxidation of ammonia by elementalchlorine is analyzed in the same terms. The analysis is extended to the reactivity of the carbonyl group andpredicts the trajectory for attack by a high HOMO. This predicted trajectory was validated experimentally byBürgi 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
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