CHEM 125A - Freshman Organic Chemistry I
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 Burgi and Dunitz, who compared numerous crystal structures determined by X-ray diffraction. (from oyc.yale.edu)
| Lecture 17 - Reaction Analogies and Carbonyl Reactivity |
| Time | Lecture Chapters |
| [00:00:00] | 1. Similarities among Acid-Base, SN2 Substitution, and E2 Elimination Reactions |
| [00:15:23] | 2. The Oxidation of Ammonia by Chlorine in Molecular Orbital Terms |
| [00:26:06] | 3. Reactivity of the Carbonyl Group |
| [00:36:11] | 4. Dunitz and Burgi's Experimental Results on Carbonyl Attack Trajectory |
| References |
| Lecture 17 - Reaction Analogies and Carbonyl Reactivity Instructor: Professor J. Michael McBride. Resources: Professor McBride's website resource for CHEM 125 (Fall 2008). Transcript [html]. Audio [mp3]. Download Video [mov]. |
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