CHEM 125a - Lecture 17 - Reaction Analogies and Carbonyl Reactivity

Lecture 17 - Reaction Analogies and Carbonyl Reactivity

Overview

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.

Resources

Professor McBride's website resource for CHEM 125 (Fall 2008)

http://webspace.yale.edu/chem125_oyc/#L17

This website may include third-party materials pertaining to relevant topics, provided for the user's convenience. Yale does not control or take responsibility for the content of any off-site pages or linked sites.

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.

Course Media

Transcript

html

Audio

mp3

Low Bandwidth Video

mov [100MB]

High Bandwidth Video

mov [500MB]