Chemistry 125A: Freshman Organic Chemistry I - Lecture 17: Reaction Analogies and Carbonyl Reactivity - Professor J. Michael McBride
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.
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