
Green Chemistry: Acids and Acid Derivatives
Michael McBride continues Yale's Freshman Organic Chemistry II with a lecture on green chemistry applied to acids and their derivatives. He opens with the Mitsunobu reaction, noting its reliability but poor atom efficiency, since it generates nearly thirty times as much byproduct weight as the water it removes. He contrasts this with greener alternatives: autoxidation of aldehydes to carboxylic acids using only O2, and ruthenium catalyzed alcohol oxidation that releases H2 rather than toxic waste. McBride then turns to relative pKa values of carboxylic acids, explaining how inductive and resonance effects shape acidity, citing an analysis that attributes four times more influence to inductive effects than resonance. The lecture closes by covering methods for preparing carboxylic acids through both oxidation and reduction routes, tying mechanism back to environmental cost throughout.