Acid-base reactions are central to many reactions in Organic Chemistry. As such, it is important for Organic Chemistry students to be able to predict strengths of acids and bases as well as the direction in which acid-base reactions favor. Students are usually taught acid strength by looking at the conjugate base or by memorizing pKa and pKb values of representative functional groups. This approach doesn’t guarantee a fundamental understanding of why an acid or base is stronger and may only give a narrow view of relative strengths. Though a discussion of electron stabilizing forces, such as resonance and inductive effects, accompanies the discussion of conjugate bases, students often struggle with determining which stabilizing force will predominate to determine stability. Herein, we present a new approach to teaching electron stabilizing forces in Organic Chemistry. This new method introduces six major electron stabilizing forces in a hierarchy that allows for prediction of relative electron stability, and by extension relative acidity and basicity of molecules without memorization of pKa values. This method also assists students in predicting the most basic site on molecules by studying electron stability.

PRECHI: New way to teach electron stabilizing forces and acid-base reactions

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

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