Abstract
This article highlights some of the challenges in explaining simple substituent effects on keto–enol equilibria, particularly to an undergraduate audience. Quantum-chemical calculations were performed to identify the role of intramolecular hydrogen bonding, inductive effects due to electron-withdrawing groups, and cross-conjugation on the enolization of β-diketones and β-ketoesters. These insights could be applied by an instructor in order to enrich undergraduate chemistry students’ understanding of this fundamental reaction.
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