Discovery-Oriented Approach To Organic Synthesis: Tandem Aldol Condensation-Michael Addition Reactions. Identifying Diastereotopic Hydrogens in an Achiral Molecule by NMR Spectroscopy
Nanette Wachter-Jurcsak and Kendra Reddin
Department of Chemistry, Hofstra University, Hempstead, NY 11550-1090
We have found a beautiful example of anisochrony of diastereotopic acyclic methylene hydrogens in a symmetric diketone, synthesized by techniques traditionally performed in an introductory organic laboratory course. Synthesis of the diketone is high-yielding and easy to carry out, and the products can be directly isolated with a good degree of purity with no need of further manipulation. The reaction can be accomplished in a single laboratory session.
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Citation
Wachter-Jurcsak, Nanette; Reddin, Kendra. J. Chem. Educ.2001 78 1264.
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