Jose Juncosa

Biennial Conference on Chemical Education, University of Kentucky, Lexington

National Meeting of the American Chemical Society, San Francisco, CA

A 2- to 3- week laboratory experience has been developed for second-semester Organic Chemistry students. Through this activity, students synthesize an unknown compound and propose a mechanism for its formation after unambiguously determining its structure. The synthesis consists of a Grignard reaction and a Babler-Dauben oxidation using (-)-carvone as a starting material. The Babler-Dauben oxidation involves the oxidation of a tertiary alcohol, which is not commonly covered in the typical Organic Chemistry curriculum. This means students need to use sound reasoning and creativity to propose a plausible mechanism, a valuable skill that requires a firm grasp on the basics of chemical mechanisms and higher-order thinking.
The experimental procedure incorporates many important lab skills, including the use of anhydrous conditions, extractions, spectroscopy, and column and thin-layer chromatography. Students also perform literature searches to determine the stereochemistry of their product based on its optical rotation. Due to the similarity in structure between carvone and the final product, when similar functional groups are overlaid for comparison, the inversion of the stereogenic center is a glaring difference. This inversion helps students to realize that the reaction involves more than just a simple substitution. Details on the development of the experiment and its successful application during Spring 2023 will be presented.

Middle Atlantic Regional Meeting of the American Chemical Society, University of Maryland, Baltimore County

New, versatile synthesis of a compound that can serve as a pharmacological tool for the study of learning and the action of psychedelics, possibly leading to new treatments.