An operationally straightforward, project-like laboratory experiment has been developed in which students directly compare the reactivity of two heterocycles, a cyclic "O,O"-acetal (standard C-O protecting group) and a cyclic "N,O"-acetal (oxazolidine), toward sodium borohydride and methylmagnesium iodide. Students synthesize a…

A discovery-based undergraduate organic chemistry lab experiment has been developed in which students establish the diastereoselectivity of hydride reduction of the a-chiral ketone (±)-benzoin isopropyl ether to erythro and threo diastereomeric alcohols by two different reducing agents. Students achieve this goal by working collaboratively and…

The essential oil of "Nepeta cataria" L. (catnip), an herbaceous plant known popularly as a stimulant for the domestic cat, is enriched in two diastereomeric iridoid lactones (nepetalactones) that vary in ratio. Although the diastereomers are chromatographically separable and exhibit different 1D NMR spectra, it is not possible to…