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…