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The Sharpless epoxidation reaction is considered one of the most powerful advances in asymmetric organic synthesis (1). It is a classic example of the use of an asymmetric catalyst to provide an enantiomerically enriched mixture of epoxy alcohols. The procedure typically uses titanium(IV) tetraisopropoxide (Ti(OiPr)4) as a catalyst, a peroxide, and dialkyl tartrates to induce asymmetry in the epoxidation reaction of allylic alcohols. The experiment described in this paper illustrates the principle of asymmetric epoxidation and enables students to determine enantiomeric product ratios using chiral shift reagents and NMR spectroscopy.

An innovative, three-year seminar program was developed for undergraduates at The College of New Jersey (TCNJ) that supplements the core chemistry curriculum by teaching the auxiliary skills necessary for life as a professional chemist. Advising, good laboratory practice, and information literacy are the strategic components of this program that function as building blocks to support sequential learning objectives and outcomes for students while enriching the chemistry program at TCNJ. Although the seminar program model is not unique to the TCNJ campus, this program has novel components, including a strong faculty-embedded-librarian partnership, a three-year approach that builds new skills onto the foundation of those previously acquired, a mentoring relationship between faculty and students that is reinforced by sustained faculty interaction, a peer mentor component that builds throughout the students’ time at TCNJ, and assessment of knowledge retention at the start of each course. Details pertaining to the components of the program, the impact of the program as evidenced by assessment outcomes, along with student views on how the program influenced their learning skills, and future directions are described.