Curriculum-based undergraduate research experiences (CUREs) have been shown to increase student retention in STEM fields and are starting to become more widely adopted in chemistry curricula. Here we describe a 10-week CURE that is suitable for a second-semester organic chemistry laboratory course. Students synthesize small molecules and use…

The ACS Guidelines for bachelor's degrees in chemistry call for the curriculum to include polymer chemistry principles and the synthesis of different classes of macromolecules. Organic chemistry can provide an important introduction to polymer chemistry principles, and photochemically induced radical polymerization is one method for generating…

Strategies for teaching NMR spectral interpretation in the undergraduate organic chemistry curriculum are often faculty-centered and can lead to student reliance on rote memorization and "guess and check" methods rather than critical-thinking skills for structure determination. This article describes a student-focused methodology for the…

An organic chemistry experiment is described that is based on recent research to elucidate a novel cation-pi interaction between tetraalkammonium cations and propargyl hydrazines. This nonbonded interaction is a key component of the mechanism of ammonium-catalyzed intramolecular cycloaddition of nitrogen to the terminal carbon of a C-C triple bond…

Although stereochemistry is an important topic in second-year undergraduate organic chemistry, there are limited options for laboratory activities that allow direct visualization of macroscopic chiral phenomena. A novel, guided-inquiry experiment was developed that allows students to explore chirality in the context of cholesteric liquid crystals.…

Liquid 2-chlorobenzaldehyde was converted, by grinding with potassium hydroxide pellets, into equimolar quantities of solid 2-chlorobenzoic acid and solid 2-chlorobenzyl alcohol in a Cannizzaro reaction. TLC, IR, and NMR experiments, using authentic samples for comparison, confirmed the identity and purity of the two products. Guided-inquiry…

When FT-NMR is used to collect data without a sufficient delay time between subsequent pulses, the integrated area under certain peaks may result in a lower value than should be observed under appropriate conditions. This discrepancy in integration may deceive the inexperienced eye and consequently can lead to a wrong assignment of the NMR…

We describe the development and use of a molecular model building activity with a chocolate theme, suitable for a public presentation of chemistry through interaction with visitors to science festivals and museums, and as a special classroom activity during science weeks, and so forth. (Contains 3 figures.)

The guided-inquiry approach is applied to the reactions of sodium borohydride and phenyl magnesium bromide with benzaldehyde, benzophenone, benzoic anhydride, and ethyl benzoate. Each team of four students receives four unknowns. Students identify the unknowns and their reaction products by using the physical state of the unknown, an…

An experiment for the undergraduate chemistry laboratory in which students perform the aldol condensation on an unknown aldehyde and an unknown ketone is described. The experiment involves the use of techniques such as TLC, column chromatography, and recrystallization, and compounds are characterized by [to the first power]H NMR, GC-MS, and FTIR.…