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…

This paper describes the design and implementation of a course-based undergraduate research experience (CURE) sequence in chemistry that links a lower-division, organic chemistry course to an upper-division, analytical chemistry course. The focus of student research is on blood preservation using trehalose derivatives in order to mimic the…

As green chemistry and engineering are being integrated into chemical processes in academia and industry, it becomes equally important to equip students with the relevant tools in the fields of sustainable chemistry and processes. In this context, continuous flow technology has been identified as one of the promising strategies. Herein, we…

The synthesis of epoxidized soybean oil (ESO) provides students a vantage point on the application of green chemistry principles in a series of experiments. Qualitative tests review the reactions of alkenes, whereas spectroscopic analyses provide insight in monitoring functional group transformations.

A microscale isotopic labeling experiment is described for the introductory organic chemistry laboratory course wherein half of the students use sodium borohydride (NaBH[subscript 4]) and the other half use sodium borodeuteride (NaBD[subscript 4]) to reduce acetophenone to 1-phenylethanol and then compare spectral data. The cost is reasonable, and…

An undergraduate organic chemistry laboratory experiment involving the breakage of amide C-N bonds is reported. Whereas amides are typically considered stable species due to well-established resonance effects, this experiment allows students to cleave the amide C-N bond in a nickel-catalyzed esterification process. Moreover, students perform the…

The synthesis of a commercial fragrance, methyl cinnamate, via Fischer esterification was evaluated for use as a second-year organic chemistry course. The experiment utilizes "trans"-cinnamic acid, a commercial flavoring that possesses a mild honey floral odor, as an inexpensive starting material. Both the starting material and the…

How well does the undergraduate organic chemistry laboratory curriculum prepare students for academic research, or for a bench job in industry? Running experiments that are more representative of research chemistry has the potential to better equip students for working in a research laboratory, while at the same time giving them insight into a…

A laboratory experiment is described for beginning, nonmajor chemistry students, which allows students to examine the phenomena of fluorescence and chemiluminescence, as well as gain experience in basic organic synthesis. Students synthesize fluorescein and bis(2,4,6-trichlorophenyl) oxalate (TCPO) to explore fluorescence and chemiluminescence by…

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…

A straightforward synthesis of 2-phenylimidazo[1,2-a]pyridine is described. The reaction is designed to demonstrate to students the preparation of a bridged N-heterocycle, in which the heteroatom occupies a bridgehead position. The product is obtained in moderate to high yield and is highly crystalline. The compound can be purified either by…

A method for the synthesis of flufenamic acid, a nonstereoidal anti-inflammatory drug (NSAID) of the anthranilate family (fenams), is described as an experiment for the upper-division undergraduate organic chemistry laboratory. The key step is the formation of the diarylamine moiety of flufenamic acid by a novel reaction consisting of the coupling…

An experimental protocol that provides an excellent way to discuss concepts at the crossroads of organic chemistry and biochemistry employing biocatalysis is presented. By evaluating several reaction parameters (enzyme source, organic solvent, and acyl donor), it was possible to conduct an enzymatic kinetic resolution experiment using…

In the Spring 2021 Organic Chemistry Lab class at Penn State Schuylkill, COVID-19 restrictions and uncertainty required a flexible plan. The first 4 weeks of 15 were fully remote, and videos of standard organic techniques were used, followed by an exam. In the next 5 weeks, some students were in the lab and some were remote. A document camera was…

An experiment for an undergraduate organic chemistry class based on the application of an ionic liquid as solvent and catalyst of an organic reaction is reported. The whole experiment requires three 3-h lab sessions. First, students prepare the ionic liquid dimethylimidazolium methylsulfate, which is then used as a recyclable catalyst/reaction…