Microwave heating enhanced the rate of three reactions typically performed in our undergraduate organic chemistry laboratory: a Diels-Alder cycloaddition, a Wittig salt formation, and a Williamson ether synthesis. Ninety-minute refluxes were shortened to 10 min using a laboratory-grade microwave oven. In addition, yields improved for the Wittig…

Assigning a popular nonfiction book as a supplemental text in organic chemistry can help students learn valuable skills. An analysis of student feedback on assignments related to a nonfiction book in two different organic courses revealed that students applied the information from the book, improved their communication skills, and were more…

A novel experiment is described in which solvated electrons in liquid ammonia reduce a benzyl alcohol carbon without affecting the aromatic ring. The reductive activity of solvated electrons can be partially or completely quenched through the addition of electron scavengers to the reaction mixture. The effectiveness of these scavengers was found…

A hetero-Diels-Alder reaction that proceeds rapidly and only requires a simple filtration to purify the product is presented. The dienophile, 4-phenyl-1,2,4-triazoline-3,5-dione (PTAD), is prepared by the heterogeneous oxidation of 4-phenylurazole by the bromenium ion, Br[superscript +], generated in situ by the oxidation of potassium bromide by…

Extending the usefulness of the instruments we have has never been more important. The current economic crisis has prompted all of us to re-examine how money is spent and to try to minimize our expenditures because of future uncertainties. We have been able to breathe new life into an aging 60 MHz NMR spectrometer used by hundreds of…

We present an adaptation to an experiment previously published in this "Journal". The experiment was designed to determine the heat capacity ratios of gases by measuring the speed of sound using a modified Kundt's tube. The experiment yielded excellent results for all of the gases and gas mixtures measured. Although elegant in its simplicity, it…

In this article I support and extend the ideas presented by J. Brent Friesen in his article "Saying What You Mean; Teaching Mechanisms in Organic Chemistry" ("JCE" November, 2008). I emphasize "telling the truth" about proton transfers. The truth is that in aqueous acid most reactions are subject to "specific" acid catalysis: the only kinetically…

Students in the second-semester organic chemistry laboratory perform a Wittig reaction between butylidenetriphenylphosphorane (an ylide) and benzaldehyde and determine the relative percentages of the cis and trans isomers of the 1-phenyl-1-pentene product. Because of the highly reactive nature of this unstabilized ylide, students are introduced to…

Peptidomimetic compounds are increasingly important in drug-discovery applications. We introduce the synthesis of an N-substituted glycine oligomer, a bioactive "peptoid" trimer. The six-step protocol is conducted on solid-phase resin, enabling the synthesis to be performed by undergraduate organic chemistry students. This synthesis lab was…

Managing student needs for effective learning in a large-enrollment, introductory organic chemistry course can be a challenging task. Because instructor time is at a premium, it is imperative to find resources that engage the students in active learning and provide them with feedback about their understanding of course content. Appropriately…

Natural products play a critical role in modern organic synthesis and learning synthetic techniques is an important component of the organic laboratory experience. In addition to traditional one-step organic synthesis laboratories, a multistep natural product synthesis is an interesting experiment to challenge students. The proposed three-step…

Students at two-year colleges and small four-year colleges have often obtained their exposure to NMR spectroscopy through "canned" spectra because the cost of an NMR spectrometer, particularly a high-field spectrometer, is prohibitive in these environments. This article describes the design of a NMR site at Trinity University in which…

The central goal of this study was to characterize the mental models of acids and acid strength expressed by advanced college chemistry students when engaged in prediction, explanation, and justification tasks that asked them to rank chemical compounds based on their relative acid strength. For that purpose we completed a qualitative research…

This paper reports a genre study of the Results sections of two samples of 20 research-reporting articles from two disciplines: sociology and organic chemistry. Following the proposal of Bhatia (2004) that genre knowledge needs to be investigated from two perspectives, an "ethnographic perspective" and a "textual perspective," the Results sections…

Organic Chemistry is perceived to be one of the most challenging of undergraduate science courses, and attrition from this course may impact decisions about pursuing a professional or academic career in the biomedical and related sciences. Research suggests that chemistry students who are strategic help seekers may outperform those students who…