For the past eight years, we have used online homework software as a pedagogical tool for undergraduate students (almost all are second-year students) learning organic chemistry. Being strong proponents of homework, we were surprised to find that about half of the students who complete 90% or more of the online homework assignments received less than 50% of the available points on examinations, even though comparable problems were given. Students who combined traditional pencil–paper problem solving with the online software performed better than students who solely used the online homework package. Our findings contribute to the ongoing debate between pencil–paper and computer learning with the recommendation that they should be combined to provide students with the ultimate learning tool.

It has been found for the first time at room temperature that the reaction of an unactivated 2-alkyl or 2-aryl aziridine with carbon dioxide to generate the corresponding oxazolidinone does not need any form of catalysis or solvent to proceed in high yield, especially when using high speed ball milling.

An experiment has been developed in which the hydrogen-atom abstraction and the coupling of propionitrile, using Fenton’s reagent, are investigated. Students learn about the regiochemistry of radical formation, the stereochemistry of product formation, and the interpretation of GC–MS data, in a safe reaction that can be easily completed in one laboratory session.Keywords: Aqueous Solution Chemistry; Constitutional Isomers; Diastereomers; Free Radicals; Gas Chromatography; Laboratory Instruction; Mass Spectrometry; Organic Chemistry; Second-Year Undergraduate; Stereochemistry;

The conversion of an unactivated 2-alkylaziridine to the corresponding oxazolidinone generally requires a very high pressure of carbon dioxide, a high temperature, an expensive catalyst, and/or a long reaction time. Here, a new, high yield (over 95%), and highly regioselective (over 95%) conversion of an unactivated aziridine to an oxazolidinone is reported. This reaction is easy to perform because it requires a low pressure of carbon dioxide, low temperature, no co-solvent, and the catalyst is the salt ammonium iodide.

The ring expansion of a dimethyl-substituted vinylcyclobutene derivative to the corresponding dimethyl-substituted cyclohexadiene or aromatic compound was studied. It was found that metal complexes of Ni(I), Ti(III), Sm(II), and Fe(II), which can undergo an inner-sphere electron-transfer reaction, allow the rearrangement to occur at room temperature. Other oxidation states of these metals and complexes that can only undergo an outer-sphere electron-transfer process do not promote this ring expansion reaction.