Because they are dramatic and intriguing, chemiluminescence demonstrations have been used for decades to stimulate interest in chemistry. One of the most intense chemiluminescent reactions is the oxidation of diaryl oxalate diesters with hydrogen peroxide in the presence of a fluorescer. In typical lecture demonstrations, the commercially…

Thermotropic liquid crystal phases are ordered fluids found, for some molecules, at intermediate temperatures between the crystal and liquid states. Although technologically important, these materials typically receive little attention in the undergraduate curriculum. Here, we describe a laboratory activity for introductory organic chemistry…

A procedure for teaching green chemistry through laboratory experiments is presented in which students are challenged to use the 12 principles of green chemistry to review and modify synthesis protocols to improve greenness. A global metric, green star, is used in parallel with green chemistry mass metrics to evaluate the improvement in greenness.…

An upper-level mechanistic organic experiment is outlined where undergraduates measure kinetic rate constants for decarboxylation of pyrrole-2-carboxylic acid by the initial-rates method. UV spectroscopy is used to monitor reactant disappearance in both hydrochloric acid and deuterium chloride at different temperatures. Individual data are pooled…

The Fisher esterification reaction is ideally suited for the undergraduate organic laboratory because it is easy to carry out and often involves a suitable introduction to basic laboratory techniques including extraction, distillation, and simple spectroscopic (IR and NMR) analyses. Here, a Fisher esterification reaction is described in which the…

This two-part laboratory experiment is designed to be a cost-effective method for teaching basic organic laboratory techniques (recrystallization, thin-layer chromatography, column chromatography, vacuum filtration, and melting point determination) to large classes of introductory organic chemistry students. Students are exposed to different…

Metal-organic frameworks (MOFs) are crystalline materials that are composed of an infinite array of metal nodes (single ions or clusters) linked to one another by polyfunctional organic compounds. Because of their extraordinary surface areas and high degree of control over the physical and chemical properties, these materials have received much…

Electrospray ionization mass spectrometry (ESI-MS) and matrix-assisted laser desorption ionization mass spectrometry (MALDI-MS) have found increasing application in the analysis of biological samples. Using these techniques to solve problems in analytical chemistry should be an essential component of the training of undergraduate chemists. We…

Our understanding of carbonium ions as intermediates in chemical reaction mechanisms derives from the early work of Julius Stieglitz and the more famous Hans Meerwein, the latter studying the racemization of isobornyl chloride when treated with Lewis acids. This review analyzes how key mechanistic concepts for this reaction evolved and gives the…

Copper fungicides and bactericides are often used in tomato cultivation and can cause toxic Cu levels in soils. In order to combat this, organic matter can be applied to induce chelation reactions and form a soluble complex by which much of the Cu can leach out of the soil profile or be taken up safely by plants. Organic acids such as citric,…

The main areas of difficulty experienced by those teaching and learning organic chemistry at high school and introductory university level in Ireland have been identified, and the findings support previous studies in Ireland and globally. Using these findings and insights from chemistry education research (CER), the Organic Chemistry in Action!…

This article describes a short synthesis and many of the difficulties experienced while carrying it out (e.g., low yields, impurities, racemization, nonrepeatable literature preps, etc.). As such, students will be educated in aspects of synthetic organic chemistry that are often down-played, or even not mentioned, in published syntheses. (Contains…

The characterization of students' reasoning strategies is of central importance in the development of instructional strategies that foster meaningful learning. In particular, the identification of shortcut reasoning procedures (heuristics) used by students to reduce cognitive load can help us devise strategies to facilitate the development of more…

Hydrogenation of alkenes is an important reaction in the synthesis of organic molecules. In this experiment, students conduct a high-yield microscale hydrogenation reaction of methyl "trans"-cinnamate using a readily available, safe, and convenient hydrogen source. The conditions are similar to those seen in an organic chemistry textbook for an…

The mineral acid-catalyzed dehydration of 2-methyl-1-cyclohexanol has been a popular laboratory exercise in second-year organic chemistry for several decades. The dehydration experiment is often performed by organic chemistry students to illustrate Zaitsev's rule. However, sensitive analytical techniques reveal that the results do not entirely…