Unlike the large number of laboratory experiments on phase-transfer catalysis (PTC) that focus on a catalyzed chemical process, the present laboratory emphasizes the mechanism of phase transfer catalysis itself. Students can follow visually the actual transfer of the reagent by the catalyst, and its consumption in the organic phase, in a…

Two experiments are described which lead to the preparation of dimethyl fumarate, a compound currently used in the treatment of multiple sclerosis. Preparation of a compound with "real-world" applications is believed to increase student interest in the experiment. One experiment involves the isomerization of dimethyl maleate to the…

Aldol chemistry is highlighted in many introductory organic chemistry laboratory experiments because it provides synthesis, mechanism, and experimental challenges for students. In the experiment described here, students synthesize dibenzalacetone derivatives by crossed aldol condensation, observe reaction rates using a semiquantitative rubric, and…

Research on student argumentation in chemistry laboratories has mainly focused on evaluating the quality of students' arguments and analyzing the structure of such arguments ("i.e." claims, evidence, and rationale). Despite advances in these areas, little is known about the impact of activity framing on the nature of student…

Nuclear magnetic resonance (NMR) spectroscopy is the tool of choice for organic chemists to determine the molecular structure of organic molecules and, as a result, is a fundamental topic in the organic chemistry curriculum. A novel laboratory module has been developed to expand the scope of NMR spectroscopy beyond structure validation at the…

The electrolysis of water to produce hydrogen is a critical step in many green chemistry processes. The key to the efficiency of water electrolysis is the synthesis of an appropriate electrocatalyst. Three-dimensional (3D) printing is an increasingly important part of many industrial processes. In this study, we propose an efficient laboratory…

Heavy metals are a recognized toxic environmental contaminant, even at very low concentrations. There have been well-known events in the last decade within the US of high amounts of lead in the drinking water supplies of cities, leading to detrimental effects within its population. Ways have been found to remove this metal, and others, from water…

Reformed Experimental Activities (REActivities) is an innovative approach to the delivery of the traditional material in an undergraduate organic chemistry laboratory. To better understand the fidelity of implementing this pedagogy and what effects the framework of REActivities has on student-instructor interactions, an observational protocol…

The ability of certain organometallic reagents to react via 1,2- or 1,4-addition to an a,ß-unsaturated ketone is a fundamental example of regioselectivity at the second-year undergraduate organic level. The following two experiments were designed to demonstrate this preference by exploiting carvone as an inexpensive chiral, nonracemic substrate.…

An undergraduate experiment for the organic laboratory is described that utilizes microwave heating to prepare 5- substituted 1H-tetrazole derivatives through a (3 + 2) cycloaddition between aryl nitriles and sodium azide. The reaction mixture is analyzed by thin layer chromatography. The products are purified through an acid-base extraction and…

Gold is an increasingly prominent transition metal in organic synthesis. The air-stable, water-insensitive cationic gold(I) catalysts enable varieties of synthetic transformations with a simple reaction setup. However, this increased importance has not coincided with an increase in the application of gold in second-year organic chemistry courses.…

The nucleophilic aromatic substitution reaction and thia-Michael addition using thiourea as an odorless, cheap, and easy-to-handle sulfur source in water are described, which can be used to teach upper-division undergraduates the role of thiourea in the formation of C-S bonds and the principles of green chemistry. The use of a cheap, nontoxic…

In the past decade, C-H functionalization has been a very active topic of research in both academia and industry. When a H atom is replaced by an aryl (or heteroaryl) group, the transformation is termed "direct arylation". This approach to the formation of key (hetero)aryl-(hetero)aryl bonds is complementary to traditional methods, such…

Despite decades of reform efforts, STEM education continues to face calls for improvement, especially regarding the teaching laboratory. Establishing an empirical understanding of the types of hands-on, psychomotor skills that students need to learn to succeed in downstream careers could help ensure laboratory courses are promoting authentic…

Herein, we describe an accessible and safe organic chemistry lab experiment that can be completed at home. Liquid-liquid extraction is a fundamental organic chemistry lab experiment that touches on topics such as chemical structure, density, solubility, and acid-base chemistry. Given the increased demand for safe organic chemistry experiments that…