The central goal of the present exploratory study was to investigate the nature of the content-related interactions in study groups independently organized by college organic chemistry students. We were particularly interested in the identification of the different factors that affected the emergence of opportunities for students to co-construct…

Red yeast rice, produced by fermenting the fungus, "Monascus purpureus", on rice ("Oryza sativa" L. gramineae), is commonly used as a dietary supplement. It contains lovastatin, a member of the statin family of compounds, and is licensed for use as a cholesterol-lowering agent. This experiment involves the isolation and structure elucidation of…

An easy-to-complete, microwave-assisted, green chemistry, electrophilic nitration method for phenol using Cu(NO[subscript 3])[subscript 2] in acetic acid is discussed. With this experiment, students clearly understand the mechanism underlying the nitration reaction in one laboratory session. (Contains 4 schemes.)

"Sustainability" is a very general term and the question arises how to specify it within daily laboratory work. In this regard, appropriate metrics could support a socially acceptable, ecological and economic product development. The application of metrics for sustainability should be strengthened in education, because they do not belong…

We investigate the efficiency of domain-specific heuristic strategies in mastering and predicting pericyclic six-electron rearrangements. Based on recent research findings on these types of reactions a new concept has been developed that should help students identify and describe six-electron rearrangements more readily in complex molecules. The…

The antioxidative capacity of phytochemical compounds is often discussed in life science courses (to prevent or slow cancer) and food science courses (to prevent the oxidation of sensitive ingredients). Thus, we developed a laboratory experiment where the photochemical reaction of lightsticks is used to qualitatively demonstrate the antioxidative…

Synthesis of 4-methylumbelliferone via the acid-catalyzed Pechmann condensation introduces students to several types of organic reactions: transesterification, electrophilic aromatic substitution, and alcohol dehydration. Performed with a recyclable, solid catalyst and under solvent-free conditions, the experiment illustrates many of the…

Chemoselectivity is a central concept in organic synthesis and may be readily appreciated in the context of the fragrant, polyfunctional natural product citral. We describe three single-step reactions students may perform on citral to synthesize other natural perfumes: citronellal, geraniol, nerol, or epoxycitral. Each of the reactions uses a…

An experiment suitable for organic chemistry students is described. Biodiesel, a "green" fuel, consists of methyl or ethyl esters of long-chain fatty acids called FAMES (fatty acid methyl esters) or FAEES (fatty acid ethyl esters). A quick way to make FAMES is a base-catalyzed transesterification of oils or fats derived from plants or from animal…

In recent years, there has been an explosion of research concerning the area of organocatalysis. A multistep capstone laboratory project that combines traditional reactions frequently found in organic laboratory curriculums with this new field of research is described. In this experiment, the students synthesize a prolinamide-based organocatalyst…

A two-period organic laboratory experiment that includes fluorescence sensing is presented. The pH-sensitive sensor MorphFl is prepared using a Mannich reaction between a fluorescein derivative and the iminium ion of morpholine. During the first laboratory, students prepare MorphFl. The second session begins with characterizing the sensor using…

A simple procedure for the isolation of the cholesterol, by hydrolysis and extraction followed by column chromatography, is described. The cholesterol can be further purified by complexation with oxalic acid. It can also be oxidized and conjugated to cholestenone. The source of the cholesterol is one egg yolk, which contains about 200 mg of…

SIPCAn, an acronym for separation, isolation, purification, characterization, and analysis, is presented as a one-term, integrated project for the first-term undergraduate organic laboratory course. Students are assigned two mixtures of unknown organic compounds--a mixture of two liquid compounds and a mixture of two solid compounds--at the…

This undergraduate organic laboratory exercise involves the sulfuric acid-catalyzed conversion of waste vegetable oil into biodiesel. The acid-catalyzed method, although inherently slower than the base-catalyzed methods, does not suffer from the loss of product or the creation of emulsion producing soap that plagues the base-catalyzed methods when…

This paper describes how three technologies were utilised in combination to align student learning and assessment as part of a case study. Multiple choice questions (MCQs) were central to all these technologies. The peer learning technologies; Personal Response Devices (a.k.a. "Clickers") and "PeerWise"…