Reported herein is a multidisciplinary laboratory experiment for advanced undergraduate students that includes elements of material synthesis, in the synthesis of cyclodextrin-containing metal-organic frameworks (CD-MOFs), and environmental chemistry, in the use of these MOFs for pollutant removal. This multiday laboratory experiment starts with…

In this organic chemistry laboratory experiment, students are guided through a series of exercises to understand the behavior of compounds during liquid-liquid extraction. Aspects of density, structure, solubility, acid-base theory, and pK[subscript a] are all incorporated into activities that students complete in groups. After using their initial…

A Web-based stereochemistry tutorial is described that details the core definitions and structural representations of stereochemistry in an organic chemistry course. The Cahn-Ingold-Prelog rules and their application for assigning "R" and "S" orientations to stereocenters and "E" and "Z" orientations to…

Many students find the transition from first-year general chemistry to second-year organic chemistry a daunting task. There are many reasons for this, not the least of which is their lack of a solid understanding and appreciation of the importance of some basic concepts and principles from general chemistry that play an extremely critical role in…

A one-pot conversion of tricyclic cationic drugs to their quaternary ammonium forms is described for a widely used bioactive drug: chlorpromazine, a phenothiazine-based antipsychotic. After conversion to its free base, the parent drug was methylated using substoichiometric amounts of methyl iodide dissolved in ether; the charged quaternary…

Students of organic chemistry traditionally make 3 x 5 in. flash cards to assist learning nomenclature, structures, and reactions. Advances in educational technology have enabled flash cards to be viewed on computers, offering an endless array of drilling and feedback for students. The current generation of students is less inclined to use…

The triterpenes are a diverse class of widely distributed natural products derived from squalene. Various cyclization and subsequent rearrangement reactions produce many complex structural types. These compounds frequently display a wide divergence of biological properties. For example the pentacyclic triterpene, betulin, is isolated from white…

This paper presents a model of the epistemic development of organic chemists from student to practitioner. Key features of this model suggest that individuals first learn the language of organic chemistry, followed by the heuristics. Deep conceptual understanding of the concepts and models of organic chemistry does not occur until individuals…

When FT-NMR is used to collect data without a sufficient delay time between subsequent pulses, the integrated area under certain peaks may result in a lower value than should be observed under appropriate conditions. This discrepancy in integration may deceive the inexperienced eye and consequently can lead to a wrong assignment of the NMR…

Waste newspaper is pulped with acid and its cellulose is hydrolyzed. The resulting glucose syrup is fermented with yeast and distilled to give ethanol. The experiment highlights the potential of applied chemistry to confront problems of economic importance, that is, the effective utilization of biomass to reduce dependence on non-renewable…

Treatment of phenylacetic acid with 90% HNO[subscript 3] yields a product, I, whose observed melting point is 175-179 degrees C and whose equivalent weight is approximately 226 grams. Treatment of phenylacetic acid with 70% HNO[subscript 3] yields a product, II, whose observed melting point is 106-111 degrees C and whose equivalent weight is…

This paper describes two techniques for rendering visual concepts encountered in an organic chemistry course into tactile representations for students who have low vision. The techniques--which utilize commercially available products--facilitate communication of organic chemistry between student and instructor. (Contains 1 figure, 2 tables and 1…

The aryl sulfonate ester, menthyl N-acetylsulfanilate, is synthesized from N-acetylsulfanilyl chloride and menthol in pyridine, then pyrolyzed (thermally decomposed) at reduced pressure. The volatile (elimination) products of the reaction are analyzed using gas chromatography, and the resulting product distribution is used to determine whether the…

An experiment for the upper-level undergraduate laboratory is described in which students synthesize a ruthenium olefin metathesis catalyst, then use the catalyst to carry out the ring-closing metathesis of diethyl diallylmalonate. The olefin metathesis reaction was the subject of the 2005 Nobel Prize in chemistry. The catalyst chosen for this…

The Reaction-Map of Organic Chemistry lists all the most commonly studied reactions in organic chemistry on one page. The discussed Reaction-Map will act as another learning aide for the students, making the study of organic chemistry much easier.