The familiar word OREO (as in the cookie) is presented as a simple mnemonic for remembering the basic steps of the classical tautomerization mechanisms in organic chemistry. For acid-catalyzed tautomerizations, OREO stands for proton on, resonance, proton off. For base-catalyzed tautomerizations, OREO stands for proton off, resonance, proton on.…

A recent article by McCarty and Vitz "demonstrating that it is not true that pH = -log[H+]" is examined critically. Then, the focus shifts to underlying problems with the IUPAC definition of pH. It is shown how the potentiometric method can provide "estimates" of both the IUPAC-defined hydrogen activity "and" the hydrogen ion concentration, using…

Temperature and entropy traditionally are expressed in units of kelvin and joule/kelvin. These units obscure some important aspects of the natures of these thermodynamic quantities. Defining a rescaled temperature using the Boltzmann constant, T' = k[subscript B]T, expresses temperature in energy units, thereby emphasizing the close relationship…

The theoretical distributions of a limited amount of energy among small numbers of particles with discrete, evenly-spaced quantum levels are examined systematically. The average populations of energy states reveal the pattern of Pascal's triangle. An exact formula for the probability that a particle will be in any given energy state is derived.…

As part of a campus-wide, externally funded project to increase performance in, enthusiasm for, and retention within STEM disciplines, we developed an interdisciplinary, team-taught first-year seminar course. The construction and delivery of this course was designed to show the relevance of selected general chemistry topics such as matter and…

When grocery stores sell solutions of ammonia, they are labeled "ammonia"; however, when the same solution is purchased from chemical supply stores, they are labeled "ammonium hydroxide". The goal of this experiment is for students to determine which name is more appropriate. In this experiment, students use several different experimental methods…

Metal oxalate synthesis and pyrolysis provides an opportunity for students to (i) learn stoichiometry, (ii) experience the consequences of proper stoichiometric calculations and experimental techniques, and (iii) be introduced to the relevance of chemistry by highlighting oxalates in context, for example, usages and health effects. At our…

A series of experiments based on problem-solving and collaborative-learning pedagogies are described that encourage students to interpret results and draw conclusions from data. Different approaches including parallel library synthesis, solvent variation, and leaving group variation are used to study a nucleophilic aromatic substitution of…

This experiment investigates the methylation of 2-naphthol with dimethyl carbonate. The volatility of the substrates, products, and co-products allows the reaction to be performed using a continuous-flow gas-phase setup at ambient pressure. The reaction uses catalytic quantities of base, achieves high conversion, produces little waste, and…

A hetero-Diels-Alder reaction that proceeds rapidly and only requires a simple filtration to purify the product is presented. The dienophile, 4-phenyl-1,2,4-triazoline-3,5-dione (PTAD), is prepared by the heterogeneous oxidation of 4-phenylurazole by the bromenium ion, Br[superscript +], generated in situ by the oxidation of potassium bromide by…

This undergraduate organic laboratory experiment complements previously described and popular experiments on hydration of 1-hexene where students experimentally establish the Markovnikov regioselectivity of alkene hydration. In this experiment, students explore not only the regiochemistry but also the stereochemistry of 1-hexene hydration and…

The discovery that galantamine penetrates the blood-brain barrier has led to its clinical use in the treatment of choline-deficiency conditions in the brain, such as Alzheimer's disease. This experiment involves the isolation and structure elucidation of galantamine from "Leucojum aestivum". Isolation of the alkaloid constituents in "L. aestivum"…

Brewing beer provides a straightforward and robust laboratory counterpart to classroom discussions of fermentation, a staple of the biochemistry curriculum. An exercise is described that provides several connections between lecture and laboratory content. Students first extract fermentable carbohydrates from whole grains, then ferment these with…

In this laboratory experiment, college students are introduced to dynamic combinatorial chemistry (DCC) and apply it to determine the substrate selectivity of acetylcholinesterase (AChE). Initially, the students construct a chemical library of dynamically interchanging thioesters and thiols. Then, AChE is added and allowed to select and hydrolyze…

Lasers have transformed chemistry and the everyday world. Therefore, it is not surprising that undergraduate chemistry students are frequently exposed to fairly advanced laser techniques. The usual topics studied with lasers are molecular spectroscopy and chemical kinetics. Static and dynamic fluorescence experiments seem to be particularly…