Salicylic acid and its derivative, acetylsalicylic acid, are often encountered in introductory organic chemistry experiments, and mention is often made that salicylic acid was originally isolated from the bark of the willow tree. This biological connection, however, is typically not further pursued, leaving students with an impression that biology…

This experiment describes a discovery-based method for the regio- and stereoselective hydrochlorination of carvone, appropriate for a 3-h second-semester organic chemistry laboratory. The product is identified through interpretation of the [superscript 13]C NMR and DEPT spectra are obtained on an Anasazi EFT-60 at 15 MHz as neat samples. A…

This laboratory experiment describes the preparation of a N-protected phenylalanine ethyl ester by a zinc-mediated Mannich-like multicomponent reaction between benzyl bromide, "p"-anisidine, and ethyl glyoxylate. The one-step reaction involves the in situ metallation of benzyl bromide into a benzylzinc reagent and its addition onto imine (Barbier…

A low-cost, straightforward, rapid prototyping of whole-glass microfluidic devices is presented using glass-etching cream that can be easily purchased in local stores. A self-adhered vinyl stencil cut out by a desktop digital craft cutter was used as an etching mask for patterning microstructures in glass using the glass-etching cream. A specific…

Because of cost and time, it is difficult to relate to students how fundamental chemical principles are involved in cutting edge biomedical breakthroughs being reported in the national media. The laboratory exercise presented here is aimed at high school chemistry students and uses alginate hydrogels, a common material used in tissue engineering,…

Photocatalytic water splitting by semiconductor photocatalysts has attracted considerable attention in the past few decades. In this experiment, nanosized titanium dioxide (nano-TiO[subscript 2]) particles are used to photocatalytically split water, which is then monitored by an oxygen sensor. Sacrificial reagents such as organics (EDTA) and metal…

An investigation of the Blue Bottle Experiment, a well-known lecture demonstration reaction involving the dye-catalyzed air oxidation of a reducing sugar in alkaline solution, has delineated the sequence of reactions leading to the bleaching of the dye, the regeneration of color, and so forth. Enolization of the sugar is proposed as a key step in…

In this experiment, students learn how to find the unknown concentration of sodium acetate using both the graphical treatment of standard addition and the standard addition equation. In the graphical treatment of standard addition, the peak area of the methyl peak in each of the sodium acetate standard solutions is found by integration using…

This laboratory experiment, using proton NMR spectroscopy to determine the dissociation constant for heterocyclic bases, has been modified from a previously described experiment. A solution of a substituted pyridine is prepared using deuterium oxide (D[subscript 2]O) as the solvent. The pH of the solution is adjusted and proton NMR spectra are…

In this discovery-oriented laboratory experiment, students use solid-phase synthesis techniques to construct a dipeptide containing an unknown amino acid. Following synthesis and cleavage from the polymeric support, electrospray ionization-mass spectrometry is employed to identify the unknown amino acid that was used in the peptide coupling. This…

This article describes the successful implementation of an oral examination format in the organic chemistry curriculum at the University of Toronto. Oral examinations are used to replace traditional written midterm examinations in several courses. In an introductory organic class, each student is allotted 15 min to individually discuss one…

The measurement of trace levels of bisphenol A (BPA) leached out of household plastics using solid-phase microextraction (SPME) with gas chromatography-mass spectrometry (GC-MS) is reported here. BPA is an endocrine-disrupting compound used in the industrial manufacture of polycarbonate plastic bottles and epoxy resin can liners. This experiment…

The potential of replacing petroleum fuels with renewable biofuels has drawn significant public interest. Many states have imposed biodiesel mandates or incentives to use commercial biodiesel blends. We present an inquiry-driven experiment where students are given the tasks to gather samples, develop analytical methods using various instrumental…

A directed study for the undergraduate physical chemistry laboratory for determining the transference number of H[superscript +](aq) using a modified moving boundary method is presented. The laboratory study combines Faraday's laws of electrolysis with mole ratios and the perfect gas equation. The volume of hydrogen gas produced at the cathode is…

General chemistry students often have difficulty writing balanced equations and performing stoichiometry calculations for precipitation reactions, in part because of difficulty understanding the symbolic notation used to represent chemical reactions. We have developed a problem-based experiment to improve student learning of these concepts, and…