This experiment allows students to use [to the first power]H NMR to directly compare the relative initial rates of substitution of the benzylic and non-benzylic [alpha] hydrogens of [beta]-tetralone and correlate their findings with the predictions made by resonance theory. The experiment demonstrates that the benzylic hydrogens undergo [alpha]…

Children learn about properties of materials as they walk through a fabric store, help in the kitchen, or dig in the garden. Directed explorations in the classroom build on these early experiences. In the inquiry-based activity described here, students prepare to learn about wet and dry ingredients (liquids and solids) and how they mix together by…

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.

In introductory chemistry courses students are presented with the model that matter is composed of particles, and that weak forces of attraction exist between them. This model is used to interpret phenomena such as solubility and melting points, and aids in understanding the changes in states of matter as opposed to chemical reactions. We…

Undergraduate retention and eventual graduation is of paramount importance to universities globally. Approximately 58% of students who began their college career at a four-year institution with the intention of receiving a bachelor's degree actually received that degree in a 6-year timeframe, according to the National Center for Education…

A non-traditional teaching method that can operate as a vehicle for engaging students is group-based competitive exercises. These exercises combine cooperative learning with a competitive environment and may be employed to promote subject- and problem-based learning. Survey responses of college-level organic chemistry and biochemistry students…

Radical chemistry is a fundamental subject of undergraduate organic chemistry. While well described in organic textbooks, laboratory manuals rarely address this topic, focusing instead on syntheses using polar reactions. Herein, we describe a colorimetric assay using the persistent radical 1,1-diphenyl-2-picrylhydrazyl (DPPH) to measure the…

We developed an alternative electrophilic aromatic substitution reaction for the organic chemistry teaching laboratory. The experiment is an electrophilic iodination reaction of salicylamide, a popular analgesic, using environmentally friendly reagents--sodium iodide and household bleach. Further, we designed the lab as a guided-inquiry…

Attenuated total reflectance-Fourier transform infrared (ATR-FTIR) spectroscopy is a useful technique for measuring the infrared spectra of solids and liquids as well as probing adsorption on particle surfaces. Several examples of the use of FTIR-ATR spectroscopy in different undergraduate chemistry laboratory courses are presented here. These…

We describe an experiment for the undergraduate organic laboratory curriculum in which 2-bromoacetophenone is converted to 2-fluoroacetophenone using a solid-phase nucleophilic fluorine source. The experiment introduces students to the utility of solid-phase reagents in organic synthesis, to NMR-active nuclei other than [to the first power]H…

A microscale experiment is presented in which cyclohexene is dihydroxylated under three sets of conditions: epoxidation-hydrolysis, permanganate oxidation, and the Woodward dihydroxylation. The products of the reactions are determined by the use of thin-layer chromatography. Teams of students are presented with proposed mechanisms for each…

One of the principles of sustainable development is to replace chemicals traditionally derived from oil with alternative, renewable materials. For example, phenol and phenol derivatives currently used in the manufacture of wood adhesives can be replaced (at least in part) by biopolymers extracted from biomass. In this work, pine bark (a renewable…

A semi-quantitative model has been developed to estimate the relative effects of dispersion, dipole-dipole interactions, and H-bonding on the normal boiling points ("T[subscript b]") for a subset of simple organic systems. The model is based upon a statistical analysis using multiple linear regression on a series of straight-chain organic…

The State of Maine seeks to eliminate most mercury use. This includes removing mercury thermometers from secondary schools and discouraging Hg use in other educational institutions. Alternatives to mercury thermometers in chemical laboratory work include non-mercury thermometers, temperature probes, and thermocouples. In organic chemistry mercury…