Several articles suggest how to incorporate computer models into the organic chemistry laboratory, but relatively few papers discuss how to incorporate these models broadly into the organic chemistry lecture. Previous research has suggested that "manipulating" physical or computer models enhances student understanding; this study…

A two-semester second-year introductory organic chemistry sequence featuring one semester of accelerated organic chemistry followed by one semester of bioorganic chemistry is described. Assessment data collected over a six-year period reveal that such a course sequence can facilitate student mastery of fundamental organic chemistry in the first…

A 45 MHz benchtop NMR spectrometer is used to identify the structures and determine the amount of 1-bromoethylbenzene and 1,1-dibromoethylbenzene produced from free-radical bromination of ethylbenzene. The experiment is designed for nonchemistry majors, specifically B.S. Biology students, in a predominantly undergraduate institution with…

An efficient laboratory experiment has been developed for undergraduate students to conduct hydrogen-deuterium (H-D) exchange of resorcinol by electrophilic aromatic substitution using D[subscript 2]O and a catalytic amount of H[subscript 2]SO[subscript 4]. The resulting labeled product is characterized by [superscript 1]H NMR. Students also…

Mechanochemical syntheses avoid or considerably reduce the use of reaction solvents, thus providing green chemistry synthetic alternatives that are both environmentally friendly and economically advantageous. The increased solid-state reactivity generated by mechanical energy imparted to the reactants by grinding or milling can offer alternative…

A numerical analysis of the free radical addition polymerization system is described that provides those teaching polymer, physical, or advanced organic chemistry courses the opportunity to introduce students to numerical methods in the context of a simple but mathematically stiff chemical kinetic system. Numerical analysis can lead students to an…

Organic chemistry is often considered to be a difficult subject to teach and to learn, particularly as students prefer to resort to memorization alone rather than reasoning using models from chemical reactivity. Existing studies have led us to suggest principles for redefining the curriculum, ranging from its overall structure to the tasks given…

The traditional assignment of oxidation states to organic molecules is problematic. Accordingly, in 1999, Calzaferri proposed a simple and elegant solution that is based on the similar electronegativities of carbon and hydrogen: hydrogen would be assigned an oxidation state of zero when bonded to carbon. Here, we show that X-ray photoelectron…

Although many students learn best in different ways, the widest range of students can be reached when multiple modes of input are employed, especially if the student is simultaneously completing a set of handwritten notes. Computers, meanwhile, have led to countless changes in society, and education has not been exempt from these changes. Students…

To address third- and fourth-year chemistry students' difficulties with the challenge of interpreting [superscript 1]H NMR spectra, a problem solving-cooperative learning technique was incorporated in a Spectra of Organic Compounds course. Using this approach helped students deepen their understanding of the basics of [superscript 1]H NMR…

Esters are volatile and pleasantly smelling compounds, commonly used as food additives. Using Ti(OBu)[subscript 4]-catalyzed acyl exchange, we demonstrate a scent transmutation experiment, in which two fragrant esters swap their acyl and alkoxy substituents and are, during the course of a reactive distillation, quantitatively converted into two…

Undergraduate students in the teaching laboratory have successfully used N-heterocyclic carbenes (NHCs) as organocatalysts for the acetylation of primary alcohols, despite the high water sensitivity of uncomplexed ("free") NHCs. The free NHC readily reacted with chloroform, resulting in an air- and moisture-stable adduct that liberates…

The purpose of this study was dual: First, to develop and validate assessment schemes for assessing 11th grade students' meaningful understanding of organic chemistry concepts, as well as their systems thinking skills in the domain. Second, to explore the relationship between the two constructs of interest based on students' performance…

Benzoyl peroxide is used as a bleaching agent for flour and whey processing, a polymerization initiator in the synthesis of plastics, and the active component of acne medication. Because of its simplicity and wide application, benzoyl peroxide is a target molecule of interest. It can be affordably synthesized in three steps from bromobenzene using…

A comprehensive guided-inquiry approach was used in a combined organic and biochemistry course for prenursing and predietetics students rather than lecture. To assess its effectiveness, exam grades and final course grades of students in three instructional techniques were compared. The three groups were the following: (i) lecture only, (ii)…