A unique homework assignment has been designed as a review exercise to be implemented near the end of the one-year undergraduate organic chemistry sequence. Within the framework of the exercise, students derive potential mechanisms for glucose ring opening in the aqueous mutarotation process. In this endeavor, 21 general review principles are…

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…

Fundamental to a student's understanding of organic chemistry is the ability to interpret and use its language, including molecules' names and other key terms. A learning gap exists in that students often struggle with organic nomenclature. Although many resources describe the rules for naming molecules, there is a paucity of resources…

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…

Skill in organic chemistry nomenclature is fundamental for communicating more complex concepts. Interpreting and using functional group names is particularly important. With nomenclature101.com, students can create tailored interactive quizzes according to their learning needs; the tool is free and available in English and French. The present…

A critical factor for the increased nucleophilicity of the pyridine nitrogen in 4-(dimethylamino)pyridine (DMAP) is electron donation via resonance from the amino group into the aromatic ring that increases electron density on the pyridine nitrogen. To explore how important this resonance effect is, 4-(dimethylaminomethyl)pyridine (DMAMP) was…

Organic chemistry education is one of the youngest research areas among all chemistry related research efforts, and its published scholarly work has become vibrant and diverse over the last 15 years. Research on problem-solving behavior, students' use of the arrow-pushing formalism, the investigation of students' conceptual knowledge and…

The implementation of a web-based stereochemistry tutorial, which allows students to select their preferred structural representation and method for making stereochemical comparisons between molecules, is discussed. The tutorial was evaluated by students in three different introductory organic chemistry courses at a large midwestern university.…

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…

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…

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…

Since 2002, infrared spectroscopy (IR) and nuclear magnetic resonance (NMR) spectrometry have been introduced at the beginning of the first-semester organic chemistry lab course at this university. Starting in 2008, each individual student was given 20 unique homework problems that consisted of multiple-choice [superscript 1]H NMR and IR problems…

Natural product isolation and analysis provide an opportunity to present a variety of experimental techniques to undergraduate students in introductory organic chemistry. Eugenol, anethole, and carvone were extracted from six common spices using steam-distillation and diethyl ether as the extraction solvent. Students assessed the purity of their…

This pilot study examined students' use of ball-and-stick images versus electrostatic potential maps when asked questions about electron density, positive charge, proton attack, and hydroxide attack with six different molecules (two alcohols, two carboxylic acids, and two hydroxycarboxylic acids). Students' viewing of these dual images…

To accentuate the importance of organic chemistry in development of contemporary pharmaceuticals, a three-week unit entitled "Molecules-in-Medicine" was included in the curriculum of a comprehensive one-semester four-credit organic chemistry course. After a lecture on medicinal chemistry concepts and pharmaceutical practices, students…