A one-pot conversion of tricyclic cationic drugs to their quaternary ammonium forms is described for a widely used bioactive drug: chlorpromazine, a phenothiazine-based antipsychotic. After conversion to its free base, the parent drug was methylated using substoichiometric amounts of methyl iodide dissolved in ether; the charged quaternary…

Many students fail to develop a conceptual understanding of organic chemistry. Evidence suggests this failure goes hand-in-hand with a failure to grasp the techniques, meaning, and usefulness of curved arrow notation. Use of curved arrow notation to illustrate electrophilic addition appears to be a critical juncture in student understanding.…

A spectroscopic experiment is presented that reveals that the hydrophobically end-modified water-soluble polymeric fluorophore, pyrene end-capped poly(ethylene oxide) (PYPY), interacts differently with [alpha], [beta], and [gamma]-cyclodextrins (CD) to form supramolecular inclusion complexes. The emission spectrum of PYPY in aqueous solution shows…

An exercise on structure elucidation for advanced undergraduate students is described. To determine the structure of an unknown product, students are required to use spectra together with an organic chemistry mechanism. This exercise exemplifies the procedure commonly used in research, thus helping students develop problem-solving skills. In…

An undergraduate organic chemistry experiment demonstrating real-life application of GC-MS to arson accelerant identification is described. Students are given the task of comparing a sample recovered from a "crime scene" to that from a "suspect's clothing". Accelerants subjected to different conditions are recovered using a quick and simple…

Liquid 2-chlorobenzaldehyde was converted, by grinding with potassium hydroxide pellets, into equimolar quantities of solid 2-chlorobenzoic acid and solid 2-chlorobenzyl alcohol in a Cannizzaro reaction. TLC, IR, and NMR experiments, using authentic samples for comparison, confirmed the identity and purity of the two products. Guided-inquiry…

A novel undergraduate chemistry experiment involving superabsorbent polymers commonly used in diapers and other personal care products is described. Students observe the removal of divalent transition-metal ions from aqueous solutions by the polymers. With the procedures provided, students are able to color the superabsorbent polymers with metal…

This article reports a set of two homework assignments that can be used in a second-year undergraduate organic chemistry class. These assignments were designed to help reinforce concepts of molecular geometry and to give students the opportunity to use a technological database and data mining to analyze experimentally determined chemical…

Because Lewis structures provide a direct connection between molecular structure and properties, the ability to construct and use them is an integral component of many chemistry courses. Although a great deal of time and effort has been dedicated to development of "foolproof" rules, students still have problems with the skill. What is more, many…

Almost one half of U.S. students receiving B.S. and M.S. science degrees attend community colleges during their academic careers, yet for the large majority of community college students in the sciences, a four-year degree in a STEM discipline remains an unrealized goal. The authors describe methods intended to improve student learning, retention,…

A simple method is proposed based on energies obtained with the Huckel theory to compute the weights of the structures. The Huckel-Lewis CI technique extends to the Huckel theory the field of the resonance between Lewis structures.

This article explores the reasons that Peer Assisted Study Sessions (PASS) at the University of the Incarnate Word (UIW), commonly called PASS-UIW, has been successful in science courses at the University. The intent is to provide information for other institutions to launch, evaluate, or improve their own programs. PASS-UIW is a student-led…

In teaching organic chemistry laboratory at this university, we eliminated the use of "canned" experiments from textbooks. Instead, we present students with literature studies that form the basis of developing new unpublished experiments to answer specific questions. In this research approach, students are better exposed to the chemical…

In this introductory organic chemistry experiment, the students get an opportunity to analyze and identify an unknown compound as it is done in a real-laboratory setting. First, students are instructed on the proper operation of three major instruments, NMR, IR, and GC-MS, and are given a sample of an unknown compound. The students are expected to…

This study examines how well second-year nonmajor organic chemistry students are learning to draw, interpret, and understand resonance-related structures. Students were tested seven times throughout an academic year using a set of four tasks that reflected their understanding of what these structures represent and how they relate to each other.…