Introductory Organic Laboratory Course Research Articles

Student-Designed Green Chemistry Experiment for a Large-Enrollment, Introductory Organic Laboratory Course

A 3-week module incorporating the principles of green chemistry was developed for a large-enrollment, introductory organic chemistry laboratory course. An emphasis was placed on students planning their own experiments with the goal of obtaining a greener reaction (week 1). Students executed their designed experiments in week 2 and were given an opportunity to repeat the experiment or further optimize the reaction conditions to improve the yields during week 3. A postlab writing assignment as well as pre- and postsemester surveys were used to evaluate student learning and confidence. These data revealed an increase in students’ understanding of green chemistry concepts as well as their confidence in their ability to modify a reaction to improve the results. We anticipate that this overall framework can be adapted to other large- and small-enrollment laboratory courses.

Solution-Phase Synthesis of Dipeptides: A Capstone Project That Employs Key Techniques in an Organic Laboratory Course

A contemporary approach to the synthesis and purification of several UV-active dipeptides has been developed for the second-year organic laboratory. This experiment exposes students to the important technique of solution-phase peptide synthesis and allows an instructor to highlight the parallel between what they are accomplishing in the laboratory to the advancements being made in the pharmaceutical industry. By illustrating the importance of protecting group strategy and stereochemistry preservation, while also reinforcing the various separatory and purification techniques learned throughout the typical laboratory course, this experiment serves as an excellent candidate for a capstone project that assesses students’ mastery of important techniques learned in an introductory organic laboratory course.

Microscale Synthesis and Spectroscopic Analysis of Flutamide, an Antiandrogen Prostate Cancer Drug

The microscale preparation of flutamide, a nonsteroidal antiandrogen prescribed as Eulexin for the treatment of prostate cancer is outlined. The synthesis involves N-acylation of a trisubstituted aromatic compound, 3-trifluoromethyl-4-nitroaniline. The procedure is easily adapted to generate structural analogues of flutamide. A significant feature is the curricular flexibility afforded by this experiment. The fundamental reaction is appropriate within an introductory organic laboratory course, demonstrating amine and acid–halide reactivity. Functional group transformations can be observed by IR spectroscopy. 1H NMR spectra of reactant and products facilitate a thorough examination of shielding and deshielding effects and aromatic proton coupling. With more advanced students there exists the potential to discuss principles of retrosynthetic analysis, pharmaceutical synthesis, and structure–activity relationships.

Discovery-Oriented Approach To Organic Synthesis: Tandem Aldol Condensation-Michael Addition Reactions. Identifying Diastereotopic Hydrogens in an Achiral Molecule by NMR Spectroscopy

We have found a beautiful example of anisochrony of diastereotopic acyclic methylene hydrogens in a symmetric diketone, synthesized by techniques traditionally performed in an introductory organic laboratory course. Synthesis of the diketone is high-yielding and easy to carry out, and the products can be directly isolated with a good degree of purity with no need of further manipulation. The reaction can be accomplished in a single laboratory session.

Combinatorial Synthesis and Discovery of an Antibiotic Compound. An Experiment Suitable for High School and Undergraduate Laboratories

An exercise demonstrating solution-phase combinatorial chemistry and its application to drug discovery is described. The experiment involves the synthesis of six libraries of three hydrazones, screening the libraries for antibiotic activity, and deconvolution to determine the active individual compound. The laboratory was designed for a high school classroom, though it can easily be expanded to suit a college introductory organic laboratory course.

Esterification for the introductory organic laboratory course: A modified Dean-Stark trap

Describes a simplified construction for a Dean-Stark trap and its use to determine optimum conditions for the preparation of n-amul acetate.