The essential oil of "Nepeta cataria" L. (catnip), an herbaceous plant known popularly as a stimulant for the domestic cat, is enriched in two diastereomeric iridoid lactones (nepetalactones) that vary in ratio. Although the diastereomers are chromatographically separable and exhibit different 1D NMR spectra, it is not possible to…

Modern undergraduate organic chemistry textbooks provide detailed discussion of stoichiometric Cr- and Mn-based reagents for the oxidation of alcohols, yet the use of such oxidants in instructional and research laboratories, as well as industrial chemistry, is increasingly avoided. This work describes a laboratory exercise that uses ambient air as…

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…

Spatial information in science is often expressed through representations such as diagrams and models. Learning the strengths and limitations of these representations and how to relate them are important aspects of developing scientific understanding, referred to as "representational competence." Diagram translation is particularly…

POGIL (Process Oriented Guided Inquiry Learning) is a collaborative learning technique that employs guided inquiry within a cyclic system of exploration, concept invention, and application. This action research explores students' academic performance on a unit of organic chemistry work taught using POGIL, in addition to the effect of POGIL on…

Herein we describe a series of experiments for the undergraduate organic laboratory curriculum in which various plant oils (soybean, rapeseed, and olive) are subjected to saponification and transesterification reactions to create a set of compounds that can function as soaps or as fuels. The experiments introduce students to and asks them to…

The development of curricular problems based on the practice of synthetic organic chemistry has not been explored in the literature. Such problems have broadly been hypothesized to promote student persistence and interest in STEM fields. This study reports seven ideas about how practice-based problems can be developed for sophomore-level organic…

A multistep synthesis of 5-isopropyl-1,3-cyclohexanedione is carried out from three commodity chemicals. The sequence involves an aldol condensation, Dieckmann-type annulation, ester hydrolysis, and decarboxylation. No purification is required until after the final step, at which point gravity column chromatography provides the desired product in…

Organic chemistry is very challenging to many students pursuing science careers. Flipping the classroom presents an opportunity to significantly improve student success by increasing active learning, which research shows is highly beneficial to student learning. However, flipping an entire course may seem too daunting or an instructor may simply…

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…

A laboratory experiment was designed for undergraduate students, in which the outcome of an easy single-step organic synthesis with well-defined conditions was not elucidated until the end of the exercise. In class, students predict and discuss the possible products using their knowledge of reaction mechanisms. In the laboratory, they learn how to…

The synthesis of N-methoxycarbonyl-2-imidazolidone, an analogue of biotin, was conducted by organic chemistry students and confirmed using FT-IR and H NMR. Spectroscopy students used FT-IR to measure the rate of hydrolysis of the product and determined the rate constant for the reaction using the integrated rate law. From the magnitude of the rate…

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…

Two green chemistry courses have been introduced into the liberal arts curriculum at Susquehanna University. Green chemistry was integrated into an existing course, Chemical Concepts, and offered as Green Chemical Concepts for nonscience majors. This course is designed to instill an appreciation for green chemistry in a large and diverse group of…