A renewed experimental procedure for the unknown carbonyl experiment has been developed using hydrazone synthesis, thin layer chromatography (TLC) analysis, and melting point determination to differentiate between structurally similar ketones and aldehydes in undergraduate organic chemistry practical courses. Benzaldehyde, p-tolualdehyde,…

A new organic chemistry experiment aimed to separate the chlorophyll precursor in plant seeds by column chromatography is described. The primary pedagogical goal in developing this experiment is to establish a simple and interesting chromatographic separation to demonstrate basic concepts and the standard procedure for this important lab…

NMR spectroscopy is a powerful spectroscopic tool that not only allows the determination of structures after synthesis, as usually explained to students of Organic Chemistry, but also is useful in many other fields such as medicine imaging, real-time industrial processes, material sciences, or metabolomics. In this experiment, students performed a…

Cycloadditions in combination with multicomponent reactions are among the most valuable synthetic tools used by organic chemists to construct cyclic and heterocyclic compounds in a straightforward way. Although cycloadditions, such as the Diels--Alder reaction, are mainly covered in basic and advanced organic courses for undergraduate students,…

The demand for sustainable synthetic methods in modern industry has been increasing rapidly due to the requirements of environmental protection and energy conservation, which has brought organic electrochemical synthesis to the forefront nowadays. Here, a two-part laboratory experiment has been designed to train undergraduates in comprehending and…

The [2 + 2] photocycloaddition reaction of olefins is an effective, atom-economical approach to produce cyclobutane compounds in organic synthetic chemistry, and they usually exhibit high regioselectivity and stereoselectivity. Here we devised a solid-state [2 + 2] photocycloaddition experiment that introduces senior undergraduate students with…

In all fields of chemistry, it has become essential to use quantum chemical calculations and machine learning for explaining and predicting chemical phenomena. However, it is challenging to apply textbook knowledge to practical research. In this study, we developed teaching material based on computational chemistry to promote the integration of…

Organic chemistry students often struggle with reaction mechanisms, particularly in how they are proposed and justified. In this activity targeting second year organic undergraduates, students used infrared spectroscopy (IR) to track the reaction progress of two distinct aldol reactions and used polarimetry to analyze the stereoselectivity of…

A new undergraduate organic laboratory experiment has been developed and implemented for the Ugi three-component synthesis of the topical anesthetic lidocaine with excellent atom economy. Paraformaldehyde, diethylamine, and 2,6-dimethylphenyl isocyanide were combined and conveniently stirred at room temperature for a week in methanol with acetic…

In an effort to further develop critical thinking and problem solving skills, a guided-inquiry-based, multioutcome organic chemistry synthesis and characterization experiment was developed. Students were provided with the protocol for a time-saving microwave-assisted acetanilide synthesis reaction from acetic anhydride and an unknown primary aryl…

An introductory normal phase column chromatography experiment is described and evaluated for second year undergraduate chemistry laboratory class. The experiment involves a nucleophilic substitution yielding a crude mixture of reactant and one product, both of which are brightly colored and contrasting, creating a clearly visual separation when…

This project introduces green chemistry to the undergraduate laboratory through two pedagogical techniques: undergraduate research and guided-inquiry. Through these two learning activities, an efficient synthetic procedure for the PRINS cyclization of citronellal into isopulegol, focused on minimizing negative environmental impact, was developed.…

An organic chemistry experiment designed for senior undergraduates focuses on bifunctional catalysis, a critical yet often omitted topic at the undergraduate level, but essential for advanced studies in chemistry. By utilization of a tertiary amine-thiourea catalyst in the asymmetric Michael addition reaction, the experiment showcases the…

In primary organic chemistry, students learn about the dehydration of ethanol to ethylene with concentrated sulfuric acid. Similar reactions(the dehydration of alcohols) exist in nature. For example, various alkenes with aromas are synthesized from linalool, a monoterpene tertiary alcohol. In this laboratory experiment, we report experiments…

In this second-semester organic chemistry lab experiment, students work collaboratively using a combination of chemical synthesis and NMR spectroscopy to investigate the diastereoselectivity associated with the Meerwein-Ponndorf-Verley (MPV) reduction of two ketone substrates having carbonyl groups flanked by an [alpha]-chiral carbon with…