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…

A comprehensive laboratory-style teaching activity involving the synthesis, characterization, and analysis of structure-activity relationships of metal-organic framework (MOF) nanozymes was developed specifically for undergraduates at Tianjin University. The students acquired familiarity with the general approach in synthesizing MOFs by…

A green laboratory experiment has been developed in which students perform an aqueous oxidation/cycloaddition reaction to convert salicyl alcohol into a pentacyclic diepoxydione that is readily isolated by filtration. Drawing on their knowledge of periodate-mediated 1,2-diol cleavage, students propose a mechanism for the oxidation of salicyl…

A method for the synthesis of flufenamic acid, a nonstereoidal anti-inflammatory drug (NSAID) of the anthranilate family (fenams), is described as an experiment for the upper-division undergraduate organic chemistry laboratory. The key step is the formation of the diarylamine moiety of flufenamic acid by a novel reaction consisting of the coupling…

A discovery-based undergraduate organic chemistry lab experiment has been developed in which students establish the diastereoselectivity of hydride reduction of the a-chiral ketone (±)-benzoin isopropyl ether to erythro and threo diastereomeric alcohols by two different reducing agents. Students achieve this goal by working collaboratively and…

In order to introduce the concept of covalent organic frameworks (COFs), an important class of predictable crystalline porous polymers, an integrated laboratory experiment for advanced organic chemistry students is reported. The importance of these kind of polymers and their multiple applications are presented as a part of key concepts in polymer…

A multifaceted experiment, accessible to students either in an introductory organic chemistry course or in a more advanced laboratory setting, is described for investigating the addition of dichlorocarbene to E- and Z-[beta]-methylstyrenes. The innovative exercise, which integrates elements of synthesis, mechanisms, instrumental analysis,…

Semiconductors are an important class of materials; preparing ZnO nanorods allows semiconducting properties to be easily observed. The week before lab, groups of four students take 15 min to setup two fluorine-doped tin oxide glass (FTO) slides in a zinc nitrate and hexamethylenetetramine solution stored at 90°C until the next lab. Hexagonal ZnO…

A series of laboratory experiments were developed to introduce first-year chemistry students to nanoscience through a green chemistry approach. Students made and characterized the stability of silver nanoparticles using two different methods: UV-visible spectroscopy and dynamic light scattering. They then assessed the ecotoxicity of silver…

Many students enroll in college general chemistry with an interest in a medical career. In those (and alternative) careers, they will need to make critical decisions about data and how that data are acquired. A significant portion of introductory lab experiments are, in principle, but not necessarily in practice, devoted to understanding how…

One of the most mystifying products on the market for people at any age is the glow stick: a plastic tube that, when snapped, creates a flood of bright, brilliantly colored light without the use of electricity or significant production of heat. In this case, the chemiluminescence reaction also provides an exciting phenomenon through which we can…

This paper describes a first-year general chemistry laboratory that uses NMR spectroscopy and model building to emphasize molecular shape and structure. It is appropriate for either a traditional or an atoms-first curriculum. Students learn the basis of structure and the use of NMR data through a cooperative learning hands-on laboratory…

A simple, robust, and reproducible method was developed for the isolation of (-)-menthol from peppermint oil and to study the effect of different types of leaving groups, catalysts, solvents, and tertiary base on the extent of esterification of (-)-menthol to (-)-menthyl acetate. In this experiment, students compare leaving group properties of…

In this experiment, students build a spectrometer to explore infrared radiation and greenhouse gases in an inquiry-based investigation to introduce climate science in a general chemistry lab course. The lab is based on the exploration of the thermal effects of molecular absorption of infrared radiation by greenhouse and non-greenhouse gases. A…