A simple, microscale experiment was developed with the aim of demonstrating the concept of umpolung in synthetic organic chemistry. Starting from a common alkyl sulfinate, students perform a polarity inversion by performing a Grignard-based sulfoxide synthesis and a Mannich-type formamide synthesis. The products are purified without chromatography…

Reformed experimental activities (REActivities) are an innovative approach to the delivery of the traditional material in an undergraduate organic chemistry laboratory. A description of the design and implementation of REActivities at both a four- and two-year institution is discussed. The results obtained using a reformed teaching observational…

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…

We report a series of experiments based upon cinnamon oil that were developed to provide a practical integration of green and sustainable chemistry concepts for the organic chemistry laboratory. Five experiments centering around cinnamaldehyde as a green, plant-based chemical were performed by undergraduate students in a second-year organic…

This paper revisits the tie-dyeing process through a bioinspired and safer alternative to nucleophilic aromatic substitution (S[subscript N]Ar) reactions for an introductory organic chemistry laboratory. The simple and straightforward experiment provides students with an opportunity to gain practical experience in conducting a chemical reaction in…

Reported herein is a multidisciplinary experiment for senior-level undergraduate teaching laboratories in the synthesis of the analytes acetaminophen and phenacetin; the fabrication of paper-based devices, using eyeliner, acrylic spray paint, or wax-printing, for sensing of those analytes; and the use of the newly fabricated devices for successful…

Due to a lack of time and, thus, an inability to present every possibility in a chemical reaction, organic chemistry professors tend to present each reaction with a single outcome. In practice, this is clearly not the case. A first-semester, three-week laboratory experiment designed for undergraduate organic chemistry students is described in…

The synthesis of 1,1-diphenylethylene (DPE) via a Grignard reaction, followed by an acid-catalyzed dehydration reaction, yields a mixture of compounds. DPE is a high boiling liquid that cannot be purified using simple distillation. However, it is easily separated from the more polar starting material and intermediate alcohol using both thin layer…

In this experiment for an upper-division course in organic structure determination, each student prepares an unknown compound and characterizes the product using multiple spectroscopic techniques. The unknowns, 2-aryl-substituted 1,4-dihydro-3,1-benzoxazines and 1,2,3,4-tetrahydroquinazolines, are prepared in a single step by the condensation of…

Hands-on learning in a laboratory is an integral part of the undergraduate experience for chemistry students. However, with the onset of the COVID-19 pandemic, an opportunity for this approach was not possible. The pandemic has been forcing instructors to explore the remote setting instead of the laboratory. There are several commercially…

We present an experiment which was designed to assess the separation technique skills of the gifted high school students who attended the 50th International Chemistry Olympiad 2018. The procedure consists of two synthetic tasks and is also applicable for teaching undergraduates. The haloform reaction of 2-acetonaphthone with sodium hypochlorite in…

A synthesis of the "R,R"-tartrate salt of the popular anti-Parkinson's drug "R"-rasagiline (Azilect) was adapted to introduce the organic laboratory student to a medically relevant synthesis. It makes use of concepts found in the undergraduate organic chemistry curriculum, appropriately fits into three approximately 4 h lab…

Introductory organic laboratory courses frequently begin with a set of activities built around developing basic experimental skills and techniques, often with guided-inquiry components. A sequence of skill-based activities is described to promote reflection, analysis of, and interpersonal communication around science. A multistage process was used…

A laboratory exercise was devised that allows students to rapidly and fairly accurately determine the iodine value of oleic acid. This method utilizes the addition of elemental bromine to the unsaturated bonds in oleic acid, due to bromine's relatively fast reaction rate compared to that of the traditional Wijs solution method. This method also…

We present a novel guided inquiry second semester organic chemistry laboratory rearrangement experiment. Students performed the Favorskii Rearrangement to obtain methyl cyclopentanecarboxylate in good yields. The students learned about the individual steps of the Favorskii mechanism and were required to propose a complete reaction mechanism and…