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…

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.…

There has been dramatic growth in interest and research regarding organic photochromism in recent decades. Despite this, the topic is seldom addressed in the undergraduate chemistry curriculum. Herein, we present a straightforward and robust experiment for the second semester organic chemistry laboratory curriculum which combines multistep…

This three-part laboratory experiment investigates key aspects of the Buchwald-Hartwig amination cross-coupling reaction through guided-inquiry learning strategies. The first part of this experiment utilizes high-throughput experimentation techniques to reinforce, explore, and extend fundamental concepts that are represented in the classroom,…

The laboratory experiment regarding esterification of ethylene glycol with acetic acid to ethylene glycol diacetate using resin catalysts in a continuous flow was designed to carry out the reaction in a flow through an inquiry-guided approach. Incorporating the burgeoning field of continuous flow chemistry into the educational infrastructure, the…

The dehydration of 2- or 4-methylcyclohexanol to obtain isomers of methylcyclohexene is a classic organic chemistry experiment. Students perform a distillation, collecting samples to analyze the progress of the reaction. The reaction produces a major product that can be explained on the basis of the regiochemistry of the [pi] bond formation for…

The free radical chlorination of an alkane experiment is often used in the undergraduate laboratory curriculum to introduce students to the free radical mechanism, substituent effects, intermediate stability, and the relative reactivity of radicals. In this experiment, students monochlorinate multiple alkanes and analyze the reaction mixture using…

In this study, students' understanding of some important features of competitive elimination and substitution reactions of alcohols was examined based on their participation in a guided inquiry activity of two organic laboratory experiments: the dehydration of cyclohexanol and the conversion of tert-butyl alcohol into tert-butyl chloride. Students…

Students' expectations for their laboratory coursework are theorized to have an impact on their learning experiences and behaviors, such as engagement. Before students' expectations and engagement can be explored in different types of undergraduate chemistry laboratory courses, appropriate measures of these constructs must be identified, and…

An inquiry-based learning approach was implemented into comprehensive organic chemistry experiments focusing on the formation process of N-phenylbenzamide from the reaction between N-benzylideneaniline and benzoyl peroxide in commercial dimethyl sulfoxide. Students conducted comparative experiments using alternative reagents or reaction conditions…

A national survey on chemistry instructional laboratories was administered to faculty members at four-year postsecondary institutions in the United States for the purpose of exploring levels of inquiry-based instruction implemented in laboratory courses. Respondents were asked to rate the level of choice their students had in deciding six key…

This two-part laboratory experiment is concerned with investigating key aspects of the Suzuki-- Miyaura cross-coupling reaction. The first part of this experiment utilizes high-throughput experimentation techniques to reinforce, explore, and extend fundamental concepts that are presented in the classroom. In contrast, the second part employs…

Unlike the large number of laboratory experiments on phase-transfer catalysis (PTC) that focus on a catalyzed chemical process, the present laboratory emphasizes the mechanism of phase transfer catalysis itself. Students can follow visually the actual transfer of the reagent by the catalyst, and its consumption in the organic phase, in a…

Aldol chemistry is highlighted in many introductory organic chemistry laboratory experiments because it provides synthesis, mechanism, and experimental challenges for students. In the experiment described here, students synthesize dibenzalacetone derivatives by crossed aldol condensation, observe reaction rates using a semiquantitative rubric, and…

An undergraduate experiment for the organic laboratory is described that utilizes microwave heating to prepare 5- substituted 1H-tetrazole derivatives through a (3 + 2) cycloaddition between aryl nitriles and sodium azide. The reaction mixture is analyzed by thin layer chromatography. The products are purified through an acid-base extraction and…