Friedel-Crafts alkylation reactions using a curated set of alcohols provide students with the opportunity to combine the study of electrophilic aromatic substitution with carbocation rearrangements. In this experiment students may be presented with up to nine alcohols that yield six products, all synthesized under identical reaction conditions.…

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…

Guided-inquiry experiments are an important tool for helping students develop scientific practices such as hypothesizing and problem solving. In organic chemistry, these types of experiments can help students learn how to connect the theory of the reaction to the observation and data to decide how the reaction is proceeding or if it needs…

A chemistry course designed as an elective for chemistry, biochemistry, biology, and pharmaceutical science majors is described. The course is designed for second- through fourth-year undergraduate students. The prerequisite is first-semester, second-year undergraduate organic chemistry with the second semester of the organic sequence as a…

Given student familiarity with electronic cigarettes (e-cigs), this lab uses a student-built smoke collection apparatus to collect e-cig vapors to teach students about gas chromatography-mass spectrometry (GC-MS). Students in a second semester, introductory organic chemistry course spent 1 week collecting e-cig vapors and 1 week qualitatively…

A Sonogashira experiment was transformed into a problem-based learning platform for third-year undergraduate students. Given a target that could be synthesized in a single step, students worked in groups to investigate which method was the best for large-scale production. Through this practical scenario, students learn to conduct a literature…

The different ways microscale and green chemistry allow reducing the deleterious impacts of chemistry on human health and the environment are discussed in terms of their different basic paradigms: green chemistry follows the ecologic paradigm and microscale the risk paradigm. A study of the synthesis of 1-bromobutane at macro- ? microscale (109.3…

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…

This paper discusses laboratory activities that can improve the meaningfulness of natural product chemistry course. These laboratory activities can be useful for students from many different disciplines including chemistry, pharmacy, and medicine. Students at the third-year undergraduate level of chemistry education undertake the project to…

The Distributed Drug Discovery (D3) program trains students in three drug discovery disciplines (synthesis, computational analysis, and biological screening) while addressing the important challenge of discovering drug leads for neglected diseases. This article focuses on implementation of the synthesis component in the second-semester…

Science educators strive to teach students how to be well-rounded scientists with the ability to problem solve, anticipate errors, and adapt to unexpected roadblocks. Traditional organic chemistry experiments seldom teach these skills, no matter how novel or contemporary the subject material. This paper reports on the success of a quarter-long…

A course is described where students are engaged in an inquiry-based quarter-long research project to synthesize a known pharmaceutical target. Students use literature search engines, such as Reaxys and SciFinder, and the primary chemical literature as resources to plan and perform the synthesis of their pharmaceutical target. Through this…

Reaction workup can be a complex problem for those facing novel synthesis of difficult compounds for the first time. Workup problem solving by systematic thinking should be inculcated as mid-graduate-level is reached. A structured approach is proposed, building decision tree flowcharts to analyze challenges, and an exemplar flowchart is presented…

Academic programs generally work to make their laboratory curriculum both as instrumentation rich and up to date as possible. However, little is known about the relationship between the use of instrumentation in the curriculum and student learning. As part of our department's ongoing assessment efforts, a project was designed to probe this…

This experiment describes a discovery-based method for the regio- and stereoselective hydrochlorination of carvone, appropriate for a 3-h second-semester organic chemistry laboratory. The product is identified through interpretation of the [superscript 13]C NMR and DEPT spectra are obtained on an Anasazi EFT-60 at 15 MHz as neat samples. A…