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,…

An experiment for the synthesis of N-acyl derivatives of natural amino acids has been developed as part of the Distributed Drug Discovery (D3) program. Students use solid-phase synthesis techniques to complete a three-step, combinatorial synthesis of six products, which are analyzed using LC-MS and NMR spectroscopy. This protocol is suitable for…

The synthesis of substituted 1,4-benzoquinones, a biologically important class of compounds, was developed using [mu]-oxodi(phenyliodanyl) diacetate, a (diacetoxyiodo)benzene-based oxidizing reagent, in order to introduce second-year undergraduate organic laboratory students in their second semester or advanced organic students to increasingly…

A structured series of activities has been designed and implemented to promote analysis and data reporting skills for second-year organic chemistry students. Student report sheets were developed to assist students in reporting necessary data for their compounds. A series of rubrics have been utilized by students to promote metacognition and by…

Xerogels, exemplified by silica gel, are substances formed by drying gels, resulting in a loss of their internal solvents. Understanding the production and properties of xerogels is crucial, owing to their widespread applications. Xerogel chemistry is widely utilized in several substances; therefore, understanding this chemistry is extremely…

Research has shown that the use of practical examples in undergraduate education promotes the retention of historically underrepresented students in STEM majors and lowers achievement gaps within courses. Since many students of color and women aspire toward careers in healthcare and the pharmaceutical industry, efforts to incorporate medicinal…

An organic solar cell fabrication kit has been developed for demonstration in both undergraduate teaching classes and high school laboratories to promote the growing field of renewable energy and to facilitate empirical comprehension of solar technology. The laboratory focuses on fabricating organic photovoltaics (solar cells) and testing the…

A semester-long research project for second-semester organic chemistry lab sections was developed. Student projects were based on preliminary data from faculty research that suggested the natural product neurolenin B to be a treatment for lymphatic filariasis. Students isolated neurolenins from the Central American plant "Neurolaena…

Undergraduate chemistry laboratory instruction can be considered from many perspectives and addresses multiple educational aims. We critically assess an inventory of "Cognitive Tasks of Experimental Research" for its applicability to chemistry laboratory teaching, and then apply it to an integrated upper-level laboratory course as an…

The importance of understanding factors that contribute to surface wettability is highlighted in this new organic chemistry laboratory experiment, which aims to introduce the application of organic chemistry at the interface of polymer chemistry and material science. Polydimethylsiloxane (PDMS), a hydrophobic silicon-based rubber, is polymerized…

A multistep synthesis of quinolone antibiotic analogues was developed as a laboratory experiment for intermediate/advanced undergraduate students. Students can synthesize a range of "des"fluoroenoxacin analogues via a five-step sequence. The experiment includes a range of key practical laboratory techniques including thin-layer…

Introductory organic chemistry laboratory is often a difficult course for students in terms of translating the structural information and reactivity learned in lecture to the practical applications found in the laboratory. These concepts are even more difficult when presented through distance learning when a student cannot get hands-on experience.…

An undergraduate laboratory experiment for the synthesis of biologically significant bis-4-hydroxycoumarins using a new catalyst is described here. An experimental setup plan, monitoring the reaction by TLC, isolation of the product, safe laboratory handling procedures, and significance of data reproducibility of the result are the main learning…

An operationally straightforward, project-like laboratory experiment has been developed in which students directly compare the reactivity of two heterocycles, a cyclic "O,O"-acetal (standard C-O protecting group) and a cyclic "N,O"-acetal (oxazolidine), toward sodium borohydride and methylmagnesium iodide. Students synthesize a…

One dimensional (1-D)[superscript 1] H and [superscript 13]C NMR experiments are common tools used in undergraduate organic laboratories to characterize synthesized molecules. However, 1-D NMR spectra cannot always provide unambiguous structure determination. In research laboratories, advanced NMR spectroscopy methods are employed for structural…