Physical Sciences and Mathematics Commons^™

Adding Gas Chromatography-Mass Spectrometry Data To A Melting Point And Thin-Layer Chromatography Laboratory, Adam Azman, Julie Barrett, Megan Darragh, John Esteb, Luanne Mcnulty, Paul Morgan, Stacy O'Reilly, Anne Wilson

John Esteb

The addition of gas chromatography–mass spectrometry (GC–MS) data interpretation to a thin-layer chromatography (TLC) and melting point (mp) laboratory for an introductory organic course is described.

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Technology For The Organic Chemist: Three Exploratory Modules, John Esteb, Luanne Mcnulty, John Magers, Paul Morgan, Anne Wilson

John Esteb

The ability to use computer-based technology is an essential skill set for students majoring in chemistry. This exercise details the introduction of appropriate uses for this technology in the organic chemistry series. The incorporation of chemically appropriate online resources (module 1), scientific databases (module 2), and the use of a chemical drawing program (module 3) are detailed here.

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A Simple Sn2 Reaction For The Undergraduate Organic Laboratory, John Esteb

John Esteb

A simple procedure for the synthesis of n-butyl naphthyl ether is presented. This procedure represents an easy method for the production of an aryl ether by an SN2 reaction, uses ethanol as an environmentally friendly solvent, and does not require the use of a lachrymator. Product isolation is done by pouring the reaction mixture over ice and collecting the solid by suction filtration. Students typically recover from 7–95% of the ether.

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A Flexible Solvolysis Experiment For The Undergraduate Organic Laboratory, John Esteb, John Magers, Luanne Mcnulty, Paul Morgan, Kathryn Tindell, Anne Wilson

John Esteb

A simple SN1 reaction is presented that uses bromotriphenylmethane and a range of oxygen-based nucleophiles including water and various alcohols. This procedure represents a process that affords easy isolation of solid products. Typical student yields ranged from 17–128% with the average yield of 50%. Students obtained products with a melting point range of 140 to 164 °C. This procedure offers multiple ways to adapt this experiment from a straight solvolysis reaction to a discovery-based experiment that explores the effect of nucleophile (for a more advanced group) or the method of product isolation. Note: Link is to the article in a …

Projects That Assist With Content In A Traditional Organic Chemistry Course, John Esteb, John Magers, Luanne Mcnulty, Anne Wilson

John Esteb

Projects that engage undergraduate students in content-based courses, such as organic chemistry, must relate to the material and provide useful tools for the divergent needs of the students. There are few examples of these types of projects in the literature. Herein, we describe two projects, the reaction notebook and the end-of-semester synthesis activity. Each project is designed to stimulate student ownership of the material and leads to engagement with the content of the course.

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A Solvent-Free Baeyer–Villiger Lactonization For The Undergraduate Organic Laboratory: Synthesis Of Γ-T-Butyl-Ε-Caprolactone, John Esteb, James Hohman, Diana Schlamadinger, Anne Wilson

John Esteb

We present an experiment involving the Baeyer–Villiger oxidation reactionfor a first-year organic chemistry class. The Baeyer–Villiger reactionprovides an efficient method to convert ketones to esters or lactones. Most organictextbooks cover the Baeyer–Villiger reaction but owing to a lack of suitableexperiments, students seldom get to explore the reaction in the undergraduateteaching laboratory. In this experiment, m-chloroperoxybenzoic acid(m-CPBA) and4-tert-butylcyclohexanone are mixed together for 30 minutes under solvent-freeconditions to produce γ-t-butyl-ε-caprolactone in 95%yield. The solvent-free nature of this procedure greatly limits the quantityof waste generated by students and keeps costs low by removing the need for solvent.

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Solvent-Free Conversion Of Alpha-Naphthaldehyde To 1-Naphthoic Acid And 1-Naphthalenemethanol: Application Of The Cannizzaro Reaction, John Esteb, Keith Gligorich, Stacy O'Reilly, Jeremy Richter

John Esteb

The Cannizzaro reaction is routinely covered in organic textbooks, but owing to the shortage of suitable procedures for the undergraduate teaching laboratory, this reaction is seldom performed in a first-year organic chemistry class. In this experiment, powdered potassium hydroxide and α-naphthaldehyde are heated under solvent-free conditions to produce 1-naphthoic acid and 1-naphthalenemethanol in 86% and 79% yields, respectively. The solvent-free nature of this procedure greatly reduces the quantity of waste generated by students relative to the typical solvent-based method of preparation. Note:Link is to the article in a subscription database available to users affiliated with Butler University. Appropriate login information …

Cautionary Comments (Author Response), John Esteb, Anne Wilson

John Esteb

Reply to concerns about a safety factor in the paper, “A Solvent-Free Oxidation of Alcohols in an Organic Laboratory."

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Simple Epoxide Formation For The Organic Laboratory Using Oxone, John Esteb

John Esteb

We present an epoxide formation experiment for a second-semester organic chemistry laboratory. This oxidation utilizes Oxone, a commercially available oxidizing agent, in the industrially relevant process of epoxide formation. The oxidant performing the oxidation is dimethyldioxirane, which is formed in situ. This experiment demonstrates a simple synthesis of an epoxide and formation of a secondary oxidizing agent.

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A Solvent-Free Claisen Condensation Reaction For The Organic Laboratory, John Esteb, Matthew Stockton

John Esteb

An experiment involving the Claisen condensation reaction for a first-year organic chemistry laboratory is presented. Claisen condensations are routinely covered in organic textbooks but owing to the long reaction times required to reach equilibrium in solution they are seldom explored in the undergraduate teaching laboratory. In this experiment, potassium tert-butoxide and ethyl phenylacetate are heated to 100 °C for 30 minutes under solvent-free conditions to produce 2,4-diphenyl acetoacetate in 80% yield. The solvent-free nature of this procedure greatly reduces the quantity of waste generated by students relative to typical carbonyl condensation experiments.

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A Solvent-Free Oxidation Of Alcohols In An Organic Laboratory, John Esteb, Michael Schelle, Anne Wilson

John Esteb

An oxidation experiment for a first-year organic chemistry class is presented. This oxidation utilizes a solid mixture of CuSO4•5H2O and KMnO4 prepared by mortar and pestle. The oxidations take place under solvent-free conditions and near quantitative yields are obtained for the reactions. Thin-layer chromatography is used to monitor the progress of the reaction. This experiment provides for the simple oxidation of a secondary alcohol to a ketone using a relatively nontoxic oxidizing agent under solvent-free conditions.

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