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Organic chemistry

Selected Works

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Full-Text Articles in Physical Sciences and Mathematics

Application Of The Picoloyl Substituent In Carbohydrate Chemistry, Michael Mannino, Alexei V. Demchenko May 2019

Application Of The Picoloyl Substituent In Carbohydrate Chemistry, Michael Mannino, Alexei V. Demchenko

Michael Mannino

Stereocontrol of glycosylation reactions is a constant struggle in the field of synthetic carbohydrate chemistry. The application of the picoloyl (Pico) substituent can offer a numerous stereocontrolling avenues. The most popular application is the Hydrogen-bond-mediated Aglycone Delivery (HAD) method that provides excellent selectivity in the glycosylation of a variety of sugar substrates. The HAD method relies on the formation of an intermolecular hydrogen bond between the nitrogen atom of the Pico substituent on the glycosyl donor with the hydroxyl group of the glycosyl acceptor. This interaction provides a facial preference for the nucleophilic attack and hence provides powerful stereocontrol for …

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Arrow Pushing In Organic Chemistry: An Easy Approach To Understanding Reaction Mechanisms (Book Review), Jeffrey H. Glans Jan 2014

Arrow Pushing In Organic Chemistry: An Easy Approach To Understanding Reaction Mechanisms (Book Review), Jeffrey H. Glans

Jeffrey H. Glans

A book review by Jeffrey Glans. Levy, Daniel E. Arrow Pushing in Organic Chemistry: An Easy Approach to Understanding Reaction Mechanisms. New York: Wiley, 2008. ISBN 9780470171103

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Molecular Orbitals And Organic Chemical Reactions (Book Review), Jeffrey H. Glans Sep 2013

Molecular Orbitals And Organic Chemical Reactions (Book Review), Jeffrey H. Glans

Jeffrey H. Glans

Book review by Jeffrey Glans. Fleming, Ian. Molecular Orbitals and Organic Chemical Reactions. Wiley-Blackwell, 2010, c2009. ISBN: 9780470746608; 9780470746592 (pbk.)

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Organic Chemistry: A Survival Guide For Students, Ethan C. Levine Apr 2012

Organic Chemistry: A Survival Guide For Students, Ethan C. Levine

Anton Geiler

This project reviews material from undergraduate Organic Chemistry I and II. It is meant to function as a supplement to the textbook and lecture material for the course as it is taught in universities throughout the United States. Complex ideas are broken down into simpler ones. Material is presented in conversational language, using as little scientific jargon as possible.

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The Discovery-Oriented Approach To Organic Chemistry. 5. Stereochemistry Of E2 Elimination: Elimination Of Cis- And Trans-2-Methylcyclohexyl Tosylate, Ram S. Mohan, Marcus E. Cabay, Brad J. Ettlie, Adam J. Tuite, Kurt A. Welday Dec 2000

The Discovery-Oriented Approach To Organic Chemistry. 5. Stereochemistry Of E2 Elimination: Elimination Of Cis- And Trans-2-Methylcyclohexyl Tosylate, Ram S. Mohan, Marcus E. Cabay, Brad J. Ettlie, Adam J. Tuite, Kurt A. Welday

Ram S. Mohan

The E2 elimination is one of the most important reactions in organic chemistry and is discussed in considerable detail in a sophomore organic course. We have developed a discovery-oriented lab that illustrates the stereochemistry of the E2 elimination reaction and is a good exercise in 1H NMR spectroscopy. The added element of discovery insures that student interest and enthusiasm are retained.

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The Discovery-Oriented Approach To Organic Chemistry. 4. Epoxidation Of P-Methoxy-Trans-Β-Methylstyrene. An Exercise In 1H Nmr And 13C Nmr Spectroscopy For Sophomore Organic Laboratories, Ram S. Mohan, Rebecca S. Centko Dec 2000

The Discovery-Oriented Approach To Organic Chemistry. 4. Epoxidation Of P-Methoxy-Trans-Β-Methylstyrene. An Exercise In 1H Nmr And 13C Nmr Spectroscopy For Sophomore Organic Laboratories, Ram S. Mohan, Rebecca S. Centko

Ram S. Mohan

Epoxidation of alkenes using peroxyacids is one of the most fundamental reactions in organic chemistry, yet there are very few examples of laboratory experiments that illustrate this important reaction. We have developed a discovery-oriented lab experiment that illustrates epoxidation of alkenes as well as the reactivity of epoxides toward acids. The experiment involves reaction of p-methoxy-trans-β-methylstyrene (trans-anethole) with m-chloroperoxybenzoic acid (MCPBA), in both the absence and presence of a buffer, followed by product identification using 1H NMR, 13C NMR, and IR spectroscopy. The added element of discovery ensures that students' interest and enthusiasm are retained.

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The Discovery-Oriented Approach To Organic Chemistry. 3. Boron-Trifluoride Catalyzed Rearrangement Of Cis- And Trans-Stilbene Oxides. An Exercise In 1H Nmr Spectroscopy For Sophomore Organic Laboratories, Ram S. Mohan, Erik A. Sgariglia, Regina Schopp, Kostas Gavardinas Dec 1999

The Discovery-Oriented Approach To Organic Chemistry. 3. Boron-Trifluoride Catalyzed Rearrangement Of Cis- And Trans-Stilbene Oxides. An Exercise In 1H Nmr Spectroscopy For Sophomore Organic Laboratories, Ram S. Mohan, Erik A. Sgariglia, Regina Schopp, Kostas Gavardinas

Ram S. Mohan

Epoxides, or oxiranes, are among the most versatile intermediates in organic synthesis. Yet very few examples of laboratory experiments involving reactions of epoxides are to be found in lab texts. We have developed a discovery-oriented laboratory experiment that involves the rearrangement of both cis- and trans-stilbene oxides with boron trifluoride etherate. The identity of the product can be easily determined by 1H NMR spectroscopy and, in case of the trans isomer, by preparation of the semicarbazone derivative as well. In spite of the simplicity of the experiment, the element of discovery ensures that student interest and enthusiasm are retained.

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The Discovery-Oriented Approach To Organic Chemistry. 2. Selectivity In Alcohol Oxidation. An Exercise In 1H Nmr Spectroscopy For Sophomore Organic Laboratories, Ram S. Mohan, Steven R. Shadwick Jul 1999

The Discovery-Oriented Approach To Organic Chemistry. 2. Selectivity In Alcohol Oxidation. An Exercise In 1H Nmr Spectroscopy For Sophomore Organic Laboratories, Ram S. Mohan, Steven R. Shadwick

Ram S. Mohan

We have developed a simple oxidation experiment that presents the student with a puzzle and is a good exercise in 1H NMR spectroscopy. The experiment, which illustrates the important concept of selectivity in organic synthesis, involves selective oxidation of a mixture of 1-heptanol and 2-heptanol using commercial swimming pool chlorine. 1H NMR analysis of the product mixture allows the student to determine the selectivity exhibited by the reagent.

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The Discovery-Oriented Approach To Organic Chemistry 1. Nitration Of Unknown Organic Compounds. An Exercise In 1H Nmr And 13C Nmr Spectroscopy For Sophomore Organic Laboratories, Ram S. Mohan, Sonia R. Mcelveen, Kostas Gavardinas, Jean A. Stamberger Mar 1999

The Discovery-Oriented Approach To Organic Chemistry 1. Nitration Of Unknown Organic Compounds. An Exercise In 1H Nmr And 13C Nmr Spectroscopy For Sophomore Organic Laboratories, Ram S. Mohan, Sonia R. Mcelveen, Kostas Gavardinas, Jean A. Stamberger

Ram S. Mohan

Nitration is one of the most fundamental reactions in organic chemistry. However, the majority of the nitration experiments found in the standard lab textbooks are of the "cookbook" variety and convey none of the excitement associated with discovery in experimental chemistry. We have developed two simple nitration experiments that present the student with a puzzle and are a good exercise in 1H NMR and 13C NMR spectroscopy. 13 C NMR spectroscopy is a powerful structure elucidation tool and yet not many examples of the use of 13C NMR spectroscopy in organic lab experiments can be found. The experiment involves nitration …

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