| Journal Articles: 14 results |
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Synthesis Explorer: A Chemical Reaction Tutorial System for Organic Synthesis Design and Mechanism Prediction Jonathan H. Chen and Pierre Baldi
Synthesis Explorer is an interactive tutorial system for organic chemistry that enables students to learn chemical reactions in ways previously unrealized. Pedagogical experiments in undergraduate classes at UC Irvine indicate that the system can improve average student examination performance by ~10%.
Chen, Jonathan H.; Baldi, Pierre. J. Chem. Educ. 2008, 85, 1699.
Mechanisms of Reactions |
Reactions |
Synthesis
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The Discovery-Oriented Approach to Organic Chemistry. 7. Rearrangement of trans-Stilbene Oxide with Bismuth Trifluoromethanesulfonate and Other Metal Triflates James E. Christensen, Matthew G. Huddle, Jamie L. Rogers, Herbie Yung, and Ram S. Mohan
Presents a microscale, green organic chemistry laboratory experiment that illustrates the utility of metal triflates, especially bismuth triflate, as a Lewis acid catalyst. Bismuth compounds are especially attractive for use as catalysts in organic synthesis because of their low toxicity, low cost, and ease of handling.
Christensen, James E.; Huddle, Matthew G.; Rogers, Jamie L.; Yung, Herbie; Mohan, Ram S. J. Chem. Educ. 2008, 85, 1274.
Catalysis |
Epoxides |
Green Chemistry |
Lewis Acids / Bases |
Mechanisms of Reactions |
Microscale Lab |
NMR Spectroscopy
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Keeping Your Students Awake: Facile Microscale Synthesis of Modafinil, a Modern Anti-Narcoleptic Drug Evangelos Aktoudianakis, Rui Jun Lin, and Andrew P. Dicks
Describes the microscale preparation of modafinil, a pharmaceutical recently approved for the treatment of narcolepsy, by a sulfide oxidation reaction. An unusual feature of modafinil is the presence of a chiral sulfoxide functionality where a sulfur atom acts as a stereocenter, demonstrating that atoms other than carbon can act as centers of chirality.
Aktoudianakis, Evangelos; Lin, Rui Jun; Dicks, Andrew P. J. Chem. Educ. 2006, 83, 1832.
Chirality / Optical Activity |
Drugs / Pharmaceuticals |
Synthesis |
Mechanisms of Reactions |
IR Spectroscopy |
NMR Spectroscopy |
Microscale Lab |
Stereochemistry
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Regiospecific Epoxidation of Carvone: A Discovery-Oriented Experiment for Understanding the Selectivity and Mechanism of Epoxidation Reactions Kendrew K. W. Mak, Y. M. Lai, and Yuk-Hong Siu
Peroxy acids and alkaline H2O2 are two commonly used reagents for alkene epoxidation. The former react preferentially with electron-rich alkenes while the latter works better with a,-unsaturated carbonyl compounds. The selectivity of these two reagents on carvone, a naturally occurring compound that contains both types of C=C bonds, is investigated.
Mak, Kendrew K. W.; Lai, Y. M.; Siu, Yuk-Hong. J. Chem. Educ. 2006, 83, 1058.
Alkenes |
Chromatography |
Epoxides |
IR Spectroscopy |
NMR Spectroscopy |
Synthesis |
Mechanisms of Reactions
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Just Click It: Undergraduate Procedures for the Copper(I)-Catalyzed Formation of 1,2,3-Triazoles from Azides and Terminal Acetylenes William D. Sharpless, Peng Wu, Trond Vidar Hansen, and James G. Lindberg
In keeping with the defining aspects of click chemistry, this reaction is high-yielding, requires no chromatography, is easily monitored by TLC, and displays distinct peaks in both IR and 1H-NMR. Virtually all products precipitate, and with just a few different starting blocks, every student, or pair of lab partners, can produce a unique "clicked" compound.
Sharpless, William D.; Wu, Peng; Hansen, Trond Vidar; Lindberg, James G. J. Chem. Educ. 2005, 82, 1833.
Catalysis |
Heterocycles |
Alkynes |
IR Spectroscopy |
NMR Spectroscopy |
Reactions |
Thin Layer Chromatography |
Synthesis
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Conversion of an Aziridine to an Oxazolidinone Using a Salt and Carbon Dioxide in Water Justin R. Wallace, Deborah L. Lieberman, Matthew T. Hancock, and Allan R. Pinhas
An undergraduate laboratory experiment that allows for optimization of experimental reaction conditions for the conversion of a readily-available aziridine to the corresponding oxazolidinone using only carbon dioxide and a salt in water is discussed. A variety of salts were used to determine their effect on the reaction. In all cases, either no reaction occurred or a high yield of product was obtained. Ring opening of the less substituted carbonnitrogen bond predominates. This experiment allows students to optimize reaction conditions to obtain predominantly one of two regioisomers.
Wallace, Justin R.; Lieberman, Deborah L.; Hancock, Matthew T.; Pinhas, Allan R. J. Chem. Educ. 2005, 82, 1229.
Heterocycles |
Synthesis |
Aqueous Solution Chemistry |
Constitutional Isomers |
Mechanisms of Reactions |
NMR Spectroscopy |
Quantitative Analysis
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Epoxide Reactions Thomas Bertolini
Puzzle involving epoxide reactions.
Bertolini, Thomas. J. Chem. Educ. 2002, 79, 828.
Synthesis |
Epoxides |
Ethers
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Epoxide Chemistry: Guided Inquiry Experiment Emphasizing Structure Determination and Mechanism H. G. Krishnamurty, Niveta Jain, and Kiran Samby
An operationally simple three-step synthesis of an a-hydroxy acid based on epoxide chemistry. The focus of the experiment is on the preparation of the chalcone epoxide and its reaction with hot alcoholic alkali. The experiment leads to an unpredicted reaction product.
Krishnamurty, H. G.; Jain, Niveta; Samby, Kiran. J. Chem. Educ. 2000, 77, 511.
Epoxides |
Molecular Properties / Structure |
Mechanisms of Reactions |
Synthesis
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The Discovery-Oriented Approach to Organic Chemistry. 3. Rearrangement of cis- and trans-Stilbene Oxides with Boron Trifluoride Etherate. An Exercise in 1H NMR Spectroscopy for Sophomore Organic Laboratories Erik A. Sgariglia, Regina Schopp, Kostas Gavardinas, and Ram S. Mohan
A discovery-oriented laboratory experiment that involves the rearrangement of both cis- and trans-stilbene oxides with boron trifluoride etherate.
Sgariglia, Erik A.; Schopp, Regina; Gavardinas, Kostas; Mohan, Ram S. J. Chem. Educ. 2000, 77, 79.
Mechanisms of Reactions |
NMR Spectroscopy |
Constitutional Isomers
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Inadequacies of the SN1 Mechanism Johannes Dale
A planar free carbocation intermediate is used as a simple model to explain racemization in solvolysis; but the problem is that racemization is never complete, the enantiomer in excess having the inverted configuration. Also, the unimolecularity has never been demonstrated, but is an assumption only.
Dale, Johannes. J. Chem. Educ. 1998, 75, 1482.
Mechanisms of Reactions
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Diastereospecific Synthesis of an Epoxide: An Introductory Experiment in Organic Synthetic and Mechanistic Chemistry James A. Ciaccio
A two-step epoxide synthesis that can be presented to students in the form of two mechanistic "puzzles" that probe the stereoselectivity of two important reactions: halohydrin formation from alkenes and epoxide formation via intramolecular Williamson ether synthesis.
Ciaccio, James A. J. Chem. Educ. 1995, 72, 1037.
Stereochemistry |
Molecular Properties / Structure |
Mechanisms of Reactions |
Synthesis |
Epoxides |
Alkenes
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The AC Rule: An Algorithm for Organic Reactions Edgar F. Kiefer
Algorithm for predicting organic reaction mechanisms.
Kiefer, Edgar F. J. Chem. Educ. 1995, 72, 906.
Mechanisms of Reactions |
Synthesis |
Reactions
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Disconnect by the numbers: A beginner's guide to synthesis Smith, Michael B.
A protocol for planning organic syntheses using the disconnection method.
Smith, Michael B. J. Chem. Educ. 1990, 67, 848.
Synthesis |
Mechanisms of Reactions
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Chemical toxicology. Part I. Organic compounds Carter, D. E.; Fernando, Quintus
General principles of toxicology, and particular consideration of aliphatics, aromatic, and halogenated hydrocarbons; alcohols, aldehydes, esters, ethers, and ketones; sulfides, mercaptans, and carbon disulfide; nitrogen-containing compounds; and carcinogens.
Carter, D. E.; Fernando, Quintus J. Chem. Educ. 1979, 56, 284.
Toxicology |
Alcohols |
Aldehydes / Ketones |
Esters |
Ethers |
Aromatic Compounds |
Amines / Ammonium Compounds |
Lipids
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