TIGER

Journal Articles: 66 results
Synthesis of Albendazole Metabolite: Characterization and HPLC Determination  Graciela Mahler, Danilo Davyt, Sandra Gordon, Marcelo Incerti, Ivana Núñez, Horacio Pezaroglo, Laura Scarone, Gloria Serra, Mauricio Silvera, and Eduardo Manta
In this laboratory activity, students are introduced to the synthesis of an albendazole metabolite obtained by a sulfide oxidation reaction. Albendazole as well as its metabolite, albendazole sulfoxide, are used as anthelmintic drugs. The oxidation reagent is H2O2 in acetic acid. The reaction is environmental friendly, fast, and proceeds with high yield. The crude reaction is analyzed by HPLC chromatography to determine purity. The simplicity of the experiment allows students to study chiral concepts, physicochemical and spectroscopic properties of the compounds, and HPLC determinations.
Mahler, Graciela; Davyt, Danilo; Gordon, Sandra; Incerti, Marcelo; Núñez, Ivana; Pezaroglo, Horacio; Scarone, Laura; Serra, Gloria; Silvera, Mauricio; Manta, Eduardo. J. Chem. Educ. 2008, 85, 1652.
Chirality / Optical Activity |
Drugs / Pharmaceuticals |
HPLC |
Medicinal Chemistry |
Organosulfur Compounds |
Oxidation / Reduction |
Synthesis
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
Isolation of Betulin and Rearrangement to Allobetulin  Brian Green, Michael D. Bentley, Bong Y. Chung, Nicholas G. Lynch, and Bruce L. Jensen
Betulin is obtained by extraction from birch bark and converted to allobetulin. Both compounds display 1H NMR spectra that include axialequatorial coupling characteristic of a C3-alcohol, conformational analysis by the use of dihedral angles and the Karplus equation, coupling patterns caused by diastereotopic protons and long-range interactions, and chemical shift values that are influenced by electronegativity and stereochemistry.
Green, Brian; Bentley, Michael D.; Chung, Bong Y.; Lynch, Nicholas G.; Jensen, Bruce L. J. Chem. Educ. 2007, 84, 1985.
Biosynthesis |
IR Spectroscopy |
Microscale Lab |
NMR Spectroscopy |
Synthesis |
Natural Products
A Knoevenagel Initiated Annulation Reaction Using Room Temperature or Microwave Conditions  A. Gilbert Cook
The product of a Knoevenagel initiated annulation reaction is identified through a guided prelab exercise of the synthesis of the Hagemann ester, and then through the analysis of GCMS, NMR, and IR spectra. The stereochemistry of the product is determined through the NMR spectrum and Karplus curve, and the student is required to write a mechanism for the reaction.
Cook, A. Gilbert. J. Chem. Educ. 2007, 84, 1477.
Aldehydes / Ketones |
Conformational Analysis |
Gas Chromatography |
IR Spectroscopy |
Mass Spectrometry |
Mechanisms of Reactions |
NMR Spectroscopy |
Stereochemistry |
Synthesis
Polar Addition to C=C Group: Why Is Anti-Markovnikov Hydroboration–Oxidation of Alkenes Not "Anti-"?  Predrag-Peter Ilich, Lucas S. Rickertsen, and Erienne Becker
The authors redefine Markovnikov or anti-Markovnikov regioselectivity and propose that the teaching of organic chemistry should be based on robust and portable concepts such as energy difference and atomic charge rather than historical labels.
Ilich, Predrag-Peter; Rickertsen, Lucas S.; Becker, Erienne. J. Chem. Educ. 2006, 83, 1681.
Addition Reactions |
Alkenes |
Computational Chemistry |
Mechanisms of Reactions |
Molecular Modeling
Reductive Amination: A Remarkable Experiment for the Organic Laboratory  Kim M. Touchette
The synthesis of N-(2-hydroxy-3-methoxybenzyl)-N-p-tolylacetamide is a fast, simple three-step sequence that serves as a useful example of the reductive amination reaction for the organic chemistry laboratory.
Touchette, Kim M. J. Chem. Educ. 2006, 83, 929.
Aldehydes / Ketones |
Amines / Ammonium Compounds |
Green Chemistry |
Instrumental Methods |
IR Spectroscopy |
NMR Spectroscopy |
Oxidation / Reduction |
Solids
Synthesis of Methyl Diantilis, a Commercially Important Fragrance  William H. Miles and Katelyn B. Connell
Describes the synthesis of a family of fragrances, including the commercially important Methyl Diantilis, and provides an excellent introduction to intellectual property laws.
Miles, William H.; Connell, Katelyn B. J. Chem. Educ. 2006, 83, 285.
Alcohols |
Food Science |
Catalysis |
Ethers |
Industrial Chemistry |
IR Spectroscopy |
Lewis Acids / Bases |
NMR Spectroscopy |
Oxidation / Reduction |
Synthesis
Derivatization of Fullerenes: An Organic Chemistry Laboratory  Charles T. Cox Jr. and Melanie M. Cooper
Presents two undergraduate organic chemistry laboratories detailing the synthesis of fullerene derivatives, using the Bingel (carbene insertion) and Prato (1,3-dipolar addition) protocols.
Cox, Charles T., Jr.; Cooper, Melanie M. J. Chem. Educ. 2006, 83, 99.
Acids / Bases |
Addition Reactions |
Chromatography |
Heterocycles |
IR Spectroscopy |
Microscale Lab |
NMR Spectroscopy |
Synthesis |
UV-Vis Spectroscopy
Monitoring the Rate of Solvolytic Decomposition of Benzenediazonium Tetrafluoroborate in Aqueous Media Using a pH Electrode  Floyd L. Wiseman
This article discusses the use of pH electrodes to monitor the aqueous solvolysis of the benzenediazonium ion and shows that the results are in reasonable agreement with literature values.
Wiseman, Floyd L. J. Chem. Educ. 2005, 82, 1841.
Calorimetry / Thermochemistry |
Kinetics |
Thermodynamics |
Amines / Ammonium Compounds |
Aqueous Solution Chemistry |
Mechanisms of Reactions |
pH |
Rate Law
A Solvent-Free Baeyer–Villiger Lactonization for the Undergraduate Organic Laboratory: Synthesis of γ-t-Butyl-ε-caprolactone  John J. Esteb, J. Nathan Hohman, Diana E. Schlamadinger, and Anne M. Wilson
The BaeyerVilliger reaction provides an efficient method to convert ketones to esters or lactones. In this experiment, m-chloroperoxybenzoic acid and 4-tert-butylcyclohexanone are mixed together for under solvent-free conditions to produce ?-t-butyl-e-caprolactone.
Esteb, John J.; Hohman, J. Nathan; Schlamadinger, Diana E.; Wilson, Anne M. J. Chem. Educ. 2005, 82, 1837.
Green Chemistry |
Synthesis |
Esters |
Oxidation / Reduction
A Microwave-Assisted Reduction of Cyclohexanone Using Solid-State-Supported Sodium Borohydride  Lori L. White and Kevin W. Kittredge
We report a microwave-assisted reduction of cyclohexanone by sodium borohydride that is supported on SiO2. The reaction was completed in less than 3 minutes. Workup and analysis by GCMS, IR, and 1H NMR was possible in a two and half-hour laboratory session. This reduction was used successfully in a second-year organic chemistry laboratory. Students were exposed to a green chemistry reaction using solid-state-supported reactants in the absence of solvent.
White, Lori L.; Kittredge, Kevin W. J. Chem. Educ. 2005, 82, 1055.
Oxidation / Reduction |
Solid State Chemistry |
Green Chemistry |
Alcohols |
Aldehydes / Ketones
Circular Dichroism Investigation of Dess–Martin Periodinane Oxidation in the Organic Chemistry Laboratory  Nicole A. Reed, Robert D. Rapp, Christian S. Hamann, and Pamela G. Artz
Using circular dichroism, organic laboratory students investigated the change in absolute stereochemistry upon oxidation of menthol to menthone. In the first laboratory period, the oxidation was performed with DessMartin periodinane, which is a facile and less toxic oxidizing agent. Half the laboratory group performed the oxidation with ()-menthol and the other half used (+)-menthol to produce ()-menthone and (+)-menthone, respectively. The products were analyzed in the second laboratory period using infrared spectroscopy and gas chromatography/mass spectrometry to determine the fraction of starting alcohol converted to ketone. Comparison was made between CD spectra both for the menthol reactant and menthone product and for the (+)- and ()-menthone enantiomers.
Reed, Nicole A.; Rapp, Robert D.; Hamann, Christian S.; Artz, Pamela G. J. Chem. Educ. 2005, 82, 1053.
Instrumental Methods |
Molecular Properties / Structure |
Oxidation / Reduction |
Reactions |
Enantiomers
The Evolution of a Green Chemistry Laboratory Experiment: Greener Brominations of Stilbene  Lallie C. McKenzie, Lauren M. Huffman, and James E. Hutchison
We describe two new greener alkene bromination reactions that offer enhanced laboratory safety and convey important green chemistry concepts, in addition to illustrating the chemistry of alkenes. The two alternative reactions, one involving pyridinium tribromide and a second using hydrogen peroxide and hydrobromic acid, are compared to the traditional bromination of stilbene through the application of green metrics, including atom economy, percent experimental atom economy, E factor, and effective mass yield.
McKenzie, Lallie C.; Huffman, Lauren M.; Hutchison, James E. J. Chem. Educ. 2005, 82, 306.
Synthesis |
Green Chemistry |
Aromatic Compounds |
Addition Reactions |
Alkenes
The Conversion of Carboxylic Acids to Ketones: A Repeated Discovery  John W. Nicholson and Alan Wilson
This article describes the history of the reaction converting carboxylic acids to ketones. The reaction has been rediscovered several times, yet has actually been known for centuries.
Nicholson, John W.; Wilson, Alan. J. Chem. Educ. 2004, 81, 1362.
Synthesis |
Carboxylic Acids |
Aldehydes / Ketones
Solvent-Free Synthesis of Chalcones  Daniel R. Palleros
The solvent-free synthesis of 20 chalcones was carried out by grinding the benzaldehyde (unsubstituted, 4-methyl, 4-methoxy, 3-chloro, or 4-chloro) and the acetophenone (unsubstituted, 4-methyl, 4-bromo, or 4-methoxy) in the presence of solid sodium hydroxide with a mortar and pestle. In general, the chalcones were obtained in high yields and high purity. Minor quantities of ketol and Michael addition product were detected by NMR spectroscopy. These side-products were easily removed by recrystallization.
Palleros, Daniel R. J. Chem. Educ. 2004, 81, 1345.
Green Chemistry |
NMR Spectroscopy |
Synthesis |
Solids |
Laboratory Management
The Darzens Condensation: Structure Determination through Spectral Analysis and Understanding Substrate Reactivity  R. David Crouch, Michael S. Holden, and Candice A. Romany
The Darzens condensation involves two steps that are typically included in the sophomore organic curriculum: an aldol reaction followed by an intramolecular nucleophilic substitution.
Crouch, R. David; Holden, Michael S.; Romany, Candice A. J. Chem. Educ. 2004, 81, 711.
NMR Spectroscopy |
Synthesis |
Stereochemistry |
Mechanisms of Reactions |
Aldehydes / Ketones
Developing Investigation Skills in an Introductory Multistep Synthesis Using Fluorene Oxidation and Reduction  Mark G. Stocksdale, Steven E. S. Fletcher, Ian Henry, Paul J. Ogren, Michael A. G. Berg, Roy D. Pointer, and Barrett W. Benson
A two-step reaction sequence in the beginning organic laboratory provides a useful introduction to the importance of multistep synthesis. In addition to introducing several common synthetic methods and techniques, a two-step preparation can quickly establish the importance of testing alternative reactions in order to optimize intermediate yields.
Stocksdale, Mark G.; Fletcher, Steven E. S.; Henry, Ian; Ogren, Paul J.; Berg, Michael A. G.; Pointer, Roy D.; Benson, Barrett W. J. Chem. Educ. 2004, 81, 388.
Chromatography |
IR Spectroscopy |
NMR Spectroscopy |
Synthesis |
Aromatic Compounds |
Oxidation / Reduction
Microscale Synthesis of 1-Bromo-3-chloro-5-iodobenzene: An Improved Deamination of 4-Bromo-2-chloro-6-iodoaniline  Michael W. Pelter, Libbie S.W. Pelter, Dusanka Colovic, and Regina Strug
Overall, we find this procedure to be advantageous to the published methods owing to its requirement of less starting material, higher product yields, and a greatly simplified procedure.
Pelter, Michael W.; Pelter, Libbie S.W.; Colovic, Dusanka; Strug, Regina. J. Chem. Educ. 2004, 81, 111.
Microscale Lab |
Synthesis |
Aromatic Compounds |
Amines / Ammonium Compounds
A Series of Small-Scale, Discovery-Based Organic Laboratory Experiments Illustrating the Concepts of Addition, Substitution, and Rearrangement  Judith S. Moroz, Janice L. Pellino, and Kurt W. Field
Multistep, microscale organic laboratory experiments are presented that illustrate addition, substitution, and rearrangement reactions.
Moroz, Judith S.; Pellino, Janice L.; Field, Kurt W. J. Chem. Educ. 2003, 80, 1319.
IR Spectroscopy |
Mass Spectrometry |
Microscale Lab |
NMR Spectroscopy |
Synthesis |
Addition Reactions |
Mechanisms of Reactions
A Solvent-Free Oxidation of Alcohols in an Organic Laboratory  John J. Esteb, Michael W. Schelle, and Anne M. Wilson
Oxidation of alcohols using potassium permanganate and copper(II) sulfate pentahydrate.
Esteb, John J.; Schelle, Michael W.; Wilson, Anne M. J. Chem. Educ. 2003, 80, 907.
IR Spectroscopy |
Synthesis |
Solids
Preparing Students for Research: Synthesis of Substituted Chalcones as a Comprehensive Guided-Inquiry Experience  James R. Vyvyan, Donald L. Pavia, Gary M. Lampman, and George S. Kriz Jr.
An aldol condensation of substituted benzaldehydes with substituted acetophones to produce substituted benzalacetophenones (chalcones) in a guided-inquiry approach.
Vyvyan, James R.; Pavia, Donald L.; Lampman, Gary M.; Kriz, George S., Jr. J. Chem. Educ. 2002, 79, 1119.
Medicinal Chemistry |
Microscale Lab |
Natural Products |
NMR Spectroscopy |
Synthesis |
Aromatic Compounds |
Aldehydes / Ketones
Chiral Compounds and Green Chemistry in Undergraduate Organic Laboratories: Reduction of a Ketone by Sodium Borohydride and Baker's Yeast  Nicola Pohl, Allen Clague, and Kimberly Schwarz
Students compare biological and chemical means of introducing chirality into a molecule by investigating the reduction of a ketoester with two different reducing agents.
Pohl, Nicola; Clague, Allen; Schwarz, Kimberly. J. Chem. Educ. 2002, 79, 727.
Chirality / Optical Activity |
Oxidation / Reduction |
Synthesis |
Green Chemistry
The Mechanism of the Ritter Reaction in Combination with Wagner-Meerwein Rearrangements. A Cooperative Learning Experience  María I. Colombo, María L. Bohn, and Edmundo A. Rúveda
Procedure in which students develop analytical and problem-solving skills by investigating an organic reaction mechanism, predicting the most likely products, and suggesting experiments to test the postulated mechanistic pathways and possible intermediates.
Colombo, María I.; Bohn, María L.; Rúveda, Edmundo A. J. Chem. Educ. 2002, 79, 484.
Mechanisms of Reactions |
Reactive Intermediates |
Amides |
Thin Layer Chromatography |
NMR Spectroscopy
Synthesis and Analysis of a Solvatochromic Dye, 1-(p-Dimethylaminophenyl)-2-nitroethylene. An Advanced Undergraduate Laboratory Experiment  Dana L. Richter-Egger, Aaron Tesfai, Spencer J. Flamm, and Sheryl A. Tucker
Synthesis and analysis of 1-(p-dimethylaminophenyl)-2-nitroethylene.
Richter-Egger, Dana L.; Tesfai, Aaron; Flamm, Spencer J.; Tucker, Sheryl A. J. Chem. Educ. 2001, 78, 1375.
Fluorescence Spectroscopy |
Synthesis |
Undergraduate Research |
UV-Vis Spectroscopy |
Dyes / Pigments |
Amines / Ammonium Compounds |
Aromatic Compounds |
Alkenes
A More Realistic Teaching Style in Spectroscopic Instruction  Mar Gómez Gallego, Santiago Romano, Miguel A. Sierra, and Enrique Nieto
A practical application of spectroscopic analysis in intermediate and advanced organic chemistry to determine reaction mechanisms and identify products; provides three specific problems.
Gallego, Mar Gómez; Romano, Santiago; Sierra, Miguel A.; Nieto, Enrique. J. Chem. Educ. 2001, 78, 765.
Mechanisms of Reactions |
NMR Spectroscopy |
Learning Theories |
Spectroscopy |
Molecular Properties / Structure |
Qualitative Analysis
Synthesis of Substituted Butenolides. An Undergraduate Organic Laboratory Experiment Utilizing Two 3-Step Preparatory Sequences  Géraldine Maheut, Liang Liao, Jean-Marie Catel, Paul-Alain Jaffrès, and Didier Villemin
The synthesis of substituted butenolide in two, 3-step sequences that illustrate five basic organic reactions (alkyne hydration, Knoevenagel condensation, lactonization, aldolization-type reaction, and hydration of nitrile); the products have pedagogical interest for IR and NMR spectroscopy (diastereotopic effect).
Maheut, Géraldine; Liao, Liang; Catel, Jean-Marie; Jaffrès, Paul-Alain; Villemin, Didier. J. Chem. Educ. 2001, 78, 654.
IR Spectroscopy |
Molecular Modeling |
NMR Spectroscopy |
Synthesis |
Undergraduate Research |
Reactions
A Practical Procedure for the Solid-Phase Synthesis of Azo Compounds in the Undergraduate Organic Laboratory  Cailan Wang, Yulu Wang, Xiaoyang Wang, Xiaoxia Wang, and Hong Wang
A new solid-phase reaction method used to synthesize a new type of azo compound is described. The procedure is short, safe, and simple enough to serve as a laboratory exercise for undergraduate students in the middle weeks of a course when azo compounds or synthesis methods have been discussed in the lecture.
Wang, Cailan; Wang, Yulu; Wang, Xiaoyang; Wang, Xiaoxia; Wang, Hong. J. Chem. Educ. 2000, 77, 903.
Synthesis |
Undergraduate Research |
Aromatic Compounds
The Heck Reaction: A Microscale Synthesis Using a Palladium Catalyst  William B. Martin and Laura J. Kateley
The microscale synthesis described uses a reaction between a bromoiodobenzene and acrylic acid to produce a bromocinnamic acid. Structure verification for the product uses IR and 1H NMR spectroscopy.
Martin, William B.; Kateley, Laura J. J. Chem. Educ. 2000, 77, 757.
Catalysis |
Microscale Lab |
Synthesis |
IR Spectroscopy |
NMR Spectroscopy |
Aromatic Compounds |
Mechanisms of Reactions
Microwave Irradiation Reactions: Synthesis of Analgesic Drugs  Gholam A. Mirafzal and Jolene M Summer
Over-the-counter analgesics such as aspirin, acetanilide, phenacetin, and acetaminophen are conveniently prepared in a microwave at 30% power for five minutes. Recrystallization from appropriate solvents results in solid products in good to excellent yields.
Mirafzal, Gholam A.; Summer, Jolene M. J. Chem. Educ. 2000, 77, 356.
Drugs / Pharmaceuticals |
Synthesis |
Medicinal Chemistry |
Aromatic Compounds |
Amines / Ammonium Compounds |
Esters
Chemiluminescence Demonstration Illustrating Principles of Ester Hydrolysis Reactions  Andrew G. Hadd, David W. Lehmpuhl, Laura R. Kuck, and John W. Birks
Peroxyoxalate chemiluminescence, the most efficient nonenzymatic chemiluminescence reaction known, is used to demonstrate mechanistic features of analogous ester hydrolysis reactions.
Hadd, Andrew G.; Lehmpuhl, David W.; Kuck, Laura R.; Birks, John W. J. Chem. Educ. 1999, 76, 1237.
Kinetics |
Photochemistry |
Mechanisms of Reactions |
Atomic Properties / Structure |
Esters
Sharpless Asymmetric Dihydroxylation: Effect of Alkene Structure on Rates and Selectivity  Alan C. Spivey, R. Hanson, N. Scorah, and S. J. Thorpe
Each student is assigned an alkene and performs three dihydroxylation reactions: one racemic and two enantioselective variants. The products are characterized by 1H NMR, IR, MS, [a]D20, and chiral chromatography (HPLC or GC). Comparison by the students of their results with those reported in the literature, particularly the extensive work of Sharpless, allows an exploration of the validity of Sharpless's mnemonic for predicting the stereochemical outcome of these reactions.
Spivey, Alan C.; Hanson, R.; Scorah, N.; Thorpe, S. J. J. Chem. Educ. 1999, 76, 655.
Synthesis |
Catalysis |
Stereochemistry |
Organometallics |
Molecular Properties / Structure
The Art and Science of Organic and Natural Products Synthesis  K. C. Nicolaou, E. J. Sorensen, and N. Winssinger
In this article, the history of the art and science of organic and natural products synthesis is briefly reviewed and the state of the art is discussed. The impact of this discipline on biology and medicine is amply demonstrated with examples, and projections for future developments in the field are made.
Nicolaou, K. C.; Sorensen, E. J.; Winssinger, N. J. Chem. Educ. 1998, 75, 1225.
Natural Products |
Synthesis |
Medicinal Chemistry |
Applications of Chemistry |
Drugs / Pharmaceuticals
A Microscale Synthesis of Mauve  Rhonda L. Scaccia, David Coughlin, and David W. Ball
We have reproduced Perkin's synthesis of mauve and have scaled it down to microscale levels. As such, we present a synthesis of mauve that can be performed in a microscale organic chemistry laboratory.
Scaccia, Rhonda L.; Coughlin, David; Ball, David W. J. Chem. Educ. 1998, 75, 769.
Microscale Lab |
Dyes / Pigments |
Applications of Chemistry |
Synthesis
A Simple Organic Microscale Experiment Illustrating the Equilibrium Aspect of the Aldol Condensation  Ernest A. Harrison Jr.
A simple microscale experiment has been developed that illustrates the equilibrium aspect of the aldol condensation by using two versions of the standard preparation of tetraphenylcyclopentadienone from benzil and 1,3-diphenyl- 2-propanone.
Harrison, Ernest A., Jr. J. Chem. Educ. 1998, 75, 636.
Equilibrium |
Reactions |
Mechanisms of Reactions |
Microscale Lab |
Aldehydes / Ketones
Incorporating Organic Name Reactions and Minimizing Qualitative Analysis in an Unknown Identification Experiment  Claire Castro and William Karney
The authors have developed a new type of unknown identification experiment for the introductory organic chemistry laboratory. The unknown sample the student is provided with is the product of an organic name reaction. The student is only informed of the starting material and conditions used in the compound's synthesis, and must then: (1) deduce the compound's structure, (2) determine the name reaction and corresponding mechanism that yields the compound, and (3) present his/her results to the class.
Claire Castro and William Karney. J. Chem. Educ. 1998, 75, 472.
IR Spectroscopy |
NMR Spectroscopy |
Qualitative Analysis |
Nomenclature / Units / Symbols |
Reactions |
Mechanisms of Reactions |
Molecular Properties / Structure
An Aldehyde Derivative  J. Hodge Markgraf and Bo Yoon Choi
A system in which aldehydes are condensed with 1,2-benzenedimethylthiol in the presence of anhydrous ferric chloride on silica gel to give 3-substituted 1,5-dihyhdro-2,4-benzodithiepines. Melting points of the derivatives were taken as a means of identification of unknown compounds.
Markgraf, J. Hodge; Choi, Bo Yoon. J. Chem. Educ. 1998, 75, 222.
Aldehydes / Ketones |
Synthesis
The Diels-Alder Reaction of 2,4-Hexadien-1-ol with Maleic Anhydride: A Novel Preparation for the Undergraduate Organic Chemistry Laboratory Course  Keith F. McDaniel and R. Matthew Weekly
The reaction of 2,4-hexadien-1-ol with maleic anhydride provides an excellent exercise for undergraduate laboratory courses. In addition to the expected Diels-Alder reaction, which takes place readily in refluxing toluene, subsequent intramolecular cleavage of the resulting bicyclic anhydride by the pendant hydroxy group generates a lactone. Thus, two important organic reactions can be carried out in a single laboratory session.
McDaniel, Keith F.; Weekley, R. Matthew. J. Chem. Educ. 1997, 74, 1465.
Synthesis |
NMR Spectroscopy |
Molecular Properties / Structure |
Alcohols
Simple Preparation of Palladium(II) Complexes and Determination of Their Structures by Infrared Spectrosopy  José María Casas and Antonio Martín
The complex [PdCl2(bopy-N,O)] (1) is prepared by addition of the 2-benzoylpyridine, NC5H4 - CO - C6H5 (bopy) ligand to a refluxing suspension of PdCl2 (1:1 molar ratio). The bopy ligand is coordinated in a chelate fashion, but the Pd - O=C bond is weak and easily displaced by ligands resulting complexes cis-[PdCl2(bopy-N)(L)] (L = bopy (2), PPh3 (3)) or [NMe4][PdCl3(bopy-N)].
Casas, Jose Maria; Martin, Antonio. J. Chem. Educ. 1997, 74, 1327.
Coordination Compounds |
Group Theory / Symmetry |
IR Spectroscopy |
Synthesis
An Experiment to Demonstrate Magnetic Nonequivalence in Proton NMR  Christopher J. Welch
The bicyclic compound, 3a,6a-diethoxycarbonyl-2,5-dimethyl-1,4-dioxo-octahydropyrrolo[3,4-c]pyrrole, prepared by a literature procedure is used to demonstrate magnetic nonequivalence for methylene protons in the proton NMR experiment.
Welch, Christopher J. J. Chem. Educ. 1997, 74, 247.
Spectroscopy |
NMR Spectroscopy |
Stereochemistry |
Aldehydes / Ketones
Infrared Spectroscopy: A Versatile Tool in Practical Chemistry Courses   Volker Wiskam, Wolfgang Fichtner, Volker Kramb, Alexander Nintschew, and Jens Stefan Schneider
Procedure for preparing samples of basic inorganic compounds and analyzing them through IR spectroscopy in freshman chemistry.
Wiscamp, Volker; Fichtner, Wolfgang; Kramb, Volker; Nintschew, Alexander; Schneider, Jens Stefan. J. Chem. Educ. 1995, 72, 952.
IR Spectroscopy |
Synthesis |
Coordination Compounds
The Addition of Hydrogen Bromide to Simple Alkenes  Hilton M. Weiss
Synthesis of 1-bromohexane.
Weiss, Hilton M. . J. Chem. Educ. 1995, 72, 848.
Synthesis |
Mechanisms of Reactions |
Addition Reactions |
Alkenes
A Centenary Synthesis of Carone and Dicarvelone  Armstead, D. E. F.
Procedure for synthesizing carone and dicarvelone.
Armstead, D. E. F. J. Chem. Educ. 1995, 72, 550.
Synthesis |
Aldehydes / Ketones
Preparation of (S)-(+)-5,8a-Dimethyl-3,4,8,8a-tetrahydro-1,6(2H,7H)-naphthalenedione: An Undergraduate Experiment in Asymmetric Synthesis  Markgraf, J. Hodge; Fei, John F.; Ruckman, Robert E.
An asymmetric Robinson annelation suitable for the undergraduate organic laboratory.
Markgraf, J. Hodge; Fei, John F.; Ruckman, Robert E. J. Chem. Educ. 1995, 72, 270.
Synthesis |
Chirality / Optical Activity |
Aldehydes / Ketones
High-Temperature Synthesis of Anhydrous CrCl3 and the Thermally Controlled Formation of C6Cl6 and C2Cl6  Stevenson, Cynthia; Rudman, Reuben
Results of a systematic investigation of the synthesis of anhydrous chromium chloride and the various products produced under varying reaction conditions.
Stevenson, Cynthia; Rudman, Reuben J. Chem. Educ. 1994, 71, 704.
Synthesis |
Solid State Chemistry
Nitration of phenols: A two-phase system  Zeegers, Petrus J.
Nitration of phenols is often overlooked in undergraduate organic chemistry courses.
Zeegers, Petrus J. J. Chem. Educ. 1993, 70, 1036.
Phenols |
Aromatic Compounds |
Reactions |
Quantitative Analysis |
Mechanisms of Reactions |
Chromatography |
NMR Spectroscopy
Kinetics of the reaction of p-nitrobenzyl chloride with cyanide ion: An undergraduate organic chemistry experiment  Hurst, Michael O.; Hill, John W.
The title reaction is used to develop an undergraduate organic kinetics experiment in which the student determines the order and rate constant of the reaction, as well as the effect of solvent upon the rate of the reaction.
Hurst, Michael O.; Hill, John W. J. Chem. Educ. 1993, 70, 429.
Reactions |
Rate Law |
Kinetics |
Aromatic Compounds |
Alcohols |
Solutions / Solvents |
Organosulfur Compounds
A laboratory study of 1,3-dipole-dipolarophile addition: An extension of the Diels Alder reaction  Gingrich, Henry L.; Pickering, Miles
Some easy organic reactions that can also be used as the basis for puzzles, or as facile heterocyclic syntheses: an area neglected in the student experiment literature.
Gingrich, Henry L.; Pickering, Miles J. Chem. Educ. 1991, 68, 614.
Mechanisms of Reactions |
Addition Reactions |
Synthesis |
Heterocycles |
Physical Properties |
NMR Spectroscopy
Decarboxylative elimination of 2,3-dibromo-3-phenylpropanoic acid to E or Z 1-bromo-2-phenylethylene (Beta-Bromostyrene): An experiment illustrating solvent effect on the stereochemical course of a reaction  Mestdagh, Helene; Puechberty, Anne
An experiment illustrating solvent effect on the stereochemical course of a reaction.
Mestdagh, Helene; Puechberty, Anne J. Chem. Educ. 1991, 68, 515.
Elimination Reactions |
Alkenes |
Stereochemistry |
Solutions / Solvents
A convenient synthesis of 3,4-pentadien-1-ol from 3-butyn-1-ol: Spectral analysis and unusual durability of the allene moiety  Price, William A.; Patten, Timothy E.
Description of a convenient synthesis of 3,4-pentadien-1-ol from 3-butyn-1-ol: Spectral analysis and unusual durability of the allene moiety.
Price, William A.; Patten, Timothy E. J. Chem. Educ. 1991, 68, 256.
Synthesis |
Alcohols |
Alkenes |
NMR Spectroscopy
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
Three easy puzzles based on the Diels-Alder reaction  Pickering, Miles.
This paper recasts some classic systems so that they can be done at room temperature on a small scale in a large lab course without sophisticated instrumentation. Furthermore, they start the student using experimental results to solve mechanistic problems.
Pickering, Miles. J. Chem. Educ. 1990, 67, 524.
Mechanisms of Reactions |
Stereochemistry
Steric course of lactonization in the deamination of glutamic acid: An organic mechanism experiment  Markgraf, J. Hodge; Davis, Howard A.
The stereochemical consequences of a reaction at a chiral center offer a unique way to distinguish among mechanistic hypothesis.
Markgraf, J. Hodge; Davis, Howard A. J. Chem. Educ. 1990, 67, 173.
Mechanisms of Reactions |
Stereochemistry |
Alcohols
Microscale synthesis and analysis of a dipeptide  Blatchly, Richard A.; Allen, Timothy R.; Bergstrom, Dirk T.; Shinozaki, Yuji
The synthesis of a dipeptide from its component amino acids and its analysis by chiral-phase thin-layer chromatography.
Blatchly, Richard A.; Allen, Timothy R.; Bergstrom, Dirk T.; Shinozaki, Yuji J. Chem. Educ. 1989, 66, 965.
Microscale Lab |
Synthesis |
Proteins / Peptides |
Thin Layer Chromatography |
Amino Acids
Isomerization of dimethyl maleate to dimethyl fumarate: An undergraduate experiment utilizing high performance liquid chromatography  Ledlie, David B.; Wenzel, Thomas J.; Hendrickson, Susan M.
Introduces students to liquid chromatography, the stereoisomerization of alkenes, certain aspects of free radical chemistry, and thermodynamics.
Ledlie, David B.; Wenzel, Thomas J.; Hendrickson, Susan M. J. Chem. Educ. 1989, 66, 781.
HPLC |
Mechanisms of Reactions |
Esters |
Stereochemistry |
Free Radicals |
Alkenes |
Thermodynamics
A tandem Michael-aldol reaction sequence: An undergraduate research organic experiment  Coutlangus, Marilyin L.; Filla, Sandra A.; Rowland, Alex T.
A short reaction sequence that allows students to determine by spectroscopic methods the constitutions of and stereochemistry in the reaction products.
Coutlangus, Marilyin L.; Filla, Sandra A.; Rowland, Alex T. J. Chem. Educ. 1989, 66, 520.
Mechanisms of Reactions |
Spectroscopy |
Stereochemistry |
IR Spectroscopy |
UV-Vis Spectroscopy |
NMR Spectroscopy
The preparation of 4-hydroxy-2,3,4,5-tetraphenyl-2-cyclopenten-1-one and its base catalyzed conversion into 2,3,4,5-tetraphenycyclopentadienone: An organic laboratory experiment   Harrison, Ernest A., Jr.
An organic laboratory experiment that permits direct observation of a pedagogically interesting transformation.
Harrison, Ernest A., Jr. J. Chem. Educ. 1988, 65, 828.
Aldehydes / Ketones |
Phenols |
Alkanes / Cycloalkanes |
IR Spectroscopy |
Synthesis
A synthesis of o-chlorocinnamic acid utilizing a Meerwein reaction. An undergraduate organic experiment  Cleland, George H.
The authors share an experimental procedure that converts an o-chloroaniline to o-chlorocinnamic acid.
Cleland, George H. J. Chem. Educ. 1978, 55, 814.
Carboxylic Acids |
Synthesis
Project for problem-oriented undergraduate organic or integrated undergraduate laboratory  Silveira, Augustine, Jr.
This paper reports on an open-ended project which allows a great degree of flexibility in the laboratory. The project provided about a 6-week study for groups of 24 students each.
Silveira, Augustine, Jr. J. Chem. Educ. 1978, 55, 57.
Synthesis |
Undergraduate Research |
Spectroscopy |
Diastereomers |
Addition Reactions |
MO Theory |
Elimination Reactions |
Thermodynamics |
Kinetics
Substituent effects in electrophilic aromatic substitution. A laboratory in organic chemistry  Gilow, Helmuth
The acid catalyzed bromination of aromatic substrates with hydrobromous acid.
Gilow, Helmuth J. Chem. Educ. 1977, 54, 450.
Molecular Properties / Structure |
Aromatic Compounds |
Electrophilic Substitution |
Mechanisms of Reactions |
Catalysis
Analysis of an important air pollutant: Peroxyacetyl nitrate  Stephens, Edgar R.; Price, Monty A.
Synthesis and IR analysis of peroxyacetyl nitrate (PAN).
Stephens, Edgar R.; Price, Monty A. J. Chem. Educ. 1973, 50, 351.
Atmospheric Chemistry |
Chromatography |
IR Spectroscopy |
Synthesis
Organic chemistry laboratory. A non-traditional approach  Nugent, Maurice J.
A problem-solving approach to the organic chemistry laboratory in which students are asked to identify and then synthesize two unknowns.
Nugent, Maurice J. J. Chem. Educ. 1972, 49, 491.
Synthesis |
Qualitative Analysis
Alkylations in organic chemistry  Mundy, Bradford P.
Examines some of the subtle factors involved in alkylations, including alkylations via enolates, alkylations via enamines, and alkylation of enolates derived from reduction of enone systems.
Mundy, Bradford P. J. Chem. Educ. 1972, 49, 91.
Synthesis |
Alkylation |
Aldehydes / Ketones |
Mechanisms of Reactions
The historical and current interest in coumarin  Abernethy, John Leo
Examines the historic isolation of coumarin, its uses, and an industrial synthesis.
Abernethy, John Leo J. Chem. Educ. 1969, 46, 561.
Applications of Chemistry |
Synthesis
Infrared spectrometry to study second order reaction kinetics  Gastambide, B.; Blanc, J.; Allamagny, Y.
The change studied is a synthesis reaction between menthol and phenyl isocyanate.
Gastambide, B.; Blanc, J.; Allamagny, Y. J. Chem. Educ. 1964, 41, 613.
Spectroscopy |
IR Spectroscopy |
Reactions |
Kinetics |
Synthesis
The amine catalyzed Perkin condensation: A class project  Ketcham, Roger
In this exercise students carry out the amine catalyzed Perkin condensations of substituted benzaldehydes with substituted phenylacetic acids to give alpha-phenyl-cis- and trans-cinnamic acids.
Ketcham, Roger J. Chem. Educ. 1964, 41, 565.
Amines / Ammonium Compounds |
Catalysis |
Reactions |
Synthesis
Student preparation and manipulation of a gasMethyl ethyl ether  Casanova, Joseph, Jr.
This laboratory involves the preparation of methyl ethyl ether by a Williamson synthesis.
Casanova, Joseph, Jr. J. Chem. Educ. 1963, 40, 41.
Ethers |
Synthesis |
Gases