TIGER

Journal Articles: 42 results
Acylation of Ferrocene: A Greener Approach  Kurt R. Birdwhistell, Andy Nguyen, Eric J. Ramos, and Robert Kobelja
This article describes an acylation of ferrocene that is more eco-friendly than the conventional experiment, which has been modified by replacing mineral acid with a polymeric acid catalyst and using microwave instead of conventional heating.
Birdwhistell, Kurt R.; Nguyen, Andy; Ramos, Eric J.; Kobelja, Robert. J. Chem. Educ. 2008, 85, 261.
Catalysis |
Chromatography |
Green Chemistry |
Organometallics |
Synthesis |
Transition Elements |
Brønsted-Lowry Acids / Bases
Microwave-Assisted Organic Synthesis in the Organic Teaching Lab: A Simple, Greener Wittig Reaction  Eric Martin and Cynthia Kellen-Yuen
A microwave-assisted Wittig reaction has been developed for the organic teaching laboratory. Utilizing this technique, a variety of styrene derivatives have been synthesized from aromatic aldehydes in good yields. The mixture of cis and trans alkenes produced also provides instructors with opportunities to emphasize the spectroscopic analysis of product mixtures.
Martin, Eric; Kellen-Yuen, Cynthia. J. Chem. Educ. 2007, 84, 2004.
Aldehydes / Ketones |
Alkenes |
Chromatography |
Green Chemistry |
Mass Spectrometry |
NMR Spectroscopy |
Spectroscopy |
Synthesis
Synthesis and Characterization of Aldol Condensation Products from Unknown Aldehydes and Ketones  Nicholas G. Angelo, Laura K. Henchey, Adam J. Waxman, James W. Canary, Paramjit S. Arora, and Donald Wink
Describes an experiment in which students perform the aldol condensation on an unknown aldehyde and ketone and make use of TLC, column chromatography, recrystallization, and characterization by 1H NMR, GCMS, and FTIR.
Angelo, Nicholas G.; Henchey, Laura K.; Waxman, Adam J.; Canary, James W.; Arora, Paramjit S.; Wink, Donald. J. Chem. Educ. 2007, 84, 1816.
Aldehydes / Ketones |
Chromatography |
Gas Chromatography |
IR Spectroscopy |
Mass Spectrometry |
NMR Spectroscopy |
Spectroscopy |
Thin Layer Chromatography
A Guided-Inquiry Approach to the Sodium Borohydride Reduction and Grignard Reaction of Carbonyl Compounds  Robert E. Rosenberg
Students teams identify unknowns and their reaction products and use their data to deduce that esters are less electrophilic than the other carbonyl compounds present, that Grignard reagents are more nucleophilic than sodium borohydride, and that carboxylic acid derivatives do not undergo the nucleophilic addition reactions that are characteristic of aldehydes and ketones.
Rosenberg, Robert E. J. Chem. Educ. 2007, 84, 1474.
Addition Reactions |
Aldehydes / Ketones |
Esters |
Grignard Reagents |
IR Spectroscopy |
Oxidation / Reduction |
Reactions |
Student-Centered Learning
Using a Premade Grignard Reagent To Synthesize Tertiary Alcohols in a Convenient Investigative Organic Laboratory Experiment  Michael A. G. Berg and Roy D. Pointer
Describes the use of a commercially available Grignard reagent in a Grignard synthesis that avoided the failures typically associated with the Grignard reaction.
Berg, Michael A. G.; Pointer, Roy D. J. Chem. Educ. 2007, 84, 483.
Aldehydes / Ketones |
Grignard Reagents |
IR Spectroscopy |
NMR Spectroscopy |
Organometallics |
Synthesis
A Research-Based Laboratory Course in Organic Chemistry  Thomas A. Newton, Henry J. Tracy, and Caryn Prudenté
Describes the development, implementation, evolution, and evaluation of a unique approach to laboratory instruction in organic chemistry. The new course involves a combinatorial strategy that offers every student a different group of 14 metallole as their personal synthetic target.
Newton, Thomas A.; Tracy, Henry J.; Prudenté, Caryn. J. Chem. Educ. 2006, 83, 1844.
Combinatorial Chemistry |
Organometallics |
Synthesis |
Undergraduate Research
Incorporation of Microwave Synthesis into the Undergraduate Organic Laboratory  Alan R. Katritzky, Chunming Cai, Meghan D. Collins, Eric F. V. Scriven, Sandeep K. Singh, and E. Keller Barnhardt
Describes a simple way to effectively implement microwave synthesis into the undergraduate organic laboratory curriculum.
Katritzky, Alan R.; Cai, Chunming; Collins, Meghan D.; Scriven, Eric F. V.;Singh, Sandeep K.; Barnhardt, E. Keller. J. Chem. Educ. 2006, 83, 634.
Aromatic Compounds |
Laboratory Equipment / Apparatus |
Reactions |
Synthesis
Grubbs's Cross Metathesis of Eugenol with cis-2-Butene-1,4-diol To Make a Natural Product. An Organometallic Experiment for the Undergraduate Lab   Douglass F. Taber and Kevin J. Frankowski
Describes the ruthenium catalyzed cross metathesis of eugenol with cis-1,4-butenediol. The experiment is an excellent example of the powerful selectivity possible with the Grubbs' catalyst, demonstrating the preference for trans over cis alkene formation and for cross metathesis over homodimerization.
Taber, Douglass F.; Frankowski, Kevin J. J. Chem. Educ. 2006, 83, 283.
Alkenes |
Catalysis |
IR Spectroscopy |
Mass Spectrometry |
Mechanisms of Reactions |
Microscale Lab |
Natural Products |
NMR Spectroscopy |
Organometallics |
Stereochemistry |
Synthesis |
Thin Layer Chromatography |
Transition Elements
Quantitative Thermodynamic Descriptions of Aromaticity. A Computational Exercise for the Organic Chemistry Laboratory  Terrence Gavin
This article describes an exercise that enables students to establish a quantitative scale of aromaticity via computer-driven quantum mechanical calculations using Spartan software. The method utilizes a group of analogous isodesmic reactions from which the energy difference between two isomeric cyclic polyenes is calculated from their optimized geometries. The energy differences found are used to characterize structures as aromatic, nonaromatic, or antiaromatic depending on the value obtained. A representative group of structures, including hydrocarbons, hydrocarbon ions, and heterocycles are studied.
Gavin, Terrence. J. Chem. Educ. 2005, 82, 953.
Aromatic Compounds |
Computational Chemistry |
Heterocycles |
Molecular Modeling |
Thermodynamics
A Convenient Method for Dispensing Organometallic Reagents  Thomas A. Newton
The construction of a simple apparatus for dispensing air-sensitive organometallic reagents is described.
Newton, Thomas A. J. Chem. Educ. 2005, 82, 936.
Organometallics |
Instrumental Methods |
Synthesis
Solvent-Free Wittig Reaction: A Green Organic Chemistry Laboratory Experiment  Sam H. Leung and Stephen A. Angel
In this experiment (E)- and (Z)-1-(4-bromophenyl)-2-phenylethene are synthesized by a solvent-free Wittig reaction. The reaction is effected by grinding the reactants in a mortar with a pestle. Both the E and Z isomers of the product are produced as evidenced by thin-layer chromatography and 1H NMR analysis. The E isomer is isolated by crystallization with ethanol in this experiment. In addition to learning about the Wittig reaction, students are also introduced to the ideas of mechanochemistry and green chemistry.
Leung, Sam H.; Angel, Stephen A. J. Chem. Educ. 2004, 81, 1492.
Chromatography |
Green Chemistry |
Microscale Lab |
NMR Spectroscopy |
Synthesis |
Reactions |
Aldehydes / Ketones |
Alkenes
Dendrimers: Branching Out of Polymer Chemistry  Eric E. Simanek and Sergio O. Gonzalez
Addresses synthetic concepts surrounding dendrimers including the use of protecting groups, functional group interconversions, and convergent and divergent synthetic strategies.
Simanek, Eric E.; Gonzalez, Sergio O. J. Chem. Educ. 2002, 79, 1222.
Materials Science |
Synthesis |
Molecular Properties / Structure |
Addition Reactions |
Aromatic Compounds |
Alkylation |
Nucleophilic Substitution
Discovery-Oriented Approach To Organic Synthesis: Tandem Aldol Condensation-Michael Addition Reactions. Identifying Diastereotopic Hydrogens in an Achiral Molecule by NMR Spectroscopy  Nanette Wachter-Jurcsak and Kendra Reddin
Procedure illustrating aldol condensation and Michael addition reactions.
Wachter-Jurcsak, Nanette; Reddin, Kendra. J. Chem. Educ. 2001, 78, 1264.
NMR Spectroscopy |
Synthesis |
Stereochemistry |
Aromatic Compounds |
Aldehydes / Ketones |
Addition Reactions |
Mechanisms of Reactions
Suzuki Cross-Coupling Reactions: Synthesis of Unsymmetrical Biaryls in the Organic Laboratory  Christopher S. Callam and Todd L. Lowary
Laboratory that exposes students to organometallic chemistry and application of the Suzuki reaction.
Callam, Christopher S.; Lowary, Todd L. J. Chem. Educ. 2001, 78, 947.
Aromatic Compounds |
Metals |
Synthesis |
Organometallics |
Transition Elements |
Mechanisms of Reactions
Diastereoselective Synthesis of (+/-)-1,2-Diphenyl-1,2-propanediol. A Discovery-Based Grignard Reaction Suitable for a Large Organic Lab Course  James A. Ciaccio, Roxana P. Bravo, Antoinette L. Drahus, John B. Biggins, Rosalyn V. Concepcion, and David Cabrera
An experiment that probes the diastereoselectivity of the reaction between a Grignard reagent and a common, inexpensive alpha-chiral ketone; introduces students to pi-facial discrimination by having them establish the stereochemical course of kinetically controlled nucleophilic addition to a carbonyl.
Ciaccio, James A.; Bravo, Roxana P.; Drahus, Antoinette L.; Biggins, John B.; Concepcion, Rosalyn V.; Cabrera, David. J. Chem. Educ. 2001, 78, 531.
Mechanisms of Reactions |
Synthesis |
Organometallics |
Stereochemistry |
Grignard Reagents |
Aldehydes / Ketones
Molecular Orbital Animations for Organic Chemistry  Steven A. Fleming, Greg R. Hart, and Paul B. Savage
Introduces the application of highest occupied and lowest unoccupied molecular orbitals (HOMOs and LUMOs) in animated form.
Fleming, Steven A.; Hart, Greg R.; Savage, Paul B. J. Chem. Educ. 2000, 77, 790.
MO Theory |
Molecular Modeling |
Mathematics / Symbolic Mathematics |
Mechanisms of Reactions |
Electrophilic Substitution |
Nucleophilic Substitution
Keep Going with Cyclooctatetraene!  Addison Ault
This paper shows how some simple properties of cyclooctatetraene can indicate important ideas about the structure of cyclooctatetraene.
Ault, Addison. J. Chem. Educ. 2000, 77, 55.
Aromatic Compounds |
NMR Spectroscopy |
Mechanisms of Reactions |
Molecular Properties / Structure
The Wittig synthesis of alkenes by phase-transfer catalysis: The syntheses of 4,4'-dichlorostilbenes and of E, E-1,4 -diphenylbutadiene   Breuer, Stephen W.
The syntheses of 4,4'-dichlorostilbenes and of E, E-1,4 -diphenylbutadiene.
Breuer, Stephen W. J. Chem. Educ. 1991, 68, A58.
Synthesis |
Microscale Lab |
Alkenes |
Aromatic Compounds
Synthesis of an isolable quinodimethane  Rosenfeld, Stuart; VanDyke, Sarah
A new lab sequence where the primary goal is to generate a situation in which students have the ability to extend knowledge independently using the tools and models available following a yearlong organic chemistry course. To accomplish this, the authors created a structured lab within a relatively poorly studied area so that some independent work could be done in a setting that is neither contrived nor too loosely defined to afford a useful experience.
Rosenfeld, Stuart; VanDyke, Sarah J. Chem. Educ. 1991, 68, 691.
Aromatic Compounds |
Undergraduate Research
Synthesis of a bicyclo[2.2.1]heptene Diels-Alder adduct: An organic chemistry experiment utilizing NMR spectroscopy to assign endo stereochemistry  Harrison, Ernest A., Jr.
An organic chemistry experiment utilizing NMR spectroscopy to assign endo stereochemistry via synthesis of a bicyclo[2.2.1]heptene Diels-Alder adduct.
Harrison, Ernest A., Jr. J. Chem. Educ. 1991, 68, 426.
Alkanes / Cycloalkanes |
Synthesis |
Alkenes |
Aromatic Compounds |
NMR Spectroscopy |
Thin Layer Chromatography
Friedel Crafts acylation and alkylation with acid chlorides  Jarret, Ronald M.; Keil, Nora; Allen, Susan; Cannon, Lisa; Coughlan, Julie; Cusumano, Leonarda; Nolan, Brian
A shortened Friedel-Crafts experiment; the extra time available allows for additional experiments designed to illustrate the finer points of the reaction, such as electrophile rearrangements and decarbonylation of acyl cations.
Jarret, Ronald M.; Keil, Nora; Allen, Susan; Cannon, Lisa; Coughlan, Julie; Cusumano, Leonarda; Nolan, Brian J. Chem. Educ. 1989, 66, 1056.
Electrophilic Substitution |
Aromatic Compounds |
Mechanisms of Reactions |
Microscale Lab
The early history of organotin chemistry  Nicholson, John W.
Survey of the first 35 years of organotin chemistry.
Nicholson, John W. J. Chem. Educ. 1989, 66, 621.
Organometallics
Organic lecture demonstrations  Silversmith, Ernest F.
Organic chemistry may not be known for its spectacular, attention getting chemical reactions. Nevertheless, this author describes a few organic chemistry reactions that put points across and generate interest. This article provides a convenient sources of demonstrations and urges others to add to the collection. Demonstrations concerning: carbohydrates, spectroscopy, proteins, amines, carbohydrates, carboxylic acids, and much more.
Silversmith, Ernest F. J. Chem. Educ. 1988, 65, 70.
Molecular Properties / Structure |
Nucleophilic Substitution |
Acids / Bases |
Physical Properties |
Alkenes |
Stereochemistry |
Enantiomers |
Chirality / Optical Activity |
Aldehydes / Ketones |
Alcohols
Oxidation numbers and their limitations  Woolf, A. A.
An in-depth look at oxidation numbers of various elements in a number of different compounds.
Woolf, A. A. J. Chem. Educ. 1988, 65, 45.
Organometallics |
Oxidation State |
Oxidation / Reduction
Microscale organic laboratory: IV: A simple and rapid procedure for carrying out Wittig reactions  Pike, R. M.; Mayo, D. W.; Butcher, D. W.; Butcher, S. S.; Hinkle, R. J.
This paper offers two examples that illustrate a new synthetic method. This synthesis is the first feasible preparation of a particular group available for the introductory organic laboratory.
Pike, R. M.; Mayo, D. W.; Butcher, D. W.; Butcher, S. S.; Hinkle, R. J. J. Chem. Educ. 1986, 63, 917.
Synthesis |
Aromatic Compounds |
Heterocycles |
Alkenes |
Alcohols
Starting recalcitrant Grignard reactions  Clough, S.; Goldman, E.; Williams, S.; George, B.
This note offers a tip on starting a Gringard reaction.
Clough, S.; Goldman, E.; Williams, S.; George, B. J. Chem. Educ. 1986, 63, 176.
Laboratory Management |
Grignard Reagents |
Organometallics
An undergraduate laboratory program project involving photocyclizations in independent syntheses of novel chrysenes and phenanthrenes  Letcher, R. M.
This experiment attempts to fulfill such objectives as providing meaningful and viable preparative reactions, providing an opportunity for independent laboratory work within a project framework and under conditions of nearly equal opportunity and experience.
Letcher, R. M. J. Chem. Educ. 1981, 58, 1020.
Undergraduate Research |
Synthesis |
Aromatic Compounds |
Photochemistry |
Diastereomers |
NMR Spectroscopy |
Alcohols |
Thin Layer Chromatography
Structure-resonance theory for pericyclic transition states  Herndon, William C.
The purpose of this article is to show that structure-resonance theory can be used to understand the effects of structure or substituents on the rates of thermal pericyclic reactions.
Herndon, William C. J. Chem. Educ. 1981, 58, 371.
Aromatic Compounds |
Resonance Theory |
Molecular Properties / Structure
Diphenylbutadienes syntheses by means of the Wittig reaction: Experimental introduction to the use of phase transfer catalysis  Gillois, J.; Guillerm, G.; Stephen, E.; Vo-Quang, L.
Intended as a project carried out by students at the end of introductory organic chemistry.
Gillois, J.; Guillerm, G.; Stephen, E.; Vo-Quang, L. J. Chem. Educ. 1980, 57, 161.
Synthesis |
Catalysis |
Alkenes |
Aldehydes / Ketones |
Stereochemistry
Synthesis of 4-methyl-3-heptanol and 4-methyl-3-heptanone. Two easily synthesized insect pheromones  Einterz, Robert M.; Ponder, Jay W.; Lenox, Ronald S.
A two step reaction sequence involving the Grignard synthesis of an alcohol followed by oxidation of this alcohol to the corresponding ketone.
Einterz, Robert M.; Ponder, Jay W.; Lenox, Ronald S. J. Chem. Educ. 1977, 54, 382.
Natural Products |
Synthesis |
Applications of Chemistry |
Grignard Reagents |
Mechanisms of Reactions |
Stereochemistry |
Alcohols |
Aldehydes / Ketones
Syntheses and rearrangements of cage molecules related to cubane  Jefford, Charles W.
This article looks at the synthesis of cubane, basketene, miscellaneous homocubane chemistry, snoutene, triqunacene, hypostrophene, tris-homocubane, and catalysis by transition metals.
Jefford, Charles W. J. Chem. Educ. 1976, 53, 477.
Catalysis |
Transition Elements |
Alkenes |
Synthesis |
Aromatic Compounds |
Heterocycles |
Alcohols
Imidazole - Versatile today, prominent tomorrow  Matuszak, C. A.; Matuszak, A. J.
Imidazole chemistry has pedagogical utility for all the organic chemistry students pursing careers in the life sciences.
Matuszak, C. A.; Matuszak, A. J. J. Chem. Educ. 1976, 53, 280.
Grignard Reagents |
Aromatic Compounds |
Heterocycles |
Phenols |
Acids / Bases |
Catalysis |
Coordination Compounds |
Hydrogen Bonding
Experimental illustration of chemical principles in organic chemistry lectures  Haberfield, Paul
Lists a series of demonstrations used in the second semester of a one year organic chemistry course.
Haberfield, Paul J. Chem. Educ. 1972, 49, 702.
Electrophilic Substitution |
Aromatic Compounds |
Amines / Ammonium Compounds |
Nucleophilic Substitution
Fluorine compounds as teaching aids in organic theory  Young, John A.
Fluorine compounds do obey the fundamental tenets of organic theory, but their frequent reversal of polarity, relative to hydrocarbon analogs, and the change in emphasis from a positive hydrogen ion to a negative fluoride ion allow the instructor to frame questions that demand reasoning rather than reiteration on the part of the student.
Young, John A. J. Chem. Educ. 1970, 47, 733.
Aromatic Compounds |
Mechanisms of Reactions
The photoaddition of maleic anhydride to benzene: A simple organic experiment in a complicated system  Bozak, R. E.; Alvarez, V. E.
Presents the photochemical synthesis of benzopinacol as a pedagogical example of organic photochemistry suitable for the first-year organic course.
Bozak, R. E.; Alvarez, V. E. J. Chem. Educ. 1970, 47, 589.
Photochemistry |
Aromatic Compounds |
Synthesis
One hundred years of organosilicon chemistry  Muller, Richard
Summarizes the history organosilicon chemistry to commemorate the early contributions of Charles Friedel and James Mason Crafts.
Muller, Richard J. Chem. Educ. 1965, 42, 41.
Organometallics
A pseudo first-order-second-order kinetics experiment: An illustration of the Guggenheim method  Ahmad, Mushlaq; Hamer, Jan
The rate of one of the typical reactions of the aromatic nitroso group is determined spectrophotometrically employing the Guggenheim method.
Ahmad, Mushlaq; Hamer, Jan J. Chem. Educ. 1964, 41, 249.
Kinetics |
Rate Law |
Aromatic Compounds |
Spectroscopy
The pyrolytic decomposition of carboxylate salts to ketones  Schultz, H. P.; Sichels, J. P.
Suggestions for research to accompany a previously published article.
Schultz, H. P.; Sichels, J. P. J. Chem. Educ. 1963, 40, A463.
Undergraduate Research |
Reactions |
Aldehydes / Ketones
Multicenter and assisted mechanistic pathways in the reactions of organometallic compounds  Dessy, Raymond E.; Paulik, Frank
Examines a variety of nucleophilic and electrophilic, multicenter and assisted mechanistic pathways in the reactions of organometallic compounds.
Dessy, Raymond E.; Paulik, Frank J. Chem. Educ. 1963, 40, 185.
Organometallics |
Mechanisms of Reactions |
Nucleophilic Substitution |
Electrophilic Substitution
The chemistry of benzyne  Bunnett, Joseph F.
Examines the chemistry of benzyne and alkynes.
Bunnett, Joseph F. J. Chem. Educ. 1961, 38, 278.
Aromatic Compounds |
Reactions |
Mechanisms of Reactions |
Alkynes
The organization of subject matter in elementary organic chemistry  MacKenzie, Charles A.
Describes a curricular approach in which aliphatic and aromatic compounds are treated simultaneously rather than separately.
MacKenzie, Charles A. J. Chem. Educ. 1953, 30, 243.
Aromatic Compounds |
Alkanes / Cycloalkanes
The Friedel-Crafts reaction in elementary organic laboratories  Wright, Oscar L.; Fuhlhage, Donald; Sheridan, Earl
Presents a modification of the Perrier ketone synthesis.
Wright, Oscar L.; Fuhlhage, Donald; Sheridan, Earl J. Chem. Educ. 1952, 29, 620.
Reactions |
Aldehydes / Ketones |
Synthesis