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Journal Articles: 30 results
Identification of Secondary Metabolites in Citrus Fruit Using Gas Chromatography and Mass Spectroscopy  Jean-Michel Lavoie, Esteban Chornet, and André Pelletier
Using a simple extraction and a gas chromatograph coupled with a mass spectrometer, this protocol allows students in analytical or organic chemistry to quantify and qualify monoterpenes from the peels of limes, grapefruits, and oranges.
Lavoie, Jean-Michel; Chornet, Esteban; Pelletier, André. J. Chem. Educ. 2008, 85, 1555.
Alkenes |
Food Science |
Gas Chromatography |
Mass Spectrometry |
Natural Products |
Plant Chemistry |
Qualitative Analysis |
Quantitative Analysis
The Aromaticity of Pericyclic Reaction Transition States  Henry S. Rzepa
Presents an approach that combines two fundamental concepts in organic chemistry, chirality and aromaticity, into a simple rule for stating selection rules for pericyclic reactions in terms of achiral Hckel-aromatic and chiral Mbius-aromatic transition states.
Rzepa, Henry S. J. Chem. Educ. 2007, 84, 1535.
Alkanes / Cycloalkanes |
Alkenes |
Aromatic Compounds |
Mechanisms of Reactions |
Stereochemistry
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
A Template-Controlled Solid-State Reaction for the Organic Chemistry Laboratory  Tomislav Friscic, Tamara D. Hamilton, Giannis S. Papaefstathiou, and Leonard R. MacGillivray
Describes a laboratory experiment that employs linear hydrogen-bond templates to direct [2 + 2] photodimerization in the solid state. The experiment introduces undergraduates to supramolecular and solid-state chemistry, as well as aspects of green chemistry.
Friscic, Tomislav; Hamilton, Tamara D.; Papaefstathiou, Giannis S.; MacGillivray, Leonard R. J. Chem. Educ. 2005, 82, 1679.
Green Chemistry |
Solid State Chemistry |
Crystals / Crystallography |
Alkenes |
Alkanes / Cycloalkanes |
Hydrogen Bonding |
Materials Science |
NMR Spectroscopy
Diels–Alder Synthesis of endo-cis-N-Phenylbicyclo[2.2.2]oct-5-en-2,3-dicarboximide  Marsha R. Baar and Kristin Wustholz
endo-cis-N-Phenylbicyclo[2.2.2]oct-5-en-2,3-dicarboximide was synthesized by a DielsAlder cycloaddition of 1,3-cyclohexadiene and N-phenylmaleimide in ethyl acetate. 1,3-Cyclohexadiene and N-phenylmaleimide were selected to illustrate the Alder rule, which reflects a preference for endo products and to overcome the difficulties associated with the traditional combination of 1,3-cyclopentadiene and maleic anhydride.
Baar, Marsha R.; Wustholz, Kristin. J. Chem. Educ. 2005, 82, 1393.
Asymmetric Synthesis |
Microscale Lab |
Stereochemistry |
Addition Reactions |
Alkenes |
IR Spectroscopy |
NMR Spectroscopy
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
A Substitute for “Bromine in Carbon Tetrachloride”  Joshua M. Daley and Robert G. Landolt
Benzotrifluoride (BTF) is a suitable solvent substitute for carbon tetrachloride in experiments requiring application of bromine (Br2) in free radical or addition reactions with organic substrates. A 1 M solution of Br2 in BTF may be used to distinguish hydrocarbons based on the ease of abstraction of hydrogen atoms in thermally or light-induced free radical substitutions. Efficacy of minimization of solvent use, by aliquot addition to neat samples, has been established.
Daley, Joshua M.; Landolt, Robert G. J. Chem. Educ. 2005, 82, 120.
Alkenes |
Free Radicals |
Green Chemistry |
Qualitative Analysis |
Reactions
Cis and Trans Isomerization in Cyclic Alkenes: A Topic for Discovery Using the Results of Molecular Modeling  Susan E. Barrows and Thomas H. Eberlein
This article describes an activity in which students are led to discover the fundamental reasons behind the unusual instability of the trans isomers in medium-sized cycloalkenes by using the results of molecular modeling. Notably, students will make the unexpected discovery that twisting about p bonds is perhaps more facile than they had been led to believe.
Barrows, Susan E.; Eberlein, Thomas H. J. Chem. Educ. 2004, 81, 1529.
Covalent Bonding |
Computational Chemistry |
Molecular Modeling |
Alkenes |
Molecular Properties / Structure
Regioselective Synthesis of a Stereodefined Heterocyclic Push–Pull Alkene. 1H NMR Studies and Two-Dimensional TLC Illustrating Z/E Isomerization  Rade Markovi, Marija Baranac, Vesna Jovanovi, and Zdravko Dambaski
Facile and direct regioselective synthesis of the 4-oxothiazolidine derivative from inexpensive chemicals as an example of kinetic versus thermodynamic control is described.
Markovi, Rade; Baranac, Marija; Jovanovi, Vesna; Dambaski, Zdravko. J. Chem. Educ. 2004, 81, 1026.
Heterocycles |
Alkenes |
Stereochemistry |
Synthesis |
NMR Spectroscopy
The Study of Elimination Reactions Using Gas Chromatography: An Experiment for the Undergraduate Organic Laboratory  Devin Latimer
This article describes an investigation of elimination reactions of alkyl halides. 1-Bromopentane or 2-bromopentane are reacted with either sodium ethoxide or potassium tert-butoxide. Gas chromatography is used to monitor the relative amounts of 1-pentene, (E)-2-pentene, and (Z)-2-pentene produced.
Latimer, Devin. J. Chem. Educ. 2003, 80, 1183.
Chromatography |
Instrumental Methods |
Synthesis |
Gas Chromatography |
Elimination Reactions |
Mechanisms of Reactions |
Alkenes |
Stereochemistry
Organic Functional Group Playing Card Deck  Michael J. Welsh
Organic functional group playing card deck used for review of the name and structure of organic functional groups that can be used to play any game that a normal deck of cards is used for.
Welsh, Michael J. J. Chem. Educ. 2003, 80, 426.
Nomenclature / Units / Symbols |
Nonmajor Courses |
Enrichment / Review Materials |
Alcohols |
Aldehydes / Ketones |
Alkanes / Cycloalkanes |
Alkenes |
Alkynes |
Amides |
Amines / Ammonium Compounds |
Aromatic Compounds |
Carboxylic Acids |
Esters |
Ethers |
Mechanisms of Reactions |
Synthesis
Fractional Distillation and GC Analysis of Hydrocarbon Mixtures  Craig J. Donahue
Separating and identifying the components of a three-hydrocarbon mixture through fractional distillation and gas chromatography.
Donahue, Craig J. J. Chem. Educ. 2002, 79, 721.
Chromatography |
Gas Chromatography |
Separation Science |
Alkanes / Cycloalkanes |
Alkenes |
Aromatic Compounds |
IR Spectroscopy |
NMR Spectroscopy |
Qualitative Analysis
Colorful Azulene and Its Equally Colorful Derivatives  Robert S. H. Liu
Analysis of azulene and related compounds for an explanation of their respective colors.
Liu, Robert S. H. J. Chem. Educ. 2002, 79, 183.
Atomic Properties / Structure |
MO Theory |
UV-Vis Spectroscopy |
Aromatic Compounds |
Alkenes
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
Photodimerization of Maleic Anhydride  Zhang, Zhijun
Why the photodimerization of maleic anhydride produces the cis, tans, cis product.
Zhang, Zhijun J. Chem. Educ. 1998, 75, 1515.
Photochemistry |
Stereochemistry |
Molecular Properties / Structure |
Alkenes
S. M. Tanatar and His Contribution to the Field of Thermal Rearrangements  Ludmila Birladeanu
Thermal rearrangements constitute an important chapter in organic chemistry. Surprisingly, the name of its discoverer remains unknown. The present article is meant to remedy this situation by describing some of the work of the 19th century Russian chemist S. M. Tanatar (1849 - 1917) who, based on the thermochemical data provided by Berthelot, envisaged the possibility of transforming cyclopropane into propene under the influence of heat alone.
Birladeanu, Ludmila. J. Chem. Educ. 1998, 75, 603.
Gases |
Thermodynamics |
Synthesis |
Alkanes / Cycloalkanes |
Alkenes
A History of the Double-Bond Rule  Bernard E. Hoogenboom
From his experience as an industrial chemist, Otto Schmidt recognized the bond weakening in hydrocarbons and in 1932 postulated the "Double-Bond Rule," stating that the presence of a double bond in a hydrocarbon has an alternating strengthening and weakening effect on single bonds throughout the molecule, diminishing with distance from the double bond.
Hoogenboom, Bernard E. J. Chem. Educ. 1998, 75, 596.
Learning Theories |
Mechanisms of Reactions |
Alkenes
Old MacDonald Named a Compound: Branched Enynenynols  Dennis Ryan
An imaginary teacher of organic chemistry thinks up some whimsical compounds for his students to name using IUPAC nomenclature rules.
Ryan, Dennis. J. Chem. Educ. 1997, 74, 782.
Learning Theories |
Nomenclature / Units / Symbols |
Alcohols |
Alkenes |
Alkynes |
Molecular Properties / Structure
Preparation and Solution Polymerization of Diacetylenes  Bruce A. Hathaway and Angela M. Scates
Most published student laboratory syntheses of symmetrical diacetylenes follow Hay's procedure, with some modifications for using air as a source of oxygen. We report a simpler procedure, which has been useful in preparing a variety of diacetylenes. In addition, we have developed conditions suitable for solution polymerization of these diacetylenes to PDA's, using short-wave UV light.
Hathaway, Bruce A.; Scates, Angela M. J. Chem. Educ. 1997, 74, 111.
Synthesis |
Alkenes
Playing with the Soccer Ball-an Experimental Introduction to Fullerene Chemistry  Achim Hildebrand, Uwe Hilgers, Rudiger Blume, Dagmar Wiechoczek,
For the first time a selection of simple experiments with C60 on high-school and university level are presented: the bromination with Winkler's solution, hydroxylation with an alkaline permanganate solution, cycloadditions of dichlorcarbene and cyclopentadiene and the formation of a molecular complex with o-dimethoxybenzene.
Hildebrand, Achim; Hilgers, Uwe; Blume, Rudiger; Wiechoczek, Dagmar. J. Chem. Educ. 1996, 73, 1066.
Alkenes
Using High Performance Liquid Chromatography to Determine the C60:C70 Ratio in Fullerene Soot: An Undergraduate Chemistry Lab  Michael C. Zumwalt and M. Bonner Denton
Apparatus for producing fullerene soot and procedure for determining its C60-C70 ratio.
Zumwalt, Michael C.; Denton, M. Bonner. J. Chem. Educ. 1995, 72, 939.
Chromatography |
Separation Science |
Main-Group Elements |
Laboratory Equipment / Apparatus |
Alkenes |
HPLC |
Quantitative Analysis
Quantitative analysis by FTIR: Thin films of copolymers of ethylene and vinyl acetate.  Mathias, Lon J.; Hankins, Marie G.; Bertolucci, Craig M.; Grubb, Tina L.; Muthiah, Jeno.
Quantitation of coploymers of ethylene and vinyl acetate using FTIR.
Mathias, Lon J.; Hankins, Marie G.; Bertolucci, Craig M.; Grubb, Tina L.; Muthiah, Jeno. J. Chem. Educ. 1992, 69, A217.
IR Spectroscopy |
Fourier Transform Techniques |
Quantitative Analysis |
Alkenes |
Carboxylic Acids
C60 and C70 made simply.  Craig, Norman C.; Gee, Gilbert C.; Johnson, Adam R.
Procedure and apparatus for synthesizing C60 and C70.
Craig, Norman C.; Gee, Gilbert C.; Johnson, Adam R. J. Chem. Educ. 1992, 69, 664.
Laboratory Equipment / Apparatus |
Synthesis |
Alkenes
The diverse nature of the C6H6 molecule  Potgeiter, J. H.
The purpose of this discussion is to show that C6H6 describes more than just one kind of benzene.
Potgeiter, J. H. J. Chem. Educ. 1991, 68, 280.
Aromatic Compounds |
Alkenes |
Reactions |
Constitutional Isomers
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
A safe, convenient method of generating bromine for qualitative analysis  Slayden, Suzauee W.; Do, Thuy H.; Smiley, Kimberly Y.; Nelson, Donna J.
A safe, convenient method of generating bromine used as a qualitative test for unsaturation, active methylene groups, phenols, and amines.
Slayden, Suzauee W.; Do, Thuy H.; Smiley, Kimberly Y.; Nelson, Donna J. J. Chem. Educ. 1987, 64, 368.
Qualitative Analysis |
Alkenes |
Phenols |
Amines / Ammonium Compounds |
Laboratory Management
Balloon models for organic molecules  Niac, G.
A balloon model can be used to demonstrate properties of small, organic molecules.
Niac, G. J. Chem. Educ. 1978, 55, 303.
Molecular Properties / Structure |
Alcohols |
Alkenes |
VSEPR Theory
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
Indene reactions: An organic chemistry laboratory problem  Garrison, James A.
Students are given a problem in which they are to determine which of two published accounts of reaction products involving derivatives of idene is correct.
Garrison, James A. J. Chem. Educ. 1970, 47, 300.
Alkenes |
Alcohols
Polymerization of ethylene at atmospheric pressure: A demonstration using a "Ziegler" type catalyst  Zilkha, Albert; Calderon, Nissim; Rabani, Joseph; Frankel, Max
A simple experiment on the polymerization of ethylene at atmospheric pressure is described using a "Ziegler" type catalyst prepared from amyl lithium and titanium tetrachloride.
Zilkha, Albert; Calderon, Nissim; Rabani, Joseph; Frankel, Max J. Chem. Educ. 1958, 35, 344.
Polymerization |
Reactions |
Catalysis |
Alkenes