| Journal Articles: 20 results |
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Catalytic Hydrogenation of Maleic Acid at Moderate Pressures Kwesi Amoa
This article demonstrates the reduction of maleic acid in about 90 minutes using moderate-pressure catalytic hydrogenation.
Amoa, Kwesi. J. Chem. Educ. 2007, 84, 1948.
Alkenes |
Catalysis |
Chromatography |
IR Spectroscopy |
Laboratory Equipment / Apparatus |
Spectroscopy |
Thin Layer Chromatography
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Quantitative Measurement of Trans-Fats by Infrared Spectroscopy Edward B. Walker, Don R. Davies, and Mike Campbell
FTIR-ATR spectroscopy provides an efficient analytical tool to measure the percentage of trans-fat in several commercially available lipids and the degree of alkene isomerization induced by brominationdebromination chemical reactions.
Walker, Edward B.; Davies, Don R.; Campbell, Mike. J. Chem. Educ. 2007, 84, 1162.
Alkenes |
Calibration |
Food Science |
Instrumental Methods |
IR Spectroscopy |
Lipids |
Quantitative Analysis |
Fatty Acids
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Stereospecific Synthesis of the Geometrical Isomers of a Natural Product T. Grove, D. DiLella, and E. Volker
Presents an experiment for the synthesis of (Z) and (E) isomers that is presented to students as a puzzle in which they must determine the identity of the major component in anise oil. A necessary part of the analysis is the preparation the (E) and (Z) isomers of anethole. Molecular modeling is used to explore the conformation of and energy difference between isomers.
Grove, T.; DiLella, D.; Volker, E. J. Chem. Educ. 2006, 83, 1055.
Alkenes |
Computational Chemistry |
Gas Chromatography |
IR Spectroscopy |
NMR Spectroscopy |
Stereochemistry |
Synthesis
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Ozonolysis Problems That Promote Student Reasoning Ray A. Gross Jr.
The structural features inherent in acyclic monoterpenes that follow the isoprene rule often lead to unique sets of ozonolysis products from which their structures, excluding stereochemistry, can be determined from molecular formulas only. This article shows how students may elucidate the structures of these compounds by analysis of the oxidative and reductive workup products.
Gross, Ray A., Jr. J. Chem. Educ. 2006, 83, 604.
Aldehydes / Ketones |
Alkenes |
Alkynes |
Carboxylic Acids |
Oxidation / Reduction |
Student-Centered Learning
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Cis and Trans Isomers of Cycloalkenes Susan E. Barrows and Thomas H. Eberlein
The purpose of this article is to provide that analysis. In order for a cycloalkene to accommodate a trans double bond one or more of the following nonideal geometries must occur: a twisted p bond; pyramidal sp2-carbon atoms; nonideal sp3 bond angles; or longer than normal CC single and double bonds. This article provides a list of experimentally determined relative energies of the cis and trans isomers within the series cycloheptenecycloundecene, along with computationally derived energies at several levels of theory. It also examines the geometric distortions through which cycloalkenes relieve the strain introduced by a trans double bond.
Barrows, Susan E.; Eberlein, Thomas H. J. Chem. Educ. 2005, 82, 1334.
Computational Chemistry |
Molecular Modeling |
Alkenes |
Diastereomers
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Understanding Rotation about a C=C Double Bond Susan E. Barrows and Thomas H. Eberlein
We present a simple method of introducing the concept of a flexible C=C pi bond into beginning organic chemistry courses. We report the energetic demands of partial twisting about the C=C bond in 2-butene as calculated using DFT, LMP2, and MCSCF methods. Finally, using the results of these calculations, we assessed the degree of strain introduced by the twisted nature of the C=C bond in trans cycloalkenes.
Barrows, Susan E.; Eberlein, Thomas H. J. Chem. Educ. 2005, 82, 1329.
Computational Chemistry |
Molecular Mechanics / Dynamics |
Molecular Modeling |
Alkenes
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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
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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
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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
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On the Disproportionations of Cyclohexene and Related Compounds Alex Bunjes, Ingo Eilks, Manfred Pahlke, and Bernd Ralle*
The catalytic hydrogenation of liquid hydrocarbons is easy to realize in a simple laboratory experiment using a palladium catalyst. In the case of hydrogenation cyclohexen or cyclohexadiene in addition to the expected finding of cyclohexane among the hydrogenation products, the formation of benzene can be observed. In absence of hydrogen, the disproportionation of both starting materials to cyclohexane and benzene takes place.
Bunjes, Alex; Eilks, Ingo; Pahlke, Manfred; Ralle, Bernd. J. Chem. Educ. 1997, 74, 1323.
Alkanes / Cycloalkanes |
Aromatic Compounds |
Alkenes |
Synthesis
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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
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A Simple and Safe Catalytic Hydrogenation of 4-Vinylbenzoic Acid De, Shantanu; Gambhir, Geetu; Krishnamurty, H. G.
An alternative procedure to catalytic hydrogenation is catalytic transfer hydrogenation. In this technique, the reduction of an organic compound is achieved with the aid of a donor substance in the presence of a catalyst.
De, Shantanu; Gambhir, Geetu; Krishnamurty, H. G. J. Chem. Educ. 1994, 71, 992.
Catalysis |
Oxidation / Reduction |
Alkanes / Cycloalkanes |
Alkenes |
Alkynes
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The electrophilic addition to alkynes Weiss, Hilton M.
Electrophilic additions to alkynes traditionally do not receive as much attention in organic textbooks as electrophilic addition to alkenes.
Weiss, Hilton M. J. Chem. Educ. 1993, 70, 873.
Addition Reactions |
Alkynes
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The catalytic hydrogenation of methyl oleate by in situ hydrogen generation Plummer, Ben
Modification of the catalytic hydrogenation of methyl oleate into methyl stearate.
Plummer, Ben J. Chem. Educ. 1989, 66, 518.
Catalysis |
Alkenes |
Laboratory Equipment / Apparatus
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The evaluation of strain and stabilization in molecules using isodesmic reactions Fuchs, Richard
The stabilities of cyclic hydrocarbons are analyzed using isodesmic and metathetical isodesmic reactions.
Fuchs, Richard J. Chem. Educ. 1984, 61, 133.
Molecular Properties / Structure |
Alkanes / Cycloalkanes |
Alkenes |
Aromatic Compounds
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Oil shale - Heir to the petroleum kingdom Schachter, Y.
A discussion of oil shale provides students with real-world problems that require chemical literacy.
Schachter, Y. J. Chem. Educ. 1983, 60, 750.
Applications of Chemistry |
Alkenes |
Alkanes / Cycloalkanes |
Green Chemistry
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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
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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
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The dehydration of 3,3-dimethyl-2-butanol Taber, Richard L.; Grantham, Gary D.; Champion, William C.
Presents an experiment that demonstrates the usefulness of gas chromatography as an analytical technique, emphasizes structural rearrangement, makes use of elementary thermodynamics, and gives the student some experience in the original literature.
Taber, Richard L.; Grantham, Gary D.; Champion, William C. J. Chem. Educ. 1969, 46, 849.
Alcohols |
Alkenes |
Gas Chromatography
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Hyperconjugation: An elementary approach Ferreira, Ricardo Carvalho
Presents kinetic, thermochemical, and spectroscopic evidence for hyperconjugation in organic species.
Ferreira, Ricardo Carvalho J. Chem. Educ. 1952, 29, 554.
Alkenes
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