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Journal Articles: 41 results
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
Hydration of Acetylene: A 125th Anniversary  Dmitry A. Ponomarev and Sergey M. Shevchenko
The discovery the hydration of alkynes catalyzed by mercury ions by Mikhail Kucherov made possible industrial production of acetaldehyde from acetylene and had a profound effect on the development of industrial chemistry in the 1920th centuries.
Ponomarev, Dmitry A.; Shevchenko, Sergey M. J. Chem. Educ. 2007, 84, 1725.
Addition Reactions |
Aldehydes / Ketones |
Alkynes |
Catalysis |
Industrial Chemistry |
Reactions
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 brominationdebromination 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
The Aldol Addition and Condensation: The Effect of Conditions on Reaction Pathway  R. David Crouch, Amie Richardson, Jessica L. Howard, Rebecca L. Harker, and Kathryn H. Barker
Describes an experiment offering the opportunity for students to observe the critical role that reaction temperature and base strength have in determining the product of the base-mediated addition of a ketone to an aldehyde.
Crouch, R. David; Richardson, Amie; Howard, Jessica L.; Harker, Rebecca L.; Barker, Kathryn H. J. Chem. Educ. 2007, 84, 475.
Addition Reactions |
Aldehydes / Ketones |
Green Chemistry |
NMR Spectroscopy |
Reactions |
Synthesis
Was Markovnikov's Rule an Inspired Guess?  Peter Hughes
A study of 19th century literature shows that neither Markovnikov nor any of his contemporaries carried out the reactions often attributed to himthe addition of hydrogen bromide or hydrogen chloride to propene. Since there is little evidence for Markovnikov's rule in his 1870 article, it is likely that it was more of an inspired guess than a rational conclusion.
Hughes, Peter. J. Chem. Educ. 2006, 83, 1152.
Addition Reactions |
Alkenes |
Mechanisms of Reactions
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
A Sequence of Linked Experiments, Suitable for Practical Courses of Inorganic, Organic, Computational Chemistry, and NMR Spectroscopy  Grigoriy A. Sereda
A sequence of investigations associated with the iodochlorination of styrene and 1-hexene is described. The sequence is flexible enough to be used in inorganic, organic, computational, and instrumental courses.
Sereda, Grigoriy A. J. Chem. Educ. 2006, 83, 931.
Alkenes |
Computational Chemistry |
Constitutional Isomers |
MO Theory |
NMR Spectroscopy |
Synthesis
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
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 CC single and double bonds. This article provides a list of experimentally determined relative energies of the cis and trans isomers within the series cycloheptenecycloundecene, 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
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
"You're Repulsive!"Teaching VSEPR in a Not-So-Elegant Way  Robert S. H. Liu
Valence shell electron pair repulsive (VSEPR) interaction is an important concept particularly in discussing structural properties of molecules. In this article we showed five organic examples not commonly associated with VSEPR but yet all involving repulsive interactions of valence electrons, which provides ready explanations for altered chemical reactivity and spectroscopic properties of organic compounds. The ready catchy phrase Youre Repulsive! is the common thread used throughout these five examples.
Liu, Robert S. H. J. Chem. Educ. 2005, 82, 558.
Mechanisms of Reactions |
UV-Vis Spectroscopy |
Reactions |
Addition Reactions |
Electrophilic Substitution
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
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
Moving Past Markovnikov's Rule  E. Eugene Gooch
Extension of the Markovnikov Rule for addition reactions across a carbon-carbon double bond.
Gooch, E. Eugene. J. Chem. Educ. 2001, 78, 1358.
Synthesis |
Reactions |
Alkenes |
Addition Reactions |
Mechanisms of Reactions
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
Mechanism Templates: Lecture Aids for Effective Presentation of Mechanism in Introductory Organic Chemistry  Brian J. McNelis
To promote active student learning of mechanism in introductory organic chemistry, hand-outs have been developed with incomplete structures for reaction processes depicted, which are called mechanism templates. The key to these lecture aids is to provide only enough detail in the diagram to facilitate notetaking, ensuring that these templates are dynamic learning tools that must be utilized by an engaged and alert student.
Brian J. McNelis. J. Chem. Educ. 1998, 75, 479.
Learning Theories |
Mechanisms of Reactions |
Reactions |
Addition Reactions |
Acids / Bases |
Electrophilic Substitution |
Nucleophilic Substitution
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
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
Further Comments upon the Electrophilic Addition to Alkynes: A Response to Criticism from Professor Thomas T.Tidwell  Hilton M. Weiss
This paper responds to the preceding article by Professor T. Tidwell in which he provides arguments for vinyl cations being an intermediate in most electrophilic additions to alkynes.
Weiss, Hilton M. J. Chem. Educ. 1996, 73, 1082.
Addition Reactions |
Alkynes |
Mechanisms of Reactions
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
A New Approach To Teaching Organic Chemical Mechanisms  Wentland, Stephen H.
Describing the mechanisms of organic reactions using five simple steps or operations.
Wentland, Stephen H. J. Chem. Educ. 1994, 71, 3.
Mechanisms of Reactions |
Addition Reactions |
Nucleophilic Substitution |
Electrophilic Substitution |
Elimination Reactions |
Resonance Theory |
Molecular Properties / Structure
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
Hydrochlorination of 1-propynylbenzene on alumina: A demonstration of kinetic and thermodynamic control using HCl produced in situ and molecular modeling  Pienta, Norbert J.; Crawford, Scott D.; Kropp, Paul J.
A hydrochlorination experiment that provides sufficient latitude in choice of conditions.
Pienta, Norbert J.; Crawford, Scott D.; Kropp, Paul J. J. Chem. Educ. 1993, 70, 682.
Molecular Modeling |
Alkynes |
Alkenes |
Gas Chromatography |
NMR Spectroscopy |
Microscale Lab
An operationally simple hydroboration-oxidation experiment  Kabalka, George W.; Wadgaonkar, Prakash P.; Chatla, Narayana
The reactions involve the use of in situ generated diborane as the hydroborating reagent and sodium perborate as the oxidizing agent to convert cyclopentene to cyclopentanol.
Kabalka, George W.; Wadgaonkar, Prakash P.; Chatla, Narayana J. Chem. Educ. 1990, 67, 975.
Synthesis |
Mechanisms of Reactions |
Alkenes |
Alcohols
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
Markownikoff's rule: What did he say and when did he say it?  Tierney, John
The author traces the origin of this important rule.
Tierney, John J. Chem. Educ. 1988, 65, 1053.
Alkenes |
Synthesis
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
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
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
Student preparation of alkanols from alkenes  McKee, J. R.; Kauffman, J. M.
The hydration of 1-hexene to form 2-hexanol demonstrates Markovnikov addition, produces a higher yield of alcohol, and starts with a less expensive alkene than cyclohexene hydrations.
McKee, J. R.; Kauffman, J. M. J. Chem. Educ. 1982, 59, 695.
Alcohols |
Alkenes |
Mechanisms of Reactions |
Addition Reactions
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
The hydroboration-oxidation of alkenes. A convenient anti-Markownikoff hydration experiment  Kabalka, George W.; Hedgecock, Herbert C., Jr.
A hydroboration-oxidation sequence that relies on the borane dimethylsulfide complex as the hydroborating agent and trimethylamine-N-oxide dihydrate as the oxidizing agent.
Kabalka, George W.; Hedgecock, Herbert C., Jr. J. Chem. Educ. 1975, 52, 745.
Alkenes |
Oxidation / Reduction |
Addition Reactions
Classification of the electrophilic addition reactions of olefins and acetylenes  Wilson, Michael A.
Summarizes a wide variety of electrophiles and substrates and the mechanisms by which they react.
Wilson, Michael A. J. Chem. Educ. 1975, 52, 495.
Addition Reactions |
Reactions |
Mechanisms of Reactions
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
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
A modern look at Markovnikov's rule and the peroxide effect  Isenberg, Norbert; Grdinic, Marcel
Presents a "carbonium ion" definition of Markovnikov's Rule and examines the peroxide effect.
Isenberg, Norbert; Grdinic, Marcel J. Chem. Educ. 1969, 46, 601.
Mechanisms of Reactions |
Stereochemistry |
Diastereomers |
Free Radicals |
Alkenes |
Addition Reactions
Preparation of p-anisole: An organic chemistry experiment  Smith, Richard F.; Bates, Alvin C.
In this experiment, p-anisaldehyde is converted to p-anisonitrile by a modification of the three-step aldehyde-nitrile synthesis of Smith and Walker.
Smith, Richard F.; Bates, Alvin C. J. Chem. Educ. 1969, 46, 174.
Synthesis |
Mechanisms of Reactions |
Addition Reactions |
Nucleophilic Substitution |
Elimination Reactions |
Catalysis
Bromination of alkanes: Experiment illustrating relative reactivities and synthetic utility  Warkentin, J.
The radical halogenation of alkanes lend themselves well to the teaching of basic material such as bond dissociation energies, potential energy profiles, enthalpy of reaction, activation energy, and reaction rate.
Warkentin, J. J. Chem. Educ. 1966, 43, 331.
Electrochemistry |
Alkanes / Cycloalkanes |
Rate Law |
Kinetics |
Synthesis |
Alkenes |
Mechanisms of Reactions |
Free Radicals
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