| Journal Articles: 25 results |
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Pyrolysis of Aryl Sulfonate Esters in the Absence of Solvent: E1 or E2? A Puzzle for the Organic Laboratory John J. Nash, Marnie A. Leininger, and Kurt Keyes
An aryl sulfonate ester is synthesized and then pyrolyzed at reduced pressure. The volatile products are analyzed using gas chromatography to determine whether the thermal decomposition occurs via an E1 or E2 mechanism.
Nash, John J.; Leininger, Marnie A.; Keyes, Kurt . J. Chem. Educ. 2008, 85, 552.
Alkenes |
Carbocations |
Elimination Reactions |
Gas Chromatography |
Mechanisms of Reactions |
Synthesis
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A Discovery-Based Experiment Involving Rearrangement in the Conversion of Alcohols to Alkyl Halides Richard A. Kjonaas and Ryand J. F. Tucker
This article reports a discovery-based experiment in which students convert three alcohols to alkyl halides under acidic conditions and record the 13C NMR spectrum in each case. By comparing the number of resonances observed with the number of resonances predicted for each possible product, students draw several conclusions about the resulting rearrangement.
Kjonaas, Richard A.; Tucker, Ryand J. F. J. Chem. Educ. 2008, 85, 100.
Alcohols |
Carbocations |
Gas Chromatography |
NMR Spectroscopy |
Nucleophilic Substitution
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Spiral Puzzle for Organic Chemistry Students Ender Erdik
Puzzle to review organic reactions and their reagents.
Erdik, Ender. J. Chem. Educ. 2003, 80, 428.
Synthesis |
Learning Theories |
Enrichment / Review Materials |
Addition Reactions |
Alkylation |
Electrophilic Substitution |
Elimination Reactions |
Reactions |
Nucleophilic Substitution |
Mechanisms of Reactions |
Grignard Reagents
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Chart for Deciding Mechanism for Reaction of Alkyl Halide with Nucleophile/Base McClelland, Bruce W.
The decision chart offered here is based upon the well-known and accepted characteristics of the reaction system mechanisms described in typical introductory organic chemistry textbooks.
McClelland, Bruce W. J. Chem. Educ. 1994, 71, 1047.
Mechanisms of Reactions |
Nucleophilic Substitution
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GC/MS experiments for the organic chemistry laboratory: I. E2 elimination of 2-bromo-2-methyloctane Novak, Michael; Heinrich, Julie; Martin, Kristy A.; Green, John; Lytle, Scott
Two capillary GC/MS experiments that were designed for and tested in a sophomore organic laboratory course.
Novak, Michael; Heinrich, Julie; Martin, Kristy A.; Green, John; Lytle, Scott J. Chem. Educ. 1993, 70, A103.
Gas Chromatography |
Alkenes |
Alkanes / Cycloalkanes |
Alcohols |
Elimination Reactions |
Synthesis
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The aromatic substitution game Zanger, Murray; Gennaro, Alfonso R.; McKee, James R.
This paper describes a game used to bring attention to the need for students to reconsider substitution theories learned in earlier chapters.
Zanger, Murray; Gennaro, Alfonso R.; McKee, James R. J. Chem. Educ. 1993, 70, 985.
Nucleophilic Substitution |
Synthesis
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Pinacol rearrangement of cyclopentylcyclohexane-1,1'-diol revisited. Sands, Richard D.
Two cyclic diols are treated with ice-cold boron trifluoride etherate to make rearrangement instead of diene formation the major product.
Sands, Richard D. J. Chem. Educ. 1992, 69, 667.
Mechanisms of Reactions |
Alcohols |
Aldehydes / Ketones
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A series of synthetic organic experiments demonstrating physical organic principles Sayed, Yousry; Ahlmark, Chris A.; Martin, Ned H.
The sequence of reactions described here incorporates several common synthetic organic transformations involving alkenes, alcohols, alkyl halides, and ketones that demonstrate some important principles of physical organic chemistry.
Sayed, Yousry; Ahlmark, Chris A.; Martin, Ned H. J. Chem. Educ. 1989, 66, 174.
Synthesis |
Alkenes |
Alcohols |
Aldehydes / Ketones |
Reactions
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Two working models for the SN2 mechanism Anderson, Martin M.
Design of an articulated physical model demonstrating the mechanism of the SN2 reaction.
Anderson, Martin M. J. Chem. Educ. 1987, 64, 1023.
Nucleophilic Substitution |
Mechanisms of Reactions |
Molecular Modeling
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Aromatic substitution reactions: when you've said ortho, meta, and para you haven't said it all Traynham, James G.
The author presents a range of examples for nucleophilic, electrophilic, and free-radical reactions where the ipso is an important, predominant, or even exclusive site of reaction.
Traynham, James G. J. Chem. Educ. 1983, 60, 937.
Nucleophilic Substitution |
Electrophilic Substitution |
Free Radicals |
Diastereomers |
Stereochemistry |
Reactions
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Phase transfer catalysis. Part II: Synthetic applications Gokel, George W.; Weber, William P.
In this month's continuation of an article, the authors have catalogued a number of illustrative examples so that the range of applicability of phase transfer catalysis will be.
Gokel, George W.; Weber, William P. J. Chem. Educ. 1978, 55, 429.
Phases / Phase Transitions / Diagrams |
Catalysis |
Aromatic Compounds |
Organometallics |
Nucleophilic Substitution |
Synthesis |
Esters |
Oxidation / Reduction |
Alkylation
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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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Nucleophilic substitution reactions at secondary carbon atoms. A modification of accepted views Raber, Douglas J.; Harris, J. Milton
Considers reaction mechanisms that are intermediate between SN1 and SN2 and the possible role of ion pairs.
Raber, Douglas J.; Harris, J. Milton J. Chem. Educ. 1972, 49, 60.
Nucleophilic Substitution |
Mechanisms of Reactions
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Reaction mechanisms in organic chemistry. Concerted reactions Caserio, Marjorie C.
Examines displacement and elimination, cyclization, and rearrangement reactions, as well as theoretical considerations and generalized selection rules.
Caserio, Marjorie C. J. Chem. Educ. 1971, 48, 782.
Mechanisms of Reactions |
Reactions |
Nucleophilic Substitution |
Elimination Reactions
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Hydrolysis of benzenediazonium ion Sheats, John E.; Harbison, Kenneth G.
Presents a more convenient approach to studying the kinetics of the hydrolysis of benzenediazonium ion.
Sheats, John E.; Harbison, Kenneth G. J. Chem. Educ. 1970, 47, 779.
Aromatic Compounds |
Nucleophilic Substitution |
Kinetics
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Donor-acceptor interactions in organic chemistry Sunderwirth, S. G.
The purpose of this article is to aid teachers in making even more effective use of theoretical considerations in teaching organic chemistry; the primary objective is to emphasize the underlying principles that are common to the following four basic types of reactions: substitution, addition, elimination, and rearrangement.
Sunderwirth, S. G. J. Chem. Educ. 1970, 47, 728.
Reactions |
Mechanisms of Reactions |
Addition Reactions |
Elimination Reactions |
Nucleophilic Substitution
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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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Bimolecular nucleophilic displacement reactions Edwards, John O.
The bimolecular nucleophilic displacement reaction is important and should be included in any detailed discussion of kinetics and mechanism at an early undergraduate level.
Edwards, John O. J. Chem. Educ. 1968, 45, 386.
Reactions |
Nucleophilic Substitution |
Kinetics |
Mechanisms of Reactions
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Substitution reactions in octahedral complexes Banerjea, D.
Commentary on the cited article by one of the authors that article referenced.
Banerjea, D. J. Chem. Educ. 1967, 44, 485.
Coordination Compounds |
Nucleophilic Substitution
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Substitution reactions in octahedral complexes Jones, G. R. H.
Examines the possibility of direct substitution, in aqueous solution, of a ligand in an octahedral complex by a nucleophile other than water or OH-.
Jones, G. R. H. J. Chem. Educ. 1966, 43, 657.
Coordination Compounds |
Mechanisms of Reactions |
Aqueous Solution Chemistry |
Nucleophilic Substitution |
Transition Elements |
Metals
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Reaction mechanisms in organic chemistry. I. The experimental approach Caserio, Marjorie C.
Reviews a variety of method that may be employed to determine the mechanism of organic reactions.
Caserio, Marjorie C. J. Chem. Educ. 1965, 42, 570.
Reactions |
Mechanisms of Reactions |
Reactive Intermediates |
Kinetics |
Nucleophilic Substitution |
Addition Reactions |
Elimination Reactions
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A second order kinetics experiment Teerlink, Wilford J.; Asay, Jeanette; Sugihara, James M.
Investigates the nucleophilic displacement reaction of ethyl p-toluenesulfonate by iodide in acetone.
Teerlink, Wilford J.; Asay, Jeanette; Sugihara, James M. J. Chem. Educ. 1964, 41, 161.
Kinetics |
Nucleophilic Substitution
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Nucleophilic reactions at trigonally bonded carbon Cash, R. Vincent
Examines the mechanisms of nucleophilic displacement reactions, nucleophilic addition reactions, and nucleophilic addition with elimination, all at trigonally bonded carbon.
Cash, R. Vincent J. Chem. Educ. 1964, 41, 108.
Nucleophilic Substitution |
Reactions |
Mechanisms of Reactions |
Addition Reactions |
Elimination Reactions
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A rapid test to distinguish tertiary from primary or secondary alcohols Bordwell, Frederick C.; Wellman, Keith M.
Describes a protocol for distinguishing tertiary from primary or secondary alcohols and its application to a specific problem.
Bordwell, Frederick C.; Wellman, Keith M. J. Chem. Educ. 1962, 39, 308.
Alcohols |
Qualitative Analysis
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Nucleophilic substitution in aromatic systems Gillis, Richard G.
Classifies and examines various categories of nucleophilic substitution in aromatic systems.
Gillis, Richard G. J. Chem. Educ. 1955, 32, 296.
Nucleophilic Substitution |
Aromatic Compounds
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