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Journal Articles: 28 results
Teaching Reaction Mechanisms Using the Curved Arrow Neglect (CAN) Method  John H. Penn and Abdulrahman G. Al-Shammari
A new method for teaching organic reaction mechanisms that concentrates on intermediate reaction structures and can be used in a computer-assisted instruction environment is found to significantly enhance student performance in drawing traditional reaction mechanisms.
Penn, John H.; Al-Shammari, Abdulrahman G. J. Chem. Educ. 2008, 85, 1291.
Enrichment / Review Materials |
Mechanisms of Reactions |
Reactive Intermediates |
Student-Centered Learning
Acid-Catalyzed Enolization of β-Tetralone  Brahmadeo Dewprashad, Anthony Nesturi, and Joel Urena
This experiment allows students to use 1H NMR to compare the rates of substitution of benzylic and non-benzylic a hydrogens of -tetralone and correlate their findings with predictions made by resonance theory.
Dewprashad, Brahmadeo; Nesturi, Anthony; Urena, Joel. J. Chem. Educ. 2008, 85, 829.
Aldehydes / Ketones |
Isotopes |
Mechanisms of Reactions |
NMR Spectroscopy |
Reactive Intermediates |
Resonance Theory |
Synthesis
Six Pillars of Organic Chemistry  Joseph J. Mullins
This article focuses on a core set of conceptselectronegativity, polar covalent bonding, inductive and steric effects, resonance, and aromaticitythe proper application of which can explain and predict a wide variety of chemical, physical, and biological properties of molecules and conceptually unite important features of general, organic, and biochemistry.
Mullins, Joseph J. J. Chem. Educ. 2008, 85, 83.
Bioorganic Chemistry |
Covalent Bonding |
Hydrogen Bonding |
Mechanisms of Reactions |
Periodicity / Periodic Table |
Reactive Intermediates |
Resonance Theory
Semiempirical and DFT Investigations of the Dissociation of Alkyl Halides  Jack R. Waas
Enthalpy changes corresponding to the gas phase heats of dissociation of 12 organic halides were calculated using two semiempirical methods, the HartreeFock method, and two DFT methods. All five methods agreed generally with the expected empirically known trends in the dissociation of alkyl halides.
Waas, Jack R. J. Chem. Educ. 2006, 83, 1017.
Alkanes / Cycloalkanes |
Computational Chemistry |
Mechanisms of Reactions |
Molecular Modeling |
Reactions |
Reactive Intermediates |
Thermodynamics |
Elimination Reactions |
Nucleophilic Substitution
Using Building-Block Puzzles To Practice Drawing Organic Mechanisms  Ender Erdik
This pencil-and-paper activity is designed to test the ability of students in writing intermediates and products in the reactions of ketones. An undergraduate student who is successful in organic chemistry at the sophomore level is expected to fill in empty boxes with the appropriate "building blocks", which are atoms and atom groups (neutral or ionic). Solving the puzzle will give the formulas of reactants, reactive intermediates, and products. Students test their understanding of reaction mechanisms while having fun.
Erdik, Ender. J. Chem. Educ. 2005, 82, 1325.
Reactive Intermediates |
Synthesis |
Aldehydes / Ketones |
Mechanisms of Reactions
Ionic Activity Effects in Reaction Kinetics: What Happened to the Parsimony Principle?  Robert de Levie
The effect of ionic strength on the rates of chemical reactions highlights an often overlooked but highly relevant study by Christiansen. That work, based directly on the DebyeHckel theory, makes the BrnstedBjerrum interpretation unnecessary.
de Levie, Robert. J. Chem. Educ. 2005, 82, 885.
Kinetics |
Reactive Intermediates |
Aqueous Solution Chemistry
Exploring Organic Mechanistic Puzzles with Molecular Modeling  Gail Horowitz and Gary Schwartz
Molecular modeling projects in the form of mechanistic organic puzzles are described. Students, working in small groups, deduced reaction mechanisms and calculated heats of formation of intermediates and products in order to predict thermodynamic and kinetic selectivities of reaction. Student performance and degree of success is discussed. Projects are appropriate for students who have completed one semester of organic chemistry. A 3 - 4 hour laboratory period is required.
Horowitz, Gail; Schwartz, Gary. J. Chem. Educ. 2004, 81, 1136.
Molecular Properties / Structure |
Molecular Properties / Structure |
Computational Chemistry |
Mechanisms of Reactions |
Reactive Intermediates
The Mechanism of the Ritter Reaction in Combination with Wagner-Meerwein Rearrangements. A Cooperative Learning Experience  María I. Colombo, María L. Bohn, and Edmundo A. Rúveda
Procedure in which students develop analytical and problem-solving skills by investigating an organic reaction mechanism, predicting the most likely products, and suggesting experiments to test the postulated mechanistic pathways and possible intermediates.
Colombo, María I.; Bohn, María L.; Rúveda, Edmundo A. J. Chem. Educ. 2002, 79, 484.
Mechanisms of Reactions |
Reactive Intermediates |
Amides |
Thin Layer Chromatography |
NMR Spectroscopy
The Mechanism of Aqueous Hydrolysis of Nitro Derivatives of Phenyl Phenylmethanesulfonate. An Organic Laboratory Experiment  S. D. Mulder, B. E. Hoogenboom, and A. G. Splittgerber
Synthesis, purification, and characterization of three esters.
Mulder, S. D.; Hoogenboom, B. E.; Splittgerber, A. G. J. Chem. Educ. 2002, 79, 218.
Mechanisms of Reactions |
Molecular Properties / Structure |
Resonance Theory |
Reactive Intermediates |
Equilibrium |
Esters |
Aromatic Compounds |
Brønsted-Lowry Acids / Bases
Intermediates, Transition States, Butterflies, and Frogs  Trevor M. Kitson
The changes that occur in typical simple SN1 and SN2 reactions are compared to the metamorphoses undergone by caterpillars and tadpoles, respectively.
Kitson, Trevor M. J. Chem. Educ. 2001, 78, 504.
Mechanisms of Reactions |
Reactive Intermediates |
Nucleophilic Substitution
The Story of the Wagner-Meerwein Rearrangement  Ludmila Birladeanu
This paper tells the story of the long, arduous journey toward comprehending the mechanism of molecular rearrangements. This work involved the greatest chemists of the 19th and 20th centuries, among whom two names stand out: Georg Wagner, who showed what happens in these strange reshufflings of atoms, and Hans Meerwein, who showed how it happens. The resulting insight revolutionized the theory of organic chemistry.
Birladeanu, Ludmila. J. Chem. Educ. 2000, 77, 858.
Mechanisms of Reactions |
Reactive Intermediates |
Molecular Properties / Structure
Organic Reaction Animations, Version 1.5, CD-ROM (by Steven A. Fleming, Paul B. Savage, and Greg R. Hart)  reviewed by Michael S. Holden
Accompaniment to Organic Chemistry by the same authors. Fifty animations that can be viewed in a ball-and-stick, space-filling, HOMO, or LUMO mode. The animations can be put on a slow-motion setting to permit better visualization and are accompanied by an energy diagram, making it easy to identify transition states and intermediates. Electron flow is apparent in the HOMO and LUMO modes, allowing the student to link curved arrows and orbital interactions.
Holden, Michael S. J. Chem. Educ. 2000, 77, 447.
Reactions |
Mechanisms of Reactions |
Reactive Intermediates
Molecular Modeling to Predict Regioselectivity of Hydration Reactions  Kate J. Graham, Kathleen Skoglund, Chris P. Schaller, William P. Muldoon, and John B. Klassen
Students oxidize several isomeric alkenes using acid-catalyzed hydration, oxymercuration/demercuration, and hydroboration to compare the regioselectivity of the different techniques. The product mixtures are subsequently analyzed by GC and IR. To explain the results fully, students use the Spartan 5.0 molecular modeling package to predict the regioselectivity of these hydration reactions.
Graham, Kate J.; Skoglund, Kathleen; Schaller, Chris P.; Muldoon, William P.; Klassen, John B. J. Chem. Educ. 2000, 77, 396.
Computational Chemistry |
Mechanisms of Reactions |
Reactive Intermediates |
IR Spectroscopy |
Gas Chromatography |
Molecular Recognition |
Molecular Properties / Structure |
Molecular Modeling
A Simple and Convenient Method for Generation and NMR Observation of Stable Carbanions  Hamid S. Kasmai
A simple and convenient method for the generation and NMR study of stable carbanions is described. The data and sample spectra illustrate that reliable and good quality NMR spectra of stable carbanions may be obtained. The experiments described provide a good opportunity for students to apply the basic principles of 1H and 13C NMR spectrometry and the interesting topic of the exchange phenomenon in NMR.
Kasmai, Hamid S. J. Chem. Educ. 1999, 76, 830.
Acids / Bases |
Reactive Intermediates |
NMR Spectroscopy |
Aromatic Compounds
A Low-Cost Matrix Isolation Experiment: For the Undergraduate Laboratory   Mark Flair and T. Rick Fletcher
Method for generating and observing the reaction intermediate formed by photolysis of Cr(CO)6 in a low temperature solid matrix illustrating some of the principles of photochemistry and the relationship of spectroscopy to molecular structure.
Flair, Mark; Fletcher, T. Rick. J. Chem. Educ. 1995, 72, 753.
Photochemistry |
Organometallics |
Reactive Intermediates |
IR Spectroscopy |
Molecular Properties / Structure
Binding energy and enzymatic catalysis  Hansen, David E.; Raines, Ronald T.
The authors discuss the fundamental role that the favorable free energy of binding of the rate-determining transition state plays in catalysis and review the principle that many catalytic factors are realized by the use of this binding energy.
Hansen, David E.; Raines, Ronald T. J. Chem. Educ. 1990, 67, 483.
Enzymes |
Catalysis |
Thermodynamics
Reaction intermediates in organic chemistry: A colorful demonstration  Novaki, Luzia P.; Brotero, Paula P.; El Seoud, Omar A.
Demonstration in which the reactant, intermediates, and the final product have intense and different colors.
Novaki, Luzia P.; Brotero, Paula P.; El Seoud, Omar A. J. Chem. Educ. 1989, 66, 1040.
Reactive Intermediates |
Mechanisms of Reactions
The language of dynamics  Field, Richard J.
For a reacting chemical system, there exists a set of polynomial differential equations that describes the dynamics of how the concentrations of all chemical species change with time.
Field, Richard J. J. Chem. Educ. 1989, 66, 188.
Mechanisms of Reactions |
Equilibrium |
Thermodynamics
Organosilicon chemistry. Part II  West, Robert; Barton, Thomas J.
Stereochemistry and reaction mechanisms, reactive intermediates, bioactive organosilanes, organosilanes in organic synthesis, and sources of silicon compounds.
West, Robert; Barton, Thomas J. J. Chem. Educ. 1980, 57, 334.
Molecular Properties / Structure |
Stereochemistry |
Mechanisms of Reactions |
Reactive Intermediates
Project for problem-oriented undergraduate organic or integrated undergraduate laboratory  Silveira, Augustine, Jr.
This paper reports on an open-ended project which allows a great degree of flexibility in the laboratory. The project provided about a 6-week study for groups of 24 students each.
Silveira, Augustine, Jr. J. Chem. Educ. 1978, 55, 57.
Synthesis |
Undergraduate Research |
Spectroscopy |
Diastereomers |
Addition Reactions |
MO Theory |
Elimination Reactions |
Thermodynamics |
Kinetics
Cycloamyloses  Bergeron, Raymond J.
Examines an unusual carbohydrate system of current interest in the hope of generating some enthusiasm for the topic.
Bergeron, Raymond J. J. Chem. Educ. 1977, 54, 204.
Carbohydrates |
Molecular Properties / Structure |
Thermodynamics |
Kinetics |
Enzymes |
Spectroscopy
Sealed tube experiments  Campbell, J. A.
Lists and briefly describes a large set of "sealed tube experiments," each of which requires less than five minutes to set-up and clean-up, requires less than five minutes to run, provides dramatic results observable by a large class, and illustrates important chemical concepts.
Campbell, J. A. J. Chem. Educ. 1970, 47, 273.
Thermodynamics |
Crystals / Crystallography |
Solids |
Liquids |
Gases |
Rate Law |
Equilibrium
From stoichiometry and rate law to mechanism  Edwards, John O.; Greene, Edward F.; Ross, John
Examines the rules used by chemists as guidelines in developing mechanisms from stoichiometric and rate law observations.
Edwards, John O.; Greene, Edward F.; Ross, John J. Chem. Educ. 1968, 45, 381.
Stoichiometry |
Rate Law |
Kinetics |
Mechanisms of Reactions |
Equilibrium |
Reactive Intermediates
Biological oxidations and energy conservation  Kirschbaum, Joel
Examines the oxidative steps leading to the synthesis of ATP in living organisms and their metabolic control.
Kirschbaum, Joel J. Chem. Educ. 1968, 45, 28.
Bioenergetics |
Oxidation / Reduction |
Thermodynamics |
Metabolism
Reaction mechanisms in organic chemistry. II. The reaction intermediate  Caserio, Marjorie C.
This paper describes the more important methods that have been used to identify the various intermediates that are formed in complex reactions.
Caserio, Marjorie C. J. Chem. Educ. 1965, 42, 627.
Mechanisms of Reactions |
Reactive Intermediates
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
The reactive intermediates of organic chemistry  Stewart, Ross
The purpose of this paper is to outline a logical presentation of the more important reactive intermediates the student is likely to encounter in organic chemistry.
Stewart, Ross J. Chem. Educ. 1961, 38, 308.
Reactive Intermediates |
Free Radicals |
Mechanisms of Reactions
A convenient method for demonstration of stable carbanions  Landsbury, Peter T.
Highly colored pyridine solutions of carbanions are used as a convenient demonstration illustrating reactive intermediates.
Landsbury, Peter T. J. Chem. Educ. 1961, 38, 307.
Reactive Intermediates |
Reactions |
Free Radicals