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Journal Articles: 685 results
Synthesis Explorer: A Chemical Reaction Tutorial System for Organic Synthesis Design and Mechanism Prediction  Jonathan H. Chen and Pierre Baldi
Synthesis Explorer is an interactive tutorial system for organic chemistry that enables students to learn chemical reactions in ways previously unrealized. Pedagogical experiments in undergraduate classes at UC Irvine indicate that the system can improve average student examination performance by ~10%.
Chen, Jonathan H.; Baldi, Pierre. J. Chem. Educ. 2008, 85, 1699.
Mechanisms of Reactions |
Reactions |
Synthesis
J. Chem. Educ. 1999, 76, 1578–1583  John Andraos
Corrections to the article A Streamlined Approach to Solving Simple and Complex Kinetic Systems Analytically.
Andraos, John. J. Chem. Educ. 2008, 85, 1624.
Kinetics |
Mechanisms of Reactions |
Theoretical Chemistry
Novel Organic Courses  Arietta W. Clauss
JCE offers a wealth of materials for teaching and learning chemistry. This memo identifies some additional resources for teaching organic chemistry available through JCE.
Clauss, Arrietta W. J. Chem. Educ. 2008, 85, 1523.
Drugs / Pharmaceuticals |
Mechanisms of Reactions |
Medicinal Chemistry |
Natural Products |
Synthesis |
Student-Centered Learning
Teaching Organic Synthesis: A Comparative Case Study Approach  David A. Vosburg
This course, intended for advanced undergraduate and graduate students, studies reactions and mechanisms in the context of landmark syntheses of biologically important molecules accessed through the primary literature. Students examine and critically compare different synthetic strategies for related or identical molecules and present their results to peers.
Vosburg, David A. J. Chem. Educ. 2008, 85, 1519.
Drugs / Pharmaceuticals |
Mechanisms of Reactions |
Medicinal Chemistry |
Natural Products |
Synthesis |
Student-Centered Learning
Saying What You Mean: Teaching Mechanisms in Organic Chemistry  J. Brent Friesen
Ways to maintain clarity and consistency when teaching reaction mechanisms in organic chemistry include the use of balanced reaction equations, avoiding the use of shortcut notations, including key electrons and bonds in structural representations, and distinguishing between covalent and ionic bonds.
Friesen, J. Brent. J. Chem. Educ. 2008, 85, 1515.
Learning Theories |
Mechanisms of Reactions |
Reactions
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
The Discovery-Oriented Approach to Organic Chemistry. 7. Rearrangement of trans-Stilbene Oxide with Bismuth Trifluoromethanesulfonate and Other Metal Triflates  James E. Christensen, Matthew G. Huddle, Jamie L. Rogers, Herbie Yung, and Ram S. Mohan
Presents a microscale, green organic chemistry laboratory experiment that illustrates the utility of metal triflates, especially bismuth triflate, as a Lewis acid catalyst. Bismuth compounds are especially attractive for use as catalysts in organic synthesis because of their low toxicity, low cost, and ease of handling.
Christensen, James E.; Huddle, Matthew G.; Rogers, Jamie L.; Yung, Herbie; Mohan, Ram S. J. Chem. Educ. 2008, 85, 1274.
Catalysis |
Epoxides |
Green Chemistry |
Lewis Acids / Bases |
Mechanisms of Reactions |
Microscale Lab |
NMR Spectroscopy
A Convenient Tool for the Stochastic Simulation of Reaction Mechanisms  Nikolaos Bentenitis
Students can use Chemical Kinetics Simulator, a free, easy-to-use, and powerful program, to model reactions with both kinetically and thermodynamically controlled products and study a mechanism where the steady-state approximation gives inaccurate results.
Bentenitis, Nikolaos. J. Chem. Educ. 2008, 85, 1146.
Kinetics |
Mechanisms of Reactions
Kinetic Study of the Heck Reaction: An Interdisciplinary Experiment  Christel Gozzi and Naoual Bouzidi
The aim of this experiment is to study and calculate the kinetic constant of a Heck reaction. Students use GC analysis to quantify the reaction's reagents and products, control the global order of the reaction, prove that the two products are formed by two parallel reactions, and calculate the rate constant for each reaction.
Gozzi, Christel; Bouzidi, Naoual. J. Chem. Educ. 2008, 85, 1126.
Aromatic Compounds |
Catalysis |
Gas Chromatography |
Kinetics |
Mechanisms of Reactions |
Organometallics |
Rate Law |
Microscale Lab
Kinetics and Mechanism of Iodide Oxidation by Iron(III): A Clock Reaction Approach  Jurica Bauer, Vladislav Tomiic, and Petar B. A. Vrkljan
Describes a simple method for studying the kinetics of a chemical reaction and demonstrates the significance of reaction orders in deducing reaction mechanisms.
Bauer, Jurica; Tomiic, Vladislav; Vrkljan, Petar B. A. J. Chem. Educ. 2008, 85, 1123.
Kinetics |
Mechanisms of Reactions |
Rate Law |
Reactive Intermediates
Data Pooling in a Chemical Kinetics Experiment: The Aquation of a Series of Cobalt(III) Complexes  Richard S. Herrick, Kenneth V. Mills, and Lisa P. Nestor
Describes an experiment that introduces students to integrated rate laws, the search for a mechanism that is consistent with chemical and kinetic data, and the concept of activation barriers and their measurement in a curriculum whose pedagogical philosophy makes the laboratory the center of learning for undergraduates in their first two years of instruction.
Herrick, Richard S.; Mills, Kenneth V.; Nestor, Lisa P. J. Chem. Educ. 2008, 85, 1120.
Coordination Compounds |
Kinetics |
Mechanisms of Reactions |
Rate Law |
UV-Vis Spectroscopy
An Exercise on Structure Elucidation Based on a Tricky Aldol Reaction  Manuel González Sierra, Silvina C. Pellegrinet, María I. Colombo, and Edmundo A. Rúveda
To determine the structure of an unknown product, students are required to use spectra in conjunction with an organic chemistry mechanism. This exercise exemplifies a common research procedure, highlights the potential of modern one- and two-dimensional NMR, and helps students develop problem-solving skills.
González Sierra, Manuel; Pellegrinet, Silvina C.; Colombo, María I.; Rúveda, Edmundo A. J. Chem. Educ. 2008, 85, 1094.
IR Spectroscopy |
Mechanisms of Reactions |
Natural Products |
NMR Spectroscopy
The Iodochlorination of Styrene: An Experiment That Makes a Difference  R. Gary Amiet and Sylvia Urban
This purpose of this laboratory exercise is to determine the various substitution and elimination products generated in the iodochlorination of styrene and their relative proportions through the application of mechanistic principles and a basic knowledge of GCMS and NMR.
Amiet, R. Gary; Urban, Sylvia. J. Chem. Educ. 2008, 85, 962.
Alkenes |
Constitutional Isomers |
Gas Chromatography |
Instrumental Methods |
Mass Spectrometry |
Mechanisms of Reactions |
NMR Spectroscopy |
Synthesis |
Student-Centered Learning
Evaluating Mechanisms of Dihydroxylation by Thin-Layer Chromatography  Benjamin T. Burlingham and Joseph C. Rettig
Presents a microscale experiment in which cyclohexene is dihydroxylated under three sets of conditions and the products determined through thin-layer chromatography. Teams of students evaluate proposed mechanisms for each dihydroxylation in light of the data collected.
Burlingham, Benjamin T.; Rettig, Joseph C. J. Chem. Educ. 2008, 85, 959.
Addition Reactions |
Alkenes |
Diastereomers |
Mechanisms of Reactions |
Microscale Lab |
Stereochemistry |
Synthesis |
Thin Layer Chromatography
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
Organic Synthesis: Strategy and Control (Paul Wyatt and Stuart Warren)  Richard Pagni
Organic Synthesis is an excellent resource on organic synthesis. Because of the enormous breadth and complexity of the subject, being able to organize the material into coherent units as well as interconnecting them into a coherent whole is key to writing a successful book on organic synthesis. Wyatt and Warren show this skill in abundance.
Pagni, Richard. J. Chem. Educ. 2008, 85, 785.
Synthesis |
Mechanisms of Reactions
Acylation, Diastereoselective Alkylation, and Cleavage of an Oxazolidinone Chiral Auxiliary  Thomas E. Smith, David P. Richardson, George A. Truran, Katherine Belecki, and Megumi Onishi
Describes an introduction to the concepts and experimental techniques of diastereoselective synthesis using a chiral auxiliary that gives students the opportunity to gain proficiency with the techniques of modern organic synthesis, including the manipulation of moisture-sensitive reagents, low temperature reactions, column chromatography, TLC, and NMR analysis.
Smith, Thomas E.; Richardson, David P.; Truran, George A.; Belecki, Katherine; Onishi, Megumi. J. Chem. Educ. 2008, 85, 695.
Alkylation |
Asymmetric Synthesis |
Chromatography |
Diastereomers |
Enantiomers |
Mechanisms of Reactions |
NMR Spectroscopy |
Stereochemistry
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
Dynamic Reaction Figures: An Integrative Vehicle for Understanding Chemical Reactions  Emeric Schultz
Describes the dynamic reaction figure, a flexible learning tool that can be used to balance chemical equations, predict the results of potential reactions, present the underlying mechanism of reactions, and solve quantitative problems in a number of areas.
Schultz, Emeric. J. Chem. Educ. 2008, 85, 386.
Acids / Bases |
Aqueous Solution Chemistry |
Mechanisms of Reactions |
Nonmajor Courses
A Simple Assignment That Enhances Students' Ability To Solve Organic Chemistry Synthesis Problems and Understand Mechanisms  Jennifer Teixeira and R. W. Holman
Describes an original, easily implemented approach in which students construct a "functional group transformation" notebook which helps them to think about organic reactions in both the forward and the reverse (retrosynthetic) sense.
Teixeira, Jennifer; Holman, Robert W. J. Chem. Educ. 2008, 85, 88.
Mechanisms of Reactions |
Synthesis |
Student-Centered Learning
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
Computational Analysis of Stereospecificity in the Cope Rearrangement  Laura Glish and Timothy W. Hanks
Experimental product distributions from the Cope rearrangement of disubstituted 1,5-hexadienes can be readily understood by computer modeling of the various possible transitions states. Visual analysis of these geometries allow students to interpret the computational results by analogy to the familiar chair and boat conformations of substituted cyclohexanes.
Glish, Laura; Hanks, Timothy W. J. Chem. Educ. 2007, 84, 2001.
Alkenes |
Computational Chemistry |
Conformational Analysis |
Medicinal Chemistry |
MO Theory |
Molecular Modeling |
Mechanisms of Reactions
The Glyoxal Clock Reaction  Julie B. Ealy, Alexandra Rodriguez Negron, Jessica Stephens, Rebecca Stauffer, and Stanley D. Furrow
The glyoxal clock reaction has been adapted to a general chemistry kinetics lab to determine the order of the reacting species using a Calculator Based Laboratory or LabPro equipment.
Ealy, Julie B.; Negron, Alexandra Rodriguez; Stephens, Jessica; Stauffer, Rebecca; Furrow, Stanley D. J. Chem. Educ. 2007, 84, 1965.
Aldehydes / Ketones |
Dyes / Pigments |
Kinetics |
Lewis Acids / Bases |
Mechanisms of Reactions |
Rate Law |
Reactions
Probing the Rate-Determining Step of the Claisen–Schmidt Condensation by Competition Reactions  Kendrew K. W. Mak, Wing-Fat Chan, Ka-Ying Lung, Wai-Yee Lam, Weng-Cheong Ng, and Siu-Fung Lee
This article describes a physical organic experiment to identify the rate-determining step of the ClaisenSchmidt condensation of benzaldehyde and acetophenone by studying the linear free energy relationship.
Mak, Kendrew K. W.; Chan, Wing-Fat; Lung, Ka-Ying; Lam, Wai-Yee; Ng, Weng-Cheong; Lee, Siu-Fung. J. Chem. Educ. 2007, 84, 1819.
Aldehydes / Ketones |
Aromatic Compounds |
Gas Chromatography |
Kinetics |
Mechanisms of Reactions |
Synthesis
The A1c Blood Test: An Illustration of Principles from General and Organic Chemistry  Robert C. Kerber
The glycated hemoglobin blood test is a key measure of the effectiveness of glucose control in diabetics. The chemistry of glucose in the bloodstream, which underlies the test and its impact, provides an illustration of the importance of chemical equilibrium and kinetics to a major health problem.
Kerber, Robert C. . J. Chem. Educ. 2007, 84, 1541.
Applications of Chemistry |
Bioinorganic Chemistry |
Carbohydrates |
Mechanisms of Reactions |
Proteins / Peptides |
Bioorganic Chemistry
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
Lactate Dehydrogenase Catalysis: Roles of Keto, Hydrated, and Enol Pyruvate  J. E. Meany
Considers the reduction of pyruvate by lactate dehydrogenase in the presence of NADH. This reaction is inhibited by high concentrations of pyruvate, the physiological significance of which has long been controversial. This article summarizes the literature regarding the interactions of keto, hydrated, and enol pyruvate with lactate dehydrogenase.
Meany, J. E. J. Chem. Educ. 2007, 84, 1520.
Aldehydes / Ketones |
Bioenergetics |
Biophysical Chemistry |
Enzymes |
Equilibrium |
Mechanisms of Reactions |
Reactive Intermediates |
Thermodynamics
Appreciating Formal Similarities in the Kinetics of Homogeneous, Heterogeneous, and Enzyme Catalysis  Michael T. Ashby
The investigation of the kinetics of catalytic reactions by chemists, engineers, and biologists has lead to redundant theories, particularly with regard to homogeneous, heterogeneous, and enzyme catalysis. From a pedagogical perspective, it is useful to emphasize the common denominators among these theories.
Ashby, Michael T. J. Chem. Educ. 2007, 84, 1515.
Catalysis |
Enzymes |
Kinetics |
Mathematics / Symbolic Mathematics |
Mechanisms of Reactions
A Knoevenagel Initiated Annulation Reaction Using Room Temperature or Microwave Conditions  A. Gilbert Cook
The product of a Knoevenagel initiated annulation reaction is identified through a guided prelab exercise of the synthesis of the Hagemann ester, and then through the analysis of GCMS, NMR, and IR spectra. The stereochemistry of the product is determined through the NMR spectrum and Karplus curve, and the student is required to write a mechanism for the reaction.
Cook, A. Gilbert. J. Chem. Educ. 2007, 84, 1477.
Aldehydes / Ketones |
Conformational Analysis |
Gas Chromatography |
IR Spectroscopy |
Mass Spectrometry |
Mechanisms of Reactions |
NMR Spectroscopy |
Stereochemistry |
Synthesis
Reaction-Map of Organic Chemistry  Steven Murov
The Reaction-Map of Organic Chemistry has been designed to provide an overview of most of the reactions needed for the organic chemistry course and should help students develop synthetic routes from one functional group to another.
Murov, Steven. J. Chem. Educ. 2007, 84, 1224.
Addition Reactions |
Electrophilic Substitution |
Elimination Reactions |
Nucleophilic Substitution |
Oxidation / Reduction |
Periodicity / Periodic Table |
Reactions |
Synthesis |
Enrichment / Review Materials
Teaching a Modified Hendrickson, Cram, and Hammond Curriculum in Organic Chemistry  Joel M. Karty, Gene Gooch, and B. Gray Bowman
Describes a new organic chemistry curriculum in which fundamental concepts are introduced before mechanisms, and mechanisms are introduced before reactions. Reactions are introduced according to similarities among mechanisms rather than the functional group involved.
Karty, Joel M.; Gooch, Gene; Bowman, B. Gray. J. Chem. Educ. 2007, 84, 1209.
Learning Theories |
Mechanisms of Reactions
A Student Laboratory Experiment Based on the Vitamin C Clock Reaction  Ed Vitz
Describes an adaptation of the vitamin C clock reaction to a student laboratory experiment in which the orders with respect to peroxide and iodide, the rate constant, and the activation energy are determined by the method of initial rates.
Vitz, Ed. J. Chem. Educ. 2007, 84, 1156.
Consumer Chemistry |
Kinetics |
Mechanisms of Reactions |
Rate Law
Markovnikov's Rule  Predrag-Peter Ilich
More insight into the mechanisms of addition reactions to alkenes is needed before completely abandoning Markovnikov and anti-Markovnikov terminology
Ilich, Predrag-Peter. J. Chem. Educ. 2007, 84, 1109.
Addition Reactions |
Reactions |
Mechanisms of Reactions
Markovnikov's Rule  Robert C. Kerber
The use of Markovniknov and anti-Markovnikov to describe addition reactions and their products has long outlived its utility.
Kerber, Robert C. . J. Chem. Educ. 2007, 84, 1109.
Addition Reactions |
Reactions |
Mechanisms of Reactions
Markovnikov's Rule  Robert C. Kerber
The use of Markovniknov and anti-Markovnikov to describe addition reactions and their products has long outlived its utility.
Kerber, Robert C. . J. Chem. Educ. 2007, 84, 1109.
Addition Reactions |
Reactions |
Mechanisms of Reactions
Oxidation of Aromatic Aldehydes Using Oxone  Rajani Gandhari, Padma P. Maddukuri, and Thottumkara K. Vinod
Describes an eco-friendly procedure for the oxidation of aldehydes to carboxylic acids in water or a water-ethanol mixture using Oxone as the oxidant. The use of eco-friendly solvents, a non-toxic reagent, and the elimination of extraction solvents in the procedure demonstrate important green chemistry themes to students.
Gandhari, Rajani; Maddukuri, Padma P.; Vinod, Thottumkara K. J. Chem. Educ. 2007, 84, 852.
Aldehydes / Ketones |
Aromatic Compounds |
Aqueous Solution Chemistry |
Carboxylic Acids |
Green Chemistry |
Mechanisms of Reactions |
NMR Spectroscopy |
Oxidation / Reduction
The GC–MS Observation of Intermediates in a Stepwise Grignard Addition Reaction  Devin Latimer
This article describes a three-hour laboratory experiment for the third-year organic chemistry lab whereby the stable organic intermediates and final product of the Grignard addition of 3 equivalents of phenylmagnesium bromide to diethyl carbonate are observed.
Latimer, Devin. J. Chem. Educ. 2007, 84, 699.
Aldehydes / Ketones |
Grignard Reagents |
Synthesis |
Chromatography |
Instrumental Methods |
Mass Spectrometry |
Mechanisms of Reactions
Sterically Hindered Square-Planar Nickel(II) Organometallic Complexes: Preparation, Characterization, and Substitution Behavior  Manuel Martínez, Guillermo Muller, Mercè Rocamora, and Carlos Rodríguez
Presents a series of experiments for advanced undergraduate students dealing with both standard organometallic preparative methods in dry anaerobic conditions and with a kinetic study of the mechanisms operating in the substitution of square-planar complexes.
Martínez, Manuel; Muller, Guillermo; Rocamora, Mercè; Rodríguez, Carlos. J. Chem. Educ. 2007, 84, 485.
Coordination Compounds |
Grignard Reagents |
Kinetics |
Mechanisms of Reactions |
Organometallics |
Synthesis |
UV-Vis Spectroscopy
A "Classic Papers" Approach to Teaching Undergraduate Organometallic Chemistry  Andrew P. Duncan and Adam R. Johnson
Describes an upper-level undergraduate course in organometallic chemistry based on "classic" publications in the field, an approach that offers students a richly contextual introduction to many of the fundamental tenets of the discipline.
Duncan, Andrew P.; Johnson, Adam R. J. Chem. Educ. 2007, 84, 443.
Catalysis |
Mechanisms of Reactions |
MO Theory |
Organometallics
The Roles of Acids and Bases in Enzyme Catalysis  Hilton M. Weiss
In enzyme reactions, only weak acids and bases are available to hydrogen bond to reactants and to transfer protons in response to developing charges. Understanding this difference goes a long way toward applying organic concepts to the mechanisms of bioorganic chemistry.
Weiss, Hilton M. J. Chem. Educ. 2007, 84, 440.
Bioorganic Chemistry |
Catalysis |
Enzymes |
Hydrogen Bonding |
Mechanisms of Reactions |
Acids / Bases |
Aqueous Solution Chemistry |
Brønsted-Lowry Acids / Bases
A Pollutant Transformation Laboratory Exercise for Environmental Chemistry: The Reduction of Nitrobenzenes by Anaerobic Solutions of Humic Acid  Frank M. Dunnivant and Mark-Cody Reynolds
Presents a laboratory for advanced undergraduate- or graduate-level environmental chemistry in which students study the reduction of substituted nitrobenzenes by natural organic matter under anaerobic conditions. The exercise involves solution preparation, pH and EH buffers, organic reaction mechanisms, reaction kinetics, and instrumental analysis.
Dunnivant, Frank M.; Reynolds, Mark-Cody. J. Chem. Educ. 2007, 84, 315.
Instrumental Methods |
pH |
Solutions / Solvents |
Mechanisms of Reactions |
Kinetics |
Oxidation / Reduction
General Acid and General Base Catalysis  Addison Ault
General catalysis is indicated when the rate of a reaction depends upon buffer concentration and pH; it is most likely to be observed when the pH of the solution is near the pKa of the buffer and the reaction mechanism involves proton transfer in the rate-determining step.
Ault, Addison. J. Chem. Educ. 2007, 84, 38.
Acids / Bases |
Aqueous Solution Chemistry |
Catalysis |
pH |
Mechanisms of Reactions |
Kinetics
A Green Enantioselective Aldol Condensation for the Undergraduate Organic Laboratory  George D. Bennett
The proline-catalyzed aldol condensation between acetone and isobutyraldehyde proceeds in good yield and with high enantioselectivity at room temperature. This multi-week experiment also illustrates a number of principles and trade-offs of green chemistry.
Bennett, George D. J. Chem. Educ. 2006, 83, 1871.
Addition Reactions |
Aldehydes / Ketones |
Asymmetric Synthesis |
Catalysis |
Chirality / Optical Activity |
Green Chemistry |
Mechanisms of Reactions |
Stereochemistry
Keeping Your Students Awake: Facile Microscale Synthesis of Modafinil, a Modern Anti-Narcoleptic Drug  Evangelos Aktoudianakis, Rui Jun Lin, and Andrew P. Dicks
Describes the microscale preparation of modafinil, a pharmaceutical recently approved for the treatment of narcolepsy, by a sulfide oxidation reaction. An unusual feature of modafinil is the presence of a chiral sulfoxide functionality where a sulfur atom acts as a stereocenter, demonstrating that atoms other than carbon can act as centers of chirality.
Aktoudianakis, Evangelos; Lin, Rui Jun; Dicks, Andrew P. J. Chem. Educ. 2006, 83, 1832.
Chirality / Optical Activity |
Drugs / Pharmaceuticals |
Synthesis |
Mechanisms of Reactions |
IR Spectroscopy |
NMR Spectroscopy |
Microscale Lab |
Stereochemistry
Projects That Assist with Content in a Traditional Organic Chemistry Course  John J. Esteb, John R. Magers, LuAnne McNulty, and Anne M. Wilson
Describes two projects in organic chemistry, the reaction notebook and the end-of-semester synthesis activity, that are designed to stimulate student ownership of and engagement with course content.
Esteb, John J.; Magers, John R.; McNulty, LuAnne; Wilson, Anne M. J. Chem. Educ. 2006, 83, 1807.
Enrichment / Review Materials |
Mechanisms of Reactions |
Reactions |
Synthesis |
Student-Centered Learning
Let Us Give Lewis Acid–Base Theory the Priority It Deserves  Alan A. Shaffer
The Lewis concept is simple yet powerful in its scope, and can be used to help beginning students understand reaction mechanisms more fully. However, traditional approaches to acid-base reactions at the introductory level ignores Lewis acid-base theory completely, focusing instead on proton transfer described by the Br?nsted-Lowry concept.
Shaffer, Alan A. J. Chem. Educ. 2006, 83, 1746.
Acids / Bases |
Lewis Acids / Bases |
Lewis Structures |
Mechanisms of Reactions |
Molecular Properties / Structure |
VSEPR Theory |
Covalent Bonding |
Brønsted-Lowry Acids / Bases
Polar Addition to C=C Group: Why Is Anti-Markovnikov Hydroboration–Oxidation of Alkenes Not "Anti-"?  Predrag-Peter Ilich, Lucas S. Rickertsen, and Erienne Becker
The authors redefine Markovnikov or anti-Markovnikov regioselectivity and propose that the teaching of organic chemistry should be based on robust and portable concepts such as energy difference and atomic charge rather than historical labels.
Ilich, Predrag-Peter; Rickertsen, Lucas S.; Becker, Erienne. J. Chem. Educ. 2006, 83, 1681.
Addition Reactions |
Alkenes |
Computational Chemistry |
Mechanisms of Reactions |
Molecular Modeling
Creatine Synthesis: An Undergraduate Organic Chemistry Laboratory Experiment  Andri L. Smith and Paula Tan
Describes the synthesis of creatine monohydratea popular supplement used in sports requiring short bursts of energyfor introductory organic chemistry laboratory courses. The synthesis illustrates the electrophilic nature of nitriles, as well as the nucleophilic nature of amines.
Smith, Andri L.; Tan, Paula. J. Chem. Educ. 2006, 83, 1654.
Amines / Ammonium Compounds |
Aqueous Solution Chemistry |
Bioorganic Chemistry |
Chromatography |
Dyes / Pigments |
Mechanisms of Reactions |
Microscale Lab |
Thin Layer Chromatography
Chemistry Comes Alive!, Volume 8. Abstract of Special Issue 34  Rachel Bain, Jerrold J. Jacobsen, James H. Maynard, John W. Moore, and C. Jonathan Mitschele
Chemistry Comes Alive! Volume 8 can help move students understanding of waves from mechanical models to the chemical phenomena those models explain.
Bain, Rachel; Jacobsen, Jerrold J.; Maynard, James H.; Moore, John W.; Mitschele, C. Jonathan. J. Chem. Educ. 2006, 83, 1406.
Mechanisms of Reactions |
Reactions
The Hammett Equation: Probing the Mechanism of Aromatic Semicarbazone Formation  Glenn K. Ikeda, Karen Jang, Scott O. C. Mundle, and Andrew P. Dicks
An organic class project is described where upper-level undergraduates measure kinetic rate constants for semicarbazone formation by reacting semicarbazide with a meta- or para-substituted benzaldehyde.
Ikeda, Glenn K.; Jang, Karen; Mundle, Scott O. C.; Dicks, Andrew P. J. Chem. Educ. 2006, 83, 1341.
Addition Reactions |
Aldehydes / Ketones |
Kinetics |
Mechanisms of Reactions |
UV-Vis Spectroscopy
Colorful Chemical Demonstrations on the Extraction of Anionic Species from Water into Ether Mediated by Tricaprylylmethylammonium Chloride (Aliquat 336), a Liquid–Liquid Phase-Transfer Agent  Anil Joseph Pezhathinal, Kerensa Rocke, Louis Susanto, Derek Handke, Roch Chan-Yu-King, and Patrick Gordon
Provides a list of safe and easy experiments to demonstrate the extraction of colorful, water-soluble reagents by Aliquat 336 into ether. The demonstrations simulate the preliminary extractive step of an ionic species in liquidliquid phase transfer-catalyzed reactions and introduce various undergraduate chemistry concepts and principles to students.
Pezhathinal, Anil Joseph; Rocke, Kerensa; Susanto, Louis; Handke, Derek; Chan-Yu-King, Roch; Gordon, Patrick. J. Chem. Educ. 2006, 83, 1161.
Alkanes / Cycloalkanes |
Amines / Ammonium Compounds |
Catalysis |
Dyes / Pigments |
Reactions |
Mechanisms of Reactions
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
Rapid and Stereoselective Conversion of a trans-Cinnamic Acid to a β-Bromostyrene  Thomas A. Evans
The stereoselective synthesis of an aryl vinyl bromide is accomplished in a rapid microscale reaction of trans-4-methoxycinnamic acid with N-bromosuccinimide in dichloromethane. This guided-inquiry experiment links reactivity, stereochemistry, and mechanism in electrophilic addition reactions of alkenes and in E1 and E2 elimination reactions that form alkenes.
Evans, Thomas A. J. Chem. Educ. 2006, 83, 1062.
Alkenes |
Carbocations |
Gas Chromatography |
Mechanisms of Reactions |
Microscale Lab |
NMR Spectroscopy |
Stereochemistry
Regiospecific Epoxidation of Carvone: A Discovery-Oriented Experiment for Understanding the Selectivity and Mechanism of Epoxidation Reactions  Kendrew K. W. Mak, Y. M. Lai, and Yuk-Hong Siu
Peroxy acids and alkaline H2O2 are two commonly used reagents for alkene epoxidation. The former react preferentially with electron-rich alkenes while the latter works better with a,-unsaturated carbonyl compounds. The selectivity of these two reagents on carvone, a naturally occurring compound that contains both types of C=C bonds, is investigated.
Mak, Kendrew K. W.; Lai, Y. M.; Siu, Yuk-Hong. J. Chem. Educ. 2006, 83, 1058.
Alkenes |
Chromatography |
Epoxides |
IR Spectroscopy |
NMR Spectroscopy |
Synthesis |
Mechanisms of Reactions
Reactivity of the Monoterpenoid Nerol with p-Toluenesulfonic and Chlorosulfonic Acids: Selective Syntheses of α-Terpineol and α-Cyclogeraniol. An Activity for the Undergraduate Organic Lab  Pablo J. Linares-Palomino, Sofía Salido, Joaquín Altarejos, Manuel Nogueras, and Adolfo Sánchez
Describes the selective syntheses of the cyclic monoterpenoids a-terpineol or a-cyclogeraniol from the acyclic monoterpenoid nerol using p-toluenesulfonic acid or chlorosulfonic acid as cyclizing agents.
Linares-Palomino, Pablo J.; Salido, Sofía; Altarejos, Joaquín; Nogueras, Manuel; Sánchez, Adolfo. J. Chem. Educ. 2006, 83, 1052.
Alcohols |
Carbocations |
Gas Chromatography |
Mechanisms of Reactions |
Microscale Lab |
Synthesis |
Natural Products |
Alkenes
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
Mannich Reactions in Room Temperature Ionic Liquids (RTILs): An Advanced Undergraduate Project of Green Chemistry and Structural Elucidation  Kendrew K. W. Mak, Jane Siu, Y. M. Lai, and Pak-kei Chan
This experiment describes the synthesis of a commonly used ionic liquid, 1-butyl-3-methylimidazolium tetrafluoroborate, and the application of this ionic liquid as a recyclable medium for Mannich reactions.
Mak, Kendrew K. W.; Siu, Jane; Lai, Y. M.; Chan, Pak-kei. J. Chem. Educ. 2006, 83, 943.
Aldehydes / Ketones |
Amines / Ammonium Compounds |
Green Chemistry |
Mechanisms of Reactions |
NMR Spectroscopy |
Stereochemistry |
Synthesis |
Undergraduate Research
Iodolactonization of 4-Pentenoic Acid   R. David Crouch, Alexander Tucker-Schwartz, and Kathryn Barker
Describes an experiment in which 4-pentenoic acid is converted into a lactone via iodolactonization.
Crouch, R. David; Tucker-Schwartz, Alexander; Barker, Kathryn. J. Chem. Educ. 2006, 83, 921.
Alkenes |
Carboxylic Acids |
IR Spectroscopy |
Mechanisms of Reactions |
NMR Spectroscopy |
Reactions |
Synthesis
Taming the Barking Dog  Ché Royce Seabourne, George Maxwell, and James Wallace
This demonstration brings Liebig's famous 19th-century demonstration headlong into the 21st century, using digital video footage and other novel media.
Seabourne, Ché Royce; Maxwell, George; Wallace, James. J. Chem. Educ. 2006, 83, 751.
Gases |
Kinetics |
Mechanisms of Reactions |
Reactions
Computational Quantum Chemistry: A Reliable Tool in the Understanding of Gas-Phase Reactions  Annia Galano, J. Raúl Alvarez-Idaboy, and Annik Vivier-Bunge
The goal of this work is to show that computational quantum chemistry is a powerful tool for understanding real-world chemical problems. Several examples of gas-phase reaction kinetics are described.
Galano, Annia; Alvarez-Idaboy, J. Raúl; Vivier-Bunge, Annik. J. Chem. Educ. 2006, 83, 481.
Applications of Chemistry |
Atmospheric Chemistry |
Computational Chemistry |
Kinetic-Molecular Theory |
Kinetics |
Mechanisms of Reactions |
Quantum Chemistry |
Theoretical Chemistry
Synthesis of Unsymmetrical Alkynes via the Alkylation of Sodium Acetylides. An Introduction to Synthetic Design for Organic Chemistry Students  Jennifer N. Shepherd and Jason R. Stenzel
Teams of students design a microscale synthesis of an unsymmetrical alkyne using commercially available terminal alkynes and alkyl halides and characterize the resulting products using TLC, IR, and 1H NMR spectroscopy. Depending on the chosen reactants, students observe both substitution and elimination products, or in some cases, no reaction at all.
Shepherd, Jennifer N.; Stenzel, Jason R. J. Chem. Educ. 2006, 83, 425.
Alkylation |
Alkynes |
Elimination Reactions |
IR Spectroscopy |
Microscale Lab |
NMR Spectroscopy |
Nucleophilic Substitution |
Synthesis
Modern Physical Organic Chemistry (Eric V. Anslyn and Dennis A. Dougherty)  Richard Pagni
Modern Physical Organic Chemistry is the most well-rounded textbook on physical organic chemistry that this reviewer has seen.
Pagni, Richard. J. Chem. Educ. 2006, 83, 387.
Acids / Bases |
Bioorganic Chemistry |
Hydrogen Bonding |
Isotopes |
Kinetics |
Mechanisms of Reactions |
MO Theory |
Organometallics |
Photochemistry |
Reactive Intermediates |
Thermodynamics
Mechanisms That Interchange Axial and Equatorial Atoms in Fluxional Processes: Illustration of the Berry Pseudorotation, the Turnstile, and the Lever Mechanisms via Animation of Transition State Normal Vibrational Modes  Marion E. Cass, King Kuok Hii, and Henry S. Rzepa
Teaching the Berry pseudorotation mechanism presents particular pedagogic problems due to both its dynamic and three dimensional character. The approach described here illustrates these processes using interactive animations embedded in a Web page.
Cass, Marion E.; Hii, King Kuok; Rzepa, Henry S. J. Chem. Educ. 2006, 83, 336.
Computational Chemistry |
Enantiomers |
Molecular Mechanics / Dynamics |
Molecular Properties / Structure |
Mechanisms of Reactions |
NMR Spectroscopy |
Nonmetals
Using Jmol To Help Students Better Understand Fluxional Processes   William F. Coleman and Edward W. Fedosky
This new WebWare neatly combines instructional text and Jmol interactive, animated illustrations to teach mechanisms that need to be clearly visualized in order to be well understood.
Coleman, William F.; Fedosky, Edward W. J. Chem. Educ. 2006, 83, 336.
Computational Chemistry |
Enantiomers |
Mechanisms of Reactions |
Molecular Mechanics / Dynamics |
Molecular Properties / Structure |
NMR Spectroscopy |
Nonmetals
4-Dimethylaminopyridine or Acid-Catalyzed Syntheses of Esters: A Comparison  Annemieke W. C. van den Berg and Ulf Hanefeld
Students compare acid-catalyzed ester synthesis and the 4-dimethylaminopyridine-catalyzed reaction. Based on the outcome of the experiments, students discuss the different reaction mechanisms and reason why different products are formed.
van den Berg, Annemieke W. C.; Hanefeld, Ulf. J. Chem. Educ. 2006, 83, 292.
Acids / Bases |
Catalysis |
Chromatography |
Esters |
IR Spectroscopy |
NMR Spectroscopy |
Mass Spectrometry |
Synthesis |
Mechanisms of Reactions
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
Monitoring the Rate of Solvolytic Decomposition of Benzenediazonium Tetrafluoroborate in Aqueous Media Using a pH Electrode  Floyd L. Wiseman
This article discusses the use of pH electrodes to monitor the aqueous solvolysis of the benzenediazonium ion and shows that the results are in reasonable agreement with literature values.
Wiseman, Floyd L. J. Chem. Educ. 2005, 82, 1841.
Calorimetry / Thermochemistry |
Kinetics |
Thermodynamics |
Amines / Ammonium Compounds |
Aqueous Solution Chemistry |
Mechanisms of Reactions |
pH |
Rate Law
Strategic Applications of Named Reactions in Organic Synthesis: Background and Detailed Mechanisms (László Kürti and Barbara Czakó)  R. W. Holman
Krti and Czak use a two-page format that uses four-color graphics to address 250 reactions selected for inclusion based upon their applicability to modern natural products synthesis. Each named reaction is concisely introduced, mechanistically explained, and then set in context with example applications involving the production of natural products.
Holman, R. W. J. Chem. Educ. 2005, 82, 1780.
Synthesis |
Mechanisms of Reactions
Name Reactions and Reagents in Organic Synthesis, 2nd Edition (Bradford P. Mundy, Michael G. Ellerd, and Frank G. Favaloro)  R. W. Holman
Name Reactions and Reagents in Organic Synthesis is an exhaustive collection, addressing more than 500 reactions (and rearrangements). The breadth of coverage extends well beyond the confines of a typical undergraduatebeginning graduate organic chemistry course, although the detail presented for each reaction is minimal.
Holman, R. W. J. Chem. Educ. 2005, 82, 1780.
Synthesis |
Mechanisms of Reactions
Named Organic Reactions, 2nd Edition (Thomas Laue and Andreas Plagens)  R. W. Holman
Named Organic Reactions is a collection of 134 of the most common named organic reactions, with common being defined as those reactions most likely addressed in the combination of a typical sophomore organic chemistry sequence plus an advanced undergraduatebeginning graduate organic reactions and synthesis course.
Holman, R. W. J. Chem. Educ. 2005, 82, 1780.
Synthesis |
Mechanisms of Reactions
Named Organic Reactions, 2nd Edition (Thomas Laue and Andreas Plagens)  R. W. Holman
Named Organic Reactions is a collection of 134 of the most common named organic reactions, with common being defined as those reactions most likely addressed in the combination of a typical sophomore organic chemistry sequence plus an advanced undergraduatebeginning graduate organic reactions and synthesis course.
Holman, R. W. J. Chem. Educ. 2005, 82, 1780.
Synthesis |
Mechanisms of Reactions
A GC–MS Analysis of an SN2 Reaction for the Organic Laboratory  Malgorzata M. Clennan and Edward L. Clennan
This experiment utilizes an SN2 reaction between an alkyl bromide and potassium acetate to introduce the use of mass spectrometry for structural identification. It also provides students with experience in organic synthesis, the use of IR to identify functional groups, and the use of gas chromatography and response factors to determine product ratios.
Clennan, Malgorzata M.; Clennan, Edward L. J. Chem. Educ. 2005, 82, 1676.
IR Spectroscopy |
Mass Spectrometry |
Synthesis |
Chromatography |
Esters |
Mechanisms of Reactions |
Microscale Lab |
Gas Chromatography
Hydrolysis of Pentaamminechlorocobalt(III): A Unified Mechanistic View  Gabriel González and Manuel Martínez
The lab experiment proposed for advanced undergraduate students deals with a comprehensive kinetic study of the hydrolysis reactions of [CoCl(NH3)5]2+. The experiment is aimed at increasing understanding of the differences between the spontaneous and assisted mechanisms operating for this dissociatively activated process.
González, Gabriel; Martínez, Manuel. J. Chem. Educ. 2005, 82, 1671.
Kinetics |
Mechanisms of Reactions |
Aqueous Solution Chemistry |
UV-Vis Spectroscopy |
Coordination Compounds |
pH
The Organic Chemistry of Biological Pathways (John E. McMurry and Tadhg P. Begley)  Alan M. Rosan
This modern, comprehensive, dense, and beautifully presented book has one goal: to make explicit the mechanistic organic chemistry underlying fundamental biochemical pathways. In this effort it succeeds admirably.
Rosan, Alan M. J. Chem. Educ. 2005, 82, 1626.
Mechanisms of Reactions
Demonstrating Energy Migration in Coupled Oscillators. A Central Concept in the Theory of Unimolecular Reactions  Ronald E. Marcotte
This physical chemistry lecture demonstration is designed to aid the understanding of intramolecular energy transfer processes as part of the presentation of the theory of unimolecular reaction rates. Coupled pendulums are used to show the rate of migration of energy between oscillators under resonant and nonresonant conditions with varying degrees of coupling and how that relates to chemical reaction.
Marcotte, Ronald E. J. Chem. Educ. 2005, 82, 1530.
Enrichment / Review Materials |
Kinetics |
Mechanisms of Reactions |
Reactions |
Reactive Intermediates
Reduction of Iodine by Phosphorus(I): Integration of the Rate Equation  Kenneth Kustin and Edward W. Ross
The reduction of iodine by phosphorus(I) (hypophosphorous acid) yields iodide and phosphorus(III) (phosphorous acid). The reaction is autocatalytic in hydrogen ion, autoinhibitory in iodide ion, and zero order in iodine over a wide concentration range. We return to the original article by A. D. Mitchell that presents a mechanism to account for these facts and devise a method to integrate numerically the complex rate equation for this reaction.
Kustin, Kenneth; Ross, Edward W. J. Chem. Educ. 2005, 82, 1413.
Chemometrics |
Kinetics |
Mechanisms of Reactions |
Oxidation / Reduction |
Reactions |
Mathematics / Symbolic Mathematics |
Rate Law
"It Gets Me to the Product": How Students Propose Organic Mechanisms  Gautam Bhattacharyya and George M. Bodner
Because practicing organic chemists use the arrow-pushing formalism in situations that are far removed from the simple contexts in which they are first presented, this study probed how students enrolled in a first-semester, graduate-level organic chemistry course approached the task of writing the mechanisms for two- to four-step reactions that lacked the typical cues that bring common mechanisms to mind. This article focuses on the students' solutions and discusses possible limitations of their strategies.
Bhattacharyya, Gautam; Bodner, George M. J. Chem. Educ. 2005, 82, 1402.
Mechanisms of Reactions |
Learning Theories |
Constructivism
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
Conversion of an Aziridine to an Oxazolidinone Using a Salt and Carbon Dioxide in Water  Justin R. Wallace, Deborah L. Lieberman, Matthew T. Hancock, and Allan R. Pinhas
An undergraduate laboratory experiment that allows for optimization of experimental reaction conditions for the conversion of a readily-available aziridine to the corresponding oxazolidinone using only carbon dioxide and a salt in water is discussed. A variety of salts were used to determine their effect on the reaction. In all cases, either no reaction occurred or a high yield of product was obtained. Ring opening of the less substituted carbonnitrogen bond predominates. This experiment allows students to optimize reaction conditions to obtain predominantly one of two regioisomers.
Wallace, Justin R.; Lieberman, Deborah L.; Hancock, Matthew T.; Pinhas, Allan R. J. Chem. Educ. 2005, 82, 1229.
Heterocycles |
Synthesis |
Aqueous Solution Chemistry |
Constitutional Isomers |
Mechanisms of Reactions |
NMR Spectroscopy |
Quantitative Analysis
Chemistry Comes Alive!, Volume 7 Abstract of Special Issue 32, a CD-ROM of Flames and Explosions   Rachel Bain, Jerrold J. Jacobsen, James H. Maynard, and John W. Moore
A visual library containing more than 230 QuickTime movies and more than 6700 still images, Chemistry Comes Alive! Volume 7: Flames and Explosions features the kind of chemistry that is sure to spark an interest. Organized using both the periodic table and type of reaction, CCA! 7 makes it easy for you to find the movie or image you seek to add that spark of interest to your presentation. CCA! 7 covers a broad range of spectacular chemical reactions while also offering a depth of coverage that encourages discussions that compare and contrast particular reactions.
Bain, Rachel; Jacobsen, Jerrold J.; Maynard, James H.; Moore, John W. J. Chem. Educ. 2005, 82, 1102.
Reactions |
Mechanisms of Reactions
Generation, Isolation, and Characterization of a Stable Enol from Grignard Addition to a Bis-Ester. A Microscale Experiment for the Undergraduate Organic Chemistry Laboratory  Olivier J.-C. Nicaise, Kyle F. Ostrom, and Brent J. Dalke
A microscale experiment for the undergraduate organic chemistry laboratory that consists of preparing and characterizing an alpha-ketoester and its corresponding, remarkably stable enol form, has been developed. The reaction is that of a Grignard reagent with a bis-ester. A difference in reaction temperature is responsible for the selective generation of the alpha-ketoester and the enol ester. Analysis of spectral data (1H NMR and IR) and a knowledge of organic reactions allows the students to determine the detailed structure of the two reaction products and also to suggest a mechanism for their formation. This experiment introduces students to the concept of stability of the tetrahedral intermediate in acyl-transfer reactions. It also gives them a taste of the unexpected.
Nicaise, Olivier J.-C.; Ostrom, Kyle F.; Dalke, Brent J. J. Chem. Educ. 2005, 82, 1059.
IR Spectroscopy |
Mechanisms of Reactions |
Microscale Lab |
NMR Spectroscopy |
Organometallics |
Reactive Intermediates |
Synthesis
The Ethylene Ketal Protecting Group Revisited: The Synthesis of 4-Hydroxy-4,4-diphenyl-2-butanone  Marsha R. Baar, Charles E. Russell, and Kristin L. Wustholz
The multistep synthesis of 4-hydroxy-4,4-diphenyl-2-butanone from ethyl acetoacetate illustrates the use of a ketal protecting group. Reaction of ethyl acetoacetate with ethylene glycol with p-TsOH in toluene produced the ketal ester. Reaction of the crude ketal ester with two equivalents of phenyl magnesium bromide followed by an aqueous acid workup generated the tertiary alcohol and simultaneously removed the ketal protecting group to produce the hydroxyketone. Our procedure is a modification of a previously published synthesis whose end product was 4,4-diphenyl-3-buten-2-one, the dehydrated analog.
Baar, Marsha R.; Russell, Charles E.; Wustholz, Kristin L. J. Chem. Educ. 2005, 82, 1057.
Synthesis |
Grignard Reagents |
IR Spectroscopy |
Mechanisms of Reactions |
NMR Spectroscopy
The Addition of Bromine to 1,2-Diphenylethene   Judith C. Amburgey-Peters and LeRoy W. Haynes
We investigated the reaction of (Z)-1,2-diphenylethene (cis-stilbene) with various brominating reagents and solvents following directions in standard organic chemistry manuals. We were particularly interested in learning which combination of brominating reagent and solvent gave the best yield of (d,l)-1,2-dibromo-1,2-diphenylethane without the formation of significant amounts of meso-1,2-dibromo-1,2-diphenylethane, which is essentially the sole product from the reaction of bromine with (E)-1,2-diphenylethene (trans-stilbene). Based on the results from the standard preparatory methods, some permutations of solvent and brominating reagent were tried.
Amburgey-Peters, Judith C.; Haynes, LeRoy W. J. Chem. Educ. 2005, 82, 1051.
Addition Reactions |
Alkenes |
Carbocations |
Diastereomers |
Enantiomers |
Mechanisms of Reactions |
Stereochemistry
Factors Affecting the Relative Efficiency of General Acid Catalysis  Eugene E. Kwan
Specific acid catalysis (SAC) and general acid catalysis (GAC) play an important role in many organic reactions. Elucidation of SAC or GAC mechanisms requires an understanding of the factors that affect their relative efficiency. A simple model reaction in which SAC and GAC occur concurrently is analyzed to provide guidelines for such analyses. Simple rules that predict the effect of pH on the relative efficiency of GAC are discussed. An explicit expression for determining the optimal pH at which the effects of GAC are maximized is provided as well as an analogous expression for the general base case.
Kwan, Eugene E. J. Chem. Educ. 2005, 82, 1026.
Acids / Bases |
Catalysis |
Kinetics |
Aqueous Solution Chemistry |
Mechanisms of Reactions |
Reactions
"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 Rearrangement of an Allylic Dithiocyanate: An Experiment for Organic or Physical Chemistry Using NMR Analysis  David W. Emerson, Spencer M. Steinberg, and Richard L. Titus
An experiment suitable for students who have taken either organic chemistry or organic and physical chemistry is described. The simple preparation and molecular rearrangement of thiocyanic acid, 2-methylene-1,3-propanediyl ester to 1-propene, (3-isothiocyanato-2-isothiocyanatomethyl) occurs readily in the temperature range of 6590C and progress of the reaction is readily tracked by proton NMR. The buildup and decline of the intermediate, thiocyanic acid, 2-(isothiocyanatomethyl)-2-propenyl ester, is readily seen.
Emerson, David W.; Steinberg, Spencer M.; Titus, Richard L. J. Chem. Educ. 2005, 82, 466.
Kinetics |
Mechanisms of Reactions |
NMR Spectroscopy |
Quantitative Analysis
Halide (Cl) Quenching of Quinine Sulfate Fluorescence: A Time-Resolved Fluorescence Experiment for Physical Chemistry  Jonathan H. Gutow
A time-resolved fluorescence experiment for use in physical chemistry is described. Students investigate the halide quenching of the fluorescence from quinine sulfate in water (similar to tonic water). The students are able to determine that the fluorescence is quenched dynamically by collision with the halide, not by forming an equilibrated complex. Students reproduce the literature unquenched lifetime of about 19 ns and observe a nearly diffusion-limited collisional quenching rate of 5.2 ? 109 M1 in 0.5 M H2SO4.
Gutow, Jonathan H. J. Chem. Educ. 2005, 82, 302.
Kinetics |
Laboratory Computing / Interfacing |
Lasers |
Spectroscopy |
Photochemistry |
Mechanisms of Reactions
Two-Step Semi-Microscale Preparation of a Cinnamate Ester Sunscreen Analog  Ryan G. Stabile and Andrew P. Dicks
The two-step synthesis and characterization of a sunscreen analog (ethyl trans-4-methoxycinnamate) is presented. This experiment is tailored towards students with a sound theoretical understanding of organic chemistry and related laboratory techniques. Appropriate synthetic discussion topics include carbonyl condensation reactions, carboxylic acid esterifications, and the so-called "cesium effect" in organic synthesis.
Stabile, Ryan G.; Dicks, Andrew P. J. Chem. Educ. 2004, 81, 1488.
Conductivity |
IR Spectroscopy |
Mechanisms of Reactions |
Microscale Lab |
NMR Spectroscopy |
Synthesis |
UV-Vis Spectroscopy |
Consumer Chemistry
The Molecular Structure of Penicillin  Ronald Bentley
The chemical structure of penicillin was determined between 1942 and 1945 under conditions of secrecy established by the U.S. and U.K. governments. The evidence was not published in the open literature but as a monograph. This complex volume does not present a structure proof that can be readily comprehended by a student. In this article, a basic structural proof for the penicillin molecule is provided, emphasizing the chemical work.
Bentley, Ronald. J. Chem. Educ. 2004, 81, 1462.
Drugs / Pharmaceuticals |
Applications of Chemistry |
Natural Products |
Molecular Properties / Structure |
Mechanisms of Reactions |
Stereochemistry
Competition Experiments as a Means of Evaluating Linear Free Energy Relationships. An Experiment for the Advanced Undergraduate Organic Chemistry Lab   Richard J. Mullins, Andrei Vedernikov, and Rajesh Viswanathan
A novel approach to exploring Hammett relationships in the undergraduate teaching lab is described. The use of competition experiments proved to be a reliable method for the construction of Hammett plots with good correlation. Reactions that were studied include the sodium borohydride reduction, methylmagnesium bromide addition, and oxime formation with para-substituted acetophenones. The composition of reaction mixtures was established by 1H NMR integrations. The use of competition experiments ensured consistency in the results, as relatively little control was required over the reaction conditions.
Mullins, Richard J.; Vedernikov, Andrei; Viswanathan, Rajesh. J. Chem. Educ. 2004, 81, 1357.
Kinetics |
Mechanisms of Reactions |
NMR Spectroscopy |
Synthesis
Chain Copolymerization Reactions: An Algorithm To Predict the Reaction Evolution with Conversion  Alberto Gallardo, María Rosa Aguilar, Gustavo A. Abraham, and Julio San Román
The theoretical understanding of kinetic curves is an important area of macromolecular chemistry. Modeling of these curves is important for polymer synthesis. To theoretically predict the evolution of a binary copolymerization reaction that follows the terminal model, an algorithm using the exact solution of the differential equation of this kinetic model is presented. The algorithm has been programmed in Basic language and named Conversion. The basis of the algorithm, as well as its evaluation using four different model reactions, is discussed. Conversion is a useful tool to study the behavior of chain copolymerization reactions. Moreover, the use of computer programs helps teachers and students better understand the principles and practical considerations involved in the study of polymer science.
Gallardo, Alberto; Aguilar, María Rosa; Abraham, Gustavo A.; San Román, Julio. J. Chem. Educ. 2004, 81, 1210.
Polymerization |
Mechanisms of Reactions
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
An NMR Study of Isotope Effect on Keto–Enol Tautomerization. A Physical Organic Chemistry Experiment  D. Atkinson and V. Chechik
A series of physical organic chemistry experiments suitable for second- or third-year undergraduate students is presented.
Atkinson, D.; Chechik, V. J. Chem. Educ. 2004, 81, 1030.
NMR Spectroscopy |
Isotopes |
Kinetics |
Mechanisms of Reactions
Pressure Dependence of Gas-Phase Reaction Rates  Stéphanie de Persis, Alain Dollet, and Francis Teyssandier
This article is intended to show that only simple concepts are required to qualitatively explain and describe the pressure dependence of gas-phase reaction rates.
de Persis, Stéphanie; Dollet, Alain; Teyssandier, Francis. J. Chem. Educ. 2004, 81, 832.
Qualitative Analysis |
Gases |
Kinetics |
Mechanisms of Reactions
The Darzens Condensation: Structure Determination through Spectral Analysis and Understanding Substrate Reactivity  R. David Crouch, Michael S. Holden, and Candice A. Romany
The Darzens condensation involves two steps that are typically included in the sophomore organic curriculum: an aldol reaction followed by an intramolecular nucleophilic substitution.
Crouch, R. David; Holden, Michael S.; Romany, Candice A. J. Chem. Educ. 2004, 81, 711.
NMR Spectroscopy |
Synthesis |
Stereochemistry |
Mechanisms of Reactions |
Aldehydes / Ketones
Keynotes in Organic Chemistry (Andrew F. Parsons)  Joel M. Karty
As a result of the trend towards modularization of chemistry courses, the text attempts to meet the need for smaller, highly focused and accessible organic chemistry textbooks, which complement the very detailed standard texts, to guide students through the key principles of the subject.
Karty, Joel M. J. Chem. Educ. 2004, 81, 651.
Acids / Bases |
Equilibrium |
Mechanisms of Reactions |
Thermodynamics
The Electrophilic Aromatic Substitution of Fluorobenzene   Addison Ault
Joel Rosenthal and David Schuster published a paper entitled The Anomalous Reactivity of Fluorobenzene in Electrophilic Aromatic Substitution and Related Phenomena. The authors and the reviewers, apparently, were not aware of my publication in this Journal in 1966 entitled The Activating Effect of Fluorine in Electrophilic Aromatic Substitution.
Ault, Addison. J. Chem. Educ. 2004, 81, 644.
Aromatic Compounds |
Mechanisms of Reactions |
Synthesis
The Tragedy of Hamlet, Son of an Organic Chemist of Denmark  Ronald G. Brisbois
Herein, Hamlet (the son of an organic chemist of Denmark) is the surrogate of any and every student as he uses a thoroughly Shakespearean approach to sorting out some of the key distinguishing features of SN2 versus SN1 reactions.
Brisbois, Ronald G. J. Chem. Educ. 2004, 81, 502.
Kinetics |
Mechanisms of Reactions |
Stereochemistry |
Nucleophilic Substitution
A Generalized Pre-Equilibrium Approximation in Chemical and Photophysical Kinetics  Margaret Rae and Mário N. Berberan-Santos
The pre-equilibrium approximation is one of several useful approximation methods that allow one to go from complex systems of differential equations (the kinetic rate equations) to simple explicit solutions. In this article, a relatively general view of the pre-equilibrium approximation is presented, along with the respective solution. Several applications are also discussed.
Rae, Margaret; Berberan-Santos, Mário N. J. Chem. Educ. 2004, 81, 436.
Enzymes |
Atomic Properties / Structure |
Fluorescence Spectroscopy |
Kinetics |
Photochemistry |
Mechanisms of Reactions
The Substitution–Elimination Mechanistic Disc Method  Paul T. Buonora and Yu Jin Lim
In this manuscript a mnemonic device designed to facilitate presentation of the competing SN1, SN2, E1, and E2 mechanisms is presented.
Buonora, Paul T.; Lim, Yu Jin. J. Chem. Educ. 2004, 81, 368.
Mechanisms of Reactions |
Elimination Reactions |
Nucleophilic Substitution
Why Chemical Reactions Happen (James Keeler and Peter Wothers)  John Krenos
By concentrating on a limited number of model reactions, this book presents chemistry as a cohesive whole by tying together the fundamentals of thermodynamics, chemical kinetics, and quantum chemistry, mainly through the use of molecular orbital interpretations.
Krenos, John. J. Chem. Educ. 2004, 81, 201.
Mechanisms of Reactions |
Thermodynamics |
Kinetics |
Quantum Chemistry |
MO Theory
Correction to J. Chem. Educ. 2003, 80, 833  
Corrections to original article.
J. Chem. Educ. 2004, 81, 197.
Kinetics |
Mechanisms of Reactions |
Stoichiometry
Using Conductivity Devices in Nonaqueous Solutions II: Demonstrating the SN2 Mechanism  Thomas A. Newton and Beth Ann Hill
The use of a conductivity apparatus in nonaqueous solutions to demonstrate structurereactivity correlations and solvent effects in the SN2 reaction is described.
Newton, Thomas A.; Hill, Beth Ann. J. Chem. Educ. 2004, 81, 61.
Conductivity |
Nucleophilic Substitution |
Mechanisms of Reactions
Using Conductivity Devices in Nonaqueous Solutions I: Demonstrating the SN1 Mechanism  Thomas A. Newton and Beth Ann Hill
The use of a conductivity apparatus in nonaqueous solutions to demonstrate structurereactivity correlations and solvent effects in the SN1 reaction is described.
Newton, Thomas A.; Hill, Beth Ann. J. Chem. Educ. 2004, 81, 58.
Conductivity |
Nucleophilic Substitution |
Mechanisms of Reactions
Don't Be Tricked by Your Integrated Rate Plot  Edward Urbansky
Reply to comments on original article.
Urbansky, Edward. J. Chem. Educ. 2004, 81, 32.
Kinetics |
Mechanisms of Reactions |
Chemometrics
Don't Be Tricked by Your Integrated Rate Plot: Reaction order Ambiguity  Sue Le Vent
Integrated rate equations (for constant reaction volume) may be given in terms of relative reactant concentration, C (= concentration/initial concentration) and relative time, T (= time/half-life); in these forms, the equations are independent of rate constants and initial concentrations.
Le Vent, Sue. J. Chem. Educ. 2004, 81, 32.
Kinetics |
Mechanisms of Reactions |
Chemometrics
Don't Be Tricked by Your Integrated Rate Plot: Pitfalls of Using Integrated Rate Plots  Gabor Lente
Problems with linearizing the integrated rate law.
Lente, Gabor. J. Chem. Educ. 2004, 81, 32.
Kinetics |
Mechanisms of Reactions |
Chemometrics
Don't Be Tricked by Your Integrated Rate Plot: Pitfalls of Using Integrated Rate Plots  Gabor Lente
Problems with linearizing the integrated rate law.
Lente, Gabor. J. Chem. Educ. 2004, 81, 32.
Kinetics |
Mechanisms of Reactions |
Chemometrics
Microscale Synthesis and Spectroscopic Analysis of Flutamide, an Antiandrogen Prostate Cancer Drug  Ryan G. Stabile and Andrew P. Dicks
The synthesis involves N-acylation of a trisubstituted aromatic compound, 3-trifluoromethyl-4-nitroaniline. The procedure is easily adapted to generate structural analogues of flutamide. A significant feature is the curricular flexibility afforded by this experiment.
Stabile, Ryan G.; Dicks, Andrew P. J. Chem. Educ. 2003, 80, 1439.
Drugs / Pharmaceuticals |
IR Spectroscopy |
Mechanisms of Reactions |
Microscale Lab |
NMR Spectroscopy |
Synthesis |
Aromatic Compounds
A Series of Small-Scale, Discovery-Based Organic Laboratory Experiments Illustrating the Concepts of Addition, Substitution, and Rearrangement  Judith S. Moroz, Janice L. Pellino, and Kurt W. Field
Multistep, microscale organic laboratory experiments are presented that illustrate addition, substitution, and rearrangement reactions.
Moroz, Judith S.; Pellino, Janice L.; Field, Kurt W. J. Chem. Educ. 2003, 80, 1319.
IR Spectroscopy |
Mass Spectrometry |
Microscale Lab |
NMR Spectroscopy |
Synthesis |
Addition Reactions |
Mechanisms of Reactions
The Art of Writing Reasonable Organic Reaction Mechanisms, 2nd Edition (Robert B. Grossman)  R. W. Holman
The emphasis is upon equipping the student with an intuitive sense of how to tackle a complex organic transformation and develop a reasonable mechanism to explain the chemistry.
Holman, R. W. J. Chem. Educ. 2003, 80, 1259.
Synthesis |
Mechanisms of Reactions
Reactions (→) vs Equations (=)  S. R. Logan
A recent chemical kinetics text uses an equals sign for an overall reaction, whereas an arrow is used in each of the reaction steps that are proposed to constitute the mechanism, and for any elementary process.
Logan, S. R. J. Chem. Educ. 2003, 80, 1258.
Kinetics |
Nomenclature / Units / Symbols |
Reactions |
Mechanisms of Reactions
ABC Kinetics  Jorge A. Carrazana García
In this collection of worksheets, a step-by-step study of the ABC system is accomplished with the aid of Mathcad. Working with real mathematics notation, interactive graphs, and symbolic processing allows useful equations to be obtained, transformed and applied live, with the result of clarifying the study goals and objectives.
Carrazana García, Jorge A. J. Chem. Educ. 2003, 80, 1220.
Kinetics |
Mechanisms of Reactions |
Mathematics / Symbolic Mathematics
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
Dynamic Visualization in Chemistry Abstract of Special Issue 31, a CD-ROM for Mac OS and Windows  James P. Birk, Debra E. Leedy, Rachel A. Morgan, Mark Drake, Fiona Lihs, Eleisha J. Nickoles, and Michael J. McKelvy
Each presentation is designed to help chemistry students acquire a dynamic, three-dimensional, atomic-level visualization of matter and to use this view to explain and ultimately predict the behavior of materials. It integrates video of experiments and animations of theoretical models. Students zoom in on physical and chemical processes at resolutions as high as the atomic level.
Birk, James P.; Leedy, Debra E.; Morgan, Rachel A.; Drake, Mark; Lihs, Fiona; Nickoles, Eleisha J.; McKelvy, Michael J. J. Chem. Educ. 2003, 80, 1095.
Mechanisms of Reactions |
Solid State Chemistry
Diffusion of Water through a Differentially Permeable Membrane  Maria Guadalupe Bertoluzzo, Fabio E. Quattrin, Stella Maris Bertoluzzo, and Ruben Rigatuso
Students investigate the process of osmosis through the differentially-permeable membrane formed by copper(II) hexacyanoferrate(II), a colloidal precipitate.
Bertoluzzo, Maria Guadalupe; Quattrin, Fabio E.; Bertoluzzo, Stella Maris; Rigatuso, Ruben. J. Chem. Educ. 2003, 80, 1032A.
Transport Properties |
Mechanisms of Reactions
Orgo Cards: Organic Chemistry Review (Steven Q. Wang, Babak Razani, Edward J. K. Lee, Jennifer Wu, and William Berkowitz)  Eugene Gooch
The major strength of this product lies in coverage of the reaction mechanisms. Mechanisms are written out using curved arrow notation, steps are numbered, and a sentence describes the details of each step. Efforts are made to describe both ionic and radical mechanisms accurately. Stereochemical details are integrated into the descriptions of reactions and their mechanisms.
Gooch, Eugene. J. Chem. Educ. 2003, 80, 1009.
Enrichment / Review Materials |
Reactions |
Mechanisms of Reactions |
Stereochemistry
Advanced Organic Chemistry, 4th Edition. Part B: Reactions and Synthesis, (Richard J. Sundberg and Francis A. Carey)  Thomas G. Waddell
Graduate level reference text focussing on organic reactions and syntheses.
Waddell, Thomas G. J. Chem. Educ. 2003, 80, 883.
Mechanisms of Reactions |
Synthesis |
Reactions
Mass Conservation Implications of a Reaction Mechanism  William R. Smith and Ronald W. Missen
Determining a complete set of mass-conversion equations using only the stoichiometric matrix of the equation N.
Smith, W. R.; Missen, R. W. J. Chem. Educ. 2003, 80, 833.
Kinetics |
Mechanisms of Reactions |
Stoichiometry |
Mathematics / Symbolic Mathematics
Studying a Ligand Substitution Reaction with Variable Temperature 1H NMR Spectroscopy: An Experiment for Undergraduate Inoganic Chemistry Students  Jeffery A. Orvis, Basant Dimetry, Jeffery Winge, and T. Corbin Mullis
Synthesis and characterization of two Co(III) complexes, and a mechanistic study of the aquation of one of the complexes using variable-temperature 1H NMR spectroscopy.
Orvis, Jeffery A.; Dimetry, Basant; Winge, Jeffery; Mullis, T. Corbin. J. Chem. Educ. 2003, 80, 803.
Kinetics |
Mechanisms of Reactions |
NMR Spectroscopy |
Aqueous Solution Chemistry |
Coordination Compounds |
Synthesis |
Reactions
The Anomalous Reactivity of Fluorobenzene in Electrophilic Aromatic Substitution and Related Phenomena  Joel Rosenthal and David I. Schuster
Extensive analysis of the reactivity of fluorobenzene (electrophilic substitution); includes resonance and other inductive effects, acidities of fluorinated aromatic compounds, and properties of other organofluorine compounds.
Rosenthal, Joel; Schuster, David I. J. Chem. Educ. 2003, 80, 679.
Aromatic Compounds |
Mechanisms of Reactions |
Synthesis |
Electrophilic Substitution |
Enrichment / Review Materials |
Resonance Theory
Bromination and Debromination of Cholesterol: An Inquiry-Based Lab Involving Structure Elucidation, Reaction Mechanism, and 1H NMR  Andrew Grant and Devin Latimer
An experiment designed to examine a reaction mechanism and its stereochemical consequences; students propose the product and a mechanism for its production before conducting the experiment and analyzing the product with 1H NMR.
Grant, Andrew S.; Latimer, Devin. J. Chem. Educ. 2003, 80, 670.
Mechanisms of Reactions |
NMR Spectroscopy |
Stereochemistry |
Natural Products |
Synthesis |
Steroids
Name Reactions: A Collection of Detailed Reaction Mechanisms (Jie Jack Li)  D. G. J. Young
Alphabetized collection of over 300 organic mechanisms.
Young, D. G. J. J. Chem. Educ. 2003, 80, 617.
Mechanisms of Reactions |
Reactions
What Is the Overall Stoichiometry of a Complex Reaction?  Sidney Toby and Irwin Tobias
Obtaining stoichiometric relationships from reaction mechanisms and a kinetics approach.
Toby, Sidney; Tobias, Irwin. J. Chem. Educ. 2003, 80, 520.
Kinetics |
Mechanisms of Reactions |
Stoichiometry
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
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
"Chiral Acetate": The Preparation, Analysis, and Applications of Chiral Acetic Acid  Addison Ault
Production of chiral acetic acid using deuterium and tritium and its application to understanding stereochemistry and the specificity of enzymatic reactions.
Ault, Addison. J. Chem. Educ. 2003, 80, 333.
Chirality / Optical Activity |
Enzymes |
Isotopes |
Synthesis |
Stereochemistry |
Enrichment / Review Materials |
Carboxylic Acids |
Enantiomers |
Reactions |
Mechanisms of Reactions
Teaching Chemistry Using From the Earth to the Moon  James G. Goll and Stacie L. Mundinger
Teaching chemistry using From the Earth to the Moon (an HBO original movie series).
Goll, James G.; Mundinger, Stacie L. J. Chem. Educ. 2003, 80, 292.
Electrochemistry |
Chemometrics |
Reactions |
Mechanisms of Reactions |
Applications of Chemistry
Mechanism-Based Kinetics Simulator  Robert M. Hanson
Allows simulation of the kinetics of a reaction based on its mechanism.
Hanson, Robert M. J. Chem. Educ. 2002, 79, 1379.
Kinetics |
Mechanisms of Reactions
Using Computer Graphics to Demonstrate the Origin and Applications of the "Reacting Bond Rules"  David R. Tyler and David R. Herrick
Using computer software (such as Mathematica) to visualize and manipulate reaction surfaces to facilitate understanding of "reacting bond rules".
Tyler, David R.; Herrick, David R. J. Chem. Educ. 2002, 79, 1372.
Computational Chemistry |
Mechanisms of Reactions |
Reactive Intermediates |
Mathematics / Symbolic Mathematics
A Century of Chemical Dynamics Traced through the Nobel Prizes. 1983: Henry Taube  J. Van Houten
Nobel work on the mechanisms of electron transfer reactions, especially in metal complexes.
Van Houten, J. J. Chem. Educ. 2002, 79, 788.
Coordination Compounds |
Metals |
Electrochemistry |
Mechanisms of Reactions |
Enrichment / Review Materials
Hydrogen Bonding Using NMR: A New Look at the 2,4-Pentanedione Keto–Enol Tautomer Experiment  Alexander Grushow and Theresa Julia Zielinski
Modifications to the classic keto-enol experiment that take advantage of improvements in NMR instrumentation.
Grushow, Alexander; Zielinski, Theresa Julia. J. Chem. Educ. 2002, 79, 707.
Equilibrium |
NMR Spectroscopy |
Solutions / Solvents |
Thermodynamics |
Mechanisms of Reactions |
Molecular Properties / Structure |
Hydrogen Bonding
The Application of the Concept of Extent of Reaction  Adela E. Croce
Effectively applying the concept of extent of reaction and the degree of advancement in describing the course of a chemical reaction (particularly multistep reactions) and expressing reaction rate equations.
Croce, Adela E. J. Chem. Educ. 2002, 79, 506.
Kinetics |
Mechanisms of Reactions |
Rate Law
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
A Century of Chemical Dynamics Traced through the Nobel Prizes. 1956: Hinshelwood and Semenov  Josh Van Houten
Nobel work of Sir Cyril Norman Hinshelwood and Nikolay Nikolaevich Semenov for their researches into the mechanism of chemical reactions.
Van Houten, Josh. J. Chem. Educ. 2002, 79, 414.
Reactions |
Mechanisms of Reactions
Tick Tock, a Vitamin C Clock  Stephen W. Wright
Uses supermarket chemicals to perform a clock reaction; students vary the concentration of reactants and observe the effect on the time required for the reaction to reach its endpoint.
Wright, Stephen W. J. Chem. Educ. 2002, 79, 40A.
Consumer Chemistry |
Oxidation / Reduction |
Vitamins |
Equilibrium |
Mechanisms of Reactions
Redox Redux: Recommendations for Improving Textbook and IUPAC Definitions  Ed Vitz
Defining oxidation / reduction reactions as those in which oxidation states of the reactant(s) change.
Vitz, Ed. J. Chem. Educ. 2002, 79, 397.
Electrochemistry |
Mechanisms of Reactions |
Oxidation / Reduction |
Oxidation State
Cholesterol Biosynthesis: Lanosterol to Cholesterol  John M. Risley
Analysis of the step-by-step synthesis of cholesterol from lanosterol.
Risley, John M. J. Chem. Educ. 2002, 79, 377.
Catalysis |
Enzymes |
Lipids |
Mechanisms of Reactions |
Metabolism
Chemical Kinetics and Catalysis (by Richard I. Masel)  Richard M. Pagni
Chemical kinetics text.
Pagni, Richard M. J. Chem. Educ. 2002, 79, 313.
Catalysis |
Kinetics |
Mechanisms of Reactions
The Michael Reaction  Thomas Poon, Bradford P. Mundy, and Thomas W. Shattuck
Biography, overview, computational analysis, and examples of the Michael reaction in organic syntheses and natural systems.
Poon, Thomas; Mundy, Bradford P.; Shattuck, Thomas W. J. Chem. Educ. 2002, 79, 264.
Computational Chemistry |
Synthesis |
Mechanisms of Reactions
Microscale Synthesis of a Diphenylisoxazoline by a 1,3-Dipolar Cycloaddition  William B. Martin, Laura J. Kateley, Dawn C. Wiser, and Catherine A. Brummond
Synthesis in which two possible pathways are possible; students use NMR to identify the product and molecular modeling to explain the preferred pathway.
Martin, William B.; Kateley, Laura J.; Wiser, Dawn C.; Brummond, Catherine A. J. Chem. Educ. 2002, 79, 225.
Microscale Lab |
Molecular Modeling |
NMR Spectroscopy |
Synthesis |
Mechanisms of Reactions |
Heterocycles
Use of 15N Label in Organic Synthesis and Spectroscopy. Part I: Preparation of 15N-Labeled tert-Butylamine  Erach R. Talaty, Christopher A. Boese, Sanni M. Adewale, Mohammed S. Ismail, Frank A. Provenzano, and Melissa J. Utz
Procedure for preparation of 15N-labeled tert-butylamine through the Ritter reaction followed by hydrolysis.
Talaty, Erach R.; Boese, Christopher A.; Adewale, Sanni M.; Ismail, Mohammed S.; Provenzano, Frank A.; Utz, Melissa J. J. Chem. Educ. 2002, 79, 221.
IR Spectroscopy |
NMR Spectroscopy |
Synthesis |
Amines / Ammonium Compounds |
Mechanisms of Reactions
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
Of Magnets and Mechanisms  Edward G. Neeland
Using magnets to demonstrate the electron flow (mechanism) of nucleophilic substitution reactions.
Neeland, Edward G. J. Chem. Educ. 2002, 79, 186.
Magnetic Properties |
Mechanisms of Reactions |
Learning Theories |
Nucleophilic Substitution
Synthesis of Quinolines and Their Characterization by 2-D NMR Spectroscopy  Pamela J. Seaton, R. Thomas Williamson, Abhijit Mitra, and Ali Assarpour
Synthesis of quinolines and their characterization by 2-D NMR spectroscopy.
Seaton, Pamela J.; Williamson, R. Thomas; Mitra, Abhijit; Assarpour, Ali. J. Chem. Educ. 2002, 79, 106.
NMR Spectroscopy |
Synthesis |
Mechanisms of Reactions |
Aromatic Compounds |
Heterocycles
Preparation of a D-Glucose-Derived Alkene. An E2 Reaction for the Undergraduate Organic Chemistry Laboratory  Peter Norris and Andrew Fluxe
Synthesis of four carbohydrate derivatives that highlight techniques such as inert atmosphere work, rotary evaporators, and flash column chromatography.
Norris, Peter; Fluxe, Andrew. J. Chem. Educ. 2001, 78, 1676.
Carbohydrates |
NMR Spectroscopy |
Synthesis |
Alkenes |
Elimination Reactions |
Chromatography
Organic CD, Version 3.00 [CD-ROM] (by Bryan C. Sanctuary and Neil F. Woolsey)  Robert W. Holman
Animated and interactive introductory organic chemistry electronic text.
Holman, Robert W. J. Chem. Educ. 2001, 78, 1603.
Mechanisms of Reactions
Phototropic Reaction (re J. Chem. Educ. 2000, 77, 1386-1387)  Addison Ault
Incorrect interpretation of the mechanism of a photochemical reaction.
Ault, Addison. J. Chem. Educ. 2001, 78, 1596.
Crystals / Crystallography |
Synthesis |
Photochemistry |
Mechanisms of Reactions
Phototropic Reaction (re J. Chem. Educ. 2000, 77, 1386-1387)  Paul Rademacher
Incorrect interpretation of the mechanism of a photochemical reaction.
Rademacher, Paul. J. Chem. Educ. 2001, 78, 1596.
Crystals / Crystallography |
Synthesis |
Photochemistry |
Mechanisms of Reactions
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
The Relationship between Stoichiometry and Kinetics Revisited  Jim Y. Lee
Analysis decoupling stoichiometry and kinetics in dealing with nonelementary reactions.
Lee, Jim Y. J. Chem. Educ. 2001, 78, 1283.
Kinetics |
Mechanisms of Reactions |
Stoichiometry |
Rate Law
Discovery-Oriented Approach To Organic Synthesis: Tandem Aldol Condensation-Michael Addition Reactions. Identifying Diastereotopic Hydrogens in an Achiral Molecule by NMR Spectroscopy  Nanette Wachter-Jurcsak and Kendra Reddin
Procedure illustrating aldol condensation and Michael addition reactions.
Wachter-Jurcsak, Nanette; Reddin, Kendra. J. Chem. Educ. 2001, 78, 1264.
NMR Spectroscopy |
Synthesis |
Stereochemistry |
Aromatic Compounds |
Aldehydes / Ketones |
Addition Reactions |
Mechanisms of Reactions
Ethanol Metabolism and the Transition from Organic Chemistry to Biochemistry  Richard D. Feinman
Introducing alcohol dehydrogenase and aldehyde dehydrogenase reactions in organic chemistry to ease transition to biochemistry.
Feinman, Richard D. J. Chem. Educ. 2001, 78, 1215.
Metabolism |
Oxidation / Reduction |
Reactions |
Mechanisms of Reactions |
Alcohols |
Carbohydrates
Correction to A More Realistic Teaching Style in Spectroscopic Instruction (J. Chem. Educ. 2001, 78, 765-769)  Mar Gómez Gallego, Santiago Romano, Miguel A. Sierra, and Enrique Nieto
Missing reference and incorrect citation in original article.
Gallego, Mar Gómez Romano, Santiago; Sierra, Miguel A.; Nieto, Enrique. J. Chem. Educ. 2001, 78, 1183.
Mechanisms of Reactions |
NMR Spectroscopy |
Learning Theories
Correction to Computational Investigations for Undergraduate Organic Chemistry: Modeling a TLC Exercise to Investigate Molecular Structure and Intermolecular Forces (J. Chem. Educ. 2000, 77, 203-205)  Rita K. Hessley
Missing reference and incorrect citation in original article.
Hessley, Rita K. J. Chem. Educ. 2001, 78, 1183.
Mechanisms of Reactions |
NMR Spectroscopy |
Learning Theories |
Chromatography |
Computational Chemistry |
Separation Science
The Biginelli Reaction  Michael S. Holden and R. David Crouch
Procedure illustrating the Biginelli reaction.
Holden, Michael S.; Crouch, R. David. J. Chem. Educ. 2001, 78, 1104.
Microscale Lab |
Synthesis |
Reactions |
Mechanisms of Reactions |
Esters |
Heterocycles
Suzuki Cross-Coupling Reactions: Synthesis of Unsymmetrical Biaryls in the Organic Laboratory  Christopher S. Callam and Todd L. Lowary
Laboratory that exposes students to organometallic chemistry and application of the Suzuki reaction.
Callam, Christopher S.; Lowary, Todd L. J. Chem. Educ. 2001, 78, 947.
Aromatic Compounds |
Metals |
Synthesis |
Organometallics |
Transition Elements |
Mechanisms of Reactions
Don't Be Tricked by Your Integrated Rate Plot!  Edward T. Urbansky
Using integrated rate plots to determine reaction order.
Urbansky, Edward T. J. Chem. Educ. 2001, 78, 921.
Kinetics |
Mechanisms of Reactions |
Learning Theories |
Chemometrics |
Rate Law
Systems of Chemical Equations as Reasonable Reaction Mechanisms  Sergey V. Dorozhkin
Helping students to determine reasonable reaction mechanisms among simple inorganic compounds.
Dorozhkin, Sergey V. J. Chem. Educ. 2001, 78, 917.
Stoichiometry |
Mechanisms of Reactions |
Learning Theories
Mechanisms of Pentacoordinate Pseudorotation. A Molecular Modeling Study of PF5  Craig D. Montgomery
This exercise in molecular modeling allows students to compare the two commonly suggested mechanisms for pseudorotation in pentacoordinate compounds--the Berry and turnstile mechanisms.
Montgomery, Craig D. J. Chem. Educ. 2001, 78, 844.
Computational Chemistry |
Mechanisms of Reactions |
Molecular Modeling |
Stereochemistry
A More Realistic Teaching Style in Spectroscopic Instruction  Mar Gómez Gallego, Santiago Romano, Miguel A. Sierra, and Enrique Nieto
A practical application of spectroscopic analysis in intermediate and advanced organic chemistry to determine reaction mechanisms and identify products; provides three specific problems.
Gallego, Mar Gómez; Romano, Santiago; Sierra, Miguel A.; Nieto, Enrique. J. Chem. Educ. 2001, 78, 765.
Mechanisms of Reactions |
NMR Spectroscopy |
Learning Theories |
Spectroscopy |
Molecular Properties / Structure |
Qualitative Analysis
An Idea Whose Time Has Come?
(re
J. Chem. Educ. 1999, 76, 1718-1722)  David E. Lewis
Unoccupied orbitals as the major arbiters of reactivity have been long ignored in teaching introductory organic chemistry courses.
Lewis, David E. J. Chem. Educ. 2001, 78, 727.
Covalent Bonding |
Mechanisms of Reactions |
MO Theory
An Idea Whose Time Has Come?
(re
J. Chem. Educ. 1999, 76, 1718-1722)  William B. Jensen
Past classifications related to the nine-category classification of organic electrophilic-nucleophilic reactions based on the bonding and symmetry characteristics of the reactants' frontier orbitals of the author.
Jensen, William B. J. Chem. Educ. 2001, 78, 727.
Covalent Bonding |
Mechanisms of Reactions |
MO Theory
An Idea Whose Time Has Come?
(re
J. Chem. Educ. 1999, 76, 1718-1722)  William B. Jensen
Past classifications related to the nine-category classification of organic electrophilic-nucleophilic reactions based on the bonding and symmetry characteristics of the reactants' frontier orbitals of the author.
Jensen, William B. J. Chem. Educ. 2001, 78, 727.
Covalent Bonding |
Mechanisms of Reactions |
MO Theory
Nonclassical or Reactivation Chain Polymerization: A General Scheme of Polymerization  Yen Wei
A new integrated model of polymerization is presented: the nonclassical or reactivation chain polymerization. In this model polymer growth involves chemical, physical, or biological reactivation of a dormant chain and subsequent reaction of the reactivated chain with incoming monomers to yield a new dormant chain of higher molecular weight.
Wei, Yen. J. Chem. Educ. 2001, 78, 551.
Materials Science |
Mechanisms of Reactions |
Proteins / Peptides |
Polymerization
Diastereoselective Synthesis of (+/-)-1,2-Diphenyl-1,2-propanediol. A Discovery-Based Grignard Reaction Suitable for a Large Organic Lab Course  James A. Ciaccio, Roxana P. Bravo, Antoinette L. Drahus, John B. Biggins, Rosalyn V. Concepcion, and David Cabrera
An experiment that probes the diastereoselectivity of the reaction between a Grignard reagent and a common, inexpensive alpha-chiral ketone; introduces students to pi-facial discrimination by having them establish the stereochemical course of kinetically controlled nucleophilic addition to a carbonyl.
Ciaccio, James A.; Bravo, Roxana P.; Drahus, Antoinette L.; Biggins, John B.; Concepcion, Rosalyn V.; Cabrera, David. J. Chem. Educ. 2001, 78, 531.
Mechanisms of Reactions |
Synthesis |
Organometallics |
Stereochemistry |
Grignard Reagents |
Aldehydes / Ketones
The Oxidation of Alkylbenzenes: Using Data Pooling in the Organic Laboratory to Illustrate Research in Organic Chemistry  James C. Adrian Jr. and Leslie A. Hull
Student groups are assigned the task of oxidizing various substituted alkylbenzenes with potassium permanganate in basic solution; by pooling the results from all groups it is possible to illustrate how a research project in chemistry can be used to answer simple questions - What happens when your individual alkylbenzene is oxidized?
Adrian, James C., Jr.; Hull, Leslie A. J. Chem. Educ. 2001, 78, 529.
Synthesis |
Chemometrics |
Oxidation / Reduction |
Mechanisms of Reactions |
Aromatic Compounds
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
Advanced Organic Chemistry, Part A: Structure and Mechanism, 4th Edition (by Francis A. Carey and Richard J. Sundberg)   R. Daniel Libby
Standard text / reference for upper-level undergraduate and graduate students in physical organic chemistry.
Libby, R. Daniel. J. Chem. Educ. 2001, 78, 314.
Molecular Properties / Structure |
Mechanisms of Reactions
Synthesis of [RuCl2(dppb)(PPh3)] and Identification of the cis- and trans-[RuCl2(dppb)(phen)] Geometrical Isomers via 31P{1H} NMR Spectroscopy. An Undergraduate Experiment for Inorganic Chemistry  Salete L. Queiroz, Márcio P. de Araujo, Alzir A. Batista, Kenneth S. MacFarlane, and Brian R. James
Demonstrates the use of 31P{1H} NMR to distinguish between cis and trans geometric isomers of coordination compounds in solution, describes the concept of spin-spin coupling for P atoms by assigning signals to equivalent and nonequivalent P atoms, and offers an introduction to synthesis and in situ NMR work requiring semirigorous, inert-atmosphere conditions.
Queiroz, Salete L.; de Araujo, Márcio P.; Batista, Alzir A.; MacFarlane, Kenneth S.; James, Brian R. J. Chem. Educ. 2001, 78, 87.
Coordination Compounds |
Synthesis |
Mechanisms of Reactions |
Transition Elements |
Diastereomers |
NMR Spectroscopy
The Discovery-Oriented Approach to Organic Chemistry. 5. Stereochemistry of E2 Elimination: Elimination of cis- and trans-2-Methylcyclohexyl Tosylate  Marcus E. Cabay, Brad J. Ettlie, Adam J. Tuite, Kurt A. Welday, and Ram S. Mohan
A discovery-oriented lab that illustrates the stereochemistry of the E2 elimination reaction and is a good exercise in 1H NMR spectroscopy. The added element of discovery insures that student interest and enthusiasm are retained.
Cabay, Marcus E.; Ettlie, Brad J.; Tuite, Adam J.; Welday, Kurt A.; Mohan, Ram S. J. Chem. Educ. 2001, 78, 79.
IR Spectroscopy |
Mechanisms of Reactions |
NMR Spectroscopy |
Stereochemistry |
Elimination Reactions |
Reactions |
Alkenes
Organic Reaction Mechanisms. Selected Problems and Solutions, 1st Edition by William C. Groutas  Richard Pagni
Mastering the fundamental principles of organic chemistry by using critical reasoning skills to solve a large number of mechanistic problems.
Pagni, Richard. J. Chem. Educ. 2001, 78, 33.
Mechanisms of Reactions |
Reactions
Fluorescence Measurement of Pyrene Wall Adsorption and Pyrene Association with Humic Acids. An Experiment for Physical Chemistry or Instrumental Methods  Edward C. Shane, Miranda Price-Everett, and Tonya Hanson

Shane, Edward C.; Price-Everett, Miranda; Hanson, Tonya. J. Chem. Educ. 2000, 77, 1617.
Fluorescence Spectroscopy |
Instrumental Methods |
Mechanisms of Reactions
The Illustration of Multistability  Guy Schmitz, Ljiljana Kolar-Anic, Slobodan Anic, and Zeljko Cupic
Multistability, a phenomenon that can appear in certain nonlinear systems, is usually described by discussing the possible steady-state solutions of some nonlinear process as given by an abstract mathematical model having a single variable and one or more control or bifurcation parameters. In the present paper, the model of a real reaction is offered: the illustration of multistability is carried out on a model for the hydrogen peroxide decomposition into water and oxygen in the presence of iodate and hydrogen ions, the Bray-Liebhafsky oscillatory reaction.
Schmitz, Guy; Kolar-Anic, Ljiljana; Anic, Slobodan; Cupic, Zeljko. J. Chem. Educ. 2000, 77, 1502.
Kinetics |
Mechanisms of Reactions
Periplanar or Coplanar?  Saul Kane and William H. Hersh
The prefix peri, derived from the Greek for "near", was chosen to make the meaning "approximately planar". However, the current common usage of syn and antiperiplanar is planar, which is incorrect. In the interests of proper language, we suggest that future authors instead use "syn-coplanar" and "anti-coplanar".
Kane, Saul; Hersh, William H. J. Chem. Educ. 2000, 77, 1366.
Mechanisms of Reactions |
Nomenclature / Units / Symbols |
Stereochemistry |
Molecular Properties / Structure
Kinetic Isotope Effect in the Chromic Acid Oxidation of Secondary Alcohols  Charles E. Harding, Christopher W. Mitchell, and Jozsef Devenyi
The kinetic isotope effect is an invaluable tool in studying certain organic reaction mechanisms. Two activities involving the technique that are suitable for introductory organic laboratory students are described. A simple competition experiment utilizing the benzhydrol?benzhydrol-d1 system and chromic acid oxidation is used to demonstrate qualitatively that there is a kinetic isotope effect involved in this process.
Harding, Charles E.; Mitchell, Christopher W.; Devenyi, Jozsef. J. Chem. Educ. 2000, 77, 1042.
Isotopes |
Kinetics |
Mechanisms of Reactions |
Alcohols |
Oxidation / Reduction
Photochemistry of Chloropicrin. A Physical Chemistry Project  E. A. Wade, T. P. Clemes, and K. A. Singmaster
In this experiment, students will use FTIR spectroscopy to monitor the kinetics of the photolysis of chloropicrin by an Hg arc lamp, both with and without oxygen. They will then be able to determine the mechanism of the photolytic reaction.
Wade, Elisabeth A.; Clemes, T. P.; Singmaster, Karen A. J. Chem. Educ. 2000, 77, 898.
Atmospheric Chemistry |
IR Spectroscopy |
Kinetics |
Photochemistry |
Mechanisms of Reactions
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
Computational Investigations for Undergraduate Organic Chemistry: Modeling Markovnikov and anti-Markovnikov Reactions for the Formation of Alkyl Halides and Alcohols  Rita K. Hessley
This paper describes how the early introduction of molecular modeling for the study of reaction mechanisms leading to alcohols from alkenes can increase students' involvement in their own learning and can effectively challenge their misapprehension about memorization.
Hessley, Rita K. J. Chem. Educ. 2000, 77, 794.
Computational Chemistry |
Alcohols |
Molecular Modeling |
Mechanisms of Reactions
Molecular Orbital Animations for Organic Chemistry  Steven A. Fleming, Greg R. Hart, and Paul B. Savage
Introduces the application of highest occupied and lowest unoccupied molecular orbitals (HOMOs and LUMOs) in animated form.
Fleming, Steven A.; Hart, Greg R.; Savage, Paul B. J. Chem. Educ. 2000, 77, 790.
MO Theory |
Molecular Modeling |
Mathematics / Symbolic Mathematics |
Mechanisms of Reactions |
Electrophilic Substitution |
Nucleophilic Substitution
The Heck Reaction: A Microscale Synthesis Using a Palladium Catalyst  William B. Martin and Laura J. Kateley
The microscale synthesis described uses a reaction between a bromoiodobenzene and acrylic acid to produce a bromocinnamic acid. Structure verification for the product uses IR and 1H NMR spectroscopy.
Martin, William B.; Kateley, Laura J. J. Chem. Educ. 2000, 77, 757.
Catalysis |
Microscale Lab |
Synthesis |
IR Spectroscopy |
NMR Spectroscopy |
Aromatic Compounds |
Mechanisms of Reactions
The Oxidation of Primary Alcohols to Esters: Three Related Investigative Experiments  Chriss E. McDonald

McDonald, Chriss E. J. Chem. Educ. 2000, 77, 750.
Oxidation / Reduction |
Alcohols |
Esters |
Synthesis |
Mechanisms of Reactions
Organic Reactions in Aqueous Media (by Chao-Jun Li and Tak-Hang Chan)  reviewed Alan M. Rosan
Selective review of the burgeoning literature on organic reactions conducted in water or in aqueous media as a reaction cosolvent.
Rosan, Alan M. J. Chem. Educ. 2000, 77, 707.
Aqueous Solution Chemistry |
Reactions |
Synthesis |
Mechanisms of Reactions
Epoxide Chemistry: Guided Inquiry Experiment Emphasizing Structure Determination and Mechanism  H. G. Krishnamurty, Niveta Jain, and Kiran Samby
An operationally simple three-step synthesis of an a-hydroxy acid based on epoxide chemistry. The focus of the experiment is on the preparation of the chalcone epoxide and its reaction with hot alcoholic alkali. The experiment leads to an unpredicted reaction product.
Krishnamurty, H. G.; Jain, Niveta; Samby, Kiran. J. Chem. Educ. 2000, 77, 511.
Epoxides |
Molecular Properties / Structure |
Mechanisms of Reactions |
Synthesis
Kinetics of Reduction of Toluidine Blue with Sulfite--Kinetic Salt Effect in Elucidation of Mechanism  S. B. Jonnalagadda and N. R. Gollapalli
The reaction between toluidine blue (TB+) and the sulfite ion is an ideal kinetic experiment in an undergraduate physical chemistry laboratory, to show the dependence of the reaction rate on the concentrations of reactants and ionic strength. The experiments with varying ionic strength demonstrate how kinetic salt effect can be used to predict the nature of charged species involved in the rate-limiting step.
Jonnalagadda, S. B.; Gollapalli, N. R. J. Chem. Educ. 2000, 77, 506.
Kinetics |
Oxidation / Reduction |
Mechanisms of Reactions
Reaction of Dibenzoylethylene with Hydriodic Acid  Fred H. Greenberg
Dibenzoylethylene is treated with hydriodic acid in acetone at room temperature to obtain dibenzoylethane rather than the expected dibenzoyliodoethane. Students identify the product by the use of NMR and IR spectra and are given a nonpictorial representation of a mechanism and asked to supply the structures of the relevant intermediates.
Greenberg, Fred H. J. Chem. Educ. 2000, 77, 505.
Microscale Lab |
Synthesis |
NMR Spectroscopy |
IR Spectroscopy |
Mechanisms of Reactions |
Reactive Intermediates
Gaseous-Ion Fragmentation Mechanisms in Chlorobenzenes by GC/MS and GC/MS/MS: A Physical-Chemical Approach for Undergraduates  Steven M. Schildcrout
Students use a tabletop PC-controlled ion-trap mass spectrometer with a GC inlet to obtain positive-ion electron-ionization mass spectra and collision-induced-dissociation mass spectra (MS/MS) for chlorobenzene and 1,2- and 1,4-dichlorobenzene.
Schildcrout, Steven M. J. Chem. Educ. 2000, 77, 501.
Isotopes |
Mass Spectrometry |
Mechanisms of Reactions |
Gas Chromatography
An Introduction to Nonlinear Chemical Dynamics: Oscillations, Waves, Patterns, and Chaos (by I. R. Epstein and J. A. Pojman)  reviewed by Richard J. Field
The major strength of this treatment by Epstein and Pojman is a strong connection between theory and experiment. The mechanisms of many oscillating chemical reactions are described in detail.
Field, Richard J. J. Chem. Educ. 2000, 77, 450.
Kinetics |
Reactions |
Mechanisms of Reactions
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
Using Computer Assisted Learning to Teach Molecular Reaction Dynamics  Katharine L. Reid, Richard J. Wheatley, Stephen W. Brydges, and John C. Horton
A Computer Assisted Learning program to aid in the teaching of molecular reaction dynamics to undergraduate students. Dynamic and steric factors affecting reaction outcomes are investigated by observing individual molecular collisions. Students control the reactions by experimenting with the initial trajectories of the molecules.
Reid, Katharine L.; Wheatley, Richard J.; Brydges, Stephen W.; Horton, John C. J. Chem. Educ. 2000, 77, 407.
Kinetics |
Molecular Modeling |
Molecular Mechanics / Dynamics |
Stereochemistry |
Mechanisms of Reactions
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
Dediazoniations in Water: An Integrated Physical Organic Chemistry Experiment  Ugo Costas-Costas, Román Pazo-LLorente, Elisa González-Romero, and Carlos Bravo-Díaz
An integrated physical organic experiment that includes synthesis and isolation of an arenediazonium salt in the solid state and a kinetic study of its stability in water by employing both spectrophotometric and potentiometric measurements. Spectrophotometric kinetic data can be obtained by following the decrease in absorbance due to diazonium ion disappearance.
Costas-Costas, Ugo; Pazo-LLorente, Román; González-Romero, Elisa; Bravo-Díaz, Carlos. J. Chem. Educ. 2000, 77, 384.
Kinetics |
Synthesis |
Mechanisms of Reactions |
Synthesis
Multicomponent Reactions: A Convenient Undergraduate Organic Chemistry Experiment  Ricardo Bossio, Stefano Marcaccini, Carlos F. Marcos, and Roberto Pepino
Two experiments for the synthesis of a -lactam and a succinimide, based on a 4-component Ugi condensation. The experimental procedures for both syntheses are identical except for the choice of the starting amine, whose electron richness is controlled by the presence or absence of an electron-withdrawing group.
Bossio, Ricardo; Marcaccini, Stefano; Marcos, Carlos F.; Pepino, Roberto. J. Chem. Educ. 2000, 77, 382.
Synthesis |
Drugs / Pharmaceuticals |
IR Spectroscopy |
NMR Spectroscopy |
Mechanisms of Reactions |
Molecular Properties / Structure
Introducing Chiroscience into the Organic Laboratory Curriculum  Kenny B. Lipkowitz, Tim Naylor, and Keith S. Anliker
"Chiroscience" is a young but robust industry linking science and technology with chemistry and biology; includes description of an asymmetric reduction of a ketone followed by an assessment of the enantiomeric excess by GC using a chiral stationary phase.
Lipkowitz, Kenny B.; Naylor, Tim; Anliker, Keith S. J. Chem. Educ. 2000, 77, 305.
Chirality / Optical Activity |
Chromatography |
Mechanisms of Reactions |
Synthesis |
Separation Science |
Stereochemistry |
Gas Chromatography |
Aldehydes / Ketones
Proposed Methodological Improvement in the Elucidation of Chemical Reaction Mechanisms Based on Chemist-Computer Interaction  Andrew V. Zeigarnik, Raúl E. Valdés-Pérez, and Brian S. White
Argument for a chemist-computer collaborative search for the simpler mechanistic hypotheses consistent with experiment. We have used this method elsewhere to make specialized chemical contributions that are uniquely enabled by the man-machine interaction. The methods can be useful in the classroom to teach the specific skills needed by mechanistic chemists.
Zeigarnik, Andrew V.; Valdés-Pérez, Raúl E.; White, Brian S. J. Chem. Educ. 2000, 77, 214.
Computational Chemistry |
Mechanisms of Reactions
Computational Investigations for Undergraduate Organic Chemistry: Predicting the Mechanism of the Ritter Reaction  Rita K. Hessley
Before carrying out a laboratory experiment that investigates the mechanism for the formation of N-t-butylbenzamide, students construct and obtain heats of formation for reactants, products, postulated reaction intermediates, and one transition state structure for each proposed mechanism. This is designed as a companion to an open-ended laboratory experiment that hones skills learned early in most traditional organic chemistry courses.
Hessley, Rita K. J. Chem. Educ. 2000, 77, 202.
Computational Chemistry |
Reactive Intermediates |
Mechanisms of Reactions
The Relationship between Stoichiometry and Kinetics  Sidney Toby
A mechanism consisting of several elementary steps may not have a unique stoichiometry. Even if one exists, a linear combination of the steps will not in general lead to a correct formulation of the overall stoichiometry. We consider the time dependence of stoichiometry and show how it can be obtained.
Toby, Sidney. J. Chem. Educ. 2000, 77, 188.
Kinetics |
Mechanisms of Reactions |
Stoichiometry |
Reactions
The Discovery-Oriented Approach to Organic Chemistry. 3. Rearrangement of cis- and trans-Stilbene Oxides with Boron Trifluoride Etherate. An Exercise in 1H NMR Spectroscopy for Sophomore Organic Laboratories  Erik A. Sgariglia, Regina Schopp, Kostas Gavardinas, and Ram S. Mohan
A discovery-oriented laboratory experiment that involves the rearrangement of both cis- and trans-stilbene oxides with boron trifluoride etherate.
Sgariglia, Erik A.; Schopp, Regina; Gavardinas, Kostas; Mohan, Ram S. J. Chem. Educ. 2000, 77, 79.
Mechanisms of Reactions |
NMR Spectroscopy |
Constitutional Isomers
Keep Going with Cyclooctatetraene!  Addison Ault
This paper shows how some simple properties of cyclooctatetraene can indicate important ideas about the structure of cyclooctatetraene.
Ault, Addison. J. Chem. Educ. 2000, 77, 55.
Aromatic Compounds |
NMR Spectroscopy |
Mechanisms of Reactions |
Molecular Properties / Structure
1999 Nobel Prize in Chemistry  
The Royal Swedish Academy has awarded the 1999 Nobel Prize in Chemistry to Ahmed H. Zewail (California Institute of Technology, Pasadena, CA) "for his studies of the transition states of chemical reactions using femtosecond spectroscopy".
J. Chem. Educ. 2000, 77, 14.
Kinetics |
Mechanisms of Reactions |
Lasers |
Spectroscopy |
Reactions |
Covalent Bonding
Organizing Organic Reactions: The Importance of Antibonding Orbitals  David E. Lewis
It is proposed that unoccupied molecular orbitals arbitrate much organic reactivity, and that they provide the basis for a reactivity-based system for organizing organic reactions. Such a system is proposed for organizing organic reactions according to principles of reactivity, and the system is discussed with examples of the frontier orbitals involved.
Lewis, David E. J. Chem. Educ. 1999, 76, 1718.
Covalent Bonding |
Mechanisms of Reactions |
MO Theory
The Simulation of Dynamic Systems  Sidney Toby and Frina S. Toby
A method, suitable for undergraduates, is given for simulating dynamic systems. The program used is free of copyright and when used with a fast PC will integrate a typical mechanism in a few seconds, making unnecessary any assumptions about steady states, quasi equilibrium, or rate-determining steps.
Toby, Sidney; Toby, Frina S. J. Chem. Educ. 1999, 76, 1584.
Computational Chemistry |
Kinetics |
Mechanisms of Reactions |
Learning Theories
A Streamlined Approach to Solving Simple and Complex Kinetic Systems Analytically  John Andraos
The use of Laplace transforms and integration techniques for the solution of simultaneous differential equations is demonstrated for obtaining the analytical solutions of simple and complex kinetic systems well known to students of the chemical sciences.
Andraos, John. J. Chem. Educ. 1999, 76, 1578.
Kinetics |
Mechanisms of Reactions |
Theoretical Chemistry
The Blue Bottle Reaction as a General Chemistry Experiment on Reaction Mechanisms  Steven C. Engerer and A. Gilbert Cook
Using the scientific method (observe, question, hypothesize, experiment, repeat) students propose and test possible reaction mechanisms for the methylene blue-catalyzed oxidation of dextrose with its dramatic color change. Students are led to discover the three-step mechanism through a series of questions.
Engerer, Steven C.; Cook, A. Gilbert. J. Chem. Educ. 1999, 76, 1519.
Aqueous Solution Chemistry |
Kinetics |
Mechanisms of Reactions
Author's Reply to Micropreparation of [RuH2(PPh3)4]  Linn, Donald E.
Responses to questions regarding the synthesis of [RuH2(PPh3)4].
Linn, Donald E. J. Chem. Educ. 1999, 76, 1485.
NMR Spectroscopy |
Organometallics |
Synthesis |
Microscale Lab |
Mechanisms of Reactions
Micropreparation of [RuH2(PPh3)4]  Arnaiz, Francisco J.
Questions regarding the synthesis of [RuH2(PPh3)4].
Arnaiz, Francisco J. J. Chem. Educ. 1999, 76, 1484.
NMR Spectroscopy |
Organometallics |
Synthesis |
Microscale Lab |
Mechanisms of Reactions
Teaching Students to Use Electrochemistry as a Probe of Molecular Behavior  Grant N. Holder
Incorporating into upper-level undergraduate laboratories experiments utilizing modern, computer-controlled electrochemical workstations to probe molecular behavior. To this end, exercises of appropriate difficulty are described for calculating rate constants, surface coverage, and deducing electron-transfer mechanisms.
Holder, Grant N. J. Chem. Educ. 1999, 76, 1478.
Electrochemistry |
Instrumental Methods |
Kinetics |
Mechanisms of Reactions
Chemical Kinetics in Constant-Pressure Systems  P. L. Corio
A theory is developed for treating chemical kinetics in nonflow, constant-pressure systems. The procedure is straightforward and applicable to systems in which several reactions occur, subject to any given rate laws.
Corio, Paul L. J. Chem. Educ. 1999, 76, 1452.
Kinetics |
Mechanisms of Reactions |
Theoretical Chemistry |
Learning Theories
The Stille Reaction (Vittorio Farina, Venkat Krishnamurthy, and William J. Scott)  John C. Cochran
Describes a palladium-catalyzed cross-coupling between a carbon ligand on tin and a carbon with electrophilic character.
Cochran, John C. J. Chem. Educ. 1999, 76, 1344.
Reactions |
Mechanisms of Reactions
Studying Nonlinear Dynamics with Numerical Experiments: Dynamics.mcd  John A. Pojman
Oscillating reactions are the main focus of this document. Also an Introduction of numerical integration for chemical rate expressions and examination of the limitations to standard methods and an illustration of the erroneous results that can be obtained for simple coupled differential equations using two algorithms in Mathcad. Oscillating reactions are the main focus of this document.
Pojman, John A. J. Chem. Educ. 1999, 76, 1310.
Kinetics |
Mathematics / Symbolic Mathematics |
Mechanisms of Reactions |
Theoretical Chemistry
Modeling Stratospheric Ozone Kinetics, Part I: The Chapman Cycle: OzoneModelingPartI.mcd  Erica Harvey and Robert Sweeney
The four-step Chapman cycle of stratospheric ozone reactions is used to introduce numerical solutions of complex rate laws and kinetic modeling. This document is written specifically to be accessible to novice Mathcad users and has been employed to introduce kinetics in the first weeks of undergraduate physical chemistry, immediately following completion of the Mathcad tutorial.
Harvey, Erica; Sweeney, Robert. J. Chem. Educ. 1999, 76, 1309.
Atmospheric Chemistry |
Kinetics |
Mathematics / Symbolic Mathematics |
Mechanisms of Reactions
Making Physical Chemistry Relevant with Modern Chemical Dynamics  Theresa Julia Zielinski
Three Mathcad documents that respond to the call for relevance in physical chemistry. The focus of this column is chemical dynamics applied to atmospheric chemistry and oscillating reactions.
Zielinski, Theresa Julia. J. Chem. Educ. 1999, 76, 1308.
Kinetics |
Atmospheric Chemistry |
Mathematics / Symbolic Mathematics |
Mechanisms of Reactions |
Rate Law
Electrophilic Substitution in Naphthalene: Kinetic vs Thermodynamic Control  Leslie D. Field, Sever Sternhell, and Howard V. Wilton
Deuterium-protium exchange in naphthalene effected by trifluoroacetic acid and aluminium tris-trifluoroacetate was followed by proton NMR spectroscopy. These results are a potential "textbook" example of kinetic versus thermodynamic control, which is much clearer than the usually quoted reversible sulfonation of naphthalene.
Field, Leslie D.; Sternhell, Sever; Wilton, Howard V. J. Chem. Educ. 1999, 76, 1246.
Kinetics |
Thermodynamics |
Mechanisms of Reactions |
NMR Spectroscopy |
Electrophilic Substitution
Chemiluminescence Demonstration Illustrating Principles of Ester Hydrolysis Reactions  Andrew G. Hadd, David W. Lehmpuhl, Laura R. Kuck, and John W. Birks
Peroxyoxalate chemiluminescence, the most efficient nonenzymatic chemiluminescence reaction known, is used to demonstrate mechanistic features of analogous ester hydrolysis reactions.
Hadd, Andrew G.; Lehmpuhl, David W.; Kuck, Laura R.; Birks, John W. J. Chem. Educ. 1999, 76, 1237.
Kinetics |
Photochemistry |
Mechanisms of Reactions |
Atomic Properties / Structure |
Esters
Motivating Students in Sophomore Organic Chemistry by Examining Nature's Way- Why Are Vitamins E and C Such Good Antioxidants?  Bruce D. Beaver
Motivating students in sophomore organic chemistry by integrating material from an area of contemporary research activity into the course. This article contains an overview of the antioxidant function of vitamins E and C.
Beaver, Bruce D. J. Chem. Educ. 1999, 76, 1108.
Nutrition |
Mechanisms of Reactions |
Free Radicals |
Learning Theories |
Applications of Chemistry
Molecular Modeling as an Aid to Understanding Stereoselectivity  John B. Klassen, Kate J. Graham, and William P. Muldoon
Students use a molecular mechanics calculation program within Spartan to determine the Boltzmann distribution of conformers of 2-, 3-, and 4-methylcyclohexanone. On the basis of these data, they predict the face of the carbonyl most susceptible to attack by hydride.
Klassen, John B.; Graham, Kate J.; Muldoon, William P. J. Chem. Educ. 1999, 76, 985.
Computational Chemistry |
Mechanisms of Reactions |
Quantum Chemistry |
Stereochemistry |
MO Theory |
Molecular Modeling
Natural Product Chemistry: A Mechanistic, Biosynthetic and Ecological Approach, Second Edition (by Kurt B. G. Torssell)  Pamela K. Kerrigan
With the increased awareness of the beauty of biochemical pathways, this book provides an excellent chance for students to become aware of the natural chemistry that occurs around them.
Kerrigan, Pamela K. J. Chem. Educ. 1999, 76, 759.
Natural Products |
Mechanisms of Reactions |
Bioorganic Chemistry
Pericyclic Reactions: FMO Approach-Abstract of Issue 9904M  Albert W. M. Lee, C. T. So, C. L. Chan, and Y. K. Wu
Pericyclic Reactions: FMO Approach is a program for Macintosh computers in which the frontier molecular orbital approaches to electrocyclic and cycloaddition reactions are animated. The bonding or antibonding interactions of the frontier molecular orbital(s) determine whether the reactions are thermally or photochemically allowed or forbidden.
Lee, Albert W. M.; So, C. T.; Chan, C. L.; Wu, Y. K. J. Chem. Educ. 1999, 76, 720.
MO Theory |
Mechanisms of Reactions
Ring-Opening Metathesis Polymerization with a Well-Defined Ruthenium Carbene Complex: An Experiment for the Undergraduate Inorganic or Polymer Laboratory  Marcia B. France and Erich S. Uffelman
Ring-opening metathesis polymerization (ROMP) experiment for our inorganic laboratory that makes use of a 7-oxanorbornene monomer prepared by students. The catalyst utilized is a commercially available, well-defined ruthenium carbene complex that promotes the living polymerization of norbornene derivatives. This experiment provides students with the opportunity to gain firsthand experience performing reactions in an area of polymer chemistry that is at the forefront of modern research.
France, Marcia B.; Uffelman, Erich S. J. Chem. Educ. 1999, 76, 661.
NMR Spectroscopy |
Mechanisms of Reactions |
Catalysis
Organic Chemistry (by Joseph M. Hornback)  R. Daniel Libby
This text uses reaction mechanisms as the organizing principle, introduces structure where it is necessary to support the reactions to be studied, and considers synthesis after the mechanisms of appropriate reactions have been discussed.
Libby, R. Daniel. J. Chem. Educ. 1999, 76, 611.
Mechanisms of Reactions |
Synthesis |
Molecular Properties / Structure
Photon-Initiated Hydrogen-Chlorine Reaction  Schwenz, Richard; Geiger, Lynn
Incorrect termination step for the H2 + Cl2 reaction mechanism.
Schwenz, Richard; Geiger, Lynn J. Chem. Educ. 1999, 76, 470.
Mechanisms of Reactions
General Potential Energy Surfaces for Catalytic Processes  S. H. Bauer
Here we argue that one may describe, in general terms, how catalysts modify reaction mechanisms by entering and leaving a conversion sequence, using potential energy surfaces that are conceptually correct. Thermochemical and kinetic constraints providing bounds that limit catalytic processes are formulated. 3-D diagrams are proposed. These clearly illustrate the basic principle that catalysts initially associate with the substrates and thus directly participate in modified conversion pathways, but are regenerated in the final step, thereby providing for a turnover number greater than unity.
Bauer, S. H. J. Chem. Educ. 1999, 76, 440.
Catalysis |
Kinetics |
Mechanisms of Reactions
An Easy Experiment To Compare Factors Affecting the Reaction Rate of Structurally Related Compounds  Sandra Signorella, Silvia García, and Luis F. Sala*
An exercise for training students in chemical kinetics that involves the oxidation of polyols with potassium dichromate. The reactivities of the different polyols are compared and differences are interpreted in terms of stereoelectronic factors. In each case, the relative value of the experimental rate constant is used to infer the role of the substituents in the reaction pathway.
Signorella, Sandra; Garca, Silvia; Sala, Luis F. J. Chem. Educ. 1999, 76, 405.
Kinetics |
Mechanisms of Reactions |
Molecular Modeling
Understanding Organic Reaction Mechanisms (by Adam Jacobs)  Daniel Berger
A good buy for any organic chemist, particularly for those teaching organic chemistry, and should be strongly considered as a supplementary text. It is also useful as a main text (supplemented by other material) for an intermediate-to-advanced undergraduate course in organic reaction mechanisms.
Berger, Daniel. J. Chem. Educ. 1999, 76, 167.
Mechanisms of Reactions
Understanding Organic Reaction Mechanisms (by Adam Jacobs)  Samuel S. Stradling
This no-nonsense, well-organized book divides a study of reaction mechanism into nine chapters that discuss, in order, chemical structure, ionic species, why reactions happen, reactive carbon species, the effect of heteroatoms, types of reaction, investigative techniques, analyzing for mechanistic type, and four case histories.
Stradling, Samuel S. J. Chem. Educ. 1999, 76, 167.
Mechanisms of Reactions
Side Reactions in a Grignard Synthesis  Hilton M. Weiss
This experiment describes a standard Grignard synthesis of a secondary alcohol, 3-heptanol. It brings attention to a significant side product, 3-heptanone, and suggests ways of understanding and utilizing the formation of this product. The experiment is intended to stimulate creative thought in the undergraduate organic chemistry course.
Weiss, Hilton M. J. Chem. Educ. 1999, 76, 76.
Mechanisms of Reactions |
Synthesis |
Grignard Reagents
The Design and Synthesis of a Large Interactive Classroom  Laurel L. Clouston and Mark H. Kleinman
The use of group learning techniques in large classes has been used to effectively convey the central concepts of SN1 and SN2 reactions in an introductory organic chemistry class. The activities described are best used as an introduction to these mechanisms.
Clouston, Laurel L.; Kleinman, Mark H. J. Chem. Educ. 1999, 76, 60.
Mechanisms of Reactions |
Learning Theories
The Pechmann Reaction  Michael S. Holden and R. David Crouch
A solid acid-catalyzed version of the Pechmann reaction for the synthesis of coumarins is described. The Pechmann reaction is a multiple-transformation process which is not a part of the normal organic chemistry curriculum.
Holden, Michael S.; Crouch, R. David. J. Chem. Educ. 1998, 75, 1631.
Catalysis |
Mechanisms of Reactions |
Microscale Lab |
Synthesis |
Reactions |
Phenols
Advanced Organic Chemistry: Reactions and Mechanisms (by Bernard Miller)  Daniel J. Berger
The pedagogic philosophy behind Advanced Organic Chemistry: Reactions and Mechanisms is pithily explained in Miller's introduction: in order to maintain student interest, advanced topics are introduced early and theory is presented in context.
Berger, Daniel J. J. Chem. Educ. 1998, 75, 1558.
Reactions |
Mechanisms of Reactions
Inadequacies of the SN1 Mechanism  Johannes Dale
A planar free carbocation intermediate is used as a simple model to explain racemization in solvolysis; but the problem is that racemization is never complete, the enantiomer in excess having the inverted configuration. Also, the unimolecularity has never been demonstrated, but is an assumption only.
Dale, Johannes. J. Chem. Educ. 1998, 75, 1482.
Mechanisms of Reactions
Organic Reactions Involving Bromine: Puzzles for the Organic Laboratory  Sarita I. McGowens and Ernest F. Silversmith
Five puzzles for the organic chemistry laboratory are described. All involve bromine, which is generated in a safe, convenient way that makes it possible to control the amount of bromine precisely. Three of the puzzles involve orientation in electrophilic aromatic substitution, one is a determination of the stereochemistry of addition to alkenes, and the other one looks at the possibility of dehydrohalogenation following addition.
McGowens, Sarita I.; Silversmith, Ernest F. J. Chem. Educ. 1998, 75, 1293.
NMR Spectroscopy |
Synthesis |
Stereochemistry |
Mechanisms of Reactions
Use of Theoretical Chemistry To Explain Baeyer-Villiger Oxidations of Methoxy Aromatic Aldehydes  N. Anoune, H. Hannachi, P. Lantéri, R. Longeray, and C. Arnaud
This is a project for advanced students in two parts. First: A study of the Baeyer-Villiger reaction on para-methoxybenzaldehyde. Such a reaction is commonly used to oxidize ketones into esters. Second: The experiment is extended to various polymethoxybenzaldehydes and theoretical calculations are used to explain their particular behaviors.
Anoune, N.; Hannachi, H.; Lantéri, P.; Longeray, R.; Arnaud, Christian. J. Chem. Educ. 1998, 75, 1290.
Mechanisms of Reactions |
Theoretical Chemistry |
Aldehydes / Ketones |
Aromatic Compounds
Synthesis of Aspirin: A General Chemistry Experiment  John A. Olmsted III
An experiment is described that is suitable for the early portion of the laboratory in a general chemistry course and integrates organic examples. It is the two-step synthesis of aspirin starting from oil of wintergreen. The mechanism for this synthesis provides examples of three major classes of chemical reactions: hydrolysis, condensation, and proton transfer.
Olmsted, John A., III. J. Chem. Educ. 1998, 75, 1261.
Drugs / Pharmaceuticals |
Medicinal Chemistry |
Mechanisms of Reactions |
Aromatic Compounds |
Carboxylic Acids |
Aldehydes / Ketones
The Quasi-Steady-State Approximation: Numerical Validation  Richard A. B. Bond, Bice S. Martincigh, Janusz R. Mika , and Reuben H. Simoyi
In this note, we explore first the graphical representation of exact numerical solutions of partially nondimensionalized forms of the kinetic equations of some small systems of pedagogic interest, and thereby show that the QSSA is more widely applicable than is often assumed. Secondly, qualitative discussions of singular perturbation theory and of numerical stiffness are shown to lead to a simple computational test of QSSA validity, which works with intricate and large systems. This procedure is illustrated for the case of the Oregonator.
Bond, Richard A. B.; Martincigh, Bice S.; Mika , Janusz R.; Simoyi, Reuben H. J. Chem. Educ. 1998, 75, 1158.
Computational Chemistry |
Kinetics |
Mechanisms of Reactions |
Equilibrium
On the Meaning of Km and V/K in Enzyme Kinetics  Dexter B. Northrop
In the reactions of all enzymes except isomerases and mutases, V/K fails to encompass a complete turnover. Instead, it can be shown that V/K actually provides a measure of the rate of capture of substrate by free enzyme into a productive complex or complexes destined to form products and complete a turnover at some later time.
Northrop, Dexter B. J. Chem. Educ. 1998, 75, 1153.
Enzymes |
Catalysis |
Transport Properties |
Mechanisms of Reactions |
Kinetics
Anatomy of an Elementary Chemical Reaction  Andrew J. Alexander and Richard N. Zare
An essential aim of this article is to bring the reader to a favorable vantage point with a brief introduction to reactive dynamics, and from there to describe some examples of recent strategies that have been employed to promote a fundamental understanding of the anatomy of elementary chemical reactions. In the final section we ponder future directions for this rapidly evolving field of research.
Alexander, Andrew J.; Zare, Richard N. J. Chem. Educ. 1998, 75, 1105.
Kinetics |
Lasers |
Spectroscopy |
Mechanisms of Reactions |
Molecular Modeling |
Molecular Mechanics / Dynamics |
Photochemistry
Mechanisms in Motion-Organic Chemistry Animations v 1.5 (by Bruce H. Lipshutz)  Alan M. Rosan
This single CD-ROM presents 17 short (2-3-minute) Quicktime, full-color movie animations of selected organic reaction mechanisms, most of which are discussed at the sophomore level.
Rosan, Alan M. J. Chem. Educ. 1998, 75, 980.
Reactions |
Mechanisms of Reactions
Chemistry from Telephone Numbers: The False Isokinetic Relationship  George C. McBane
The standard technique for determining whether an isokinetic relationship holds for a particular group of reactions is incorrect, and will "discover" the relationship where it does not exist. The paper describes an amusing example of its failure, shows why the false correlations occur, and gives brief descriptions of correct approaches and references to them.
McBane, George C. J. Chem. Educ. 1998, 75, 919.
Kinetics |
Mechanisms of Reactions
Audience-Appropriate Analogies: Collision Theory  Kent W. Piepgrass
This article presents two new analogies for collision theory based on arcade games and on the interactions between salesclerks and customers in a store. The uses, limitations, and possible extensions of the analogies are discussed.
Piepgrass, Kent W. J. Chem. Educ. 1998, 75, 724.
Learning Theories |
Mechanisms of Reactions |
Kinetics
A Simple Organic Microscale Experiment Illustrating the Equilibrium Aspect of the Aldol Condensation  Ernest A. Harrison Jr.
A simple microscale experiment has been developed that illustrates the equilibrium aspect of the aldol condensation by using two versions of the standard preparation of tetraphenylcyclopentadienone from benzil and 1,3-diphenyl- 2-propanone.
Harrison, Ernest A., Jr. J. Chem. Educ. 1998, 75, 636.
Equilibrium |
Reactions |
Mechanisms of Reactions |
Microscale Lab |
Aldehydes / Ketones
Kinetic Demonstration of Intermolecular General Acid (GA) Catalysis in Thiolysis of 9-Anilinoacridine   Mohammad Niyaz Khan
After nearly five decades of active research and numerous publications on GA-GB catalysis, introduction of an experiment on GA for students majoring in enzymology/physical organic chemistry at advanced undergraduate/postgraduate level is appropriate. A kinetic experiment involving the reaction of 2-mercaptoethanol (2-ME) with 9-anilinoacridine (9-ANA) is designed to demonstrate intermolecular GA catalysis.
Khan, Mohammad Niyaz. J. Chem. Educ. 1998, 75, 632.
Bioinorganic Chemistry |
Bioorganic Chemistry |
Mechanisms of Reactions |
Catalysis |
Acids / Bases |
Kinetics
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
Incorporating Organic Name Reactions and Minimizing Qualitative Analysis in an Unknown Identification Experiment  Claire Castro and William Karney
The authors have developed a new type of unknown identification experiment for the introductory organic chemistry laboratory. The unknown sample the student is provided with is the product of an organic name reaction. The student is only informed of the starting material and conditions used in the compound's synthesis, and must then: (1) deduce the compound's structure, (2) determine the name reaction and corresponding mechanism that yields the compound, and (3) present his/her results to the class.
Claire Castro and William Karney. J. Chem. Educ. 1998, 75, 472.
IR Spectroscopy |
NMR Spectroscopy |
Qualitative Analysis |
Nomenclature / Units / Symbols |
Reactions |
Mechanisms of Reactions |
Molecular Properties / Structure
Perspectives on Structure and Mechanism in Organic Chemistry (by Felix A. Carroll)  William J. le Nobel
In his preface, Carroll writes that he hoped to meet two goals: to present the concepts that are central to the understanding and practice of physical organic chemistry, and to emphasize the role of complementary models in the formulation of these concepts.
William J. le Nobel. J. Chem. Educ. 1998, 75, 417.
Molecular Properties / Structure |
Mechanisms of Reactions
A Closer Look at the Addition of Equations and Reactions  Damon Diemente
Chemists occasionally find it convenient or even necessary to express an overall reaction as the sum of two or more component reactions. A close examination, however, reveals that the resemblance between chemical algebraic equations is entirely superficial, and that the real meaning of addition in chemical equations is subtle and varies from case to case. In high-school courses, students are likely to encounter the addition of equations in thermochemistry, in electrochemistry, and in kinetics.
Diemente, Damon. J. Chem. Educ. 1998, 75, 319.
Calorimetry / Thermochemistry |
Electrochemistry |
Mechanisms of Reactions |
Stoichiometry |
Reactions
Nucleophilic Addition vs. Substituion: A Puzzle for the Organic Laboratory  Ernest F. Silversmith
The chemistry of beta-carbonyl compounds is studied. Beta-carbonyl compounds react with hydrazines to give products with a 5-membered ring containing two nitrogens. The experiment makes students determine whether ethyl 2-acetyl-3-oxobutanoate reacts like a beta-diketone or like a beta-keto ester.
Silversmith, Ernest F. J. Chem. Educ. 1998, 75, 221.
Learning Theories |
Nucleophilic Substitution |
Aldehydes / Ketones |
Esters |
Mechanisms of Reactions
How Does the Gibbs Free Energy Evolve in a System Undergoing Coupled Competitive Reactions?  Ludovic Jullien, Anna Proust, and Jean-Christophe Le Menn
The article discusses the meaning of kinetic/thermodynamic controls and kinetic stability. The authors show how the Gibbs free energy of a reacting system varies when successively submitted to kinetic and then thermodynamic controls.
Jullien, Ludovic; Proust, Anna; Le Menn, Jean-Christophe. J. Chem. Educ. 1998, 75, 194.
Equilibrium |
Mechanisms of Reactions |
Thermodynamics
A Kinetics Experiment To Demonstrate the Role of a Catalyst in a Chemical Reaction: A Versatile Exercise for General or Physical Chemistry Students  Christine L. Copper and Edward Koubek
By modifying the iodine clock reaction, students can use the initial rate method to observe the role of a catalyst in a chemical reaction via activation energy calculations and evaluate a proposed mechanism. They can also determine the order with respect to each reactant and the rate constants of the noncatalyzed and catalyzed reactions.
Copper, Christine L.; Koubek, Edward. J. Chem. Educ. 1998, 75, 87.
Catalysis |
Kinetics |
Mechanisms of Reactions
Grignard Synthesis of Various Tertiary Alcohols  T. Stephen Everett
A general Grignard procedure is presented for the synthesis of aliphatic, tertiary alcohols containing six to nine carbons. Without revealing the specific starting materials, students are challenged to identify their unknown products from physical (boiling points, refractive indices) and spectral (infrared O-H, C-H and fingerprint regions) data.
Everett, T. Stephen. J. Chem. Educ. 1998, 75, 86.
IR Spectroscopy |
Alcohols |
Mechanisms of Reactions |
Synthesis
A Grignard-like Organic Reaction in Water  Gary W. Breton and Christine A. Hughey
A known Grignard-like reaction between allyl bromide and benzaldehyde mediated by zinc metal in aqueous media. The procedure retains the desirable features of the traditional Grignard reaction, while eliminating some of the commonly encountered difficulties.
Breton, Gary W.; Hughey, Christine A. J. Chem. Educ. 1998, 75, 85.
Microscale Lab |
Aromatic Compounds |
Aldehydes / Ketones |
Alcohols |
Synthesis |
Mechanisms of Reactions
Following Glycolysis Using 13C NMR: An Experiment Adaptable to Different Undergraduate Levels  T. L. Mega, C. B. Carlson, and D. A. Cleary
This paper describes a laboratory exercise where the glycolysis of [1-13C] glucose under anaerobic conditions was followed using 13C NMR spectroscopy. The exercise is described in terms of its suitability for a variety of different undergraduate levels, although the emphasis in this paper is on its use in an advanced chemistry laboratory course.
Mega, T. L.; Carlson, C.B.; Cleary, D. A. J. Chem. Educ. 1997, 74, 1474.
Instrumental Methods |
Carbohydrates |
Mechanisms of Reactions |
NMR Spectroscopy |
Kinetics |
Glycolysis
Assessing the Fate of Organic Contaminants in Aquatic Environments: Mechanism and Kinetics of Hydrolysis of a Carboxylic Ester  Jorg Klausen, Markus A. Meier , and Rene P. Schwarzenbach
An integrated experiment is proposed for an upper level undergraduate environmental chemistry laboratory. Using 2,4-dinitrophenylacetate (DNPA) as an example, the mechanisms of the abiotic hydrolysis of carboxylic esters are presented and the kinetic expressions are derived. The proposed experimental set-up uses isocratic reversed phase HPLC with UV detection to follow the decrease of DNPA concentration during hydrolysis experiments.
Klausen, Jorg; Meier, Markus A.; Schwarzenbach, Rene P. J. Chem. Educ. 1997, 74, 1440.
Kinetics |
Mechanisms of Reactions |
Chromatography |
Esters |
Water / Water Chemistry
An Easy and Cheap Flash Spectroscopy Experiment  Mauro Maestri*, Roberto Ballardini, Fernando Jorge Silva Pina, and Maria João Melo
Application of a flash photolysis technique to the study of the kinetic behavior of a synthetic flavylium salt in aqueous solution. The kinetic processes, triggered by a camera flash, are followed by means of a slightly modified, computer controlled, spectrophotometer. Light induces reversible absorbance changes and two different transient species are evidenced prior the full recovery of the system.
Maestri, Mauro; Ballardini, Roberto; Pina, Ferando Jorge Silva; Melo, Maria Joao. J. Chem. Educ. 1997, 74, 1314.
Instrumental Methods |
Kinetics |
Mechanisms of Reactions |
Photochemistry |
UV-Vis Spectroscopy |
Spectroscopy |
Reactive Intermediates
Ozonolysis Experiments Using Gas Chromatography-Mass Spectrometry: An Undergraduate Organic Chemistry Laboratory Experiment  Charlene M. Rhoads, George R. Farquar, and William F. Wood
A general method was developed for undergraduate laboratory instruction using ozonolysis at room temperature followed by gas chromatography-mass spectrometry (GC-MS). The simple ozonolysis apparatus described can be constructed from material found in most chemistry laboratories.
Rhoads, Charlene M.; Farquar, George R.; Wood, William F. J. Chem. Educ. 1997, 74, 1220.
Mechanisms of Reactions |
Microscale Lab |
Synthesis |
Spectroscopy |
Gas Chromatography |
Mass Spectrometry
Kinetics without Steady State Approximations  Robert R. Pavlis
The availability of powerful and inexpensive computers coupled with advances in applied mathematics make it possible to use numerical methods to integrate virtually any of the ordinary differential equations that arise in chemical kinetics.
Pavlis, Robert R. J. Chem. Educ. 1997, 74, 1139.
Kinetics |
Laboratory Computing / Interfacing |
Mechanisms of Reactions |
Mathematics / Symbolic Mathematics
Organic Chemistry, 2nd ed. and Core Organic Chemistry by Marye Anne Fox and James K. Whitesell  reviewed by Samuel S. Stradling
An introductory organic text developed around the structure/mechanism format.
Stradling, Samuel S. J. Chem. Educ. 1997, 74, 1045.
Molecular Properties / Structure |
Mechanisms of Reactions
A Three-Dimensional Energy Surface for the Conformational Inversion of Cyclohexane  Nicholas Leventis*, Samir B. Hanna, Chariklia Sotiriou-Leventis
While it is well known that chair forms of cyclohexane can interconvert without passing through the boat conformation, the same statement frequently comprises a source of confusion regarding the location of the boat conformation on the energy surface of the conformational inversion of cyclohexane. To alleviate this problem, a novel three-dimensional energy diagram has been introduced showing explicitly how the chair forms of cyclohexane interconvert.
Leventis, Nicholas; Hanna , Samir B. ; Sotiriou-Leventis, Chariklia . J. Chem. Educ. 1997, 74, 813.
Learning Theories |
Mechanisms of Reactions |
Stereochemistry |
Alkanes / Cycloalkanes |
Conformational Analysis |
Molecular Properties / Structure
Making Organic Concepts Visible  Robert S. H. Liu and Alfred E. Asato
Graphic illustrations, with a Hawaiian flavor, have been introduced to clarify the following concepts encountered in introductory organic chemistry: functional groups, resonance structures, polarizability, ionization in mass spectroscopy and difference in reactivities between alkyl and vinyl halides
Liu, Robert S. H.; Asato, Alfred E. J. Chem. Educ. 1997, 74, 783.
Mechanisms of Reactions |
Resonance Theory
Database vs. Expert System Teaching Paradigms: Using Organic Reaction Mechanisms To Teach Chemical Intuition  Paul H. Scudder
This paper presents an expert-system-designed course that has worked well to teach students how to formulate reasonable hypotheses in organic chemistry. The course organizes reactants into generic electron sources and sinks, and treats reaction mechanisms as assemblies of a limited number of recognizable mechanistic steps.
Scudder, Paul H. J. Chem. Educ. 1997, 74, 777.
Learning Theories |
Mechanisms of Reactions
Catalytic Transfer Hydogenation Reactions for Undergraduate Practical Programs  R. W. Hanson
A brief review of catalytic transfer hydrogenation (CTH) reactions is given. Attention is drawn, particularly, to the utility of ammonium formate as the hydrogen donor in this type of reaction.
Hanson, R. W. J. Chem. Educ. 1997, 74, 430.
Catalysis |
Aldehydes / Ketones |
Alcohols |
Amines / Ammonium Compounds |
Mechanisms of Reactions
Methylene Blue - Ascorbic Acid: An Undergraduate Experiment in Kinetics  T. Snehalatha, K. C. Rajanna, P. K. Saiprakash
Clock reaction experiments with methylene blue (MB) and L-ascorbic acid (H2 A) were designed in aqueous sulfuric and hydrochloric acid media with a view to demonstrate and explain the concepts in chemical kinetics such as order of the reaction, effect of ionic strength, dielectric constant and temperature. On the basis of the obtained results, a plausible mechanism for the reduction of MB by H2 A has been proposed.
Snehalatha, T.; Rajanna, K. C.; Saiprakash, P. K. J. Chem. Educ. 1997, 74, 228.
Kinetics |
Mechanisms of Reactions |
Oxidation / Reduction
A Primer to Mechanism in Organic Chemistry  reviewed by Stephen E. Branz
A book of this length and scope would be most appropriate as a supplement to the second-year organic lecture course in the United States.
Branz, Stephen E. J. Chem. Educ. 1996, 73, A313.
Mechanisms of Reactions
Organic Chemistry, Third Edition  reviewed by Timothy D. Lash
The author continues to stress the use of reaction mechanisms, and this remains a strong point in the new edition. The heart and soul of modern organic chemistry revolves around these concepts, and this framework is essential for a textbook of this type.
Lash, Timothy D. J. Chem. Educ. 1996, 73, A312.
Mechanisms of Reactions
Visualizing the SN2 Inversion  Rosan, Alan M.
Slight modification to the construction of the model presented.
Rosan, Alan M. J. Chem. Educ. 1996, 73, A228.
Nucleophilic Substitution |
Mechanisms of Reactions
Following Microscale Organic Reactions Using FT-IR  Janice Ems-Wilson
This article describes an experiment that encourages discussion of carbohydrate chemistry in terms of reaction mechanisms, conformational analysis, and spectroscopy. The specific experiment involves the preparation of the bis(acetonide) of D-(+)-mannose.
Ems-Wilson, Janice. J. Chem. Educ. 1996, 73, A170.
Microscale Lab |
Carbohydrates |
Mechanisms of Reactions |
Conformational Analysis |
Spectroscopy |
Synthesis |
Aldehydes / Ketones |
Alcohols
Inexpensive Small-Scale Sonochemistry with Magnetic Agitation  Fernando G. Braga
A reduction, esterification, acetylation, an ether synthesis, and an aryl nucleophilic substitution are performed in a microwave oven.
Braga, Fernando G. J. Chem. Educ. 1996, 73, A104.
Microscale Lab |
Synthesis |
Mechanisms of Reactions
Carbonyl and Conjugate Additions to Cyclohexenone: Experiments Illustrating Reagent Selectivity  Michael G. Organ and Paul Anderson
Undergraduate students leaving an organic chemistry program should have exposure to these concepts and hands-on experience in dealing practically with the issue of selectivity. In this paper, selective addition of a nucleophile to either end of the enone moiety in cyclohexenone is examined.
Organ, Michael G.; Anderson, Paul. J. Chem. Educ. 1996, 73, 1193.
Addition Reactions |
Aldehydes / Ketones |
Mechanisms of Reactions
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
The Electrophilic Addition to Alkynes Revisited  Thomas T. Tidwell
A recent claim that vinyl cations are not the predominant intermediates in the electrophilic addition to alkynes is disputed.
Tidwell, Thomas T. J. Chem. Educ. 1996, 73, 1081.
Addition Reactions |
Alkynes |
Mechanisms of Reactions
A Glycosidation Reaction Employing Montmorillonite K-10 as Catalyst  Brooke L. Bedell, R. David Crouch, Michael S. Holden, Heidi E. Martinson
The large number of biology majors and prehealth students enrolled in Organic Chemistry makes it desirable to have laboratories that involve biologically interesting molecules. Although many laboratory manuals contain sections on carbohydrate chemistry, the experiments are typically limited to esterification or hydrolysis reactions.
Bedell, Brooke L.; Crouch, R. David; Holden, Michael S.; Martinson, Heidi E. J. Chem. Educ. 1996, 73, 1041.
Catalysis |
Mechanisms of Reactions
Symmetry Elements and Operations  Albert W.M. Lee, K.M. Leung, W.J Daniel, C.L. Chan
Symmetry Elements and Operations is a multimedia presentation that illustrates the basics of symmetry with three dimensional molecular models and simple text explanations.
Lee, Albert W.M.; Leung, K.M.; Kwong, Daniel W.J.; Chan, C.L. . J. Chem. Educ. 1996, 73, 924.
Molecular Modeling |
Spectroscopy |
Stereochemistry |
Mechanisms of Reactions |
Group Theory / Symmetry |
Quantum Chemistry |
Enrichment / Review Materials
A New Photochemistry Experiment, A Simple 2+2 Photocycloaddition that Poses an Interesting NMR Problem   John T. Magner, Matthias Selke, Arlene A. Russell, Orville L. Chapman
The cycloaddition of -nitrostyrene to 2,3-dimethyl-1,3-butadiene provides an extremely clean example of 2 + 2 cycloaddition. This laboratory exercise combines theory, technique, spectroscopy, and data interpretation.
J. Chem. Educ. 1996, 73, 854.
Photochemistry |
NMR Spectroscopy |
Qualitative Analysis |
Instrumental Methods |
Addition Reactions |
Mechanisms of Reactions
Cascade Sequences in Organic Synthesis: A Lesson from Nature?  Shelagh T. Dennison and David C. Harrowven
This article addresses the attempts of synthetic chemists to mimic nature's syntheses of terpene natural products in the laboratory.
Dennison, Shelagh T.; Harrowven, David C. J. Chem. Educ. 1996, 73, 697.
Synthesis |
Applications of Chemistry |
Mechanisms of Reactions |
Natural Products
Examination of a Reaction Mechanism by Polarimetry: An Experiment for the Undergraduate Organic Chemistry Laboratory  Michael D. Mosher, Chad O. Kelly, and Melvyn W. Mosher
The experiment has been shown to be successful with chiral mandelic acid and POCl3 and with chiral lactic acid and HBr. The substitution mechanisms of these reactions proceed with 1% and 38% SN2 character respectively.
Mosher, Michael D.; Kelly, Chad O.; Mosher, Melvyn W. J. Chem. Educ. 1996, 73, 567.
Instrumental Methods |
Mechanisms of Reactions |
Gas Chromatography
A Mixed Aldol Condensation-Michael Addition Experiment  Thomas P. Clausen, Beverly Johnson, and Jim Wood
This article describes the analysis of the recrystallized products of a mixed aldol condensation between symmetrical ketones and aromatic aldehydes.
Clausen, Thomas P.; Johnson, Beverly; Wood, Jim. J. Chem. Educ. 1996, 73, 266.
Aldehydes / Ketones |
NMR Spectroscopy |
Mechanisms of Reactions
A Simple Algorithm for the Distinction of Reaction Mechanisms Based on the Measurement of Additive Properties  Galvez Alvarez J. and Soler Roca R. M.
This study shows that, in a reacting system containing three compounds, previously identified, only one of them being a reactive, it is possible, through measures of global absorbence or any other additive property, to distinguish between different, very frequent reaction mechanisms, such as irreversible, reversible, consecutive, and simultaneous processes.
Alvarez J., Galvez; Roca R. M., Soler. J. Chem. Educ. 1996, 73, 214.
Mechanisms of Reactions |
Kinetics
Methylene-bis-amide (MBA) Derivatives for Characterization of Nitriles  Edgar F. Kiefer and Kenn M. Takauye
Nitriles (RCN) react with formaldehyde in 80% H2SO4 to form solid derivatives (RCONH)2CH2 useful for characterization. Melting points are tabulated for derivatives of 18 common nitriles.
Kiefer, Edgar F.; Takauye, Kenn M. J. Chem. Educ. 1996, 73, 190.
Qualitative Analysis |
Mechanisms of Reactions
Olefin Metathesis Polymerization: The Unexpected Role of Carbenoid Species in Formation of Macromolecules  Donald M. Snyder
One particularly interesting topic still rarely seen outside of the research literature is the subject of metathesis polymerization. This article is intended to present the interested reader with a brief introduction to the mechanism of this unique process, its historical background, and some recent developments in the field.
Snyder, Donald M. J. Chem. Educ. 1996, 73, 155.
Polymerization |
Alkenes |
Mechanisms of Reactions
Small-Scale Experiments Involving Gas Evolution  Brouwer, H.
Apparatus for measuring very small volume changes of gases and several experimental procedures involving the evolution of gases.
Brouwer, H. J. Chem. Educ. 1995, 72, A100.
Gases |
Laboratory Equipment / Apparatus |
Stoichiometry |
Acids / Bases |
Reactions |
Mechanisms of Reactions |
Microscale Lab
Microscale Electrophilic Aromatic Substitution of p-Toluidine  Kady, Ismail O.
Experimental procedure for first-year organic chemistry students to apply the principles of group protection and study the effect of ring substituents on reaction orientation.
Kady, Ismail O. J. Chem. Educ. 1995, 72, A9.
Synthesis |
Mechanisms of Reactions |
Aromatic Compounds |
Microscale Lab |
Electrophilic Substitution
The Baylis-Hillman Reaction: Synthesizing a Compound and Explaining Its Formation  Crouch, R. David; Nelson, Todd D.
Experimental procedure for the synthesis of an unpredictable and unknown mechanism to be identified and described by students through analytical techniques (spectroscopy).
Crouch, R. David; Nelson, Todd D. J. Chem. Educ. 1995, 72, A6.
Synthesis |
Mechanisms of Reactions |
NMR Spectroscopy |
IR Spectroscopy |
UV-Vis Spectroscopy |
Microscale Lab
Baeyer-Villiger Oxidation of Indane-1-ones: Monitoring of the Reaction by VPC and IR Spectroscopy  Elie Stephan
Procedure for the Baeyer-Villiger oxidation of indane-1-ones.
Stephan, Elie. J. Chem. Educ. 1995, 72, 1142.
IR Spectroscopy |
Synthesis |
Mechanisms of Reactions |
Oxidation / Reduction |
Aldehydes / Ketones
Synthesis of a Bromohydrin: An Experiment Demonstrating Markovnikov Addition  Diane J. Porter, Andrea T. Stewart, and Carl T. Wigal
Microscale procedure that demonstrates Markovnikov addition without the production of noxious products (i.e. mercury).
Porter, Diane J.; Stewart, Andrea T.; Wigal, Carl T. J. Chem. Educ. 1995, 72, 1039.
Mechanisms of Reactions |
Synthesis |
Microscale Lab |
Microscale Lab
Diastereospecific Synthesis of an Epoxide: An Introductory Experiment in Organic Synthetic and Mechanistic Chemistry  James A. Ciaccio
A two-step epoxide synthesis that can be presented to students in the form of two mechanistic "puzzles" that probe the stereoselectivity of two important reactions: halohydrin formation from alkenes and epoxide formation via intramolecular Williamson ether synthesis.
Ciaccio, James A. J. Chem. Educ. 1995, 72, 1037.
Stereochemistry |
Molecular Properties / Structure |
Mechanisms of Reactions |
Synthesis |
Epoxides |
Alkenes
Template Synthesis of Macrocyclic Complexes: A Laboratory Project for Advanced Undergraduate Students  James H. Cameron
Procedure for template synthesis of a macrocyclic (Jager) complex.
Cameron, James H. J. Chem. Educ. 1995, 72, 1033.
Synthesis |
Coordination Compounds |
Organometallics |
Mechanisms of Reactions
The AC Rule: An Algorithm for Organic Reactions  Edgar F. Kiefer
Algorithm for predicting organic reaction mechanisms.
Kiefer, Edgar F. J. Chem. Educ. 1995, 72, 906.
Mechanisms of Reactions |
Synthesis |
Reactions
Mechanism of Electrode Reactions and the Stoichiometric Number  P. Radhakrishnamurty and R. Arun Mozhi Selvan
Calculating the rate determining step for a multielectron transfer reaction.
Radhakrishnamurty, P.; Selvan, R. Arun Mozhi. J. Chem. Educ. 1995, 72, 895.
Kinetics |
Mechanisms of Reactions |
Stoichiometry |
Rate Law |
Electrochemistry
Regioselective Methoxybromination of Styrene Using TBABr3 in Methanol: An Organic Laboratory Experiment   Jacques Berthelot, Yamina Benammar, and Catherine Lange
Methoxybromination of styrene using TBABr3 in methanol.
Bertholet, Jacques; Benammar, Yamina; Lange, Catherine. J. Chem. Educ. 1995, 72, 850.
Synthesis |
Mechanisms of Reactions |
Alkenes |
Addition Reactions
The Addition of Hydrogen Bromide to Simple Alkenes  Hilton M. Weiss
Synthesis of 1-bromohexane.
Weiss, Hilton M. . J. Chem. Educ. 1995, 72, 848.
Synthesis |
Mechanisms of Reactions |
Addition Reactions |
Alkenes
Animation of Imaginary Frequencies at the Transition State  Higgins, Robert H.
176. Computer simulations of reactions mechanisms using HyperChem and ChemPlus software.
Higgins, Robert H. J. Chem. Educ. 1995, 72, 703.
Mechanisms of Reactions |
Molecular Properties / Structure |
Reactive Intermediates |
Computational Chemistry |
Nucleophilic Substitution
Breaking Bonds versus Chopping Heads: The Enzyme as Butcher  Todd P. Silverstein
Analogy to help biochemistry students understand concepts of Michaelis-Menten kinetics; active site/binding site; activation energy; substrate saturation; cooperativity; allosteric effects; and inhibitors.
Silverstein, Todd P. J. Chem. Educ. 1995, 72, 645.
Catalysis |
Enzymes |
Kinetics |
Proteins / Peptides |
Mechanisms of Reactions |
Reactions |
Rate Law
Propylene Oxide Addition to Hydrochloric Acid: A Textbook Error  Rebecca E. Phillips and Robert L. Soulen
Procedure illustrating organic synthesis involving propylene oxide, a major industrial chemical, and important features of the SN1 and SN2 mechanisms (there are some differences on how this reaction is described in several organic textbooks).
Phillips, Rebecca E.; Soulen, Robert L. J. Chem. Educ. 1995, 72, 624.
Synthesis |
Mechanisms of Reactions |
Nucleophilic Substitution
Charge Distribution in 1,1-Dicyano-2-Arylethenes: An Undergraduate Organic Experiment Utilizing the Knoevenagel Condensation and NMR Spectroscopy  Rowland, Alex T.
Organic synthesis illustrating the effect of ring substituents on an aromatic ring.
Rowland, Alex T. J. Chem. Educ. 1995, 72, 548.
Mechanisms of Reactions |
Synthesis |
NMR Spectroscopy |
Aromatic Compounds
A Textbook Error or Failure of the Saytzeff Rule?  Reinecke, Manfred G.; Smith, William B.
Analysis of an apparent failure of the Saytzeff rule.
Reinecke, Manfred G.; Smith, William B. J. Chem. Educ. 1995, 72, 541.
Mechanisms of Reactions
Bromination of Disubstituted Arenes: Kinetics and Mechanism: GC/MS Experiments for the Instrumental Analysis and Organic Chemistry Labs  Annis, D. Allen; Collard, David M.; Bottomley, Lawrence A.
Experimental procedure using gas chromatography and mass spectroscopy to trace the progression of a reaction over time and determine the several possible steps of its mechanism; sample data and analysis included.
Annis, D. Allen; Collard, David M.; Bottomley, Lawrence A. J. Chem. Educ. 1995, 72, 460.
Synthesis |
Mechanisms of Reactions |
Kinetics |
Chromatography |
Mass Spectrometry |
Separation Science |
Gas Chromatography |
Instrumental Methods |
Aromatic Compounds
Electrophilic Aromatic Substitution Discovery Lab  Jarret, Ronald M.; New, Jamie; Patraitis, Cynthia
An organic chemistry lab for introductory chemistry in which students must determine the reaction mechanism of an organic synthesis; includes sample data and analysis.
Jarret, Ronald M.; New, Jamie; Patraitis, Cynthia J. Chem. Educ. 1995, 72, 457.
Synthesis |
Mechanisms of Reactions |
Electrophilic Substitution
Acetylation of Ferrocene: A Study of the Friedel-Crafts Acylation Mechanism as Measured by HPLC Using an Internal Standard  Newirth, Terry L.; Srouji, Nadine
An experimental procedure that allows students to reach conclusions about the mechanism of an organic reaction (Friedel-Crafts acylation) based on their own data analysis; includes sample data and analysis.
Newirth, Terry L.; Srouji, Nadine J. Chem. Educ. 1995, 72, 454.
Mechanisms of Reactions |
Synthesis |
Chromatography |
HPLC
A Model To Show the SN2 Inversion  Sands, Richard D.; Dressman, Devin C.; Wyatt, Shawn R.
Paper model illustrating the SN2 inversion.
Sands, Richard D.; Dressman, Devin C.; Wyatt, Shawn R. J. Chem. Educ. 1995, 72, 428.
Mechanisms of Reactions |
Nucleophilic Substitution |
Molecular Modeling
Organic Chemistry (Fox, Marye Anne; Whitesell, James)  Levine, Samuel G.
Organic chemistry text that relies on a mechanistic rather than functional group organization.
Levine, Samuel G. J. Chem. Educ. 1994, 71, A261.
Mechanisms of Reactions
The Ritter Reaction: Trapping a Carbocation with a Nitrile  Crouch, R. David
An organic experiment involving the Ritter reaction that yields an unpredictable product.
Crouch, R. David J. Chem. Educ. 1994, 71, A200.
Mechanisms of Reactions |
Amides |
Amines / Ammonium Compounds
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
Pictorial Analogies XIII: Kinetics and Mechanism  Fortman, John J.
Pictorial analogies for first order kinetics, the effect of concentration and temperature on reaction rate, and the requirement for proper molecular orientation for reaction.
Fortman, John J. J. Chem. Educ. 1994, 71, 848.
Mechanisms of Reactions |
Rate Law |
Reactions
The Sol-Gel Preparation of Silica Gels  Buckley, A. M.; Greenblatt, M.
Background and procedure for the sol-gel preparation of silica from molecular precursors.
Buckley, A. M.; Greenblatt, M. J. Chem. Educ. 1994, 71, 599.
Mechanisms of Reactions |
Colloids
The Dehydration of 2-Methylcyclohexanol Revisited: The Evelyn Effect  Todd, David
Modification to an earlier procedure that allows students to observe the results of a hydride shift mechanism.
Todd, David J. Chem. Educ. 1994, 71, 440.
Alcohols |
Mechanisms of Reactions |
Gas Chromatography |
Alkenes |
Elimination Reactions
Deprotonation of Nitroalkanes: Semiempirical Determination of Solvation Effects on a Simple Reaction Coordinate  Pietro, William J.
161. Using computational chemistry to arrive at mechanistic and kinetic information for nitromethane and its deprotonated anion.
Pietro, William J. J. Chem. Educ. 1994, 71, 416.
Alkanes / Cycloalkanes |
Computational Chemistry |
Molecular Properties / Structure |
Mechanisms of Reactions |
Kinetics
The Blue Bottle Experiment Revisited: How Blue? How Sweet?  Cook, A. Gilbert; Tolliver, Randi M.; Williams, Janelle E.
Determining whether other colors and carbohydrates are possible with the "Blue Bottle" reaction.
Cook, A. Gilbert; Tolliver, Randi M.; Williams, Janelle E. J. Chem. Educ. 1994, 71, 160.
Aromatic Compounds |
Reactions |
Rate Law |
Mechanisms of Reactions |
Carbohydrates |
Oxidation / Reduction
Chemical Oscillations and Waves in the Physical Chemistry Lab  Pojman, John A.; Craven, Richard; Leard, Danna C.
A three-experiment module based on the most widely studied oscillating system, the Belousov-Zhabotinskii (BZ) reaction.
Pojman, John A.; Craven, Richard; Leard, Danna C. J. Chem. Educ. 1994, 71, 84.
Reactions |
Mechanisms of Reactions |
Rate Law
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
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
Bean counter's caution   Schwartz, Leslie J.
The article "The "Bean Lab' is useful only for elementary mechanisms.
Schwartz, Leslie J. J. Chem. Educ. 1993, 70, 1042.
Equilibrium |
Mechanisms of Reactions
Nitration of phenols: A two-phase system  Zeegers, Petrus J.
Nitration of phenols is often overlooked in undergraduate organic chemistry courses.
Zeegers, Petrus J. J. Chem. Educ. 1993, 70, 1036.
Phenols |
Aromatic Compounds |
Reactions |
Quantitative Analysis |
Mechanisms of Reactions |
Chromatography |
NMR Spectroscopy
Kinetics of the hydrolysis of orthoesters: A general acid-catalyzed reaction. An undergraduate physical organic chemistry experiment using NMR to determine both rate constants of a two-route mechanism  Potts, Richard A.; Schaller, Ruth A.
As more advanced instrumentation is made available for use by undergraduates, suitable experiments are needed. Due to the great importance of NMR spectroscopy in chemistry, this experiment was developed to give students some experience in this area.
Potts, Richard A.; Schaller, Ruth A. J. Chem. Educ. 1993, 70, 421.
NMR Spectroscopy |
Mechanisms of Reactions |
Esters |
Catalysis
Microscale elimination reactions: Experiments for organic chemistry using the small scale approach  Gilow, Helmuth M.
Procedure illustrating E1 and E2 reactions.
Gilow, Helmuth M. J. Chem. Educ. 1992, 69, A265.
Microscale Lab |
Reactions |
Elimination Reactions |
Alcohols |
Alkenes |
Catalysis
Microscale synthesis of azulene  Brieger, Gottfried
Procedure for the microscale synthesis of azulene.
Brieger, Gottfried J. Chem. Educ. 1992, 69, A262.
Microscale Lab |
Synthesis |
Aromatic Compounds |
Alkenes |
Dyes / Pigments |
Mechanisms of Reactions
The dehydrohalogenation of 2-bromobutane: A simple illustration of anti-Saytzeff elimination as a laboratory experiment for organic chemistry.  Leone, Stephen A.; Davis, J. David.
A quantitative microscale experiment of the dehydrohalogenation of 2-bromobutane to explore how increasing the base size affects the distribution of products.
Leone, Stephen A.; Davis, J. David. J. Chem. Educ. 1992, 69, A175.
Microscale Lab |
Elimination Reactions |
Mechanisms of Reactions
Mass spectra of multi-halogen compounds: A student practical project  Holdsworth, David; Ching, Goh Siah; Hamid, Mohd Jamil bin Hj Abd
Synthesis of bromochloro analogues of DDT and examination of the products by gas chromatography-mass spectroscopy.
Holdsworth, David; Ching, Goh Siah; Hamid, Mohd Jamil bin Hj Abd J. Chem. Educ. 1992, 69, 856.
Mass Spectrometry |
Gas Chromatography |
Synthesis |
Reactions |
Mechanisms of Reactions
Structure, chirality, and FT-NMR in sophomore organic chemistry  Chapman, Orville L.; Russell, Arlene A.
An experimental approach (NMR) to teaching organic structure.
Chapman, Orville L.; Russell, Arlene A. J. Chem. Educ. 1992, 69, 779.
NMR Spectroscopy |
Fourier Transform Techniques |
Molecular Properties / Structure |
Chirality / Optical Activity |
Stereochemistry |
Elimination Reactions
Two-cycle organic chemistry: A sound pedagogic alternative to the traditional year-long course  Sartoris, Nelson E.
Philosophy, advantages, and disadvantages to a two-cycle organic chemistry course.
Sartoris, Nelson E. J. Chem. Educ. 1992, 69, 750.
Mechanisms of Reactions
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
The synthesis of E-beta-bromostyrene: An experiment illustrating the use of IR bending modes to distinguish E and Z isomers and the concept of kinetic and thermodynamic controlled reactions.  Strom, Laura A.; Anderson, James R.; Gandler, Joseph R.
An experiment illustrating the concept of thermodynamic and kinetically controlled reactions to produce E and Z isomers (respectively); the use of IR to distinguish E and Z isomers; and the different properties of E and Z isomers (only the E isomer has a pleasant odor).
Strom, Laura A.; Anderson, James R.; Gandler, Joseph R. J. Chem. Educ. 1992, 69, 588.
Synthesis |
IR Spectroscopy |
Stereochemistry |
Kinetics |
Thermodynamics |
Alkenes |
Diastereomers |
Mechanisms of Reactions |
Molecular Properties / Structure
Corn chip aroma: A classroom demonstration on the preparation of a Schiff base  Sartori, Antony T.; Wood, William F.
Preparing 3-methylimino-2-butanone.
Sartori, Antony T.; Wood, William F. J. Chem. Educ. 1992, 69, 572.
Aldehydes / Ketones |
Synthesis |
Reactions |
Mechanisms of Reactions
Application of graph theory to chemical kinetics: Part 1. Kinetics of complex reactions  Temkin, Oleg N.; Bonchev, Danail G.
The major trends in applying graph theory to chemical kinetics and the mechanistic theory of complex reactions.
Temkin, Oleg N.; Bonchev, Danail G. J. Chem. Educ. 1992, 69, 544.
Kinetics |
Reactions |
Mechanisms of Reactions |
Rate Law
The nitric acid/nitrous acid and ferroin/ferriin system: A reaction that demonstrates autocatalysis, reversibility, pseudo orders, chemical waves, and concentration jump  Bazsa, Gyorgy; Nagy, Istvan P.; Lengyel, Istvan
A reaction that demonstrates autocatalysis, reversibility, pseudo orders, chemical waves, and concentration jump.
Bazsa, Gyorgy; Nagy, Istvan P.; Lengyel, Istvan J. Chem. Educ. 1991, 68, 863.
Kinetics |
Oxidation / Reduction |
Spectroscopy |
Catalysis |
Rate Law |
Stoichiometry |
Mechanisms of Reactions
Determination of rates of proton exchange of thiamine hydrochloride by 1H NMR spectroscopy: A bioorganic experiment for the undergraduate laboratory  Murray, Christopher J.; Duffin, Kay L.
A lab demonstrating the reactivity of carbon acids.
Murray, Christopher J.; Duffin, Kay L. J. Chem. Educ. 1991, 68, 683.
Kinetics |
NMR Spectroscopy |
Thermodynamics |
Bioorganic Chemistry |
Mechanisms of Reactions |
Catalysis
A laboratory study of 1,3-dipole-dipolarophile addition: An extension of the Diels Alder reaction  Gingrich, Henry L.; Pickering, Miles
Some easy organic reactions that can also be used as the basis for puzzles, or as facile heterocyclic syntheses: an area neglected in the student experiment literature.
Gingrich, Henry L.; Pickering, Miles J. Chem. Educ. 1991, 68, 614.
Mechanisms of Reactions |
Addition Reactions |
Synthesis |
Heterocycles |
Physical Properties |
NMR Spectroscopy
Decarboxylative elimination of 2,3-dibromo-3-phenylpropanoic acid to E or Z 1-bromo-2-phenylethylene (Beta-Bromostyrene): An experiment illustrating solvent effect on the stereochemical course of a reaction  Mestdagh, Helene; Puechberty, Anne
An experiment illustrating solvent effect on the stereochemical course of a reaction.
Mestdagh, Helene; Puechberty, Anne J. Chem. Educ. 1991, 68, 515.
Elimination Reactions |
Alkenes |
Stereochemistry |
Solutions / Solvents
Terminology: Helping students cope with name reactions in organic chemistry  Ganem, Bruce
Using limericks to help students understand and remember name reactions in organic chemistry.
Ganem, Bruce J. Chem. Educ. 1990, 67, 1009.
Nomenclature / Units / Symbols |
Mechanisms of Reactions
From cyclohexanol to 2-alkylated cyclopentanones: An open-ended set of experiments for an upper level organic laboratory  Wintner, Claude E.
Students are given 50 g of cyclohexanol and asked to convert this to the maximum amount of adipic acid that they can.
Wintner, Claude E. J. Chem. Educ. 1990, 67, 984.
Alcohols |
Aldehydes / Ketones |
IR Spectroscopy |
NMR Spectroscopy |
Gas Chromatography |
Mass Spectrometry |
Synthesis |
Mechanisms of Reactions
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
Disconnect by the numbers: A beginner's guide to synthesis  Smith, Michael B.
A protocol for planning organic syntheses using the disconnection method.
Smith, Michael B. J. Chem. Educ. 1990, 67, 848.
Synthesis |
Mechanisms of Reactions
Industrial chemistry in the organic laboratory: C4 alkylations  Teegarden, David M.; Varco-Shea, Theresa C.; Conklin, Karen T.; Markle, Cynthia A.; Anderson, Scott D.
A set of experiments to illustrate reactions of the tertiary-butyl group; the products are all compounds that occur in consumer products and have received considerable attention in the popular press (BHT, BHA, TBHQ, and MTBE).
Teegarden, David M.; Varco-Shea, Theresa C.; Conklin, Karen T.; Markle, Cynthia A.; Anderson, Scott D. J. Chem. Educ. 1990, 67, 619.
Industrial Chemistry |
Aromatic Compounds |
Phenols |
Synthesis |
Mechanisms of Reactions
Synthesis of 3-(2'-methoxy,5'-bromophenyl)-2,3-epoxy phenyl propanone, A novel epoxidated chalcone derivative: An undergraduate organic chemistry experiment  Moloney, Gerard P.
Synthesis of 3-(2'-methoxy,5'-bromophenyl)-1-phenyl-prop-2-enone and its subsequent epoxidation to 3-(2'-methoxy,5'- bromophenyl)-2,3-epoxy phenyl propanone.
Moloney, Gerard P. J. Chem. Educ. 1990, 67, 617.
Synthesis |
Aromatic Compounds |
Aldehydes / Ketones |
Ethers |
Mechanisms of Reactions
A simple procedure for the base-catalyzed cleavage of benzopinacolone to triphenylmethane: An undergraduate experiment  Stranberg, Michael; Anselme, J. -P.
A simple procedure for the base-catalyzed cleavage of benzopinacolone to triphenylmethane: An undergraduate experiment.
Stranberg, Michael; Anselme, J. -P. J. Chem. Educ. 1990, 67, 616.
Catalysis |
Aldehydes / Ketones |
Mechanisms of Reactions |
Synthesis
Saccharin alkylation: O vs. N substitution  Greenberg, Fred H.
Illustrates charge delocalization of an ambident anion in an SN2 reaction, the comparative deshielding of oxygen and nitrogen in proton NMR, and the use of the NMR integral in assessing isomer distribution.
Greenberg, Fred H. J. Chem. Educ. 1990, 67, 611.
Nucleophilic Substitution |
Mechanisms of Reactions |
Aromatic Compounds |
Heterocycles |
NMR Spectroscopy |
Stereochemistry
The stereochemistry of additions to trans-anethole  McGahey, Lawrence
Trans-anethole is brominated with pyridinium bromide perbromide in dichloromethane.
McGahey, Lawrence J. Chem. Educ. 1990, 67, 554.
Addition Reactions |
Stereochemistry |
Mechanisms of Reactions |
Alkenes |
Diastereomers |
Enantiomers
A new approach to the generation of sigma complex structures  Young, Joseph G.
An alternative to the electron pushing approach for determining intermediate resonance structures for electrophilic aromatic substitutions.
Young, Joseph G. J. Chem. Educ. 1990, 67, 550.
Aromatic Compounds |
Electrophilic Substitution |
Resonance Theory |
Mechanisms of Reactions
Three easy puzzles based on the Diels-Alder reaction  Pickering, Miles.
This paper recasts some classic systems so that they can be done at room temperature on a small scale in a large lab course without sophisticated instrumentation. Furthermore, they start the student using experimental results to solve mechanistic problems.
Pickering, Miles. J. Chem. Educ. 1990, 67, 524.
Mechanisms of Reactions |
Stereochemistry
The addition of hydrogen bromide to unsymmetrical alkenes: Introductory experiments in NMR spectroscopy and mechanistic chemistry  Brown, Trevor M.; Dronsfield, Alan T.; Ellis, Robert
As an introduction to NMR the authors center their work around the addition of hydrogen bromide to unsymmetrical alkenes and use the coupling patterns in the proton NMR spectra to establish whether the addition product is consistent with the Markovnikov rule.
Brown, Trevor M.; Dronsfield, Alan T.; Ellis, Robert J. Chem. Educ. 1990, 67, 518.
NMR Spectroscopy |
Alkenes |
Mechanisms of Reactions
Graphic characterization and taxonomy of organic reactions  Fujita, Shinsaku
This paper deals with the substructures of imaginary transition structures as one of the integrated systems for representing organic reactions.
Fujita, Shinsaku J. Chem. Educ. 1990, 67, 290.
Mechanisms of Reactions
An omission   Quellette, Robert J.
Melvin S. Newman's model was overlooked in an article on the SN2 mechanism.
Quellette, Robert J. J. Chem. Educ. 1990, 67, 277.
Mechanisms of Reactions
Steric course of lactonization in the deamination of glutamic acid: An organic mechanism experiment  Markgraf, J. Hodge; Davis, Howard A.
The stereochemical consequences of a reaction at a chiral center offer a unique way to distinguish among mechanistic hypothesis.
Markgraf, J. Hodge; Davis, Howard A. J. Chem. Educ. 1990, 67, 173.
Mechanisms of Reactions |
Stereochemistry |
Alcohols
Organic Reaction Chemistry, Review II (Flash, P.; Bendall, V.)  Chipman, Wilmon B.
Six different programs which allow the user to identify functional groups, supply the missing reagent necessary to complete a given reaction, deduce the product of a given reaction, ascertain whether a given reaction will go, search the reaction database for functional group conversions, and search for the utility of a certain reagent.
Chipman, Wilmon B. J. Chem. Educ. 1989, 66, A171.
Enrichment / Review Materials |
Reactions |
Mechanisms of Reactions |
Nomenclature / Units / Symbols
Organic Reaction Chemistry, Review I (Flash, P.; Bendall, V.)  Hargis, J. H.
Six different programs which allow the user to identify functional groups, supply the missing reagent necessary to complete a given reaction, deduce the product of a given reaction, ascertain whether a given reaction will go, search the reaction database for functional group conversions, and search for the utility of a certain reagent.
Hargis, J. H. J. Chem. Educ. 1989, 66, A170.
Reactions |
Enrichment / Review Materials |
Mechanisms of Reactions |
Nomenclature / Units / Symbols
Mechanism and Theory in Organic Chemistry, Third Edition (Lowry, Thomas H.; Richardson, Kathleen Schuller)  Baumgarten, Henry E.
Overall this edition retains the value of its predecessors as a text for a first-year graduate course in organic reaction mechanisms.
Baumgarten, Henry E. J. Chem. Educ. 1989, 66, A131.
Mechanisms of Reactions
Friedel Crafts acylation and alkylation with acid chlorides  Jarret, Ronald M.; Keil, Nora; Allen, Susan; Cannon, Lisa; Coughlan, Julie; Cusumano, Leonarda; Nolan, Brian
A shortened Friedel-Crafts experiment; the extra time available allows for additional experiments designed to illustrate the finer points of the reaction, such as electrophile rearrangements and decarbonylation of acyl cations.
Jarret, Ronald M.; Keil, Nora; Allen, Susan; Cannon, Lisa; Coughlan, Julie; Cusumano, Leonarda; Nolan, Brian J. Chem. Educ. 1989, 66, 1056.
Electrophilic Substitution |
Aromatic Compounds |
Mechanisms of Reactions |
Microscale Lab
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
A study of the E2 reaction for the microscale organic lab  Flash, Patrick; Galle, Fred; Radil, Mark
Students determine the pseudo-first-order rate constant for the elimination of HBr from 2-bromobutane and measure the yield and approximate composition of the alkene products, determine the yield of alkenes from 1-bromobutane under the same conditions, and examine the effect of changing solvent polarity on alkene yields for the two halides.
Flash, Patrick; Galle, Fred; Radil, Mark J. Chem. Educ. 1989, 66, 958.
Elimination Reactions |
Mechanisms of Reactions |
Rate Law |
Kinetics
A Diels-Alder reaction for the overhead projector  Kolb, Kenneth E.
Reacting the strong dienophile tetracyanothylene with anthracene as the diene.
Kolb, Kenneth E. J. Chem. Educ. 1989, 66, 955.
Alkenes |
Mechanisms of Reactions
A valence isomer trapping procedure for introductory organic laboratory: Synthesis of a homobarrelene derivative  Kurtz, David W.; Johnson, Richard P.
Norcaradiene is trapped out of its cycloheptatriene valence isomer in a Diels-Alder reaction with maleic anhydride.
Kurtz, David W.; Johnson, Richard P. J. Chem. Educ. 1989, 66, 873.
Alkenes |
Mechanisms of Reactions
The iodine clock reaction: A surprising variant  Autuori, Marcos Alberto; Brolo, Alexandre Guimaraes; Mateus, Alfredo Luis M. L.
Substituting malonic acid for sulfuric acid.
Autuori, Marcos Alberto; Brolo, Alexandre Guimaraes; Mateus, Alfredo Luis M. L. J. Chem. Educ. 1989, 66, 852.
Reactions |
Kinetics |
Mechanisms of Reactions
Borodin and the benzidine rearrangement  Shine, Henry J.
It is evident now that Borodin's work really had no impact at all on the mechanism of the benzidine rearrangement.
Shine, Henry J. J. Chem. Educ. 1989, 66, 793.
Catalysis |
Mechanisms of Reactions |
Aromatic Compounds
Polymer principles (the author replies)  Rodriquez, F.
The decomposition of benzoyl peroxide.
Rodriquez, F. J. Chem. Educ. 1989, 66, 790.
Mechanisms of Reactions |
Free Radicals
Polymer principles  Abraham, Tonson
The decomposition of benzoyl peroxide.
Abraham, Tonson J. Chem. Educ. 1989, 66, 790.
Mechanisms of Reactions |
Free Radicals
Concerning orientations of certain syn-elimination reactions  Ho, Tse-Lok
Explanation of an interesting aspect of the orientation of unsymmetrically substituted oxides.
Ho, Tse-Lok J. Chem. Educ. 1989, 66, 785.
Elimination Reactions |
Mechanisms of Reactions
Isomerization of dimethyl maleate to dimethyl fumarate: An undergraduate experiment utilizing high performance liquid chromatography  Ledlie, David B.; Wenzel, Thomas J.; Hendrickson, Susan M.
Introduces students to liquid chromatography, the stereoisomerization of alkenes, certain aspects of free radical chemistry, and thermodynamics.
Ledlie, David B.; Wenzel, Thomas J.; Hendrickson, Susan M. J. Chem. Educ. 1989, 66, 781.
HPLC |
Mechanisms of Reactions |
Esters |
Stereochemistry |
Free Radicals |
Alkenes |
Thermodynamics
An investigation into the mechanism of the Ritter reaction  Hathaway, Bruce A.
Students are asked to propose a reaction mechanism; experimentation then demonstrates the most reasonable proposal.
Hathaway, Bruce A. J. Chem. Educ. 1989, 66, 776.
Mechanisms of Reactions |
Thin Layer Chromatography
The SRN1 mechanism as a route to nucleophilic substitution on alkyl halides  Rossi, Roberto A.; Pierini, Adriana B.; Pallacios, Sara M.
A series of haloaliphatic compounds that react with nucleophiles by the SRN1 mechanism due to steric, electronic, or strain factors.
Rossi, Roberto A.; Pierini, Adriana B.; Pallacios, Sara M. J. Chem. Educ. 1989, 66, 720.
Nucleophilic Substitution |
Mechanisms of Reactions
Evolution of the morphinan synthesis  Lednicer, Daniel
The key reaction to the preparation of morphinans is the Grewe carbocation cyclization.
Lednicer, Daniel J. Chem. Educ. 1989, 66, 718.
Synthesis |
Medicinal Chemistry |
Drugs / Pharmaceuticals |
Mechanisms of Reactions |
Aromatic Compounds
A kinetic study of the Diels-Alder reaction: An experiment illustrating simple second-order reaction kinetics  Silvestri, Michael G.; Dills, Charles E.
The Diels-Alder reaction between cyclopentadiene and dimethyl fumarate, when followed by gas chromatography, exhibits clear second-order reaction kinetics.
Silvestri, Michael G.; Dills, Charles E. J. Chem. Educ. 1989, 66, 690.
Kinetics |
Mechanisms of Reactions |
Gas Chromatography
Reactions of borohydride in carboxylic acid media: A summary  Nutaitis, Charles F.
Sodium borohydride / carboxylic acid systems represent a paradox of reactivity; depending on the substrate being transformed and the method sued to mix the reagents, this methodology can lead to reaction media that are either more or less reactive than sodium borohydride itself.
Nutaitis, Charles F. J. Chem. Educ. 1989, 66, 673.
Carboxylic Acids |
Mechanisms of Reactions
Selective reductions in the teaching laboratory  Jones, Alan G.
Reductions of nitrophenylethanone, aminophenylethanone, and nitrophenylethanol.
Jones, Alan G. J. Chem. Educ. 1989, 66, 611.
Aromatic Compounds |
Amines / Ammonium Compounds |
Oxidation / Reduction |
Mechanisms of Reactions |
IR Spectroscopy
The Grignard reagent: Preparation, structure, and some reactions  Orchin, Milton
Structure, formation, reactions of and the effect of transition metals and their halides on Grignard reagents.
Orchin, Milton J. Chem. Educ. 1989, 66, 586.
Mechanisms of Reactions |
Transition Elements
A tandem Michael-aldol reaction sequence: An undergraduate research organic experiment  Coutlangus, Marilyin L.; Filla, Sandra A.; Rowland, Alex T.
A short reaction sequence that allows students to determine by spectroscopic methods the constitutions of and stereochemistry in the reaction products.
Coutlangus, Marilyin L.; Filla, Sandra A.; Rowland, Alex T. J. Chem. Educ. 1989, 66, 520.
Mechanisms of Reactions |
Spectroscopy |
Stereochemistry |
IR Spectroscopy |
UV-Vis Spectroscopy |
NMR Spectroscopy
Cobalt(II) and cobalt(III) coordination compounds  Thomas, Nicholas C.; Pringle, Katrina; Deacon, Glen B.
This experiment illustrates the formation of tris(phenanthroline)cobalt complexes in the +2 and +3 oxidation states, the effect of coordination on reactions of the ligand, and the use of a ligand displacement reaction in recovering the transformed ligand.
Thomas, Nicholas C.; Pringle, Katrina; Deacon, Glen B. J. Chem. Educ. 1989, 66, 516.
Coordination Compounds |
Crystal Field / Ligand Field Theory |
Mechanisms of Reactions
The interconversion of cis and trans isomers  McGinn, Clifford J.; Wheatley, William B.
Trans-alkene oxides are converted to cis-alkenes on treatment with tributylphosphine, yet this reaction does not appear in most organic textbooks.
McGinn, Clifford J.; Wheatley, William B. J. Chem. Educ. 1989, 66, 486.
Stereochemistry |
Diastereomers |
Alkenes |
Mechanisms of Reactions
The formaldehyde-sulfite clock reaction revisited  Warneck, Peter
The purpose of this present note is to discuss the mechanism and the change of pH during the reaction.
Warneck, Peter J. Chem. Educ. 1989, 66, 334.
Mechanisms of Reactions |
pH |
Rate Law
Oscillating chemical reactions and nonlinear dynamics  Field, Richard J.; Schneider, F. W.
The field of oscillating chemical reactions has grown dramatically over the last 15 years. The reasons for this activity are the intrinsic chemical interest in the behavior and mechanisms of oscillating chemical reactions and the connection between oscillating reactions and the properties of nonlinear differential equations.
Field, Richard J.; Schneider, F. W. J. Chem. Educ. 1989, 66, 195.
Reactions |
Equilibrium |
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
The art of problem solving in organic chemistry (Alonso, Miguel E.)  Wade, L. G., Jr.
A review of a book intended to teach students how one goes about proposing mechanisms for complicated organic reactions. The book would be most useful in advanced chemistry courses.
Wade, L. G., Jr. J. Chem. Educ. 1988, 65, A140.
Mechanisms of Reactions
A guidebook to mechanism in organic chemistry; sixth edition (Sykes,P.)  Merijanian, Aris
A quick review of the sixth edition of this text shows the degree of improvement made in this classic text where the author is skilled at explaining concept matters in a simple, elegant way.
Merijanian, Aris J. Chem. Educ. 1988, 65, A139.
Mechanisms of Reactions
Advanced organic chemistry: reactions mechanisms, and structure (Mach, Jerry)  Norcorss, Bruce E.
A review of an advanced organic chemistry text that was first published in 1968 and has enjoyed monumental success.
Norcorss, Bruce E. J. Chem. Educ. 1988, 65, A139.
Mechanisms of Reactions |
Molecular Properties / Structure |
Reactions
Determination of the relative rates of alkaline hydrolysis of esters by the method of competition  Paredes, Rodrigo; Gil, Jimmy; Ocampo, Pamela
A method is presented for further illustration of the electronic and steric factors in the saponification of selected groups of esters.
Paredes, Rodrigo; Gil, Jimmy; Ocampo, Pamela J. Chem. Educ. 1988, 65, 1109.
Esters |
Mechanisms of Reactions |
Kinetics
The kinetics and inhibition of gamma-glutamyl transpeptidase: A biochemistry laboratory experiment  Splittgerber, A. G.; Sohl, Julie
This lab differs from typical kinetics experiments in that it uses a two-substrate system and the wide range of possible kinetic procedures.
Splittgerber, A. G.; Sohl, Julie J. Chem. Educ. 1988, 65, 928.
Biophysical Chemistry |
Enzymes |
Proteins / Peptides |
Applications of Chemistry |
Mechanisms of Reactions
Flow charting leaving group reactions  Hagen, James P.
The authors present a handy way of organizing information for organic chemistry learners.
Hagen, James P. J. Chem. Educ. 1988, 65, 620.
Mechanisms of Reactions |
Elimination Reactions
Just what is a transition state?  Laidler, Keith J.
The term "transition state" needs to be used in a universally consistent manner.
Laidler, Keith J. J. Chem. Educ. 1988, 65, 540.
Thermodynamics |
Reactions |
Mechanisms of Reactions |
Photochemistry
Rate controlling step: A necessary or useful concept?  Laidler, Keith J.
This author questions the presence of the concept of rate controlling steps and points out several misconceptions that seem to be prevalent among students and experienced chemists.
Laidler, Keith J. J. Chem. Educ. 1988, 65, 250.
Rate Law |
Kinetics |
Mechanisms of Reactions
Nucleophilic substitution by benzodithioate anions  Bonnans-Plaisance, Chantal; Gressier, Jean-Claude
The experiment described in this paper has been used to illustrate the Gringnard reaction and nucleophilic substitution.
Bonnans-Plaisance, Chantal; Gressier, Jean-Claude J. Chem. Educ. 1988, 65, 93.
Nucleophilic Substitution |
Grignard Reagents |
Mechanisms of Reactions
Solid state kinetic parameters and chemical mechanism of the dehydration of CoCl26H2O: An inorganic solid state experiment  Ribas, Joan; Escuer, Albert; Serra, Miquel; Vicente, Ramon
In this article, authors present a description of an experimental example illustrating the most common methods for determination of kinetic parameters, the different theories and equations applied, and the discussion of the mechanisms derived from the kinetic results.
Ribas, Joan; Escuer, Albert; Serra, Miquel; Vicente, Ramon J. Chem. Educ. 1988, 65, 85.
Kinetics |
Solid State Chemistry |
Mechanisms of Reactions |
Thermodynamics
Computer-Assisted Blackboard (Soltzberg, L. J.)  Kruger, J. D.
8-disk set of programs (Apple II) designed to help a lecturer illustrate gas laws, the Rutherford atomic model, quantization in a Bohr atom, wave-functions and orbitals, heat and changes in state, kinetics and simple reaction mechanisms, equilibrium, acid-base reactions, and titrations.
Kruger, J. D. J. Chem. Educ. 1987, 64, A135.
Acids / Bases |
Gases |
Atomic Properties / Structure |
Phases / Phase Transitions / Diagrams |
Kinetics |
Mechanisms of Reactions |
Equilibrium |
Titration / Volumetric Analysis
New stoichiometry for copper dissolution in nitric acid (the authors reply)  El-Chelkh, F. M.; Khalil, S. A.; Ei-Manguch, M. A.; Omar, H. A.
Disagreement over the balanced equation representing this reaction.
El-Chelkh, F. M.; Khalil, S. A.; Ei-Manguch, M. A.; Omar, H. A. J. Chem. Educ. 1987, 64, 1070.
Stoichiometry |
Reactions |
Mechanisms of Reactions
New stoichiometry for copper dissolution in nitric acid  Hill, William D, Jr.
Disagreement over the balanced equation representing this reaction.
Hill, William D, Jr. J. Chem. Educ. 1987, 64, 1069.
Stoichiometry |
Mechanisms of Reactions |
Reactions
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
Hydroformylation of 1-hexene utilizing homogeneous rhodium catalysts: Regioselectivity as a function of conversion  Hanson, Brian E.; Davis, Mark E.
Possible reaction pathways for isomerization, hydroformylation, and hydrogenation of 1-alkenes using HRh(CO)L3 catalyst precursors.
Hanson, Brian E.; Davis, Mark E. J. Chem. Educ. 1987, 64, 928.
Catalysis |
Alkenes |
Mechanisms of Reactions
Lewis acid catalysis of a Diels-Alder cycloaddition: An undergraduate organic experiment  Marchand, Alan P.; Vidyasagar, V.; Buckner, Mark B.; Holman, Philmore O.
Experiment based upon the Diels-Alder cycloaddition of methylcyclopentadiene to p-benzoquinone with characterization of the products through proton NMR.
Marchand, Alan P.; Vidyasagar, V.; Buckner, Mark B.; Holman, Philmore O. J. Chem. Educ. 1987, 64, 642.
NMR Spectroscopy |
Lewis Acids / Bases |
Catalysis |
Mechanisms of Reactions
Ring opening and ring forming polymerizations: An organic and polymer laboratory experiment  Mathias, Lon J.; Viswnathan, Tito
Polymer synthesis involving ring-opening polymerization to yield a polyamide from oxazoline and cyclopolymerization of a diallylamine derivative to give a polymer containing pyrrolidine units.
Mathias, Lon J.; Viswnathan, Tito J. Chem. Educ. 1987, 64, 639.
Polymerization |
Synthesis |
Heterocycles |
Amides |
Mechanisms of Reactions
Decarboxylation of a keto acids  Hanson, R. W.
Rectifies the lack of information concerning the nonenzymatic decarboxylation of alpha-keto acids found in many textbooks and to correct errors found in others.
Hanson, R. W. J. Chem. Educ. 1987, 64, 591.
Mechanisms of Reactions |
Catalysis
The misuse of Markownikov's rule  Newton, Thomas A.
Many organic textbooks site an incorrect example as a simple anti-Markownikov addition reaction.
Newton, Thomas A. J. Chem. Educ. 1987, 64, 531.
Catalysis |
Mechanisms of Reactions
Another auto analogy: Rate-determining steps  Ball, David W.
An analogy to describe the physical meaning of a rate-determining step.
Ball, David W. J. Chem. Educ. 1987, 64, 486.
Kinetics |
Mechanisms of Reactions
The reactivity selectivity principle: Should it ever be used?  Buncel, Erwin; Wilson, Harold
Applications and failures of the reactivity selectivity principle; quantitative aspects of the reactivity selectivity principle; and rationalization of reactivity selectivity principle failures.
Buncel, Erwin; Wilson, Harold J. Chem. Educ. 1987, 64, 475.
Mechanisms of Reactions |
Free Radicals |
Carbocations |
Nucleophilic Substitution
The induction by iron(II) of the oxidation of iodide by dichromate  Jolly, William L.
A surprising mechanism for an inorganic reaction in aqueous solution.
Jolly, William L. J. Chem. Educ. 1987, 64, 444.
Oxidation / Reduction |
Aqueous Solution Chemistry |
Reactions |
Mechanisms of Reactions |
Catalysis
Kinetics and mechanism of the iodine azide reaction: A videotaped experiment  Haight, Gilbert P.; Jones, Loretta L.
A clock reaction suitable for videotaping and presenting to a large lecture class of general chemistry for analysis.
Haight, Gilbert P.; Jones, Loretta L. J. Chem. Educ. 1987, 64, 271.
Kinetics |
Mechanisms of Reactions |
Rate Law
The use of fluoromethanes in organic synthesis  Everett, T. Stephen
A review of advances in selective fluorination; mechanisms and applications of fluoromethanes in organic synthesis.
Everett, T. Stephen J. Chem. Educ. 1987, 64, 143.
Synthesis |
Mechanisms of Reactions
Kinetics of oxidation of bromcresol green  Pickering, Miles; Heiler, David
Study of the bleaching of bromcresol green by hypochlorite.
Pickering, Miles; Heiler, David J. Chem. Educ. 1987, 64, 81.
Kinetics |
Oxidation / Reduction |
Dyes / Pigments |
Acids / Bases |
Mechanisms of Reactions
The synthesis of 5,5'-diphenylhydantoin: A novel benzil-benzilic acid rearrangement  Pankaskie, Marvin C.; Small, Laverne
A novel benzil-benzilic acid rearrangement.
Pankaskie, Marvin C.; Small, Laverne J. Chem. Educ. 1986, 63, 650.
Synthesis |
Heterocycles |
Mechanisms of Reactions |
Amines / Ammonium Compounds
A complex analysis of kinetic results for the base hydrolysis of iron(II) complexes: An advanced undergraduate kinetic experiment  Rodenas, Elvira; Ortega, Franciseo
This article describes a lab experiment that is suitable for an advanced undergraduate experimental exercise in kinetics where a complex analysis of kinetic results could be done.
Rodenas, Elvira; Ortega, Franciseo J. Chem. Educ. 1986, 63, 448.
Kinetics |
Mechanisms of Reactions
Application of organometallic catalysis to the commercial production of L-DOPA  Knowles, W. S.
This paper describes the application of a novel technology to the commercial preparation of L-DOPA.
Knowles, W. S. J. Chem. Educ. 1986, 63, 222.
Industrial Chemistry |
Enantiomers |
Stereochemistry |
Aromatic Compounds |
Alkenes |
Heterocycles |
Mechanisms of Reactions |
Catalysis |
Organometallics |
Alcohols
Selective oxidation and ammoxidation of olefins by heterogeneous catalysis  Grasselli, Robert K.
In this symposium paper, the author shows how the complex process of the ammoxidation of olefins can be understood in terms of free radicals and surface bound organometallic intermediates.
Grasselli, Robert K. J. Chem. Educ. 1986, 63, 216.
Organometallics |
Oxidation / Reduction |
Catalysis |
Amines / Ammonium Compounds |
Aromatic Compounds |
Alkenes |
Mechanisms of Reactions
Shell higher olefins process  Lutz, E. F.
The author shows how olefin isomerization and the exotic olefin metathesis reactions can be harnessed in industrial processes.
Lutz, E. F. J. Chem. Educ. 1986, 63, 202.
Alkenes |
Mechanisms of Reactions |
Industrial Chemistry |
Organometallics |
Catalysis
Steric and electronic effects in olefin hydrocyanation at Du Pont: A scientific and industrial success story  Tolman, C. A.
An outline of the mechanistic studies that made the development of an important technology possible.
Tolman, C. A. J. Chem. Educ. 1986, 63, 199.
Organometallics |
Coordination Compounds |
Molecular Properties / Structure |
Catalysis |
Mechanisms of Reactions |
Alkenes
A simple demonstration of a gas evolution oscillator  Kaushick, A.M.; Yuan, Zhi; Noyes, Richard M.
A demonstration is suggested that demonstrates the decomposition of aqueous ammonium nitrate into nitrogen gas and water.
Kaushick, A.M.; Yuan, Zhi; Noyes, Richard M. J. Chem. Educ. 1986, 63, 76.
Amines / Ammonium Compounds |
Gases |
Reactions |
Transport Properties |
Phases / Phase Transitions / Diagrams |
Mechanisms of Reactions
Musical mechanisms  Jones, Peter
Portraying the mechanism of the catalysis of hydrogen peroxide decomposition by catalase using an adaptation of musical notation.
Jones, Peter J. Chem. Educ. 1985, 62, 1093.
Catalysis |
Enzymes |
Mechanisms of Reactions
The catalytic function of enzymes  Splittgerber, Allan G.
Review of the structure, function, and factors that influence the action of enzymes.
Splittgerber, Allan G. J. Chem. Educ. 1985, 62, 1008.
Catalysis |
Enzymes |
Mechanisms of Reactions |
Proteins / Peptides |
Molecular Properties / Structure
Molybdenum enzymes, cofactors, and systems: The chemical uniqueness of molybdenum  Burgmayer, S. J. N.; Stiefel, E. I.
Sources, composition, and substrate reactions of molybdoenzymes. From the "State of the Art Symposium: Bioinorganic Chemistry", held at the ACS meeting, Miami, 1985.
Burgmayer, S. J. N.; Stiefel, E. I. J. Chem. Educ. 1985, 62, 943.
Enzymes |
Bioinorganic Chemistry |
Mechanisms of Reactions
Spectroscopic studies of the catechol dioxygenases  Que, Lawrence, Jr.
The catechol dioxygenases are bacterial iron-containing enzymes that catalyze the oxidative cleavage a catechols; these enzymes serve as a component of nature's mechanism for cleaving aromatic compounds in the environment. From the "State of the Art Symposium: Bioinorganic Chemistry", held at the ACS meeting, Miami, 1985.
Que, Lawrence, Jr. J. Chem. Educ. 1985, 62, 938.
Spectroscopy |
Enzymes |
Catalysis |
Raman Spectroscopy |
Molecular Properties / Structure |
Mechanisms of Reactions |
Aromatic Compounds
An aldol condensation-photochemical bromination sequence with emphasis on spectroscopic interpretations: An undergraduate organic experiment  Rowland, Alex T.; Brechbiel, Martin W.; Gerelus, Anne Sykes
The focus in these procedures is to extend students' abilities in the interpretation of spectral data in order to reach sound conclusions regarding the constitution and stereochemistry of reaction products.
Rowland, Alex T.; Brechbiel, Martin W.; Gerelus, Anne Sykes J. Chem. Educ. 1985, 62, 908.
Photochemistry |
Mechanisms of Reactions |
IR Spectroscopy |
UV-Vis Spectroscopy |
NMR Spectroscopy |
Stereochemistry
Phase-transfer-catalyzed alkylation of ethyl acetoacetate and diethyl malonate  Thompson, Douglas L.; Reeves, Perry C.
Improved method that requires shorter reaction times and safer reagents than traditional procedures.
Thompson, Douglas L.; Reeves, Perry C. J. Chem. Educ. 1985, 62, 907.
Catalysis |
Mechanisms of Reactions |
Synthesis
Interstellar chemistry  Carbo, R.; Ginebreda, A.
Surveys some of the features that characterize interstellar chemistry, particularly the composition of the interstellar medium and the nature of the changes that occur there.
Carbo, R.; Ginebreda, A. J. Chem. Educ. 1985, 62, 832.
Astrochemistry |
Gases |
Reactions |
Mechanisms of Reactions
The NBS reaction: A simple explanation for the predominance of allylic substitution over olefin addition by bromine at low concentrations  Wamser, Carl C.; Scott, Lawrence T.
What factors govern the reaction of Br2 with an alkene to give either allylic substitution or double bond addition?
Wamser, Carl C.; Scott, Lawrence T. J. Chem. Educ. 1985, 62, 650.
Mechanisms of Reactions |
Free Radicals |
Kinetics |
Alkenes
Auto analogies  Potts, Richard A.
Four analogies involving electron density, reaction mechanisms, rate-determining step, the kinetic and thermodynamic factors of a process, and automobiles.
Potts, Richard A. J. Chem. Educ. 1985, 62, 579.
Atomic Properties / Structure |
Mechanisms of Reactions |
Rate Law |
Kinetics |
Thermodynamics
The design of laboratory experiments in the 1980's: A case study on the oxidation of alcohols with household bleach  Mohrig, Jerry R.; Nienhuis, David M.; Linck, Catherine F.; Van Zoeren, Carol; Fox, Brian G.; Mahaffy, Peter G.
Improved safety by replacing chromium(VI) with bleach in the oxidation of an alcohol.
Mohrig, Jerry R.; Nienhuis, David M.; Linck, Catherine F.; Van Zoeren, Carol; Fox, Brian G.; Mahaffy, Peter G. J. Chem. Educ. 1985, 62, 519.
Oxidation / Reduction |
Alcohols |
Mechanisms of Reactions
Chain reaction wheel: An approach to free radical reactions  Monroe, Manus; Abrams, Karl
Using a "chain reaction wheel" to help students understand the mechanism of free radical reactions.
Monroe, Manus; Abrams, Karl J. Chem. Educ. 1985, 62, 467.
Free Radicals |
Reactions |
Mechanisms of Reactions
Solvation energies of organic ions  Arnett, Edward M.
Examination of recent advances in understanding regarding the role solvation factors play in determining the course of reactions in solution.
Arnett, Edward M. J. Chem. Educ. 1985, 62, 385.
Solutions / Solvents |
Nucleophilic Substitution |
Mechanisms of Reactions |
Acids / Bases |
Aqueous Solution Chemistry
The Wittig reaction in the undergraduate organic laboratory  Warner, John C.; Anastas, Paul T.; Anselme, Jean-Pierre
Using phase-transfer catalysis to prepare cis- and trans-stilbenes from the Wittig condensation of benzaldehyde.
Warner, John C.; Anastas, Paul T.; Anselme, Jean-Pierre J. Chem. Educ. 1985, 62, 346.
Mechanisms of Reactions |
Synthesis |
Catalysis |
Diastereomers |
Stereochemistry
Organic chemistry for health-science students   Schumm, Margot K.
It is important to teach health-science students reaction mechanisms when teaching them organic and biochemistry.
Schumm, Margot K. J. Chem. Educ. 1985, 62, 272.
Medicinal Chemistry |
Nonmajor Courses |
Mechanisms of Reactions
Kinetics and mechanism-a games approach  Harsch, Gunther
Using statistical games to simulate and illustrate a variety of chemical kinetics.
Harsch, Gunther J. Chem. Educ. 1984, 61, 1039.
Kinetics |
Mechanisms of Reactions |
Catalysis |
Rate Law
Iodine clock reaction mechanisms  Lambert, Jack L.; Fina, Gary T.
Outlines the mechanism for the simple iodine clock reaction and the "Old Nassau" modification.
Lambert, Jack L.; Fina, Gary T. J. Chem. Educ. 1984, 61, 1037.
Mechanisms of Reactions |
Reactions |
Kinetics |
Oxidation / Reduction
Hydrogen-ion dependence of reaction rates and mechanism  Gupta, K. S.; Gupta, Y. K.
Presents some of the most important kinds of hydrogen-ion dependence that a student of kinetics is likely to encounter.
Gupta, K. S.; Gupta, Y. K. J. Chem. Educ. 1984, 61, 972.
Rate Law |
Reactions |
Mechanisms of Reactions |
Acids / Bases
Mechanistic enzyme models: Pyridoxal and metal ions  Hamilton, S. E.; Mason, S. R.; Zerner, Burt
Experiment that introduces catalysis through Schiff's base formation between aldehydes or ketones and primary amines, and catalysis by metal ions.
Hamilton, S. E.; Mason, S. R.; Zerner, Burt J. Chem. Educ. 1984, 61, 811.
Enzymes |
Mechanisms of Reactions |
Catalysis
The kinetics and mechanism of the decomposition of murexide in acid solution  Knoche, Wilhelm; Rees, Norman H.
The experimental results show the dependence of reaction rate on ionic strength - described as a primary salt effect; the experiment can be extended in two interesting ways: at low pH the dissociation constant of an unstable acid can be evaluated, and the influence of complexing metal ions on the kinetics enables the stability constant of the metal / murexide complex to be determined.
Knoche, Wilhelm; Rees, Norman H. J. Chem. Educ. 1984, 61, 724.
Kinetics |
Mechanisms of Reactions |
Thermodynamics
Catalysis of radical chain reactions  Bardsley, W. D.; Failes, R. L.; Hunter, R.; Stimson, V. R.
Examples where "catalysts" enter into reaction in a consistent manner, to increase the rate in one case and decrease it in the other.
Bardsley, W. D.; Failes, R. L.; Hunter, R.; Stimson, V. R. J. Chem. Educ. 1984, 61, 657.
Catalysis |
Free Radicals |
Reactions |
Mechanisms of Reactions |
Kinetics |
Rate Law
Preparation of 4-phenylbut-3-yn-2-one: An organic chemistry project  Wollard, J. M.
An experiment that avoids the use of liquid ammonia and of ethyne, yet illustrates the acidity of terminal alkynes and the use of the resulting anion to form new carbon-carbon bonds.
Wollard, J. M. J. Chem. Educ. 1984, 61, 648.
Synthesis |
Alkynes |
Mechanisms of Reactions
Concertedness of 1,3-dipolar cycloadditions  Haque, M. Serajul
The 1,3-dipolar cycloaddition is the union of a 1,3-dipole with a multiple bond system (a dipolarophile) to form a five-membered ring; the process is regarded as one of the most general methods for the synthesis of five-membered heterocycles.
Haque, M. Serajul J. Chem. Educ. 1984, 61, 490.
Addition Reactions |
Alkanes / Cycloalkanes |
Mechanisms of Reactions |
Heterocycles |
Synthesis |
MO Theory
Penicillin hydrolysis, a kinetic study of a multistep, multiproduct reaction  McCarrick, Thomas A.; McLafferty, Fred W.
By the application of kinetic theory the reaction pathways for the hydrolysis of potassium benzyl penicillin can be elucidated.
McCarrick, Thomas A.; McLafferty, Fred W. J. Chem. Educ. 1984, 61, 463.
Kinetics |
Drugs / Pharmaceuticals |
Mechanisms of Reactions
Who is anti-Markovnikov?  Tedder, J. M.
What are the factors that control the rate and orientation of free radical addition to alkenes?
Tedder, J. M. J. Chem. Educ. 1984, 61, 237.
Mechanisms of Reactions |
Addition Reactions |
Free Radicals |
Alkenes
Reactions of thiocyanate ions with acid  Glidewell, Christopher; McKechnie, James S.; Pogorzelec, Peter J.
Students must identify the products of the reaction of KNCS with sulfuric acid.
Glidewell, Christopher; McKechnie, James S.; Pogorzelec, Peter J. J. Chem. Educ. 1984, 61, 78.
Mechanisms of Reactions |
Qualitative Analysis
Kinetics - Rates and mechanisms  Campbell, J. Arthur
Reasons for teaching kinetics early and often.
Campbell, J. Arthur J. Chem. Educ. 1984, 61, 40.
Kinetics |
Rate Law |
Mechanisms of Reactions
Ferrocenylmethylation of aniline: nonkinetic determination of a reaction mechanism  Lombardo, Anthony; Bieber, Theodore I.
The series of experiments described here is adapted from an original investigation and is intended to approximate the research experience. This study has been used with great success in an integrated laboratory program for advanced undergraduates.
Lombardo, Anthony; Bieber, Theodore I. J. Chem. Educ. 1983, 60, 1080.
Undergraduate Research |
Reactions |
Mechanisms of Reactions |
Organometallics
Chromium(III)-polypyridyls: A case study  Serpone, Nick; Hoffman, Morton Z.
The authors examine the photochemical and photophysical behavior of chromium (III)-polypyridyl complexes, Cr(NN)3+, in which NN is (bpy) or (phen) or one of their substituted derivatives. From the State-of-the-Art Symposium: Inorganic Photochemistry, held at the ACS meeting, Seattle, 1983.
Serpone, Nick; Hoffman, Morton Z. J. Chem. Educ. 1983, 60, 853.
Heterocycles |
Group Theory / Symmetry |
MO Theory |
Spectroscopy |
Photochemistry |
Quantum Chemistry |
Coordination Compounds |
Mechanisms of Reactions
Photochemical pathways  Endicott, John F.
The purpose of this paper is to outline some of the general principles which are likely to govern various photoreaction pathways. From the State-of-the-Art Symposium: Inorganic Photochemistry, held at the ACS meeting, Seattle, 1983.
Endicott, John F. J. Chem. Educ. 1983, 60, 824.
Photochemistry |
Reactions |
Mechanisms of Reactions |
Coordination Compounds
Programmed study aids for solving problems in advanced undergraduate organic chemistry  Chenier, Philip J.; Jenson, Todd M.
The study aids presented here offer several advantages: a student gets just the amount of help that he or she needs; students learn how to do problems by solving part of a problem and are able to monitor how well they understand an idea.
Chenier, Philip J.; Jenson, Todd M. J. Chem. Educ. 1983, 60, 409.
Mechanisms of Reactions
Hydride ion and sulfite ion attack on pyridine derivatives: Correspondence between biochemical and chemical reactions as demonstrated by UV spectroscopy  Larsen, Peder Olesen; Sundahl, Maria; Wieczorkowska, Elzbieta
Familiarizes students with nicotinamide coenzymes and use of UV-spectroscopy as a tool for investigating reaction mechanisms.
Larsen, Peder Olesen; Sundahl, Maria; Wieczorkowska, Elzbieta J. Chem. Educ. 1982, 59, 1080.
UV-Vis Spectroscopy |
Enzymes |
Mechanisms of Reactions
An NMR kinetics experiment  Kaufman, Don; Sterner, Carl; Masek, Brian; Svenningsen, Ralph; Samuelson, Greg
Uses NMR spectroscopy to obtain rate data for the synthesis of p-methoxyphenylacetylene.
Kaufman, Don; Sterner, Carl; Masek, Brian; Svenningsen, Ralph; Samuelson, Greg J. Chem. Educ. 1982, 59, 885.
NMR Spectroscopy |
Kinetics |
Catalysis |
Synthesis |
Mechanisms of Reactions |
Rate Law
The synthesis of 2-acetyl-1,4-naphthoquinone: A multi-step synthesis  Green, Ivan R.
Synthesis of the title compound is carried out through two different pathways that are then compared for their relative merits.
Green, Ivan R. J. Chem. Educ. 1982, 59, 698.
Synthesis |
Aromatic Compounds |
Mechanisms of Reactions
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
Pi bonding without tears  Akeroyd, F. Michael
A non-mathematical treatment of sigma-pi bonding applied to conjugation, hyperconjugation, Markovnikoff addition, aromaticity, and aromatic substitution.
Akeroyd, F. Michael J. Chem. Educ. 1982, 59, 371.
Alkenes |
Mechanisms of Reactions |
Addition Reactions |
Aromatic Compounds
The problem of syn- versus anti-addition: An organic chemistry laboratory experiment  Silversmith, Ernest F.
An experiment that allows a student to determine whether an addition to a carbon-carbon double bond proceeds in syn- or anti-fashion.
Silversmith, Ernest F. J. Chem. Educ. 1982, 59, 346.
Addition Reactions |
Mechanisms of Reactions |
Molecular Properties / Structure |
Stereochemistry |
Synthesis |
Alkenes
Stepwise metathesis: A promising strategy in organic synthesis  Mehta, Goverdhan
An article to stimulate interest in metathetical approaches to diverse organic molecules and highlight recent achievements in this area.
Mehta, Goverdhan J. Chem. Educ. 1982, 59, 313.
Mechanisms of Reactions |
Molecular Properties / Structure |
Synthesis |
Catalysis
Coupling of an aryl radical with a nucleophile and the reaction pathway  Rossi, Roberto A.
A qualitative description of the reaction coordinate for the process of coupling an aryl radical and a nucleophile from a molecular point of view.
Rossi, Roberto A. J. Chem. Educ. 1982, 59, 310.
MO Theory |
Mechanisms of Reactions |
Nucleophilic Substitution
Markov chain simulation of chemical reactions in nonhomogeneous systems  Formosinho, Sebastiao J.
A Markov chain method is used to study the effect of molecular diffusion in spatially inhomogeneous chemical reacting systems.
Formosinho, Sebastiao J. J. Chem. Educ. 1982, 59, 281.
Reactions |
Mechanisms of Reactions |
Kinetics |
Transport Properties
The mechanism of the formaldehyde clock reaction: Methylene glycol dehydration  Burnett, M. G.
Results of investigation to determine the mechanism of the formaldehyde clock reaction.
Burnett, M. G. J. Chem. Educ. 1982, 59, 160.
Mechanisms of Reactions |
Kinetics |
Rate Law
Techniques and Applications of Fast Reactions in Solution (Gettins, W. J.; Wyn-Jones, E.; ed.s)  Rodgers, M. A. J.

Rodgers, M. A. J. J. Chem. Educ. 1981, 58, A30.
Reactions |
Mechanisms of Reactions |
Kinetics |
Rate Law
Mechanical properties of polymers  Aklonis, J. J.
In this paper, an overview of the study of mechanical properties of polymers will be presented.
Aklonis, J. J. J. Chem. Educ. 1981, 58, 892.
Mechanisms of Reactions |
Polymerization |
Kinetics
Step-growth polymerization  Stille, J. K.
In step-growth polymerization, the molecular weight of the polymer chain builds up slowly and there is only one reaction mechanism for the formation of polymer. The distinct initiation, propagation, and termination steps of chain-growth polymerization are meaningless in step-growth polymerization.
Stille, J. K. J. Chem. Educ. 1981, 58, 862.
Polymerization |
Reactions |
Mechanisms of Reactions |
Synthesis
Chain reaction polymerization  McGrath, James E.
The purpose of this paper is to attempt to present a reasonable, concise, but up-to-date overview of chain reaction polymerization. The article refers to many excellent papers and books on the subject.
McGrath, James E. J. Chem. Educ. 1981, 58, 844.
Polymerization |
MO Theory |
Synthesis |
Kinetics |
Mechanisms of Reactions
Orbital topology and reaction mechanisms  Pearson, Ralph G.
Symmetry rules have proved useful in hundred of applications so far. The number of literature references is sufficient proof of this. The rules are valid and have been accepted into the general body of knowledge dealing with chemical reaction mechanisms, structures of molecules, and more. All serious students of chemistry need to learn something about these rules.
Pearson, Ralph G. J. Chem. Educ. 1981, 58, 753.
Group Theory / Symmetry |
Applications of Chemistry |
Mechanisms of Reactions |
Molecular Properties / Structure
The driving force of addition and elimination reactions clarified through the Hellmann-Feynman theorem  Blaise, Paul; Pujol, Phillippe; Henri-Rousseau, Olivier
The energy involved in the transition state is explored in this article.
Blaise, Paul; Pujol, Phillippe; Henri-Rousseau, Olivier J. Chem. Educ. 1981, 58, 615.
Thermodynamics |
Addition Reactions |
Elimination Reactions |
Reactions
The application of high-resolution electron microscopy to problems in solid state chemistry: The exploits of a peeping TEM  Eyring, LeRoy
High-resolution electron microscopy and using this technique to elucidate the structure of real crystalline solids and the mechanism of solid state reactions.
Eyring, LeRoy J. Chem. Educ. 1980, 57, 565.
Solid State Chemistry |
Crystals / Crystallography |
Mechanisms of Reactions
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
Micelle catalysis of an ionic substitution reaction  Corsaro, Gerald
Describes kinetics experiments for students in physical chemistry and biochemistry regarding micelle catalysis of an ionic substitution reaction and discusses the electrostatic factors that may be involved in the reaction mechanism.
Corsaro, Gerald J. Chem. Educ. 1980, 57, 225.
Micelles |
Catalysis |
Kinetics |
Mechanisms of Reactions |
Rate Law
An introductory level kinetics investigation  McGarvey, J. E. B.; Knipe, A. C.
A kinetic study of the hydrolysis of 3-bromo-3-phenylpropanoic acid.
McGarvey, J. E. B.; Knipe, A. C. J. Chem. Educ. 1980, 57, 155.
Kinetics |
Rate Law |
Mechanisms of Reactions
Toward an organic chemist's periodic table  Hall, H. K., Jr.
An analogy between electron transfer reactions of the elements and those of organic molecules.
Hall, H. K., Jr. J. Chem. Educ. 1980, 57, 49.
MO Theory |
Reactions |
Mechanisms of Reactions
The second year course in inorganic chemistry at the free university of Amsterdam  Bolster, M. W. G.
Includes an outline of the experiments used in the course.
Bolster, M. W. G. J. Chem. Educ. 1979, 56, 734.
Coordination Compounds |
Crystal Field / Ligand Field Theory |
IR Spectroscopy |
Magnetic Properties |
Kinetics |
Oxidation / Reduction |
Mechanisms of Reactions |
Catalysis
Claisen ester condensation equilibria-model calculations  Garst, John F.
In a Claisen condensation of an ester with but one alpha hydrogen, promoted by a strong base, both reactants and products are deprotonated; because the products are stronger acids than the reactant ester, the net effect is a shift toward products.
Garst, John F. J. Chem. Educ. 1979, 56, 721.
Esters |
Mechanisms of Reactions |
Equilibrium
The romance of HMDA  Wittcoff, Harold
The chemistry of hexamethylenediamine.
Wittcoff, Harold J. Chem. Educ. 1979, 56, 654.
Industrial Chemistry |
Synthesis |
Mechanisms of Reactions
The perturbational MO method for saturated systems  Herndon, William C.
Outlines a molecular orbital approach to the problem of predicting and correlating bond dissociation energies in saturated hydrocarbons.
Herndon, William C. J. Chem. Educ. 1979, 56, 448.
MO Theory |
Alkanes / Cycloalkanes |
Free Radicals |
Mechanisms of Reactions
The mechanism of action of salivary amylase: A simple undergraduate experiment  Rungruangsak, Krisna; Panijpan, Bhinyo
An experiment on the kinetics of alpha-amylase digestion of starch that yields significant information on the activity and mechanism of enzyme action.
Rungruangsak, Krisna; Panijpan, Bhinyo J. Chem. Educ. 1979, 56, 423.
Catalysis |
Enzymes |
Mechanisms of Reactions |
Kinetics |
Rate Law
A dynamic carbon model capable of showing changes in hybridization  Fountain, K. R.
It is possible to construct a simple dynamic model of a carbon atom that demonstrates the Walden inversion, the SN1 reaction, and when joined with another units like itself demonstrates the full spectrum of elimination reactions.
Fountain, K. R. J. Chem. Educ. 1979, 56, 379.
Molecular Modeling |
Nucleophilic Substitution |
Elimination Reactions
Rudolf Criegee (1902-1975)  Huisgen, Rolf; Gilde, Hans-Georg, translator
Criegee's background and work with selective oxidizing agents, the mechanism of ozonolysis, and carbocyclics.
Huisgen, Rolf; Gilde, Hans-Georg, translator J. Chem. Educ. 1979, 56, 369.
Oxidation / Reduction |
Mechanisms of Reactions
Rates of bimolecular heterogeneous reactions following the Langmuir-Hinshelwood mechanism  Glasser, L.
The Langmuir-Hinshelwood deserves attention because this model serves a basis to the study of bimolecular surface-mediated reaction rates.
Glasser, L. J. Chem. Educ. 1979, 56, 22.
Catalysis |
Rate Law |
Mechanisms of Reactions |
Surface Science
Mechanisms of ligand substitution reactions of cobalt(III) complexes  Pearson, Ralph G.
A history of the explorations of kinetics of ligand substitution reactions of cobalt(III) complexes .
Pearson, Ralph G. J. Chem. Educ. 1978, 55, 720.
Coordination Compounds |
Mechanisms of Reactions |
Kinetics
Faithful couple: The electron pair  Salem, L.
The goal of this paper is to present some of the simple facts of theoretical chemistry in a language which is as close as possible to our everyday language and to introduce one of the basic principles which governs the mechanism in chemical reactions.
Salem, L. J. Chem. Educ. 1978, 55, 344.
Mechanisms of Reactions |
Theoretical Chemistry |
Reactions
Triboluminescence of new uranyl salts  Gil, Jesus Martin; Gil, Francisco J. Martin
It is the purpose of this article to show that very simple experimentation with recent uranyl salts provide special opportunities for introducing the students to this rather unclear phenomenon. It also allows students to compare the results with the excitation mechanism proposed in the literature.
Gil, Jesus Martin; Gil, Francisco J. Martin J. Chem. Educ. 1978, 55, 340.
Mechanisms of Reactions |
Photochemistry
Favorskii rearrangement in bridged polycyclic compounds  Chenier, Philip J.
Favorskii rearrangement in bridged polycyclic compounds: This can be classified as an intramolecular rearrangement from carbon to carbon, involving a migrating group Z moving without its electrons from migrating origin A to an electron-rich terminus B.
Chenier, Philip J. J. Chem. Educ. 1978, 55, 286.
Mechanisms of Reactions |
Carboxylic Acids |
Aldehydes / Ketones |
Aromatic Compounds
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
Selective reduction of functionalized carboxylic acids with borane-methyl sulfide: A convenient undergraduate organic experiment  Krishnamurthy, S.; Thompson, Kerry L.
Introduces a new selective reducing agent, borane-methyl sulfide.
Krishnamurthy, S.; Thompson, Kerry L. J. Chem. Educ. 1977, 54, 778.
Carboxylic Acids |
Oxidation / Reduction |
Mechanisms of Reactions
Preparation of vanillin from eugenol and sawdust  Lampman, Gary M.; Andrews, Jennifer; Bratz, Wayne; Hanssen, Otto; Kelley, Kenneth; Perry, Dana; Ridgeway, Anthony
Two procedures are described for the conversion of eugenol to vanillin.
Lampman, Gary M.; Andrews, Jennifer; Bratz, Wayne; Hanssen, Otto; Kelley, Kenneth; Perry, Dana; Ridgeway, Anthony J. Chem. Educ. 1977, 54, 776.
Synthesis |
Consumer Chemistry |
Food Science |
Mechanisms of Reactions |
Aromatic Compounds |
Oxidation / Reduction
Organic photochemistry  Zimmerman, H. E.
In this question, students must recognize that the protonated zwitterion is more likely to react with an external nucleophile than with the internal center of negative charge on the zwitterion.
Zimmerman, H. E. J. Chem. Educ. 1977, 54, 756.
Photochemistry |
Mechanisms of Reactions
Pharmacological projects/case studies for teaching molecular structure and reactivity  Webb, John; Rasmussen, Malcolm
Using pharmacological agents to provide projects that develop and illustrate concepts of molecular stereochemistry, functional groups, and types of reactions and reactivity.
Webb, John; Rasmussen, Malcolm J. Chem. Educ. 1977, 54, 677.
Drugs / Pharmaceuticals |
Stereochemistry |
Reactions |
Mechanisms of Reactions
Phthalimide, anthranilic acid, benzyne. An undergraduate organic laboratory sequence  Dougherty, C. M.; Baumgarten, R. L.; Sweeney, A., Jr.; Concepcion, E.
A synthetic sequence: phthalic anhydride to phthalimide to anthranilic acid to methyl anthranilate or to 1,2,3,4-tetraphenylnaphthalene.
Dougherty, C. M.; Baumgarten, R. L.; Sweeney, A., Jr.; Concepcion, E. J. Chem. Educ. 1977, 54, 643.
Aromatic Compounds |
Mechanisms of Reactions |
Synthesis
Functionality number. A new focus on an advanced organic chemistry course  Alonso, Miguel E.
A relatively simple method is proposed whereby the reactivity of carbon-containing functional groups is analyzed systematically with emphasis on carbon-carbon bond-forming reactions.
Alonso, Miguel E. J. Chem. Educ. 1977, 54, 568.
Synthesis |
Mechanisms of Reactions
"Rule of thumb" for deriving steady state rate equations  Gilbert, H. F.
A simple method for deriving steady state rate equations for first-order and pseudo-first-order reactions.
Gilbert, H. F. J. Chem. Educ. 1977, 54, 492.
Rate Law |
Kinetics |
Mechanisms of Reactions |
Reactive Intermediates
Salt and solvent effects on reaction mechanism  Corsaro, Gerald
Shows how theory accounts for the participation of cations in a reaction mechanism, the influence of a solvent and its consequences in effecting such participation, and demonstrates a correlation between cation lattice ion size and rate constants.
Corsaro, Gerald J. Chem. Educ. 1977, 54, 483.
Solutions / Solvents |
Mechanisms of Reactions |
Reactive Intermediates |
Rate Law
Substituent effects in electrophilic aromatic substitution. A laboratory in organic chemistry  Gilow, Helmuth
The acid catalyzed bromination of aromatic substrates with hydrobromous acid.
Gilow, Helmuth J. Chem. Educ. 1977, 54, 450.
Molecular Properties / Structure |
Aromatic Compounds |
Electrophilic Substitution |
Mechanisms of Reactions |
Catalysis
Photohydration of pyridine in aqueous solution. An undergraduate experiment in photochemical kinetics  Andre, J. C.; Niclause, M.; Joussot-Dubien, J.; Deglise, X.
An easy experiment that illustrates many of the physical aspects of photochemistry.
Andre, J. C.; Niclause, M.; Joussot-Dubien, J.; Deglise, X. J. Chem. Educ. 1977, 54, 387.
Photochemistry |
Kinetics |
Spectroscopy |
Alkenes |
Aldehydes / Ketones |
Mechanisms of Reactions
Synthesis of 4-methyl-3-heptanol and 4-methyl-3-heptanone. Two easily synthesized insect pheromones  Einterz, Robert M.; Ponder, Jay W.; Lenox, Ronald S.
A two step reaction sequence involving the Grignard synthesis of an alcohol followed by oxidation of this alcohol to the corresponding ketone.
Einterz, Robert M.; Ponder, Jay W.; Lenox, Ronald S. J. Chem. Educ. 1977, 54, 382.
Natural Products |
Synthesis |
Applications of Chemistry |
Grignard Reagents |
Mechanisms of Reactions |
Stereochemistry |
Alcohols |
Aldehydes / Ketones
Benzidine rearrangement and the detection of trace quantities of blood. A laboratory experiment in criminalistics  Pinkus, Jack L.; Goldman, Lyle S.
Synthesis of 3,5,3',5'-tetramethylbenzidine and its application to detect a blood stain.
Pinkus, Jack L.; Goldman, Lyle S. J. Chem. Educ. 1977, 54, 380.
Reactions |
Mechanisms of Reactions |
Forensic Chemistry |
Synthesis |
Applications of Chemistry
Probe-dependent cooperativity patterns in Hill-plots  Byers, Larry D.
The analysis of various cooperativity patterns can provide insight into the role of subunit interactions in the catalytic mechanism.
Byers, Larry D. J. Chem. Educ. 1977, 54, 352.
Proteins / Peptides |
Enzymes |
Catalysis |
Mechanisms of Reactions |
Kinetic-Molecular Theory
Sodium perborate oxidation of an aromatic amine  Huestis, Laurence
Upon learning that the mechanism and even the nature of the oxidizing species is unknown, this reaction assumes new significance and provides an excellent opportunity for speculation on the nature of the reaction and a review of factors that affect the yield.
Huestis, Laurence J. Chem. Educ. 1977, 54, 327.
Aromatic Compounds |
Amines / Ammonium Compounds |
Oxidation / Reduction |
Synthesis |
Mechanisms of Reactions
Isodiazomethane revisited. N-aminoisonitriles  Anselme, J.-P.
The structure, reactions, and preparation of N-aminoisonitriles.
Anselme, J.-P. J. Chem. Educ. 1977, 54, 296.
Reactions |
Mechanisms of Reactions |
Molecular Properties / Structure |
Amides
Ethylene by naphtha cracking. Free radicals in action  Wiseman, Peter
Ethylene manufacture, the mechanism of ethylene formation, maximizing ethylene yield, the effect of feedstock composition, and secondary reactions.
Wiseman, Peter J. Chem. Educ. 1977, 54, 154.
Free Radicals |
Industrial Chemistry |
Alkenes |
Mechanisms of Reactions |
Reactions |
Applications of Chemistry
Mechanistic study of a reaction. An experimental course offering  Fisher, Robert D.
Brief description of an integrated chemistry course, the first half of which regards reaction parameters, the second half of which focusses on nucleophilic substitution reactions.
Fisher, Robert D. J. Chem. Educ. 1977, 54, 118.
Reactions |
Mechanisms of Reactions |
Kinetics |
Stereochemistry |
Nucleophilic Substitution
The rearrangement of 1,1-dimethyl-1-phenacylhydrazinium bromide  Koga, M.; Stamegna, A. P.; Burke, D. J.; Anselme, J.-P.
The rearrangement of 1,1-dimethyl-1-phenacylhydrazinium bromide illustrates the chemistry of ylids.
Koga, M.; Stamegna, A. P.; Burke, D. J.; Anselme, J.-P. J. Chem. Educ. 1977, 54, 111.
Mechanisms of Reactions |
Reactions
Lap-dissolve slides. Multiple-use formats for pre-laboratory instruction  Fine, Leonard W.; Harpp, David N.; Krakower, Earl; Snyder, James P.
Describes and provides examples of the lap-dissolve effect, a technique that uses two 35mm slide projectors to convey changing images in a large lecture setting.
Fine, Leonard W.; Harpp, David N.; Krakower, Earl; Snyder, James P. J. Chem. Educ. 1977, 54, 72.
Reactions |
Mechanisms of Reactions
Vitalizing the lecture. Lap-dissolve projection  Harpp, David N.; Snyder, James P.
Describes and provides examples of the lap-dissolve effect, a technique that uses two 35mm slide projectors to convey changing images in a large lecture setting.
Harpp, David N.; Snyder, James P. J. Chem. Educ. 1977, 54, 68.
Molecular Properties / Structure |
Mechanisms of Reactions
Crown ethers. A new aid to synthesis and to elucidation of reaction mechanisms  Knipe, A. C.
Although there have been many recent and exciting developments in the synthesis of these compounds, no attempt will be made in this review, to update a comprehensive catalogue of such achievement. The emphasis will alternatively be on successful application of macrocyclic polyethers within the the title areas.
Knipe, A. C. J. Chem. Educ. 1976, 53, 618.
Mechanisms of Reactions |
Ethers |
Heterocycles |
Synthesis
An electrochemist's description of rectification by a pn junction  Rosseinsky, David R.
The purpose of this note is to explore the chemical mechanisms of rectification by semiconductor pn junctions.
Rosseinsky, David R. J. Chem. Educ. 1976, 53, 617.
Mechanisms of Reactions |
Electrochemistry |
Semiconductors
Planning a kinetic and mechanistic study with cerium (IV)  Hanna, Samir B.; Kessler, Robert R.; Merbach, Andre; Ruzicka, Steve
In this paper, the authors will describe an acidic sulfate medium in which various concentrations of the possible Ce(IV) species can be prescribed. Secondly, they present the computations-based on simultaneous solutions of various equilibrium of the concentration distributed of the sulfato and hydroxo species of Ce(IV). Lastly, the optimum planning of a kinetic study of a Ce(IV)-reductant system, based on the quantitative description of the medium is suggested.
Hanna, Samir B.; Kessler, Robert R.; Merbach, Andre; Ruzicka, Steve J. Chem. Educ. 1976, 53, 524.
Kinetics |
Mechanisms of Reactions |
Equilibrium |
Acids / Bases
Rate constants from initial concentration data  Hall, K. J.; Quickenden, T. I.; Watts, D. W.
The authors suggest a method of obtaining initial rates that lead to a simple and accurate method of determining rate constants. The method is particularly valuable when side reactions complicate a mechanism and thus limit the use of an integrated rate equation.
Hall, K. J.; Quickenden, T. I.; Watts, D. W. J. Chem. Educ. 1976, 53, 493.
Reactions |
Mechanisms of Reactions |
Kinetics |
Rate Law
Ketene cycloadditions  Holder, Richard W.
Mechanisms of ketene cycloadditions.
Holder, Richard W. J. Chem. Educ. 1976, 53, 81.
Aldehydes / Ketones |
Mechanisms of Reactions |
Stereochemistry |
Reactions
The selective reduction of meta- (and para-) nitroacetophenone  Jones, Alan G.
By appropriate choice of reagent and reaction conditions a nitroketone can be selectively reduced to an aminoketone or a nitroalcohol; aromatic nitro groups can be reduced to primary arylamines using various chemical reducing agents.
Jones, Alan G. J. Chem. Educ. 1975, 52, 668.
Mechanisms of Reactions |
Synthesis |
IR Spectroscopy |
Oxidation / Reduction |
Aromatic Compounds |
Amines / Ammonium Compounds
The determination of a mechanism of isomerization of maleic acid to fumaric acid  Meek, John S.
Procedure in which students attempt to determine the mechanism for the isomerization of maleic acid to fumaric acid by heating with hydrochloric acid.
Meek, John S. J. Chem. Educ. 1975, 52, 541.
Mechanisms of Reactions |
Molecular Properties / Structure |
Stereochemistry |
Carboxylic Acids
Mechanistic inorganic photochemistry. Reactivity of the excited states of chromium(III) complexes  Kutal, Charles
Relates differences in the photochemical and thermal ligand substitution of a complex to the electronic and structural parameters of the states from which the reactions originate.
Kutal, Charles J. Chem. Educ. 1975, 52, 502.
Photochemistry |
Crystal Field / Ligand Field Theory |
Mechanisms of 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
A molecular model for SN2 reactions  Newman, Melvin S.
Plan for a homemade mechanical model designed to demonstrate many of the features of SN2 reactions.
Newman, Melvin S. J. Chem. Educ. 1975, 52, 462.
Molecular Mechanics / Dynamics |
Molecular Modeling |
Molecular Properties / Structure |
Nucleophilic Substitution |
Mechanisms of Reactions |
Reactions
The appreciation of molecular transformation in organic chemistry. Part I: Analysis of a fascinating problem  Ranganathan, S.; Ranganathan, D.
Step-by-step analysis of an involved organic transformation.
Ranganathan, S.; Ranganathan, D. J. Chem. Educ. 1975, 52, 424.
Reactions |
Mechanisms of Reactions |
Nucleophilic Substitution
The reactions of ferroin complexes. A color-to-colorless freshman kinetic experiment  Edwards, John O.; Edwards, Kathleen; Palma, Jorge
A group of related reactions that can be easily followed with a colorimeter which show that the mechanism by which a reaction takes place may not be at all obvious from the stoichiometry.
Edwards, John O.; Edwards, Kathleen; Palma, Jorge J. Chem. Educ. 1975, 52, 408.
Kinetic-Molecular Theory |
Coordination Compounds |
Crystal Field / Ligand Field Theory |
Stoichiometry |
Mechanisms of Reactions
Fallacious separation of uni and bimolecular reactions  Stein, Allan R.
To avoid errors in mechanistic conclusions in processes involving ionic reactants the possibility of incomplete dissociation or ion pairings must always be considered.
Stein, Allan R. J. Chem. Educ. 1975, 52, 303.
Reactions |
Mechanisms of Reactions |
Nucleophilic Substitution
Organoboranes and organoborate anions. New classes of electrophiles and nucleophiles in organic synthesis  Negishi, Ei-ichi
Presents some of the key features common to various reactions of organoboranes and interprets them in terms of a few common mechanistic schemes.
Negishi, Ei-ichi J. Chem. Educ. 1975, 52, 159.
Synthesis |
Mechanisms of Reactions
Biological light. a[Alpha]-Peroxylates as bioluminescent intermediates  Adam, Waldemar
The chemistry of bioluminescence.
Adam, Waldemar J. Chem. Educ. 1975, 52, 138.
Photochemistry |
Natural Products |
Mechanisms of Reactions
Generation of vinyl cations by solvolysis reactions. A lesser known genre of carbenium ions  Subramanian, L. R.; Hanack, M.
Considers the structure and geometry of vinyl cations; modes of generation of vinyl cations; heterolysis of vinyl substrates; and mechanisms of solvolysis of vinyl substrates.
Subramanian, L. R.; Hanack, M. J. Chem. Educ. 1975, 52, 80.
Molecular Properties / Structure |
Alkenes |
Mechanisms of Reactions
A spectrophotometric kinetic experiment illustrating consecutive reactions. The methanolysis of methyl p-nitrophenyl sulfate  Buncel, E.; Raoult, A.; Wiltshire, J. F.
The authors report an experiment which can be carried out efficiently in a limited time and can provide experience in obtaining and processing rate data; give an idea of the scope and variety of experimental methods which can be used for rate measurements; and illustrate how kinetic results can provide information about the mechanisms of a reaction.
Buncel, E.; Raoult, A.; Wiltshire, J. F. J. Chem. Educ. 1974, 51, 814.
Mechanisms of Reactions |
Kinetics |
Rate Law
Illustration of reaction mechanism in polyatomic systems via computer movies  Raff, L. M.
Teaching chemistry is often a challenge in that instructors must discuss three dimensional phenomenon on two dimensional blackboards. These problems may be solved by use of accurate, quasi classical trajectories represented by moving three-dimensional projections.
Raff, L. M. J. Chem. Educ. 1974, 51, 712.
Reactions |
Mechanisms of Reactions
A combined infrared and kinetic study of linkage isomers. An inorganic experiment  Hohman, William H.
In this experiment, the rate of isomerization of the nitrito to the nitro isomer is followed in the solid state using an infrared technique. The order of the reaction and the mechanism for the conversion can be determined.
Hohman, William H. J. Chem. Educ. 1974, 51, 553.
Mechanisms of Reactions |
Synthesis |
Coordination Compounds |
IR Spectroscopy
Mechanisms in photographic chemistry  Sahyun, M. R. V.
The study of the chemistry of so-called conventional photography, based on the photosensitivity of silver halides, has been a part of chemical research for nearly 150 years, yet it still has many unanswered questions to deal with.
Sahyun, M. R. V. J. Chem. Educ. 1974, 51, 72.
Photochemistry |
Applications of Chemistry |
Mechanisms of Reactions |
Catalysis |
Dyes / Pigments |
Coordination Compounds
The search for organic reaction pathways (Sykes, Peter)  Chaser, Dwight W.

Chaser, Dwight W. J. Chem. Educ. 1973, 50, A511.
Mechanisms of Reactions
Polymerization as a model chain reaction  Morton, Maurice
The building of long chain macromolecules offers the best opportunity for the study of chain reactions and the free radical mechanism.
Morton, Maurice J. Chem. Educ. 1973, 50, 740.
Conferences |
Professional Development |
Polymerization |
Reactions |
Free Radicals |
Kinetics |
Mechanisms of Reactions
Dihalocarbene addition reaction  Goh, S. H.
This experiment illustrates the synthetic utility of carbenes and that of phase transfer catalysis.
Goh, S. H. J. Chem. Educ. 1973, 50, 678.
Alkenes |
Addition Reactions |
Reactions |
Mechanisms of Reactions |
Catalysis |
Synthesis
Computer simulation of kinetics by the Monte Carlo technique  Dixon, David A.; Shafer, Richard H.
Students are taught to use Fortran IV programming to apply a digital computer to the Monte Carlo analysis of chemical kinetics.
Dixon, David A.; Shafer, Richard H. J. Chem. Educ. 1973, 50, 648.
Kinetics |
Mechanisms of Reactions |
Rate Law
Mechanism of an organic reaction  Moore, John

Moore, John J. Chem. Educ. 1973, 50, 643.
Reactions |
Mechanisms of Reactions
SN1 and SN2 reactions: Paper marionette for demonstration  Sone, Yachiyo; Sone, Kozo
Describes the construction of a paper marionette for demonstrating SN1 and SN2 reactions.
Sone, Yachiyo; Sone, Kozo J. Chem. Educ. 1973, 50, 615.
Nucleophilic Substitution |
Mechanisms of Reactions |
Reactions |
Molecular Modeling
A kinetic experiment using potentiometric determination of reactant concentration  Smith, R. H.
An experiment that provides experience in obtaining and processing kinetic data, gives students an idea of the scope and variety of experimental methods that can be used for rate measurements, and illustrates how kinetic results can provide information about the mechanism of a reaction.
Smith, R. H. J. Chem. Educ. 1973, 50, 441.
Kinetics |
Rate Law |
Electrochemistry |
Mechanisms of Reactions
A visible transient intermediate  le Noble, W. J.; Chang, Yu-Sen
A demonstration or laboratory in which a transient, reactive intermediate is fleetingly visible as a momentary color change.
le Noble, W. J.; Chang, Yu-Sen J. Chem. Educ. 1973, 50, 418.
Reactive Intermediates |
Mechanisms of Reactions |
Reactions
Synthesis of a photochromic benzothiazolinic spiropyran  Guglielmetti, R.; Meyer, R.; Dupuy, C.
The purpose of this type of experiment is to elucidate structure of the different compounds gradually prepared starting from reaction mechanisms and chiefly from spectroscopic data given perviously to students.
Guglielmetti, R.; Meyer, R.; Dupuy, C. J. Chem. Educ. 1973, 50, 413.
Photochemistry |
Synthesis |
Mechanisms of Reactions |
Molecular Properties / Structure
The preparation and dehydration of 1-benzylcycloalkanols  Newkome, George R.; Allen, J. W.; Anderson, G. M.
This reaction sequence sheds light on carbocation intermediates, steric effects, conjugation, and elimination mechanisms.
Newkome, George R.; Allen, J. W.; Anderson, G. M. J. Chem. Educ. 1973, 50, 372.
Synthesis |
Alcohols |
Mechanisms of Reactions |
Elimination Reactions
The synthesis of fused cycloalkenones via annelation methods  Mundy, Bradford P.
A review of the Robinson annelation reaction, which has been invaluable for syntheses in the terpene and steroid fields.
Mundy, Bradford P. J. Chem. Educ. 1973, 50, 110.
Synthesis |
Aldehydes / Ketones |
Nucleophilic Substitution |
Mechanisms of Reactions
Organic reaction mechanisms: An introduction (Breslow, Ronald)  Kreevoy, Maurice M.

Kreevoy, Maurice M. J. Chem. Educ. 1972, 49, A182.
Mechanisms of Reactions
A new method for learning organic reactions  Perlmutter, Howard D.; Kristol, David S.
Using wooden cubes in a game to help students learn organic reactions.
Perlmutter, Howard D.; Kristol, David S. J. Chem. Educ. 1972, 49, 793.
Reactions |
Mechanisms of Reactions |
Synthesis
Arthur Lapworth. The genesis of reaction mechanism  Saltzman, Martin
Examines the contributions made by Arthur Lapworth to the mechanistic view of organic reactions.
Saltzman, Martin J. Chem. Educ. 1972, 49, 750.
Reactions |
Mechanisms of Reactions
Relaxation kinetics of ferric thiocyanate. A temperature-jump and flash-photolysis study  Goodall, David M.; Harrison, Paul W.; Hardy, Michael J.; Kirk, C. Jane
Describes two perturbation methods for determining the kinetics and mechanism of the reaction that occurs when ferric and thiocyanate solutions are mixed.
Goodall, David M.; Harrison, Paul W.; Hardy, Michael J.; Kirk, C. Jane J. Chem. Educ. 1972, 49, 675.
Kinetics |
Aqueous Solution Chemistry |
Reactions |
Mechanisms of Reactions
A simple rule underlying kinetics  Nott, P. R.; Selinger, B. K.
Presents a simple analog computer for investigating the Lindemann Mechanism.
Nott, P. R.; Selinger, B. K. J. Chem. Educ. 1972, 49, 618.
Kinetics |
Mechanisms of Reactions
End group transfers. Mechanisms of the Cannizzaro reaction  Jacobus, John
Identifies a number of conventional, seemingly unrelated reactions that are end group transfers.
Jacobus, John J. Chem. Educ. 1972, 49, 349.
Reactions |
Mechanisms of Reactions
Carbenes in insertion and addition reactions  Buehler, Calvin A.
Summarizes the reactions typical of insertion and addition.
Buehler, Calvin A. J. Chem. Educ. 1972, 49, 239.
Addition Reactions |
Reactive Intermediates |
Mechanisms of Reactions |
Synthesis
The Ene Synthesis  Keung, Edmund C.; Alper, Howard
Examines developments of an "indirect substitutive addition" or "ene synthesis" reaction.
Keung, Edmund C.; Alper, Howard J. Chem. Educ. 1972, 49, 97.
Synthesis |
Alkenes |
Mechanisms of Reactions |
Reactions
Alkylations in organic chemistry  Mundy, Bradford P.
Examines some of the subtle factors involved in alkylations, including alkylations via enolates, alkylations via enamines, and alkylation of enolates derived from reduction of enone systems.
Mundy, Bradford P. J. Chem. Educ. 1972, 49, 91.
Synthesis |
Alkylation |
Aldehydes / Ketones |
Mechanisms of Reactions
The kinetics and mechanism of a metal carbonyl substitution reaction  Dobson, Gerard R.; Paxson, John R.
This laboratory procedure examines the reaction of (2,5-dithiahexane)tetracarbonylchromium(O) or -molybdenum(O) with triethyl phosphite.
Dobson, Gerard R.; Paxson, John R. J. Chem. Educ. 1972, 49, 67.
Kinetics |
Mechanisms of Reactions
Evidence of d pi-acceptor resonance in halogen substituents  Abdulla, Riaz F.
The association of various structural and dynamic phenomena through the postulate of d pi resonance has potential additional predictive value.
Abdulla, Riaz F. J. Chem. Educ. 1972, 49, 64.
Resonance Theory |
Mechanisms of Reactions
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
Organic sulfur compounds in organic synthesis  Block, Eric
Surveys the many syntheses of organic sulfur compounds.
Block, Eric J. Chem. Educ. 1971, 48, 814.
Synthesis |
Reactions |
Mechanisms of Reactions |
Molecular Properties / Structure
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
Stereochemical course of the pinacol rearrangement  Mundy, Bradford P.; Otzenberger, Rodney D.
The authors bring to our attention some common misunderstandings about stereochemical paths that are often found in textbooks.
Mundy, Bradford P.; Otzenberger, Rodney D. J. Chem. Educ. 1971, 48, 431.
Stereochemistry |
Mechanisms of Reactions
Kinetic aspects of biological membrane transport processes  Lerner, Joseph
This article considers diffusion processes, beginning with the simplest mechanisms, and will conclude with mention of a number of complex models that allow for co-solute transport.
Lerner, Joseph J. Chem. Educ. 1971, 48, 391.
Biophysical Chemistry |
Kinetics |
Transport Properties |
Mechanisms of Reactions |
Solutions / Solvents
Nonlinear Hammett relationships  Schreck, James 0.
The author provides examples of nonlinear structure-reactivity , Hammett correlation's, and summarize most of the types of reactions in which deviations due to change in mechanism or rate-controlling step occur.
Schreck, James 0. J. Chem. Educ. 1971, 48, 103.
Mechanisms of Reactions |
Aromatic Compounds
1,2-Anionic rearrangements. An example of mechanistic evolution  Pine, Stanley H.
This article is an updated understanding on 1,2-anionic rearrangements, as many textbooks are 10 years out of date.
Pine, Stanley H. J. Chem. Educ. 1971, 48, 99.
Mechanisms of Reactions
Mechanisms of inorganic reactions in solution: An introduction (Benson, D.)  Murmann, R. Kent

Murmann, R. Kent J. Chem. Educ. 1970, 47, A300.
Reactions |
Mechanisms of Reactions |
Aqueous Solution Chemistry
Problems in organic reaction mechanisms (Menger, F. M.)  Haynes, L. W.

Haynes, L. W. J. Chem. Educ. 1970, 47, A138.
Reactions |
Mechanisms of Reactions |
Enrichment / Review Materials
The isomerization of xylenes. An experiment for the organic or instrumental laboratory  Harbison, Kenneth G.
This experiment illustrates both qualitative and quantitative applications of infrared spectroscopy for the analysis of mixtures, as well as providing an interesting study of the mechanism of Friedel-Crafts reactions.
Harbison, Kenneth G. J. Chem. Educ. 1970, 47, 837.
Instrumental Methods |
Aromatic Compounds |
IR Spectroscopy |
Mechanisms of Reactions |
Reactions |
Constitutional Isomers
Ultraviolet and fluorescence spectra of 2,5-diaryl-1,3,4-oxidiazoles: An organic laboratory experiment  Taber, Richard L.; Grantham, Gary D.
Reports on an experiment involving a two-step synthesis leading to a series of substituted 2,5-diaryl-1,3,4-oxidiazoles that can be used for a class study of substituent effects on absorption and emission spectra of aromatic molecules.
Taber, Richard L.; Grantham, Gary D. J. Chem. Educ. 1970, 47, 834.
UV-Vis Spectroscopy |
Fluorescence Spectroscopy |
Aromatic Compounds |
Mechanisms of Reactions |
Molecular Properties / Structure |
Synthesis
Kinetics as an introductory course  Beatty, James W.; Powers, Jack W.; Scamehorn, Richard G.
Describes an introductory course entitled "Reaction Kinetics and the Mechanisms of Reactions."
Beatty, James W.; Powers, Jack W.; Scamehorn, Richard G. J. Chem. Educ. 1970, 47, 797.
Kinetics |
Mechanisms of Reactions
Fluorine compounds as teaching aids in organic theory  Young, John A.
Fluorine compounds do obey the fundamental tenets of organic theory, but their frequent reversal of polarity, relative to hydrocarbon analogs, and the change in emphasis from a positive hydrogen ion to a negative fluoride ion allow the instructor to frame questions that demand reasoning rather than reiteration on the part of the student.
Young, John A. J. Chem. Educ. 1970, 47, 733.
Aromatic Compounds |
Mechanisms of Reactions
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
ESR study of organic electron transfer reactions  Chang, Raymond
This paper examines electron spin resonance (esr) theory, electron transfer reactions, and the use of esr in investigations of chemical kinetics.
Chang, Raymond J. Chem. Educ. 1970, 47, 563.
Kinetics |
Mechanisms of Reactions
Woodward-Hoffmann rules: Cycloaddition reactions  Vollmer, John J.; Servis, Kenneth L.
Applies Woodward-Hoffmann rules to a wide variety of cycloaddition reactions.
Vollmer, John J.; Servis, Kenneth L. J. Chem. Educ. 1970, 47, 491.
Mechanisms of Reactions |
Addition Reactions |
Alkenes
Synthesis of cyclopentanecarboxaldehyde: An undergraduate organic chemistry laboratory experiment  Dev, Vasu
The synthesis of cyclopentanecarboxaldehyde can be applied to develop an understanding of the behavior of compounds in many areas of organic chemistry, particularly those of alicyclic compounds.
Dev, Vasu J. Chem. Educ. 1970, 47, 476.
Synthesis |
Aldehydes / Ketones |
Mechanisms of Reactions |
Nucleophilic Substitution
Understanding a culprit before eliminating it. An application of Lewis acid-base principles to atmospheric SO2 as a pollutant  Brasted, Robert C.
The SO2 molecule offers ample opportunities for teaching practical chemistry. [Debut of first run. This feature reappeared in 1986.]
Brasted, Robert C. J. Chem. Educ. 1970, 47, 447.
Acids / Bases |
Lewis Acids / Bases |
Atmospheric Chemistry |
Mechanisms of Reactions |
Reactions |
Applications of Chemistry |
Lewis Structures |
Molecular Properties / Structure
The synthesis of 2-nitroresorcinol: An experiment with sulfonic acids  Schaffrath, Robert E.
This synthesis is an ideal example using the -SO3H as a blocking group.
Schaffrath, Robert E. J. Chem. Educ. 1970, 47, 224.
Synthesis |
Reactions |
Mechanisms of Reactions |
Molecular Properties / Structure
The rearrangement of diazotized 4-bromobenzophenone hydrazone: A stereospecific reaction  Hawbeker, Byron L.
This procedure involves the synthesis of hydrazone and its subsequent diazotization / rearrangement to produce an anilide.
Hawbeker, Byron L. J. Chem. Educ. 1970, 47, 218.
Reactions |
Stereochemistry |
Molecular Properties / Structure |
Aromatic Compounds |
Mechanisms of Reactions |
Synthesis
Organic chemistry: Neighboring group participation  Dolbier, William R., Jr.
This paper is intended to be an introduction to neighboring group participation appropriate for undergraduate instruction.
Dolbier, William R., Jr. J. Chem. Educ. 1970, 47, 42.
Kinetics |
Stereochemistry |
Mechanisms of Reactions |
Reactions |
Molecular Properties / Structure
An experiment to illustrate nucleophilic aromatic substitution and tautomerism  Farmer, J. L.; Haws, E. J.
Students hydrolyze 2-chloropyridine and then examine the tautomeric mixture produced using infrared spectroscopy.
Farmer, J. L.; Haws, E. J. J. Chem. Educ. 1970, 47, 41.
Nucleophilic Substitution |
Aromatic Compounds |
Synthesis |
Mechanisms of Reactions |
IR Spectroscopy
An integrated NMR and synthetic organic chemistry experiment  Glaros, George; Cromwell, Norman H.
Presents a synthetic sequence that involves procedures of general utility and results in products illustrative of the basic principles of NMR spectroscopy.
Glaros, George; Cromwell, Norman H. J. Chem. Educ. 1969, 46, 854.
Spectroscopy |
NMR Spectroscopy |
Synthesis |
Mechanisms of Reactions |
Aromatic Compounds
Condensation reactions of carbon disulfide  Foye, William O.
This review catalogs a number of condensation reactions involving carbon disulfide for which no parallel appears to exist in carbon dioxide chemistry.
Foye, William O. J. Chem. Educ. 1969, 46, 841.
Reactions |
Mechanisms of Reactions
Oxidative coupling: A new approach to azo chemistry  Hunig, S.
By looking for the important structural features of p-phenylenediamines that constitute their ability to couple oxidatively, it was possible to construct three new systems that are also capable of undergoing this reaction. The enormous variety possible in these systems permits the syntheses of a great number of unusual azo compounds.
Hunig, S. J. Chem. Educ. 1969, 46, 734.
Aromatic Compounds |
Oxidation / Reduction |
Mechanisms of Reactions |
Synthesis
Preparation of sulfanilamide from aniline: An organic chemistry experiment  Hurdis, Everett C.; Yang, Josephine W.
Presents the preparation of sulfanilamide from aniline, a synthesis that is shorter than the tradition method.
Hurdis, Everett C.; Yang, Josephine W. J. Chem. Educ. 1969, 46, 697.
Synthesis |
Aromatic Compounds |
Mechanisms of Reactions
The Hantzsch pyridine synthesis: A factorial design experiment for the introductory organic laboratory  Norcross, B. E.; Clement, G.; Weinstein, M.
Students carry out the two-step Hantzsch pyridine synthesis; students are required to select the oxidizing agent and conditions for the second reaction step.
Norcross, B. E.; Clement, G.; Weinstein, M. J. Chem. Educ. 1969, 46, 694.
Synthesis |
Oxidation / Reduction |
Heterocycles |
Mechanisms of Reactions
Resolution and stereochemistry of asymmetric silicon, germanium, tin, and lead compounds  Belloli, Robert
It is the purpose of this review to summarize the results of stereochemical studies on compounds containing an asymmetric group IVA atom.
Belloli, Robert J. Chem. Educ. 1969, 46, 640.
Stereochemistry |
Organometallics |
Enantiomers |
Mechanisms of Reactions |
Nucleophilic Substitution
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
Encounters and slow reactions  Langford, Copper H.
This paper reviews the formation of a metal ion and a ligand in a mechanistic language, as much derived from the collision theory as from transition state theory.
Langford, Copper H. J. Chem. Educ. 1969, 46, 557.
Aqueous Solution Chemistry |
Metals |
Kinetics |
Mechanisms of Reactions |
Coordination Compounds |
Solutions / Solvents
Advanced organic chemistry: Reactions, mechanisms, and structure (March, Jerry)  Cochran, John C.

Cochran, John C. J. Chem. Educ. 1969, 46, 537.
Reactions |
Mechanisms of Reactions |
Molecular Properties / Structure
The preparation of potassium hexacyanocobaltate(III)  Poskozim, Paul S.
This laboratory compares the reaction of aqueous solution of cobalt(II) chloride and potassium cyanide when open to the air and under an inert atmosphere of nitrogen.
Poskozim, Paul S. J. Chem. Educ. 1969, 46, 384.
Coordination Compounds |
Mechanisms of Reactions |
Aqueous Solution Chemistry
Thermochemistry of hypochlorite oxidations  Bigelow, M. Jerome
Students mix various proportions of aqueous sodium hypochlorite and sodium sulfite and plot the change in temperature to determine the stoichiometry of the reaction.
Bigelow, M. Jerome J. Chem. Educ. 1969, 46, 378.
Calorimetry / Thermochemistry |
Oxidation / Reduction |
Aqueous Solution Chemistry |
Stoichiometry |
Thermodynamics |
Mechanisms of Reactions
Organic chemistry  Dolbier, William R., Jr.
Presents an explanation that encompasses all electrophilic additions to alkenes within a single, unifying picture.
Dolbier, William R., Jr. J. Chem. Educ. 1969, 46, 342.
Addition Reactions |
Alkenes |
Mechanisms of Reactions |
Stereochemistry
Computer animation: On-line dynamic display in real time  Walton, J. Scott; Risen, William M., Jr.
Using a simple computer system to display a molecule of up to 40 atoms and make the atoms move through any specified, but arbitrary mode of vibration.
Walton, J. Scott; Risen, William M., Jr. J. Chem. Educ. 1969, 46, 334.
Molecular Modeling |
Molecular Properties / Structure |
Mechanisms of Reactions
Reactions on basic alumina  Serratosa, Felix
Provides a survey of the use of alumina in synthetic and mechanistic studies.
Serratosa, Felix J. Chem. Educ. 1969, 46, 302.
Synthesis |
Mechanisms of Reactions
The Monte Carlo method: Plotting the course of complex reactions  Rabinovitch, B.
Introduces the Monte Carlo method applied to the problem of the probability that a given molecule will spontaneously decompose in a monomolecular reaction process, or that two molecules of the same or different types will react together in a biomolecular reaction process.
Rabinovitch, B. J. Chem. Educ. 1969, 46, 262.
Reactions |
Kinetics |
Mechanisms of Reactions |
Mathematics / Symbolic Mathematics
Photochemistry of organic compounds. II, Carbonyl compounds  Swenton, John S.
Examines the electronics of the simple carbonyl group, the effect of structure on photoreduction of benzophenones and acetophenones, non-conjugated unsaturated ketones, the photochemistry of cyclic enones, and cross-conjugated cyclohexadienones.
Swenton, John S. J. Chem. Educ. 1969, 46, 217.
Photochemistry |
Aldehydes / Ketones |
Mechanisms of 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
Kinetics of proton exchange of trimethylammonium ion by NMR: A laboratory experiment  Leyden, Donald E.; Morgan, W. R.
In this experiment several plausible reactions for the hydration of pyruvic acid are suggested and the student makes use of the data collected to select the most probable ones.
Leyden, Donald E.; Morgan, W. R. J. Chem. Educ. 1969, 46, 169.
NMR Spectroscopy |
Kinetics |
Mechanisms of Reactions
Mechanisms of inorganic reactions - A study of metal complexes in solution (Basolo, Fred; Pearson, Ralph G.)  Murmann, R. Kent

Murmann, R. Kent J. Chem. Educ. 1968, 45, A146.
Coordination Compounds |
Reactions |
Mechanisms of Reactions
The Hofmann amide rearrangement  Schreck, James O.
N-bromobenzamide and phenyl isocyanate are subjected to the same conditions required to convert benzamide to aniline to demonstrate that the former two compounds could be intermediates in the Hofmann rearrangements of benzamide.
Schreck, James O. J. Chem. Educ. 1968, 45, 670.
Amides |
Synthesis |
Mechanisms of Reactions
Analog computer simulation: An experiment in chemical kinetics  Griswold, Robert E.; Haugh, John F.
The major purpose of this experiment is to study the manner in which the overall specific rate constant and the orders of reaction with respect to each reactant are dependent on the relative magnitudes of the specific rate constants for each step in the postulated mechanism.
Griswold, Robert E.; Haugh, John F. J. Chem. Educ. 1968, 45, 576.
Kinetics |
Rate Law |
Mechanisms of Reactions
Hofmann elimination  Lyle, Robert E.
Clarification regarding the products of Hofmann elimination reactions.
Lyle, Robert E. J. Chem. Educ. 1968, 45, 547.
Elimination Reactions |
Mechanisms of Reactions |
Receptors
Mechanisms of oxidation-reduction reactions  Taube, Henry
Examines the mechanisms of oxidation-reduction reactions.
Taube, Henry J. Chem. Educ. 1968, 45, 452.
Mechanisms of Reactions |
Oxidation / Reduction |
Reactions |
Oxidation State |
Coordination Compounds
Physical-organic chemistry  Richards, John H.
This article discusses some general aspects of photochemical reactions, including the role of triplet states, an illustrative case of photosensitization, and the mechanism of the photochemical rearrangement of santonin.
Richards, John H. J. Chem. Educ. 1968, 45, 398.
Photochemistry |
Reactions |
Mechanisms of Reactions
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
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
The revolution in elementary kinetics and freshman chemistry  Wolfgang, Richard
New developments in kinetics so fundamentally affect our most elementary conception of chemical change that they must inevitably be reflected in beginning courses in chemistry; includes an outline for freshmen on elementary chemical dynamics.
Wolfgang, Richard J. Chem. Educ. 1968, 45, 359.
Kinetics |
Rate Law |
Mechanisms of Reactions
Chemical dynamics for college freshmen  Hammond, George S.; Gray, Harry B.
Suggestions for topics regarding chemical dynamics to be considered in freshman chemistry.
Hammond, George S.; Gray, Harry B. J. Chem. Educ. 1968, 45, 354.
Thermodynamics |
Kinetics |
Reactions |
Mechanisms of Reactions |
Rate Law
Woodward-Hoffmann rules: Electrocyclic reactions  Vollmer, J. J.; Servis, K. L.
Presents the theory of Woodward and Hoffmann and Longuet-Higgins to rationalize electrocyclic reactions
Vollmer, J. J.; Servis, K. L. J. Chem. Educ. 1968, 45, 214.
Electrochemistry |
Reactions |
Molecular Properties / Structure |
Mechanisms of Reactions |
Photochemistry
Introduction to inorganic reaction mechanisms (Lockhart, J. C.)  Finholt, James E.

Finholt, James E. J. Chem. Educ. 1968, 45, 71.
Mechanisms of Reactions
3-Sulfolene: A butadiene source for a Diels-Alder synthesis: An undergraduate laboratory experiment  Sample, Thomas E., Jr.; Hatch, Lewis F.
By selecting a suitable diene cyclic sulfone, the common complication in performing a Diels-Alder experiment can be avoided.
Sample, Thomas E., Jr.; Hatch, Lewis F. J. Chem. Educ. 1968, 45, 55.
Alkenes |
Synthesis |
Mechanisms of Reactions
Hydrolysis of monosubstituted orthophosphate esters  Bunton, C. A.
Examines the mechanism of the hydrolyses of mono-alkyl and -aryl derivatives of orthophosphoric acid.
Bunton, C. A. J. Chem. Educ. 1968, 45, 21.
Esters |
Mechanisms of Reactions |
Nucleophilic Substitution
Reactions in solutions under pressure  le Noble, W. J.
Examines the effect of pressure on the rates of reactions in solution.
le Noble, W. J. J. Chem. Educ. 1967, 44, 729.
Reactions |
Solutions / Solvents |
Thermodynamics |
Rate Law |
Mechanisms of Reactions |
Equilibrium
A molecular orbital description of the non-classical ion in 1,2 rearrangements  Phelan, Nelson F.; Jaffe, H. H.; Orchin, Milton
This paper attempts to show semiquantitatively why various groups migrate with differing ease with respect to 1,2 rearrangements.
Phelan, Nelson F.; Jaffe, H. H.; Orchin, Milton J. Chem. Educ. 1967, 44, 626.
Mechanisms of Reactions |
MO Theory
Systematic flash cards for organic chemistry  Sands, Richard D.
Describes systematic flash cards with a punch card code, their classification, and use by students.
Sands, Richard D. J. Chem. Educ. 1967, 44, 606.
Enrichment / Review Materials |
Mechanisms of Reactions
Kinetics of the gas phase decomposition of di-tert-butyl peroxide  Guillory, William A.
This experiment should demonstrate to the student a method for obtaining a first-order rate constant, the determination of the energy of activation, and the use of ingenuity in devising a reaction mechanism.
Guillory, William A. J. Chem. Educ. 1967, 44, 514.
Kinetics |
Gases |
Rate Law |
Mechanisms of Reactions
Acid anhydride functionality  Hurd, Charles D.
Examines several different structural types, each of which posses the acid anhydride functionality, though most are named on a different basis.
Hurd, Charles D. J. Chem. Educ. 1967, 44, 454.
Acids / Bases |
Synthesis |
Mechanisms of Reactions
Chemiluminescent reactions in solution  Haas, John W., Jr.
Examines chemiluminescent reactions in solution, including examples of their occurrence and methods for investigating such systems.
Haas, John W., Jr. J. Chem. Educ. 1967, 44, 396.
Photochemistry |
Mechanisms of Reactions |
Aqueous Solution Chemistry
Ozonolysis  Diaper, D. G. M.
Incorrect emphasis in the presentation of the ozonolysis of olefins has caused misconceptions about its scope and utility.
Diaper, D. G. M. J. Chem. Educ. 1967, 44, 354.
Mechanisms of Reactions
A computer program for making steady state calculations: Notes on effective programming techniques  DeTar, DeLos F.
Describes techniques for developing a computer program for making steady state calculations.
DeTar, DeLos F. J. Chem. Educ. 1967, 44, 193.
Reactions |
Mechanisms of Reactions |
Kinetics
Simplified computer programs for treating complex reaction mechanisms  DeTar, DeLos F.
The purpose of this article is to outline general procedures for treating mechanisms that do not involve steady state intermediates nor equilibria.
DeTar, DeLos F. J. Chem. Educ. 1967, 44, 191.
Mechanisms of Reactions |
Reactions
Reaction mechanisms in organic chemistry (Tchoubar, Bianco)  Babad, Harry

Babad, Harry J. Chem. Educ. 1967, 44, 182.
Mechanisms of Reactions
Polymerization kinetics: Dead-end radical polymerization  Senogles, E.; Woolf, L. A.
The kinetics of the polymerization of n-lauryl methacrylate in an experiment based on Tobolsky's Dead-End Theory.
Senogles, E.; Woolf, L. A. J. Chem. Educ. 1967, 44, 157.
Polymerization |
Kinetics |
Mechanisms of Reactions |
Free Radicals
Stereochemical correlations in the camphor series  Markgraf, J. Hodge
This paper presents a series of experiments that require the student to interpret the effect of structure on the steric course of an oxidation and a reduction in a bicyclic system.
Markgraf, J. Hodge J. Chem. Educ. 1967, 44, 36.
Stereochemistry |
Reactions |
Oxidation / Reduction |
Mechanisms of Reactions |
Molecular Properties / Structure
Letter to the editor  Garrigan, George A.
Comments on the teaching potential of an earlier published experiment involving the acid catalyzed hydrolysis of sucrose.
Garrigan, George A. J. Chem. Educ. 1966, 43, 681.
Carbohydrates |
Mechanisms of Reactions |
Catalysis
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
Physical organic chemistry in retrospect  Hammett, Louis P.
Reviews the early history of physical organic chemistry.
Hammett, Louis P. J. Chem. Educ. 1966, 43, 464.
Kinetics |
Mechanisms of Reactions
Aliphatic deaminations in organic synthesis  Baumgarten, Ronald J.
The purpose of this article is to review aliphatic deaminations in organic synthesis.
Baumgarten, Ronald J. J. Chem. Educ. 1966, 43, 398.
Synthesis |
Amines / Ammonium Compounds |
Mechanisms of Reactions |
Nucleophilic Substitution |
Oxidation / Reduction
Mechanisms of inorganic reactions (Kleinberg, Jacob; Murmann, R. Kent; Fraser, R. T. M.; Bauman, John)  Edwards, John O.

Edwards, John O. J. Chem. Educ. 1966, 43, 394.
Mechanisms of Reactions
Selective reduction of dinitro compounds  Weiss, Hilton M.
The selective reduction of aromatic dinitro compounds by ammonium sulfide is an opportunity to consider an open-ended question.
Weiss, Hilton M. J. Chem. Educ. 1966, 43, 384.
Oxidation / Reduction |
Aromatic Compounds |
Mechanisms of Reactions
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
The activating effect of fluorine in electrophilic aromatic substitution  Ault, Addison
It is demonstrated here that in certain electrophilic aromatic substitution reactions fluorine is actually an activating substituent.
Ault, Addison J. Chem. Educ. 1966, 43, 329.
Electrophilic Substitution |
Aromatic Compounds |
Mechanisms of Reactions
Organic reaction mechanisms: An introduction (Breslow, Ronald)  Kreevoy, Maurice M.

Kreevoy, Maurice M. J. Chem. Educ. 1966, 43, 221.
Reactions |
Mechanisms of Reactions
1-bromo-3-chloro-5-iodobenzene: An eight-step synthesis from benzene  Ault, Addison; Kraig, Raymond
Presents an eight-step synthesis of 1-bromo-3-chloro-5-iodobenzene from benzene.
Ault, Addison; Kraig, Raymond J. Chem. Educ. 1966, 43, 213.
Synthesis |
Aromatic Compounds |
Mechanisms of Reactions
o-Nitrobenzaldehyde and the benzoin condensation  Stockel, R. F.; Oppelt, J. C.; Arendt, Volker
Under carefully specialized conditions, it can be stated categorically that o-nitro-benzaldehyde does not undergo the benzoin condensation.
Stockel, R. F.; Oppelt, J. C.; Arendt, Volker J. Chem. Educ. 1966, 43, 144.
Mechanisms of Reactions
The coupling of diazonium salts  Frigerio, Norman A.
Examines confusion regarding the coupling of diazonium salts in organic systems.
Frigerio, Norman A. J. Chem. Educ. 1966, 43, 142.
Mechanisms of Reactions
Aromatic substitution  Duewell, H.
Reports on the use of the molecular orbit theory in a qualitative approach to the activation and orientation of substitution in aromatic systems.
Duewell, H. J. Chem. Educ. 1966, 43, 138.
Aromatic Compounds |
MO Theory |
Mechanisms of Reactions
Optical studies in organophosphorus chemistry  Cammarata, Arthur
This paper examines those organophosphorus reactions that have been studied using optically active phosphines and phosphonium salts.
Cammarata, Arthur J. Chem. Educ. 1966, 43, 64.
Stereochemistry |
Mechanisms of Reactions
Acid-catalyzed hydrolysis of sucrose: A student study of a reaction mechanism  Dawber, J. G.; Brown, D. R.; Reed, R. A.
By extending the experimental work in a kinetic study of the hydrolysis of sucrose, the beginning student in chemistry can gather some insight into the mechanism of the reaction.
Dawber, J. G.; Brown, D. R.; Reed, R. A. J. Chem. Educ. 1966, 43, 34.
Kinetics |
Mechanisms of Reactions |
Reactions |
Carbohydrates
Triplet-triplet excitation transfer in fluid solution: Applications to organic photochemistry  Turro, Nicholas J.
Discusses issues relevant to investigations of electronic energy transfer, including theory, choice of sensitizer, examples of sensitized photosyntheses, and mechanistic studies of photoreactions.
Turro, Nicholas J. J. Chem. Educ. 1966, 43, 13.
Photochemistry |
Photosynthesis |
Mechanisms of Reactions
Investigation of rates and mechanisms of reactions. Parts 1 and 2 (Friess, S. L.; Weis, E. S.; Weissberger, Arnold; eds.)  Reinheimer, J. D.

Reinheimer, J. D. J. Chem. Educ. 1965, 42, A148.
Rate Law |
Kinetics |
Mechanisms of Reactions |
Reactions
Teaching heterocyclic chemistry  Katritzky, A. R.
Describes the aims and organization of a course in heterocyclic chemistry and presents the fundamentals of heterocyclic rings.
Katritzky, A. R. J. Chem. Educ. 1965, 42, 636.
Heterocycles |
Mechanisms of Reactions
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
A three-step synthesis: 2,4-Dinitrophenylhydrazine from benzene  Ault, Addison
Presents a synthetic sequence for use in the introductory organic chemistry laboratory: the synthesis of 2,4-dinitrophenylhydrazine from benzene by way of bromobenzene and 2,4-dinitrobromobenzene.
Ault, Addison J. Chem. Educ. 1965, 42, 267.
Synthesis |
Aromatic Compounds |
Mechanisms of Reactions |
Reactions
Chemistry of methylenes  Schreck, James O.
Examines the formation of dihalomethylenes, other reactions involving the formation of methylenes, and the reactions of methylenes.
Schreck, James O. J. Chem. Educ. 1965, 42, 260.
Reactive Intermediates |
Free Radicals |
Reactions |
Mechanisms of Reactions
Hydrogenation with diimide  Miller, Charles E.
The azo compound diimide is a short-lived species recently recognized for its ability to hydrogenate multiple bonds; its selectivity makes diimide reduction a useful alternative to catalytic hydrogenation.
Miller, Charles E. J. Chem. Educ. 1965, 42, 254.
Mechanisms of Reactions
A simple model for the SN2 mechanism.  Nyquist, H. LeRoy
Presents a simple, physical model for the SN2 mechanism.
Nyquist, H. LeRoy J. Chem. Educ. 1965, 42, 103.
Molecular Modeling |
Reactions |
Nucleophilic Substitution |
Mechanisms of Reactions
The effect of structure on chemical and physical properties of polymers  Price, Charles C.
Suggests using polymers to teach the effect of changes in structure on chemical reactivity, the effect of structure on physical properties, the role of catalysts, and the basic principles of a chain reaction mechanism.
Price, Charles C. J. Chem. Educ. 1965, 42, 13.
Physical Properties |
Molecular Properties / Structure |
Polymerization |
Kinetics |
Reactions |
Catalysis |
Mechanisms of Reactions
Polymer synthesis in the undergraduate organic laboratory  Sorenson, Wayne R.
Presents a series of experiments on polymer synthesis for the undergraduate organic laboratory.
Sorenson, Wayne R. J. Chem. Educ. 1965, 42, 8.
Synthesis |
Polymerization |
Reactions |
Mechanisms of Reactions
Inorganic Reaction Mechanisms: An Introduction (Edwards, John O.)  Archer, Ronald D.

Archer, Ronald D. J. Chem. Educ. 1964, 41, A886.
Reactions |
Mechanisms of Reactions
Homolytic, cationotropic, and anionotropic reactions: A mechanistic approach to organic chemistry  Hoogenboom, Bernard E.
Examines examples of radical, cationotropic, and anionotropic reactions.
Hoogenboom, Bernard E. J. Chem. Educ. 1964, 41, 639.
Mechanisms of Reactions |
Free Radicals |
Reactions |
Electrophilic Substitution |
Nucleophilic Substitution
A simple kinetic investigation of an organic reaction mechanism  Landgrebe, John A.
This kinetic experiment allows the student to determine what factors affect the rate of a reaction and how this information can be rationalized in terms of a logical sequence of molecular events.
Landgrebe, John A. J. Chem. Educ. 1964, 41, 567.
Kinetics |
Reactions |
Mechanisms of Reactions
Activation of small molecules by coordination  Jones, Mark M.
Examines the general principles behind and numerous examples of the coordination process as a means of activating molecules for further reaction.
Jones, Mark M. J. Chem. Educ. 1964, 41, 493.
Catalysis |
Coordination Compounds |
Crystal Field / Ligand Field Theory |
Mechanisms of Reactions |
Free Radicals |
Lewis Acids / Bases |
Reactions
Nucleophlic substitution at a saturated carbon atom; Elimination reactions (Bunton, C. A.; Banthorpe, D. V.)  Bunnett, Joseph F.

Bunnett, Joseph F. J. Chem. Educ. 1964, 41, 406.
Nucleophilic Substitution |
Elimination Reactions |
Mechanisms of Reactions
The Friedel-Crafts alkylation of benzene: A first year organic laboratory experiment  Dunathan, H. C.
This experiment involves the alkylation of benzene with each of the four butyl chlorides and aluminum chloride; the monobutylbenzenes from each reaction are then analyzed by vapor phase chromatography and IR spectroscopy.
Dunathan, H. C. J. Chem. Educ. 1964, 41, 278.
Aromatic Compounds |
Reactions |
Mechanisms of Reactions |
IR Spectroscopy
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
Three-dimensional effects in biochemistry  Ingraham, Lloyd L.
Explores stereospecificity and stereoselectivity; rigidity requirements; steric effects; and stereospecificity when not required mechanistically.
Ingraham, Lloyd L. J. Chem. Educ. 1964, 41, 66.
Molecular Properties / Structure |
Catalysis |
Enzymes |
Molecular Recognition |
Mechanisms of Reactions |
Stereochemistry |
Chirality / Optical Activity |
Enantiomers
The use of inorganic redox mechanisms in analytical chemistry  Schenk, George H.
Presents the equilibrium-controlled iodine-arsenic(III) reaction as a simple system for laboratory study with respect to inorganic redox mechanisms.
Schenk, George H. J. Chem. Educ. 1964, 41, 32.
Oxidation / Reduction |
Mechanisms of Reactions |
Electrochemistry |
Equilibrium |
Catalysis |
Kinetics
Principles of chemical reaction  Sanderson, R. T.
The purpose of this paper is to examine the nature of chemical change in the hope of recognizing and setting forth the basic principles that help us to understand why they occur.
Sanderson, R. T. J. Chem. Educ. 1964, 41, 13.
Reactions |
Thermodynamics |
Mechanisms of Reactions |
Kinetics |
Synthesis |
Covalent Bonding |
Ionic Bonding |
Metallic Bonding
Mechanism of sulfur reactions (Pryor, William A.)  Campaigne, E.

Campaigne, E. J. Chem. Educ. 1963, 40, A224.
Reactions |
Mechanisms of Reactions
A guidebook to mechanism in organic chemistry (Sykes, Peter)  Detar, D. F.

Detar, D. F. J. Chem. Educ. 1963, 40, A224.
Reactions |
Mechanisms of Reactions
Cyclobutane chemistry. 2. Reactions and mechanisms  Wilson, Armin; Goldhamer, David
This discussion on synthetic approaches to cyclobutanes is intended to acquaint the reader with more recent works in this field.
Wilson, Armin; Goldhamer, David J. Chem. Educ. 1963, 40, 599.
Alkanes / Cycloalkanes |
Reactions |
Mechanisms of Reactions |
Free Radicals
A course in kinetics based on elementary processes  Noyes, Richard M.
Outlines a course in kinetics based on elementary processes.
Noyes, Richard M. J. Chem. Educ. 1963, 40, 584.
Kinetics |
Mechanisms of Reactions
KineticsEarly and often  Campbell, J. A.
Describes an approach to investigating kinetics and its application to the "blue bottle" experiment.
Campbell, J. A. J. Chem. Educ. 1963, 40, 578.
Kinetics |
Equilibrium |
Mechanisms of Reactions
The bromonium ion  Traynham, James C.
Presents stereochemical and kinetic data regarding the hypothesized existence and structure of the bromonium ion.
Traynham, James C. J. Chem. Educ. 1963, 40, 392.
Reactive Intermediates |
Mechanisms of Reactions |
Kinetics |
Molecular Properties / Structure
alpha-Pinene, a starting material for a sequence of organic experiments  Dominguez, X. A.; Leal, G.
This paper presents a unified sequence of experiments that illustrates the unit operations and unit processes of organic chemistry and includes rearrangements and stereoisomerism exemplified by the chemistry of the terpenes.
Dominguez, X. A.; Leal, G. J. Chem. Educ. 1963, 40, 347.
Synthesis |
Reactions |
Mechanisms of Reactions |
Stereochemistry |
Molecular Properties / Structure
Letters to the editor  Arotsky, J.
Points out evidence against iodine cations existing in aqueous media.
Arotsky, J. J. Chem. Educ. 1963, 40, 270.
Rate Law |
Kinetics |
Mechanisms of Reactions |
Aqueous Solution Chemistry
The chemistry of enamines  West, Joseph A.
Presents the properties, preparation, and important applications of enamines.
West, Joseph A. J. Chem. Educ. 1963, 40, 194.
Synthesis |
Reactive Intermediates |
Reactions |
Mechanisms of Reactions |
Amines / Ammonium Compounds
Multicenter and assisted mechanistic pathways in the reactions of organometallic compounds  Dessy, Raymond E.; Paulik, Frank
Examines a variety of nucleophilic and electrophilic, multicenter and assisted mechanistic pathways in the reactions of organometallic compounds.
Dessy, Raymond E.; Paulik, Frank J. Chem. Educ. 1963, 40, 185.
Organometallics |
Mechanisms of Reactions |
Nucleophilic Substitution |
Electrophilic Substitution
The reaction of tertiary amines with nitrous acid  Hein, George E.
Examines the history of investigation into the reaction of tertiary amines with nitrous acid as an example of the inherently conservative nature of science and resistance to new concepts.
Hein, George E. J. Chem. Educ. 1963, 40, 181.
Amines / Ammonium Compounds |
Reactions |
Mechanisms of Reactions
Chemistry of the diene-iron tricarbonyl complexes  Pettit, R.; Emerson, G.; Mahler, J.
Describes the results of experimentation involving the chemistry of the diene-iron tricarbonyl complexes.
Pettit, R.; Emerson, G.; Mahler, J. J. Chem. Educ. 1963, 40, 175.
Organometallics |
Metals |
Transition Elements |
Reactions |
Mechanisms of Reactions |
Molecular Properties / Structure
Inorganic reaction mechanisms by volumetric analysis: Oxidation of iodide ion  Moody, G. J.; Thomas, J. D. R.
Uses the Andrews' method of titration as a simple means of exposing the two-step oxidation of the iodide ion to iodine in concentrated hydrochloric acid with a variety of oxidizing agents.
Moody, G. J.; Thomas, J. D. R. J. Chem. Educ. 1963, 40, 151.
Reactions |
Mechanisms of Reactions |
Titration / Volumetric Analysis |
Oxidation / Reduction
Kinetics in the study of organic reaction mechanisms  DeWolfe, Robert H.
Examines the question: What are some of the things that can, and cannot, be learned about a reaction by studying its kinetics?
DeWolfe, Robert H. J. Chem. Educ. 1963, 40, 95.
Kinetics |
Reactions |
Mechanisms of Reactions
Peroxide reaction mechanisms (Edwards, John O., ed.)  Walling, Cheves

Walling, Cheves J. Chem. Educ. 1962, 39, A980.
Reactions |
Mechanisms of Reactions
Mechanisms of organic and enzymic reactions (Waley, S, G,)  Koshland, Daniel E., Jr.

Koshland, Daniel E., Jr. J. Chem. Educ. 1962, 39, A974.
Reactions |
Mechanisms of Reactions |
Enzymes
Biochemical mechanisms (Ingraham, Lloyd L.)  Whistler, Roy L.

Whistler, Roy L. J. Chem. Educ. 1962, 39, A694.
Mechanisms of Reactions
Experiments with photoconductive cadmium sulfide  Sheehan, William F.
The objectives of this experiment are to prepare photoconductive CdS containing deliberately added traces of chlorine and copper; to determine the influence of copper content upon the electrical properties of the photoconductor; and to characterize the photoconductor by measuring certain physical properties.
Sheehan, William F. J. Chem. Educ. 1962, 39, 540.
Conductivity |
Elimination Reactions
Some aspects of chemical kinetics for elementary chemistry  Benson, Sidney W.
The author suggests greater efforts to address the issue of kinetics and reaction mechanisms in introductory chemistry.
Benson, Sidney W. J. Chem. Educ. 1962, 39, 321.
Kinetic-Molecular Theory |
Gases |
Kinetics |
Mechanisms of Reactions |
Descriptive Chemistry
The acylation of aliphatic unsaturated hydrocarbons  Sharefkin, Jacob G.
Introductory organic chemistry textbooks discuss the Friedel-Crafts synthesis of aromatic ketones but usually do not treat the corresponding reaction in the aliphatic series.
Sharefkin, Jacob G. J. Chem. Educ. 1962, 39, 206.
Aromatic Compounds |
Aldehydes / Ketones |
Reactions |
Synthesis |
Mechanisms of Reactions
The mechanism of heterogeneous catalysis (de Boer, J. H., ed.)  Emmett, Paul H.

Emmett, Paul H. J. Chem. Educ. 1961, 38, A494.
Catalysis |
Mechanisms of Reactions
Kinetics and mechanism (Frost, A. A.; Pearson, R. G.)  Eyring, Henry

Eyring, Henry J. Chem. Educ. 1961, 38, 535.
Kinetic-Molecular Theory |
Mechanisms of 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
The chemistry of benzyne  Bunnett, Joseph F.
Examines the chemistry of benzyne and alkynes.
Bunnett, Joseph F. J. Chem. Educ. 1961, 38, 278.
Aromatic Compounds |
Reactions |
Mechanisms of Reactions |
Alkynes
Oxidation-reduction mechanisms  Duke, F. R.
Summarizes various types of oxidation-reduction mechanisms.
Duke, F. R. J. Chem. Educ. 1961, 38, 161.
Oxidation / Reduction |
Mechanisms of Reactions
Depsides: A synthesis by Emil Fischer  Ratnam, C. V.
Describes the synthesis of depsides by Emil Fischer.
Ratnam, C. V. J. Chem. Educ. 1961, 38, 93.
Synthesis |
Natural Products |
Phenols |
Mechanisms of Reactions
The Foundations of Chemical Kinetics (Benson, Sidney W.)  Alberty, R. A.

Alberty, R. A. J. Chem. Educ. 1960, 37, 660.
Kinetics |
Mechanisms of Reactions
Determination of alkaloid structures. II. Chemical methods  Sangster, A. W.
This paper reviews some of the main chemical degradative methods used in determining alkaloid structure.
Sangster, A. W. J. Chem. Educ. 1960, 37, 518.
Molecular Properties / Structure |
Mechanisms of Reactions
New horizons in elastic polymers  Fisher, Harry L.
Describes the history and future applications of natural and synthetic rubbers.
Fisher, Harry L. J. Chem. Educ. 1960, 37, 369.
Reactions |
Industrial Chemistry |
Mechanisms of Reactions |
Applications of Chemistry
The hydration of carbon dioxide  Kern, David M.
Examines the historical development and mechanisms of various methods of the hydration of carbon dioxide.
Kern, David M. J. Chem. Educ. 1960, 37, 14.
Reactions |
Mechanisms of Reactions
Physical observation of radiation-induced intermediates  Livingston, R.
Examines the use of radiochemistry and the paramagnetic resonance method to investigate reaction mechanisms and identify intermediates.
Livingston, R. J. Chem. Educ. 1959, 36, 349.
Reactive Intermediates |
Nuclear / Radiochemistry |
Mechanisms of Reactions
Some aspects of anti-acetyl-cholinesterase chemistry  Rubin, Robert T.
Examines several types of anti-acetylcholinesterase compounds and their practical applications.
Rubin, Robert T. J. Chem. Educ. 1959, 36, 306.
Enzymes |
Kinetics |
Mechanisms of Reactions |
Esters
Kinetics of polymer formation by free radical mechanism  Ferington, Thomas E.
Examines the mechanism and kinetics of the vinyl chain reaction.
Ferington, Thomas E. J. Chem. Educ. 1959, 36, 174.
Free Radicals |
Mechanisms of Reactions |
Rate Law
Base-catalyzed alkylations with alcohols  Becker, Ernest I.
It is the purpose of this paper to collect the based-catalyzed alkylations with alcohols and to indicate their scope and mechanism.
Becker, Ernest I. J. Chem. Educ. 1959, 36, 119.
Acids / Bases |
Catalysis |
Alcohols |
Mechanisms of Reactions |
Reactions
Fundamental processes of autoxidation  Russell, Glen A.
It is the purpose of this review to summarize the mechanism of the autoxidation of molecular oxygen with organic materials.
Russell, Glen A. J. Chem. Educ. 1959, 36, 111.
Oxidation / Reduction |
Mechanisms of Reactions |
Reactions |
Free Radicals |
Organometallics |
Photochemistry
Transformation of organic compounds by microorganisms  Perlman, D.
It is the purpose of this review to classify some of the chemical transformations in which microbial processes have been of some use in modifying organic compounds, and to indicate some of the practical limitations that have been encountered.
Perlman, D. J. Chem. Educ. 1959, 36, 60.
Reactions |
Mechanisms of Reactions
The principle of minimum bending of orbitals  Stewart, George H.; Eyring, Henry
The authors present a theory of valency that accounts for a variety of organic and inorganic structures in a clear and easily understood manner.
Stewart, George H.; Eyring, Henry J. Chem. Educ. 1958, 35, 550.
Atomic Properties / Structure |
Molecular Properties / Structure |
Elimination Reactions
Chemistry in the manufacture of modern gasoline  Kimberlin, C. N., Jr.
This paper presents a brief review of the chemistry involved in the manufacture of gasoline, particularly catalytic cracking reactions.
Kimberlin, C. N., Jr. J. Chem. Educ. 1957, 34, 569.
Industrial Chemistry |
Applications of Chemistry |
Catalysis |
Mechanisms of Reactions
Comparative organic chemistry: Carbon and silicon  Wilk, I. J.
Contrasts silicone chemistry with that of regular organic compounds.
Wilk, I. J. J. Chem. Educ. 1957, 34, 463.
Covalent Bonding |
Ionic Bonding |
Mechanisms of Reactions |
Stereochemistry
Lecture demonstration of a kinetic isotope effect  Zollinger, Hch
The discovery of kinetic isotope effects in azo coupling reactions provides a desirable and convenient lecture demonstration.
Zollinger, Hch J. Chem. Educ. 1957, 34, 249.
Kinetics |
Isotopes |
Mechanisms of Reactions
Organic isocyanatesVersatile intermediates  Arnold, R. G.; Nelson, J. A.; Verbanc, J. J.
Considers reactions and the synthesis of organic isocyanates, polyisocyanates, fibers, foams, elastomers, adhesives, isocyanate generators, and plastics.
Arnold, R. G.; Nelson, J. A.; Verbanc, J. J. J. Chem. Educ. 1957, 34, 158.
Polymerization |
Synthesis |
Mechanisms of Reactions
New techniques in photochemistry  Davidson, Norman
This paper focusses on the use of flash photolysis and frozen free radicals in studying the mechanism of photochemical reactions and identifying reactive intermediates.
Davidson, Norman J. Chem. Educ. 1957, 34, 126.
Photochemistry |
Mechanisms of Reactions |
Reactive Intermediates
Relations between molecular structure and photodecomposition modes  Pitts, James N., Jr.
It is now possible to predict qualitatively, and in some cases semiquantitatively, the extent of free radical processes versus direct molecular rearrangements in vapor-phase studies of the direct photolysis of aldehydes and ketones.
Pitts, James N., Jr. J. Chem. Educ. 1957, 34, 112.
Photochemistry |
Molecular Properties / Structure |
Aldehydes / Ketones |
Mechanisms of Reactions
The unique properties of 2,4-dinitrobenzenesulfenyl chloride  Kharasch, Norman
The unusual characteristics of 2,4-dinitrobenzenesulfenyl chloride undoubtedly destine this substance to be of special value to researchers in a variety of organic and biochemical research projects.
Kharasch, Norman J. Chem. Educ. 1956, 33, 585.
Molecular Properties / Structure |
Reactions |
Mechanisms of Reactions
Electrochemical methods available for reaction mechanism studies  Remick, A. Edward
The purpose of this paper is to review for chemists who are not specialists in electrochemistry the electrochemical methods presently available for studying reaction mechanisms, including potentiometric methods, voltammetry, and alternating-current techniques.
Remick, A. Edward J. Chem. Educ. 1956, 33, 564.
Electrochemistry |
Mechanisms of Reactions |
Rate Law
Uses of isotopes in organic chemistry  Semenow, Dorothy A.; Roberts, John D.
The purpose of this review is to illustrate a variety of tracer applications by specific examples in the areas of structural determinations, reaction mechanisms, reactivity studies, and kinetic isotope effects.
Semenow, Dorothy A.; Roberts, John D. J. Chem. Educ. 1956, 33, 2.
Isotopes |
Molecular Properties / Structure |
Mechanisms of Reactions |
Reactions |
Kinetics |
Chromatography |
Nuclear / Radiochemistry
The preparation of 2,3,6-tri-t-butylphenol  Somers, Bruce G.; Cook, Clinton D.
This preparation has been conducted by second-semester, elementary organic chemistry students with good results.
Somers, Bruce G.; Cook, Clinton D. J. Chem. Educ. 1955, 32, 312.
Synthesis |
Phenols |
Mechanisms of Reactions
The orientation and mechanism of electrophilic aromatic substitution  Ferguson, Lloyd N.
Electrophilic aromatic substitution apparently takes place by the formation of an intermediate pentadienate cation, +ArG, where Ar is an aromatic molecule and G is a portion of the reagent.
Ferguson, Lloyd N. J. Chem. Educ. 1955, 32, 42.
Electrophilic Substitution |
Reactions |
Mechanisms of Reactions |
Aromatic Compounds
The mechanism of diazotization  Gillis, Richard G.
Recent investigation has shown conclusively that the diazotization reaction is between free base and a number of Lewis acids, of which one or more be effective at any one time.
Gillis, Richard G. J. Chem. Educ. 1954, 31, 344.
Kinetics |
Mechanisms of Reactions |
Acids / Bases |
Lewis Acids / Bases
Predicting reactions of a resonance hybrid from minor canonical structures  Gero, Alexander
Little effort seems to have been made to set up any general rules on the relative contributions of the several structural formulas (canonical structures) used to represent a resonance hybrid to the reactions of the hybrid.
Gero, Alexander J. Chem. Educ. 1954, 31, 136.
Resonance Theory |
Mechanisms of Reactions
A dynamic illustration of organic reaction mechanisms  Daub, Guido H.; Evans, D. Donald; Sorrell, Noel C.
The mechanisms of organic reactions are animated using simple flip cards.
Daub, Guido H.; Evans, D. Donald; Sorrell, Noel C. J. Chem. Educ. 1954, 31, 134.
Mechanisms of Reactions |
Molecular Modeling
An aid to teaching electronic theory  Humffray, A. A.
This paper outlines the method used by the author in presenting the ideas of tautomerism and electronic theory.
Humffray, A. A. J. Chem. Educ. 1953, 30, 635.
Molecular Properties / Structure |
Mechanisms of Reactions
The preparation of ninhydrin as a laboratory experiment  Dominguez, Xorge Alejandro
The preparation of ninhydrin, a useful but expensive colorimetric reagent, can be accomplished easily in three laboratory sessions.
Dominguez, Xorge Alejandro J. Chem. Educ. 1953, 30, 624.
Synthesis |
Mechanisms of Reactions
Some chemistry of covalent compounds with a single central atom  Clapp, Leallyn B.
Examines the preparation and reactions of the covalent halides and oxyhalides.
Clapp, Leallyn B. J. Chem. Educ. 1953, 30, 584.
Reactions |
Mechanisms of Reactions
The Fischer indole synthesis  Roussel, Philip A.
Examines the discovery of indole and Fischer's work to develop a means of its synthesis.
Roussel, Philip A. J. Chem. Educ. 1953, 30, 122.
Synthesis |
Mechanisms of Reactions |
Molecular Properties / Structure |
Aromatic Compounds
The mechanisms of the reactions of aliphatic hydrocarbons  Schmerling, Louis
Examines the formation of carbonium ions and free radicals, the polymerization of olefins, hydrogen-halogen exchange, the condensation of haloalkanes with alkenes, the alkylation of paraffins, the condensation of paraffins with chloroolefins, the cracking of paraffins and olefins, and the isomerization of paraffins.
Schmerling, Louis J. Chem. Educ. 1951, 28, 562.
Mechanisms of Reactions |
Alkanes / Cycloalkanes |
Free Radicals |
Polymerization