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Journal Articles: 388 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
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
Frank Westheimer's Early Demonstration of Enzymatic Specificity  Addison Ault
Reviews one of the most significant accomplishments of one of the most respected chemists of the 20th centurya series of stereospecific enzymatic oxidation and reduction experiments that led chemists to recognize enantiotopic and diastereotopic relationships of atoms, or groups of atoms, within molecules.
Ault, Addison. J. Chem. Educ. 2008, 85, 1246.
Asymmetric Synthesis |
Bioorganic Chemistry |
Catalysis |
Chirality / Optical Activity |
Enantiomers |
Enzymes |
Isotopes |
Nucleophilic Substitution |
Oxidation / Reduction |
Stereochemistry
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
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
Polymer-Supported Reagents and 1H–19F NMR Couplings: The Synthesis of 2-Fluoroacetophenone  Nicola Pohl and Kimberly Schwarz
Describes an experiment in which 2-bromoacetophenone is converted to 2-fluoroacetophenone using a solid-phase nucleophilic fluorine source. The experiment introduces students to the utility of solid-phase reagents in organic synthesis, to NMR-active nuclei other than 1H without the requirement of a special NMR probe, and to the unique uses of fluorine in molecular design.
Pohl, Nicola; Schwarz, Kimberly. J. Chem. Educ. 2008, 85, 834.
Aldehydes / Ketones |
NMR Spectroscopy |
Nucleophilic Substitution |
Synthesis
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
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 Discovery-Based Experiment Involving Rearrangement in the Conversion of Alcohols to Alkyl Halides  Richard A. Kjonaas and Ryand J. F. Tucker
This article reports a discovery-based experiment in which students convert three alcohols to alkyl halides under acidic conditions and record the 13C NMR spectrum in each case. By comparing the number of resonances observed with the number of resonances predicted for each possible product, students draw several conclusions about the resulting rearrangement.
Kjonaas, Richard A.; Tucker, Ryand J. F. J. Chem. Educ. 2008, 85, 100.
Alcohols |
Carbocations |
Gas Chromatography |
NMR Spectroscopy |
Nucleophilic Substitution
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
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
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
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
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
pHantastic Fluorescence  Mark Muyskens
Students easily extract a fluorescent substance from shavings of a wood called narra. The fluorescence is dramatically pH dependent and can be turned on and off repeatedly using commonly available acid and base solutions.
Muyskens, Mark. J. Chem. Educ. 2006, 83, 768A.
Fluorescence Spectroscopy |
Natural Products |
Nucleophilic Substitution |
pH |
Solutions / Solvents |
UV-Vis Spectroscopy
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
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 Finkelstein Reaction: Quantitative Reaction Kinetics of an SN2 Reaction Using Nonaqueous Conductivity  R. David Pace and Yagya Regmi
Presents a quantitative kinetics laboratory exercise featuring the Finkelstein reaction (SN2) for use in the first-semester organic chemistry course that utilizes nonaqueous conductivity as the method by which relevant structuretemperaturesolvent effects are examined.
Pace, R. David; Regmi, Yagya. J. Chem. Educ. 2006, 83, 1344.
Calibration |
Kinetics |
Nucleophilic Substitution |
Rate Law |
Reactions |
Solutions / Solvents
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
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
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
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
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
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
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
"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
"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
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
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
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
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
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
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
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
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
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
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
Dendrimers: Branching Out of Polymer Chemistry  Eric E. Simanek and Sergio O. Gonzalez
Addresses synthetic concepts surrounding dendrimers including the use of protecting groups, functional group interconversions, and convergent and divergent synthetic strategies.
Simanek, Eric E.; Gonzalez, Sergio O. J. Chem. Educ. 2002, 79, 1222.
Materials Science |
Synthesis |
Molecular Properties / Structure |
Addition Reactions |
Aromatic Compounds |
Alkylation |
Nucleophilic Substitution
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
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
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
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
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
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
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
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
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
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
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
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
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 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
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
"New" Compounds from Old Plastics: Recycling PET Plastics via Depolymerization. An Activity for the Undergraduate Organic Lab  Don Kaufman, Geoff Wright, Ryan Kroemer, and Josh Engel
This paper describes work done to develop a meaningful undergraduate organic lab activity that illustrates chemistry of the real world while utilizing reactions typically included in the organic lecture and lab. We show how a common plastic can be converted into several compounds using ester hydrolysis and SN2 reactions.
Kaufman, Don; Wright, Geoff; Kroemer, Ryan; Engel, Josh. J. Chem. Educ. 1999, 76, 1525.
Consumer Chemistry |
Synthesis |
Esters |
Nucleophilic Substitution
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
The Neglected Element in Sophomore Organic Chemistry  Kelly L. Bieda and Suzzane T. Purrington
There are many aspects of organic chemistry that would benefit from the inclusion of organofluorine chemistry. The properties of fluorine help in the clarification of many topics such as bond strength, leaving groups, substitution reactions, radical reactions, polymers, pharmaceuticals, and enzymes.
Bieda, Kelly L.; Purrington, Suzanne T. J. Chem. Educ. 1996, 73, 754.
Drugs / Pharmaceuticals |
Enzymes |
Polymerization |
Nucleophilic Substitution
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
Iron(III) Chloride as a Lewis Acid in the Friedel-Crafts Acylation Reaction  William H. Miles, Charles F. Nutaitis, and Christian A. Anderton
The Friedel-Crafts reaction receives extensive coverage in sophomore organic chemistry. The most widely used Lewis acid for the Friedel-Crafts reaction is aluminum chloride. The safety and handling problems associated with using aluminum chloride prompted us to examine iron(III) chloride as an alternative Lewis acid for the Friedel-Crafts acylation reaction.
Miles, William H.; Nutaitis, Charles F.; Anderton, Christian A. J. Chem. Educ. 1996, 73, 272.
Aromatic Compounds |
Nucleophilic Substitution
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
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
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
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
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
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
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
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
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
The aromatic substitution game  Zanger, Murray; Gennaro, Alfonso R.; McKee, James R.
This paper describes a game used to bring attention to the need for students to reconsider substitution theories learned in earlier chapters.
Zanger, Murray; Gennaro, Alfonso R.; McKee, James R. J. Chem. Educ. 1993, 70, 985.
Nucleophilic Substitution |
Synthesis
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
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
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
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
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
Cobaloximes as vehicles for college teaching  Brown, T. M.; Dronsfield, A. T.; Cooksey, C. J.; Crich, D.
Cobaloximes are probably the most accessible and "least nasty" of all organometallic compounds, are highly colored, exhibit unusual oxidation states, demonstrate a vivid nucleophilic attack, and lend themselves to chromatographic investigation without the need for UV light.
Brown, T. M.; Dronsfield, A. T.; Cooksey, C. J.; Crich, D. J. Chem. Educ. 1990, 67, 973.
Coordination Compounds |
Organometallics |
Nucleophilic Substitution
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
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
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
Nucleophilic aromatic substitution: A microscale organic experiment  Avila, Walter B.; Crow, Jeffrey L.; Utermoehlen, Clifford M.
This experiment demonstrates one feasible route in preparing ortho-substituted benzoic acids and is also an example of nucleophilic aromatic substitution chemistry.
Avila, Walter B.; Crow, Jeffrey L.; Utermoehlen, Clifford M. J. Chem. Educ. 1990, 67, 350.
Nucleophilic Substitution |
Aromatic Compounds |
Microscale Lab |
Carboxylic Acids
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
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
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
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
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
A conversion of methyl ketones into acetylenes: A project for a problem oriented or microscale organic chemistry course  Silveira, Augustine, Jr.; Orlando, Steven C.
The authors present their adaptation of an open-ended project on the conversion of methyl ketones into acetylenes for the microscale lab and describe its pedagogic utility.
Silveira, Augustine, Jr.; Orlando, Steven C. J. Chem. Educ. 1988, 65, 630.
Microscale Lab |
Aldehydes / Ketones |
Synthesis |
Nucleophilic Substitution |
Gas Chromatography
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
Organic lecture demonstrations  Silversmith, Ernest F.
Organic chemistry may not be known for its spectacular, attention getting chemical reactions. Nevertheless, this author describes a few organic chemistry reactions that put points across and generate interest. This article provides a convenient sources of demonstrations and urges others to add to the collection. Demonstrations concerning: carbohydrates, spectroscopy, proteins, amines, carbohydrates, carboxylic acids, and much more.
Silversmith, Ernest F. J. Chem. Educ. 1988, 65, 70.
Molecular Properties / Structure |
Nucleophilic Substitution |
Acids / Bases |
Physical Properties |
Alkenes |
Stereochemistry |
Enantiomers |
Chirality / Optical Activity |
Aldehydes / Ketones |
Alcohols
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
Characterizing a tetrahedral intermediate in an acyl transfer reaction: An undergraduate 1H NMR demonstration  Rzepa, Henry S.; Lobo, Ana M.; Marques, M. Matilde; Prabhakar, Sundaresan
A simple experiment involving the detection by 1H NMR spectroscopy of a stable intermediate formed by nucleophilic attack and its characterization as a chiral species.
Rzepa, Henry S.; Lobo, Ana M.; Marques, M. Matilde; Prabhakar, Sundaresan J. Chem. Educ. 1987, 64, 725.
NMR Spectroscopy |
Nucleophilic Substitution |
Chirality / Optical Activity
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
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
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
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
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
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
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
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
Aromatic substitution reactions: when you've said ortho, meta, and para you haven't said it all  Traynham, James G.
The author presents a range of examples for nucleophilic, electrophilic, and free-radical reactions where the ipso is an important, predominant, or even exclusive site of reaction.
Traynham, James G. J. Chem. Educ. 1983, 60, 937.
Nucleophilic Substitution |
Electrophilic Substitution |
Free Radicals |
Diastereomers |
Stereochemistry |
Reactions
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
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
Organic lecture demonstrations of common-ion effect, ionizing power of solvents, and first-order reaction kinetics  Danen, Wayne C.; Blecha, Sr. M. Therese
The hydrolysis of tert-butyl chloride is the basis of three demonstrations which each illustrate an important principle of organic chemistry: the common-ion or mass law effect, the effect of changing the ionizing power of a solvent on a solvolysis reaction, and the collecting and plotting of data to illustrate a first-order reaction.
Danen, Wayne C.; Blecha, Sr. M. Therese J. Chem. Educ. 1982, 59, 659.
Aqueous Solution Chemistry |
Solutions / Solvents |
Nucleophilic Substitution |
Kinetics |
Rate Law
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
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
Nucleophilic substitution reactions: Modifications and an extension  Newton, T. A.; Warren, H. W.
Modifications to a procedure comparing the reaction of n-butyl and t-butyl alcohol with equimolar amounts of HCl and HBr.
Newton, T. A.; Warren, H. W. J. Chem. Educ. 1980, 57, 747.
Nucleophilic Substitution |
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
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
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
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
Phase transfer catalysis. Part II: Synthetic applications  Gokel, George W.; Weber, William P.
In this month's continuation of an article, the authors have catalogued a number of illustrative examples so that the range of applicability of phase transfer catalysis will be.
Gokel, George W.; Weber, William P. J. Chem. Educ. 1978, 55, 429.
Phases / Phase Transitions / Diagrams |
Catalysis |
Aromatic Compounds |
Organometallics |
Nucleophilic Substitution |
Synthesis |
Esters |
Oxidation / Reduction |
Alkylation
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
Nucleophilic substitution by phase transfer catalysis  Reeves, W. Preston; White, Mitchell R.; Bier, Deana
The preparation of alkyl thiocyanates to be an excellent and versatile experiment for first year organic students.
Reeves, W. Preston; White, Mitchell R.; Bier, Deana J. Chem. Educ. 1978, 55, 56.
Nucleophilic Substitution |
Catalysis
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
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
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
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
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
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
A simple lecture demonstration of aromatic nucleophilic substitution  Smith, N. H. P.
Colors produced when various aromatic substrates are attacked by various nucleophiles (DMF, DMSO, EtOH).
Smith, N. H. P. J. Chem. Educ. 1975, 52, 238.
Aromatic Compounds |
Nucleophilic Substitution
The remarkable reactivity of aryl halides with nucleophiles   Bunnett, Joseph F.
Nucleophilic attack on carbon; nucleophilic attack on hydrogen; aryl formation by halide ion loss from o-halophenyl anions; nucleophilic attack on halogen; acceptance of an electron, and its consequences.
Bunnett, Joseph F. J. Chem. Educ. 1974, 51, 312.
Nucleophilic Substitution |
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
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
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
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
Experimental illustration of chemical principles in organic chemistry lectures  Haberfield, Paul
Lists a series of demonstrations used in the second semester of a one year organic chemistry course.
Haberfield, Paul J. Chem. Educ. 1972, 49, 702.
Electrophilic Substitution |
Aromatic Compounds |
Amines / Ammonium Compounds |
Nucleophilic Substitution
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
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
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
Free-radical bromination of p-toluic acid. An experiment in organic chemistry  Tuleen, D. L.; Hess, B. A., Jr.
This paper describes the synthesis of a-bromo-p-toluic acid (II) and the subsequent displacement of bromide ion by three nucleophiles.
Tuleen, D. L.; Hess, B. A., Jr. J. Chem. Educ. 1971, 48, 476.
Free Radicals |
Nucleophilic Substitution
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
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
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
Hydrolysis of benzenediazonium ion  Sheats, John E.; Harbison, Kenneth G.
Presents a more convenient approach to studying the kinetics of the hydrolysis of benzenediazonium ion.
Sheats, John E.; Harbison, Kenneth G. J. Chem. Educ. 1970, 47, 779.
Aromatic Compounds |
Nucleophilic Substitution |
Kinetics
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
Nucleophilic reactivities of the halide anions  Puar, Mohindar S.
Ranks the nucleophilic reactivities of free halide ions in various solvents.
Puar, Mohindar S. J. Chem. Educ. 1970, 47, 473.
Nucleophilic Substitution
A model to demonstrate the Walden inversion  Hamon, D. P. G.
Presents the design of a model capable of illustrating the Walden inversion.
Hamon, D. P. G. J. Chem. Educ. 1970, 47, 398.
Molecular Modeling |
Molecular Properties / Structure |
Nucleophilic Substitution |
Reactions
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
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
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
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
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
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
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
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
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
Substitution reactions in octahedral complexes  Banerjea, D.
Commentary on the cited article by one of the authors that article referenced.
Banerjea, D. J. Chem. Educ. 1967, 44, 485.
Coordination Compounds |
Nucleophilic Substitution
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
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
Teaching aromatic substitution: A molecular orbital approach  Meislich, Herbert
This paper presents a way of teaching aromatic substitution using the concepts of alternate polarity and electron delocalization through extended pi-bonding.
Meislich, Herbert J. Chem. Educ. 1967, 44, 153.
Aromatic Compounds |
MO Theory |
Nucleophilic Substitution |
Covalent Bonding |
Molecular Properties / Structure
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
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
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
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
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
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
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
A second order kinetics experiment  Teerlink, Wilford J.; Asay, Jeanette; Sugihara, James M.
Investigates the nucleophilic displacement reaction of ethyl p-toluenesulfonate by iodide in acetone.
Teerlink, Wilford J.; Asay, Jeanette; Sugihara, James M. J. Chem. Educ. 1964, 41, 161.
Kinetics |
Nucleophilic Substitution
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
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
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
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
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
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
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
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 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
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 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
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
Nucleophilic substitution in aromatic systems  Gillis, Richard G.
Classifies and examines various categories of nucleophilic substitution in aromatic systems.
Gillis, Richard G. J. Chem. Educ. 1955, 32, 296.
Nucleophilic Substitution |
Aromatic Compounds
Introducing stereoisomerism  Schreiber, Kurt C.
Criticizes the traditional presentation of stereochemistry in isolation and offers a more integrated approach.
Schreiber, Kurt C. J. Chem. Educ. 1955, 32, 83.
Stereochemistry |
Molecular Properties / Structure |
Nucleophilic Substitution
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
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 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