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Journal Articles: 720 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
Cocrystal Controlled Solid-State Synthesis  Miranda L. Cheney, Michael J. Zaworotko, Steve Beaton, and Robert D. Singer
Describes experiments that can easily be adapted to a typical undergraduate organic chemistry course and are inexpensive, relatively safe, require little or no solvent, have high atom economy, make use of non-toxic or low toxicity compounds, and generate negligible quantities of waste.
Cheney, Miranda L.; Zaworotko, Michael J.; Beaton, Steve; Singer, Robert D. J. Chem. Educ. 2008, 85, 1649.
Amines / Ammonium Compounds |
Calorimetry / Thermochemistry |
Green Chemistry |
IR Spectroscopy |
Microscale Lab |
Solid State Chemistry |
Synthesis
Experimental Design and Optimization: Application to a Grignard Reaction  Naoual Bouzidi and Christel Gozzi
This 5-week project, which systematically investigates optimizing the synthesis of benzyl-1-cyclopentan-1-ol, constitutes an initiation into research methodology and experimental design to prepare the student-engineer for an industry internship. Other pedagogical goals include experience in synthetic techniques, obtaining reproducible yields, and using quantitative analysis methods.
Bouzidi, Naoual; Gozzi, Christel. J. Chem. Educ. 2008, 85, 1544.
Addition Reactions |
Alcohols |
Aldehydes / Ketones |
Chemometrics |
Gas Chromatography |
Organometallics |
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
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
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
Regioselectivity in Organic Synthesis: Preparation of the Bromohydrin of α-Methylstyrene  Brad Andersh, Kathryn N. Kilby, Meghan E. Turnis, and Drew L. Murphy
In the described experiment, the regiochemical outcome of the addition of "HOBr" to a-methylstyrene is investigated. Although both "classic" qualitative analysis and instrumental techniques are described, the emphasis of this experiment is on the utilization 13C and DEPT-135 NMR spectroscopy to determine the regiochemical outcome of the addition.
Andersh, Brad; Kilby, Kathryn N.; Turnis, Meghan E.; Murphy, Drew L. J. Chem. Educ. 2008, 85, 102.
Addition Reactions |
Alcohols |
Alkenes |
Constitutional Isomers |
IR Spectroscopy |
Microscale Lab |
NMR Spectroscopy |
Synthesis
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
Synthesis of Quaternary Ammonium Salts of Tricyclic Cationic Drugs: A One-Pot Synthesis for the Bioorganic Chemistry Laboratory  Linda S. Brunauer, Abid C. Mogannam, Won B. Hwee, and James Y. Chen
Describes a one-pot conversion of tricyclic cationic drugs to their quaternary ammonium forms for a widely used bioactive drug, chlorpromazine, a phenothiazine-based antipsychotic. The conversion of parent drug to the methylated form was evaluated by qualitatively measuring its ability to induce alterations in the shape of mammalian erythrocytes.
Brunauer, Linda S.; Mogannam, Abid C.; Hwee, Won B.; Chen, James Y. J. Chem. Educ. 2007, 84, 1992.
Amines / Ammonium Compounds |
Bioorganic Chemistry |
Drugs / Pharmaceuticals |
IR Spectroscopy |
Microscale Lab |
NMR Spectroscopy |
Synthesis |
Thin Layer Chromatography
Zeroing In on Electrophilic Aromatic Substitution  David C. Forbes, Mohini Agarwal, Jordan L. Ciza, and Heather A. Landry
Presents a unique and novel illustration of reactivity trends in the formation of trisubstituted benzene derivatives from disubstituted systems using electrophilic aromatic substitution reactions.
Forbes, David C.; Agarwal, Mohini; Ciza, Jordan L.; Landry, Heather A. J. Chem. Educ. 2007, 84, 1878.
Aromatic Compounds |
Constitutional Isomers |
Electrophilic Substitution |
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
Hydration of Acetylene: A 125th Anniversary  Dmitry A. Ponomarev and Sergey M. Shevchenko
The discovery the hydration of alkynes catalyzed by mercury ions by Mikhail Kucherov made possible industrial production of acetaldehyde from acetylene and had a profound effect on the development of industrial chemistry in the 1920th centuries.
Ponomarev, Dmitry A.; Shevchenko, Sergey M. J. Chem. Educ. 2007, 84, 1725.
Addition Reactions |
Aldehydes / Ketones |
Alkynes |
Catalysis |
Industrial Chemistry |
Reactions
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
A Guided-Inquiry Approach to the Sodium Borohydride Reduction and Grignard Reaction of Carbonyl Compounds  Robert E. Rosenberg
Students teams identify unknowns and their reaction products and use their data to deduce that esters are less electrophilic than the other carbonyl compounds present, that Grignard reagents are more nucleophilic than sodium borohydride, and that carboxylic acid derivatives do not undergo the nucleophilic addition reactions that are characteristic of aldehydes and ketones.
Rosenberg, Robert E. J. Chem. Educ. 2007, 84, 1474.
Addition Reactions |
Aldehydes / Ketones |
Esters |
Grignard Reagents |
IR Spectroscopy |
Oxidation / Reduction |
Reactions |
Student-Centered Learning
Control of Chemical Equilibrium by Solvent: A Basis for Teaching Physical Chemistry of Solutions  Oleg V. Prezhdo, Colleen F. Craig, Yuriy Fialkov, and Victor V. Prezhdo
The mechanisms by which solvent can be used to control chemical equilibria are analyzed from a thermodynamic perspective and illustrated with several examples. The solvent effect is described in terms of universal- and specific-solvation components, and the practical and pedagogical means of separating these components are discussed.
Prezhdo, Oleg V.; Craig, Colleen F.; Fialkov, Yuriy; Prezhdo, Victor V. J. Chem. Educ. 2007, 84, 1348.
Equilibrium |
Reactions |
Solutions / Solvents |
Thermodynamics
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
Synthesis and NMR Spectral Analysis of Amine Heterocycles: The Effect of Asymmetry on the 1H and 13C NMR Spectra of N,O-Acetals  Shahrokh Saba, James A. Ciaccio, Jennifer Espinal, and Courtney E. Aman
Describe an undergraduate organic laboratory experiment in which students prepare two N,O-acetals that differ only in a single ring substituent that introduces asymmetry, giving each compound a distinct 1H and 13C NMR spectral pattern that must be explained by students.
Saba, Shahrokh; Ciaccio, James A.; Espinal, Jennifer; Aman, Courtney E. J. Chem. Educ. 2007, 84, 1011.
Amines / Ammonium Compounds |
Chirality / Optical Activity |
Green Chemistry |
Heterocycles |
NMR Spectroscopy |
Stereochemistry |
Synthesis
Triethylamine  Jay A. Young
The hazards of triethylamine are discussed.
Young, Jay A. J. Chem. Educ. 2007, 84, 926.
Amines / Ammonium Compounds |
Laboratory Management
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 Green Alternative to Aluminum Chloride Alkylation of Xylene  Grigoriy A. Sereda and Vikul B. Rajpara
Presents a simple laboratory experiment that introduces organic chemistry students to the basic principles of green technologies, such as lack of toxic or bulk byproducts, nontoxicity, and reusability of the catalyst.
Sereda, Grigoriy A.; Rajpara, Vikul B. J. Chem. Educ. 2007, 84, 692.
Alkylation |
Green Chemistry |
Catalysis |
NMR Spectroscopy |
Reactions |
Synthesis
Effect of a Perturbation on the Chemical Equilibrium: Comparison with Le Châtelier's Principle  Emilio Martínez Torres
This article develops a general thermodynamic treatment to predict the direction of shift in a chemical equilibrium when it is subjected to a stress. This treatment gives an inequality that relates the change in the perturbed variable and the change that the equilibrium shift produces in the conjugated variable.
Torres, Emilio Martínez. J. Chem. Educ. 2007, 84, 516.
Equilibrium |
Reactions |
Thermodynamics
The Aldol Addition and Condensation: The Effect of Conditions on Reaction Pathway  R. David Crouch, Amie Richardson, Jessica L. Howard, Rebecca L. Harker, and Kathryn H. Barker
Describes an experiment offering the opportunity for students to observe the critical role that reaction temperature and base strength have in determining the product of the base-mediated addition of a ketone to an aldehyde.
Crouch, R. David; Richardson, Amie; Howard, Jessica L.; Harker, Rebecca L.; Barker, Kathryn H. J. Chem. Educ. 2007, 84, 475.
Addition Reactions |
Aldehydes / Ketones |
Green Chemistry |
NMR Spectroscopy |
Reactions |
Synthesis
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
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
Microwave-Mediated Synthesis of Lophine: Developing a Mechanism To Explain a Product   R. David Crouch, Jessica L. Howard, Jennifer L. Zile, and Kathryn H. Barker
Describes the microwave-mediated preparation of lophine (2,4,5-triphenylimidazole). The experiment also provides an opportunity for students to employ the principles of carbonyl chemistry in devising a mechanism to explain the formation of the product.
Crouch, R. David; Howard, Jessica L.; Zile, Jennifer L.; Barker, Kathryn H. J. Chem. Educ. 2006, 83, 1658.
Aldehydes / Ketones |
Amines / Ammonium Compounds |
Aromatic Compounds |
Microscale Lab |
Molecular Modeling |
Synthesis |
NMR Spectroscopy
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
Purification and Modification of Fullerene C60 in the Undergraduate Laboratory  Tracey Spencer, Barney Yoo, and Kent Kirshenbaum
Describes an experiment for the extraction and column purification of buckminsterfullerene from fullerene-rich soot followed by a one-pot 1,3-dipolar cycloaddition of an azomethine ylide. Characterization of the starting material and product can be performed by UVVis, MS, 1H NMR, and 13C NMR.
Spencer, Tracey; Yoo, Barney; Kirshenbaum, Kent. J. Chem. Educ. 2006, 83, 1218.
Aromatic Compounds |
Chromatography |
NMR Spectroscopy |
UV-Vis Spectroscopy |
Synthesis |
Nanotechnology |
Reactions
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
Molecular Handshake: Recognition through Weak Noncovalent Interactions  Parvathi S. Murthy
This article traces the development of our thinking about molecular recognition through noncovalent interactions, highlights their salient features, and suggests ways for comprehensive education on this important concept.
Murthy, Parvathi S. J. Chem. Educ. 2006, 83, 1010.
Applications of Chemistry |
Biosignaling |
Membranes |
Molecular Recognition |
Noncovalent Interactions |
Chromatography |
Molecular Properties / Structure |
Polymerization |
Reactions
Reductive Amination: A Remarkable Experiment for the Organic Laboratory  Kim M. Touchette
The synthesis of N-(2-hydroxy-3-methoxybenzyl)-N-p-tolylacetamide is a fast, simple three-step sequence that serves as a useful example of the reductive amination reaction for the organic chemistry laboratory.
Touchette, Kim M. J. Chem. Educ. 2006, 83, 929.
Aldehydes / Ketones |
Amines / Ammonium Compounds |
Green Chemistry |
Instrumental Methods |
IR Spectroscopy |
NMR Spectroscopy |
Oxidation / Reduction |
Solids
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
The "Reaction Rolodex": A Web-Based System for Learning Reactions in Organic Chemistry  Eric Mahan
This Web-based system of note cards has been developed to aid students in learning the vast number of reactions encountered in organic chemistry.
Mahan, Eric. J. Chem. Educ. 2006, 83, 672.
Learning Theories |
Reactions
Incorporation of Microwave Synthesis into the Undergraduate Organic Laboratory  Alan R. Katritzky, Chunming Cai, Meghan D. Collins, Eric F. V. Scriven, Sandeep K. Singh, and E. Keller Barnhardt
Describes a simple way to effectively implement microwave synthesis into the undergraduate organic laboratory curriculum.
Katritzky, Alan R.; Cai, Chunming; Collins, Meghan D.; Scriven, Eric F. V.;Singh, Sandeep K.; Barnhardt, E. Keller. J. Chem. Educ. 2006, 83, 634.
Aromatic Compounds |
Laboratory Equipment / Apparatus |
Reactions |
Synthesis
Microwave-Assisted Heterocyclic Chemistry for Undergraduate Organic Laboratory  Robert Musiol, Bozena Tyman-Szram, and Jaroslaw Polanski
Microwave-assisted techniques are used to design new environmentally benign syntheses of heterocycles for the undergraduate organic laboratory.
Musiol, Robert; Tyman-Szram, Bozena; Polanski, Jaroslaw. J. Chem. Educ. 2006, 83, 632.
Green Chemistry |
Heterocycles |
Reactions |
Synthesis
A Greener Approach to Aspirin Synthesis Using Microwave Irradiation  Ingrid Montes, David Sanabria, Marilyn García,, Joaudimir Castro, and Johanna Fajardo
Presents an inquiry-based laboratory experience based on the use of a microwave oven as a means for a comparative study of the effect of different catalysts in the synthesis of aspirin.
Montes, Ingrid; Sanabria, David; García,, Marilyn; Castro, Joaudimir; Fajardo, Johanna. J. Chem. Educ. 2006, 83, 628.
Drugs / Pharmaceuticals |
Esters |
Green Chemistry |
NMR Spectroscopy |
Reactions |
Synthesis |
Thin Layer Chromatography
Electrophilic Additions to Alkenes  Thomas M. Bertolini and Phuc D. Tran
A worksheet of 18 reactions is presented as a learning aid to comprehend the regiochemistry and stereochemistry of alkene electrophilic addition.
Bertolini, Thomas M.; Tran, Phuc D. J. Chem. Educ. 2006, 83, 590.
Addition Reactions |
Alkenes |
Reactions
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
Diastereoselectivity in the Reduction of α-Hydroxyketones. An Experiment for the Chemistry Major Organic Laboratory  David B. Ball
Describes a research type, inquiry-based project where students synthesize racemic ahydroxyketones using umpolung, a polarity-reversal approach; investigate chelating versus non-chelating reducing agents; and determine the diastereoselectivity of these reducing processes by NMR spectroscopy.
Ball, David B. J. Chem. Educ. 2006, 83, 101.
Addition Reactions |
Aldehydes / Ketones |
Chirality / Optical Activity |
Chromatography |
Conferences |
Constitutional Isomers |
Enantiomers |
NMR Spectroscopy |
Stereochemistry |
Synthesis |
Conformational Analysis
Derivatization of Fullerenes: An Organic Chemistry Laboratory  Charles T. Cox Jr. and Melanie M. Cooper
Presents two undergraduate organic chemistry laboratories detailing the synthesis of fullerene derivatives, using the Bingel (carbene insertion) and Prato (1,3-dipolar addition) protocols.
Cox, Charles T., Jr.; Cooper, Melanie M. J. Chem. Educ. 2006, 83, 99.
Acids / Bases |
Addition Reactions |
Chromatography |
Heterocycles |
IR Spectroscopy |
Microscale Lab |
NMR Spectroscopy |
Synthesis |
UV-Vis Spectroscopy
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
Comparative Methylation of 1,8-Dihydroxy-9,10-anthraquinone: Chemoselectivity in the Organic Chemistry Laboratory  Grigoriy A. Sereda
Describes a laboratory experiment that gives organic chemistry students an example of an environmentally friendly pyrolytic procedure of organic synthesis. Another synthesis with the same reactants teaches the students that appropriate reaction conditions may allow the chemist to perform an organic reaction with high chemoselectivity.
Sereda, Grigoriy A. J. Chem. Educ. 2005, 82, 1839.
Reactions |
Ethers |
Green Chemistry |
Phenols |
Synthesis |
Thin Layer Chromatography |
UV-Vis Spectroscopy
Just Click It: Undergraduate Procedures for the Copper(I)-Catalyzed Formation of 1,2,3-Triazoles from Azides and Terminal Acetylenes  William D. Sharpless, Peng Wu, Trond Vidar Hansen, and James G. Lindberg
In keeping with the defining aspects of click chemistry, this reaction is high-yielding, requires no chromatography, is easily monitored by TLC, and displays distinct peaks in both IR and 1H-NMR. Virtually all products precipitate, and with just a few different starting blocks, every student, or pair of lab partners, can produce a unique "clicked" compound.
Sharpless, William D.; Wu, Peng; Hansen, Trond Vidar; Lindberg, James G. J. Chem. Educ. 2005, 82, 1833.
Catalysis |
Heterocycles |
Alkynes |
IR Spectroscopy |
NMR Spectroscopy |
Reactions |
Thin Layer Chromatography |
Synthesis
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
The Virtual ChemLab Project: A Realistic and Sophisticated Simulation of Organic Synthesis and Organic Qualitative Analysis  Brian F. Woodfield, Merritt B. Andrus, Gregory L. Waddoups, Melissa S. Moore, Richard Swan, Rob Allen, Greg Bodily, Tricia Andersen, Jordan Miller, Bryon Simmons, and Richard Stanger
Describes a set of sophisticated and realistic laboratory simulations for use in freshman- and sophomore-level chemistry classes and laboratories called Virtual ChemLab. The purpose of these simulations is to reinforce concepts taught in the classroom, provide an environment for creative learning, and emphasize the thinking behind instructional laboratory experiments.
Woodfield, Brian F.; Andrus, Merritt B.; Waddoups, Gregory L.; Moore, Melissa S.; Swan, Richard; Allen, Rob; Bodily, Greg; Andersen, Tricia; Miller, Jordan; Simmons, Bryon; Stanger, Richard. J. Chem. Educ. 2005, 82, 1728.
IR Spectroscopy |
NMR Spectroscopy |
Qualitative Analysis |
Synthesis |
Reactions |
Thin Layer Chromatography
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
Laboratory Experiments on the Electrochemical Remediation of the Environment. Part 8. Microscale Simultaneous Photocatalysis  Jorge G. Ibanez, Rodrigo Mena-Brito, and Arturo Fregoso-Infante
In this article we describe a microscale experiment in which the simultaneous oxidation of an organic compound (citric acid) and the reduction of a metal ion (Cu2+) are photocatalytically performed in an aqueous slurry containing TiO2 irradiated with UV light. This produces electrons (capable of reducing the metal ions) and holes (capable of oxidizing the organic molecule) that can be used for environmental clean up. The experiment allows students to have a better comprehension of the different phenomena involved in a typical photocatalytic process.
Ibanez, Jorge G.; Mena-Brito, Rodrigo; Fregoso-Infante, Arturo. J. Chem. Educ. 2005, 82, 1549.
Aqueous Solution Chemistry |
Electrochemistry |
Microscale Lab |
Oxidation / Reduction |
Reactions |
Photochemistry |
Semiconductors |
UV-Vis Spectroscopy
Laboratory Experiments on the Electrochemical Remediation of the Environment. Part 7: Microscale Production of Ozone  Jorge G. Ibanez, Rodrigo Mayen-Mondragon, M. T. Moran-Moran, Alejandro Alatorre-Ordaz, Bruce Mattson, and Scot Eskestrand
Ozone, a powerful oxidizing and disinfecting agent, is produced electrochemically in the undergraduate laboratory with simple equipment and under very mild conditions. Tests are given to characterize it, to observe its action in simulated environmental applications, and to measure its rate of production.
Ibanez, Jorge G.; Mayen-Mondragon, Rodrigo; Moran-Moran, M. T.; Alatorre-Ordaz, Alejandro; Mattson, Bruce; Eskestrand, Scot. J. Chem. Educ. 2005, 82, 1546.
Aqueous Solution Chemistry |
Descriptive Chemistry |
Electrochemistry |
Electrolytic / Galvanic Cells / Potentials |
Laboratory Equipment / Apparatus |
Microscale Lab |
Oxidation / Reduction |
Reactions
"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
Diels–Alder Synthesis of endo-cis-N-Phenylbicyclo[2.2.2]oct-5-en-2,3-dicarboximide  Marsha R. Baar and Kristin Wustholz
endo-cis-N-Phenylbicyclo[2.2.2]oct-5-en-2,3-dicarboximide was synthesized by a DielsAlder cycloaddition of 1,3-cyclohexadiene and N-phenylmaleimide in ethyl acetate. 1,3-Cyclohexadiene and N-phenylmaleimide were selected to illustrate the Alder rule, which reflects a preference for endo products and to overcome the difficulties associated with the traditional combination of 1,3-cyclopentadiene and maleic anhydride.
Baar, Marsha R.; Wustholz, Kristin. J. Chem. Educ. 2005, 82, 1393.
Asymmetric Synthesis |
Microscale Lab |
Stereochemistry |
Addition Reactions |
Alkenes |
IR Spectroscopy |
NMR Spectroscopy
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
Circular Dichroism Investigation of Dess–Martin Periodinane Oxidation in the Organic Chemistry Laboratory  Nicole A. Reed, Robert D. Rapp, Christian S. Hamann, and Pamela G. Artz
Using circular dichroism, organic laboratory students investigated the change in absolute stereochemistry upon oxidation of menthol to menthone. In the first laboratory period, the oxidation was performed with DessMartin periodinane, which is a facile and less toxic oxidizing agent. Half the laboratory group performed the oxidation with ()-menthol and the other half used (+)-menthol to produce ()-menthone and (+)-menthone, respectively. The products were analyzed in the second laboratory period using infrared spectroscopy and gas chromatography/mass spectrometry to determine the fraction of starting alcohol converted to ketone. Comparison was made between CD spectra both for the menthol reactant and menthone product and for the (+)- and ()-menthone enantiomers.
Reed, Nicole A.; Rapp, Robert D.; Hamann, Christian S.; Artz, Pamela G. J. Chem. Educ. 2005, 82, 1053.
Instrumental Methods |
Molecular Properties / Structure |
Oxidation / Reduction |
Reactions |
Enantiomers
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
Procedure for Decomposing a Redox Reaction into Half-Reactions  Ilie Fishtik and Ladislav H. Berka
The principle of stoichiometric uniqueness provides a simple algorithm to check whether a simple redox reaction may be uniquely decomposed into half-reactions in a single way. For complex redox reactions the approach permits a complete enumeration of a finite and unique number of ways a redox reaction may be decomposed into half-reactions. Several examples are given.
Fishtik, Ilie; Berka, Ladislav H. J. Chem. Educ. 2005, 82, 553.
Stoichiometry |
Equilibrium |
Electrochemistry |
Oxidation / Reduction |
Reactions |
Thermodynamics
The Evolution of a Green Chemistry Laboratory Experiment: Greener Brominations of Stilbene  Lallie C. McKenzie, Lauren M. Huffman, and James E. Hutchison
We describe two new greener alkene bromination reactions that offer enhanced laboratory safety and convey important green chemistry concepts, in addition to illustrating the chemistry of alkenes. The two alternative reactions, one involving pyridinium tribromide and a second using hydrogen peroxide and hydrobromic acid, are compared to the traditional bromination of stilbene through the application of green metrics, including atom economy, percent experimental atom economy, E factor, and effective mass yield.
McKenzie, Lallie C.; Huffman, Lauren M.; Hutchison, James E. J. Chem. Educ. 2005, 82, 306.
Synthesis |
Green Chemistry |
Aromatic Compounds |
Addition Reactions |
Alkenes
A Substitute for “Bromine in Carbon Tetrachloride”  Joshua M. Daley and Robert G. Landolt
Benzotrifluoride (BTF) is a suitable solvent substitute for carbon tetrachloride in experiments requiring application of bromine (Br2) in free radical or addition reactions with organic substrates. A 1 M solution of Br2 in BTF may be used to distinguish hydrocarbons based on the ease of abstraction of hydrogen atoms in thermally or light-induced free radical substitutions. Efficacy of minimization of solvent use, by aliquot addition to neat samples, has been established.
Daley, Joshua M.; Landolt, Robert G. J. Chem. Educ. 2005, 82, 120.
Alkenes |
Free Radicals |
Green Chemistry |
Qualitative Analysis |
Reactions
The Sharpless Asymmetric Dihydroxylation in the Organic Chemistry Majors Laboratory  Christopher J. Nichols and Melissa R. Taylor
A six-period laboratory exercise has been developed that uses the convenient Sharpless asymmetric dihydroxylation (AD) to illustrate the principles of a chiral synthesis. Using one particular alkene, students perform a racemic dihydroxylation, an AD using a commercially available AD-mix, and then an AD using an ester derivative of dihydroquinidine that they synthesized themselves. The structures of the products are confirmed with 1H NMR spectroscopy and the enantiomeric excesses of the diols are determined using a chiral GC column.
Nichols, Christopher J.; Taylor, Melissa R. J. Chem. Educ. 2005, 82, 105.
Chirality / Optical Activity |
Chromatography |
IR Spectroscopy |
NMR Spectroscopy |
Synthesis |
Alkenes |
Addition Reactions
Combinatorial Partial Hydrogenation Reactions of 4-Nitroacetophenone. An Undergraduate Organic Laboratory  Kevin W. Kittredge, Susan S. Marine, and Richard T. Taylor
A combinatorial organic chemistry experiment that utilizes an inexpensive commercially available parallel reactor, Argonaut's FirstMate, is described. Students perform a metal catalyzed partial hydrogenation reaction on a multi-functionalized substrate and analyze product ratios by GCMS. Students evaluate a simple organic reaction that yields four different products. The reactions are performed in the presence and absence of a reaction modifier, methanesulfonic acid. Differing product ratios are obtained with the different types of metal catalysts and with the presence or the absence of the reaction modifier.
Kittredge, Kevin W.; Marine, Susan S.; Taylor, Richard T. J. Chem. Educ. 2004, 81, 1494.
Catalysis |
Combinatorial Chemistry |
Synthesis |
Reactions
Solvent-Free Wittig Reaction: A Green Organic Chemistry Laboratory Experiment  Sam H. Leung and Stephen A. Angel
In this experiment (E)- and (Z)-1-(4-bromophenyl)-2-phenylethene are synthesized by a solvent-free Wittig reaction. The reaction is effected by grinding the reactants in a mortar with a pestle. Both the E and Z isomers of the product are produced as evidenced by thin-layer chromatography and 1H NMR analysis. The E isomer is isolated by crystallization with ethanol in this experiment. In addition to learning about the Wittig reaction, students are also introduced to the ideas of mechanochemistry and green chemistry.
Leung, Sam H.; Angel, Stephen A. J. Chem. Educ. 2004, 81, 1492.
Chromatography |
Green Chemistry |
Microscale Lab |
NMR Spectroscopy |
Synthesis |
Reactions |
Aldehydes / Ketones |
Alkenes
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
Microscale Synthesis of 1-Bromo-3-chloro-5-iodobenzene: An Improved Deamination of 4-Bromo-2-chloro-6-iodoaniline  Michael W. Pelter, Libbie S.W. Pelter, Dusanka Colovic, and Regina Strug
Overall, we find this procedure to be advantageous to the published methods owing to its requirement of less starting material, higher product yields, and a greatly simplified procedure.
Pelter, Michael W.; Pelter, Libbie S.W.; Colovic, Dusanka; Strug, Regina. J. Chem. Educ. 2004, 81, 111.
Microscale Lab |
Synthesis |
Aromatic Compounds |
Amines / Ammonium Compounds
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
Triethanolamine  Jay A. Young
Properties, hazards, and storage requirements for triethanolamine.
Young, Jay A. J. Chem. Educ. 2004, 81, 24.
Laboratory Equipment / Apparatus |
Laboratory Management |
Amines / Ammonium Compounds |
Physical Properties |
Alcohols
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 Noble Gas Configuration—Not the Driving Force but the Rule of the Game in Chemistry  Roland Schmid
Explains the covalent and ionic bonding behavior of main-group elements in terms of electromagnetic forces rather than the supposed "stability" of noble-gas configurations.
Schmid, Roland. J. Chem. Educ. 2003, 80, 931.
Molecular Modeling |
Periodicity / Periodic Table |
Main-Group Elements |
Atomic Properties / Structure |
Reactions |
Covalent Bonding |
Ionic Bonding
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
Chemical Equilibria Involving Copper(II) Ethylenediamine Complexes  Roberto Zingales
Demonstration illustrating the formation of two different complexes when copper(II) ions react with ethylenediamine.
Zingales, Roberto. J. Chem. Educ. 2003, 80, 535.
Equilibrium |
Aqueous Solution Chemistry |
Reactions |
Amines / Ammonium Compounds |
Precipitation / Solubility
Rate Controlling Factors in a Bunsen Burner Flame  Julio Andrade-Gamboa, Hugo L. Corso, and Fabiana C. Gennari
Analysis of a Bunsen burner flame and the kinetics of its combustion.
Andrade-Gamboa, Julio; Corso, Hugo L.; Gennari, Fabiana C. J. Chem. Educ. 2003, 80, 524.
Transport Properties |
Kinetics |
Gases |
Molecular Mechanics / Dynamics |
Thermal Analysis |
Thermodynamics |
Reactions |
Rate Law
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
A Demonstration of Structure–Reactivity Relationships in Organic Chemistry  Thomas A. Newton
Demonstration of the correlation between the conductivity of aqueous solutions and the pKa values of various organic compounds.
Newton, Thomas A. J. Chem. Educ. 2003, 80, 294.
Acids / Bases |
Conductivity |
Reactions |
Equilibrium |
Acids / Bases |
Electrochemistry |
Aqueous Solution Chemistry |
Conductivity
Periodic Table Live! 3rd Edition: Abstract of Special Issue 17  Nicholas B. Adelman, Jon L. Holmes, Jerrold J. Jacobsen, John W. Moore, Paul F. Schatz, Jaclyn Tweedale, Alton J. Banks, John C. Kotz, William R. Robinson, and Susan Young
CD-ROM containing an interactive journey through the periodic table; includes information about each element, biographies of discoverers, videos of reactions, sources and uses, macro and atomic properties, and crystalline structures.
Adelman, Nicholas B.; Holmes, Jon L.; Jacobsen, Jerrold J.; Moore, John W.; Schatz, Paul F.; Tweedale, Jaclyn; Banks, Alton J.; Kotz, John C.; Robinson, William R.; Young, Susan. J. Chem. Educ. 2002, 79, 1487.
Descriptive Chemistry |
Periodicity / Periodic Table |
Solid State Chemistry |
Atomic Properties / Structure |
Physical Properties |
Reactions |
Crystals / Crystallography
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
Synthesis and Analysis of a Solvatochromic Dye, 1-(p-Dimethylaminophenyl)-2-nitroethylene. An Advanced Undergraduate Laboratory Experiment  Dana L. Richter-Egger, Aaron Tesfai, Spencer J. Flamm, and Sheryl A. Tucker
Synthesis and analysis of 1-(p-dimethylaminophenyl)-2-nitroethylene.
Richter-Egger, Dana L.; Tesfai, Aaron; Flamm, Spencer J.; Tucker, Sheryl A. J. Chem. Educ. 2001, 78, 1375.
Fluorescence Spectroscopy |
Synthesis |
Undergraduate Research |
UV-Vis Spectroscopy |
Dyes / Pigments |
Amines / Ammonium Compounds |
Aromatic Compounds |
Alkenes
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
Synthesis of Substituted Butenolides. An Undergraduate Organic Laboratory Experiment Utilizing Two 3-Step Preparatory Sequences  Géraldine Maheut, Liang Liao, Jean-Marie Catel, Paul-Alain Jaffrès, and Didier Villemin
The synthesis of substituted butenolide in two, 3-step sequences that illustrate five basic organic reactions (alkyne hydration, Knoevenagel condensation, lactonization, aldolization-type reaction, and hydration of nitrile); the products have pedagogical interest for IR and NMR spectroscopy (diastereotopic effect).
Maheut, Géraldine; Liao, Liang; Catel, Jean-Marie; Jaffrès, Paul-Alain; Villemin, Didier. J. Chem. Educ. 2001, 78, 654.
IR Spectroscopy |
Molecular Modeling |
NMR Spectroscopy |
Synthesis |
Undergraduate Research |
Reactions
An Indexed Combinatorial Library: The Synthesis and Testing of Insect Repellents  William H. Miles, Kathy A. Gelato, Kristen M. Pompizzi, Aislinn M. Scarbinsky, Brian K. Albrecht, and Elaine R. Reynolds
An indexed combinatorial library of amides was prepared by the reaction of amines and acid chlorides; a simple test for insect repellency using fruit flies (Drosophila melanogaster) allowed the determination of the most repellent sublibraries.
Miles, William H.; Gelato, Kathy A.; Pompizzi, Kristen M.; Scarbinsky, Aislinn M.; Albrecht, Brian K.; Reynolds, Elaine R. J. Chem. Educ. 2001, 78, 540.
Drugs / Pharmaceuticals |
Synthesis |
Combinatorial Chemistry |
Applications of Chemistry |
Amines / Ammonium Compounds
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
Application of Hammond's Postulate. An Activity for Guided Discovery Learning in Organic Chemistry  J. E. Meany, Vicky Minderhout, and Y. Pocker
In this activity, students are given product distributions and other relevant experimental data concerning the free radical chlorination and bromination of propane. Students are guided in the use of Hammond's postulate to predict transition-state structures and to provide a rationale for the relationship between selectivity and reactivity in these and other reactions.
Meany, J. E.; Minderhout, Vicky; Pocker, Y. J. Chem. Educ. 2001, 78, 204.
Free Radicals |
Kinetics |
Reactions
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-Solvent-Free Phase-Transfer Oxidation of Alcohols Using Hydrogen Peroxide  Martin Hulce and David W. Marks
Six representative alcohols are oxidized to the corresponding aldehyde or ketone, integrating the various techniques of extraction, drying, filtration, column chromatography, gas chromatography, NMR and IR spectroscopy, and reaction kinetics.
Hulce, Martin; Marks, David W. J. Chem. Educ. 2001, 78, 66.
Catalysis |
Oxidation / Reduction |
Reactions |
Kinetics |
Chromatography |
Gas Chromatography |
Separation Science |
NMR Spectroscopy |
IR Spectroscopy |
Alcohols |
Phenols
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
A Simple Method for Demonstrating Enzyme Kinetics Using Catalase from Beef Liver Extract  Kristin A. Johnson
A simple visual method of demonstrating enzyme kinetics using beef liver catalase. Filter paper is saturated with beef liver extract and placed into a solution of hydrogen peroxide. The catalase in the extract decomposes the hydrogen peroxide to water and oxygen. Oxygen forms on the filter paper, and the filter paper rises to the top of the beaker. Catalase activity is measured by timing the rise of the enzyme-soaked filter paper to the top of beakers containing different concentrations of hydrogen peroxide.
Johnson, A. Kristin. J. Chem. Educ. 2000, 77, 1451.
Enzymes |
Kinetics |
Proteins / Peptides |
Reactions
Combustion Demonstration Using Updated Flame Tornado  Edward G. Senkbeil
This demonstration uses the combustion of different forms of cellulose and an updated version of the "flame tornado" as an ignition source to illustrate the factors affecting the combustion process. The objectives of the experiment are to illustrate the factors affecting the rate of a combustion reaction and to demonstrate the factors affecting the production of a flame by using the flame tornado.
Senkbeil, Edward G. J. Chem. Educ. 2000, 77, 1449.
Descriptive Chemistry |
Oxidation / Reduction |
Reactions |
Rate Law
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
Displacement of the Benzene Solvent Molecule from Cr(CO)5(benzene) by Piperidine: A Laser Flash Photolysis Experiment  Ashfaq A. Bengali and Samantha B. Charlton
This laboratory experiment utilizes a nitrogen laser to investigate the chemistry of the Cr(CO)5(benzene) complex on the microsecond time scale. The unique capabilities of a laser and the chemistry made possible by its use is demonstrated.
Bengali, Ashfaq A.; Charlton, Samantha B. J. Chem. Educ. 2000, 77, 1348.
Kinetics |
Lasers |
Spectroscopy |
Organometallics |
Photochemistry |
Aromatic Compounds |
Reactions
Everyday Chemical Reactions: A Writing Assignment to Promote Synthesis of Concepts and Relevance in Chemistry  Abby L. Parrill
Capturing the interest of students in required chemistry courses is a problem for which many solutions have been proposed and described. The solution proposed here is the use of a writing assignment on everyday chemical reactions. Students select their own organic reaction and apply concepts learned throughout the semester to understanding it.
Parrill, Abby L. J. Chem. Educ. 2000, 77, 1303.
Nonmajor Courses |
Reactions
When A + B Is Not Equal To B + A  Erling Antony, Lindsay Mitchell, and Lauren Nettenstrom
Many acid-base chemistry demonstrations and laboratory manuals include the "baking soda volcano". Others use the formation of calcium carbonate from calcium hydroxide and carbon dioxide in human breath. This demonstration uses principles from both as well as stoichiometry to answer the question "Does the order of mixing of reagents make a difference?"
Antony, Erling; Mitchell, Lindsay; Nettenstrom, Lauren. J. Chem. Educ. 2000, 77, 1180.
Acids / Bases |
Stoichiometry |
Reactions
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
Elucidation of Molecular Structure Using NMR Long-Range Coupling: Determination of the Single Isomer Formed in a Regiospecific Reaction  Samuel Delagrange and Françoise Nepveu
The experiment presented in this article introduces students to the main concepts of two essential NMR techniques for investigating molecular structure. Heteronuclear multiple bond connectivity (HMBC) and proton-coupled 13C NMR are used to determine which isomer, from a possible two, is formed by a regiospecific reaction. The demonstration, based on long-range coupling between quaternary carbons and protons on neighboring carbons, is presented step by step.
Delagrange, Samuel; Nepveu, Françoise. J. Chem. Educ. 2000, 77, 895.
Molecular Properties / Structure |
NMR Spectroscopy |
Synthesis |
Carboxylic Acids |
Reactions |
Diastereomers
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
Microwave Irradiation Reactions: Synthesis of Analgesic Drugs  Gholam A. Mirafzal and Jolene M Summer
Over-the-counter analgesics such as aspirin, acetanilide, phenacetin, and acetaminophen are conveniently prepared in a microwave at 30% power for five minutes. Recrystallization from appropriate solvents results in solid products in good to excellent yields.
Mirafzal, Gholam A.; Summer, Jolene M. J. Chem. Educ. 2000, 77, 356.
Drugs / Pharmaceuticals |
Synthesis |
Medicinal Chemistry |
Aromatic Compounds |
Amines / Ammonium Compounds |
Esters
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
A Simple Secondary Amine Synthesis: Reductive Amination Using Sodium Triacetoxyborohydride  Merle W. Carlson, James T. Ciszewski, Micah M. Bhatti, Wesley F. Swanson, and Anne M. Wilson
A reductive amination experiment for a second-semester organic chemistry class. It utilizes an imine intermediate and sodium triacetoxyborohydride, a mild reducing agent. The progress of the reaction is followed by TLC as the starting materials (the aldehyde and primary amine), the imine intermediate, and the secondary amine product are visible under ultraviolet light.
Carlson, Merle W.; Ciszewski, James T.; Bhatti, Micah M.; Swanson, Wesley F.; Wilson, Anne M. J. Chem. Educ. 2000, 77, 270.
Synthesis |
Chromatography |
Amines / Ammonium Compounds
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
Catalytic Oxidation of Ammonia: A Sparkling Experiment  Vladimir A. Volkovich and Trevor R. Griffiths
A lecture demonstration experiment on the catalytic oxidation of ammonia using chromium(III) oxide as a catalyst is described.
Volkovich, Vladimir A.; Griffiths, Trevor R. J. Chem. Educ. 2000, 77, 177.
Catalysis |
Oxidation / Reduction |
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
Techniques and Experiments for Organic Chemistry, 6th Edition (by Addison Ault)  reviewed by Karen C. Inman
Those who may be new to Ault's text will find a well-written laboratory manual that clearly reflects the author's years of experience. It is thorough, describing all the common lab techniques in Part 1 and giving concise, well-written directions for experiments in Part 2. The experiments provide an excellent representation of all the important reactions in a typical course. In fact, for most types of reactions there are several experiments from which to choose.
Inman, Karen C. J. Chem. Educ. 1999, 76, 1629.
Reactions
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
More on Double Replacement  Kauffman, G. B.
Reference to directions for writing double replacement reactions.
Kauffman, G. B. J. Chem. Educ. 1999, 76, 1340.
Reactions |
Stoichiometry
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
The Discovery-Oriented Approach to Organic Chemistry. 1. Nitration of Unknown Organic Compounds. An Exercise in 1H NMR and 13C NMR Spectrosopy for Sophomore Organic Laboratories  Sonia R. McElveen, Kostas Gavardinas, Jean A. Stamberger, and Ram S. Mohan
Two simple nitration experiments that present the student with a puzzle and are a good exercise in 1H NMR and 13C NMR spectroscopy. The experiment involves nitration of unknown organic compounds and product analysis by 1H NMR and 13C NMR spectroscopy, which enables the student to determine the identity of the unknown.
McElveen, Sonia R.; Gavardinas, Kostas; Stamberger, Jean A.; Mohan, Ram S. J. Chem. Educ. 1999, 76, 535.
NMR Spectroscopy |
Synthesis |
Reactions
A Safe Simple Halogenation Experiment  Hilton M. Weiss and Lara Ganz
This experiment is designed to be a safe and experimentally simple procedure appropriate to the early weeks of a course when halogenation is the only reaction which has been discussed in the lecture. It can also provide some early experience with simple interpretation of NMR spectra.
Weiss, Hilton M.; Ganz, Lara. J. Chem. Educ. 1999, 76, 534.
Synthesis |
Free Radicals |
Reactions |
NMR Spectroscopy
Using Large Glass Cylinders To Demonstrate Chemical Reactions  Wobbe de Vos
This article describes a simple laboratory experiment that aims at pedagogic as well as aesthetic aspects of chemical reactions. Experiments of this type have a high educational potential as students have the opportunity to observe the actual formation of a precipitate instead of just being able to see the result. The experiment is also suitable for demonstrating some of the fascinating beauty of chemical reactions to the general public.
de Vos, Wobbe. J. Chem. Educ. 1999, 76, 528.
Laboratory Equipment / Apparatus |
Aqueous Solution Chemistry |
Reactions
Teaching Chemistry Using the Movie Apollo 13  James G. Goll and B. J. Woods
The use of this popular movie has helped generate interest in chemistry courses.
Goll, James G.; Woods, B. J. J. Chem. Educ. 1999, 76, 506.
Undergraduate Research |
Learning Theories |
Reactions |
Applications of Chemistry
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
The Ammonia Smoke Fountain: An Interesting Thermodynamic Adventure  M. Dale Alexander
The ammonia smoke fountain demonstration utilizes a modification of the apparatus used in the standard ammonia fountain. The modification allows for the introduction of hydrogen chloride gas into a flask of ammonia rather than water. The flow rate of hydrogen chloride gas into the flask in the smoke fountain is not constant, but periodic; that is, the smoke puffs from the end of the tube. This unexpected behavior elicits an interesting thermodynamic explanation.
Alexander, M. Dale. J. Chem. Educ. 1999, 76, 210.
Acids / Bases |
Gases |
Thermodynamics |
Reactions |
Stoichiometry |
Precipitation / Solubility
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
Slide Projector Corrosion Cell  Silvia Tejada, Estela Guevara, and Esperanza Olivares
The process of corrosion can be demonstrated in a slide projector, since the cell is in the shape of a slide, or on the stage of an overhead projector by setting up a simple galvanic cell. Corrosion occurs as the result of a galvanic cell reaction, in which the corroding metal acts as the anode. Several simple demonstrations relating to corrosion are described here.
Tejada, Silvia; Guevara, Estela; Olivares, Esperanza. J. Chem. Educ. 1998, 75, 747.
Electrochemistry |
Microscale Lab |
Oxidation / Reduction |
Reactions |
Electrolytic / Galvanic Cells / Potentials |
Applications of Chemistry
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
Book Note: Concise Encyclopedia Biochemistry and Molecular Biology, 3rd edition (edited by Thomas A. Scott and E. Ian Mercer)  Martin J. Serra
An alphabetical listing of biochemical and molecular biological processes, compounds, and reactions, with bibliographic references to the original literature. This edition is extensively updated and expanded to encompass the continued growth of our understanding of biological systems.
Martin J. Serra. J. Chem. Educ. 1998, 75, 420.
Reactions
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
What Is the Geometry at Trigonal Nitrogen?  K. P. Sudlow and A. A. Woolf
The geometry of trigonal nitrogen is discussed from VSEPR, crystallographic, and computational studies. The VSEPR theory is valid unless hydrogen bonding is strong enough or dispersal of nitrogen lone pair density is possible over receptive groups.
Sudlow, K. P.; Woolf, A. A. J. Chem. Educ. 1998, 75, 108.
Learning Theories |
Molecular Properties / Structure |
Crystals / Crystallography |
Computational Chemistry |
VSEPR Theory |
Hydrogen Bonding |
Amines / Ammonium Compounds
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
Letter to the Editor about Letter to the Editor "Redox Challenges" from David M. Hart and Response from Roland Stout (J. Chem. Educ. 1996, 73, A226-7)  Andrzej Sobkowiak
Examples of a variety of redox equations.
Sobkowiak, Andrzej. J. Chem. Educ. 1997, 74, 1256.
Stoichiometry |
Reactions |
Oxidation / Reduction
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
Stable Solutions for the Iodine Clock Reaction  George B. Kauffman and Charles R. Hall
Advanced preparation of solutions for the iodine clock reaction.
Kauffman, George B.; Hall, Charles R. J. Chem. Educ. 1997, 74, 616.
Reactions |
Solutions / Solvents
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
What are Isodesmic Reactions?  D. A. Ponomarev and V. V. Takhistov
The heat of isodesmic (formal) reaction Q is systematically used as a measure of deviations from the additivity of bond energies. For molecules these Q values are applied to quantification of strain energies in cyclic compounds, to evaluation of aromaticity of benzene, to explanation of the reasons for deviation from additivity in the heats of formation for disubstituted benzenes and some alkenes.
Ponomarev, D. A.; Takhistov, V. V. J. Chem. Educ. 1997, 74, 201.
Reactions |
Molecular Properties / Structure
A -78°C Sequential Michael Addition for the Organic Lab  Michael W. Tanis
This paper introduces a cold-temperature enolate alkylation reaction that can be performed safely and inexpensively by undergraduate students in approximately two 3-hour lab sessions.
Tanis, Michael W. J. Chem. Educ. 1997, 74, 112.
Addition Reactions |
Alkenes |
Aldehydes / Ketones |
Synthesis
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
An Organoleptic Laboratory Experiment  John M. Risley
Compounds in ten different classes of organic molecules that are used in the fragrance and food industry are provided to students. Students whiff the vapors of each compound and describe the organoleptic properties using a set of terms utilized in the fragrance and food industry. A set of questions guides students to an understanding of the relationship between structure of molecules and smell.
Risley, John M. J. Chem. Educ. 1996, 73, 1181.
Molecular Properties / Structure |
Consumer Chemistry |
Physical Properties |
Nonmajor Courses |
Alcohols |
Aldehydes / Ketones |
Amines / Ammonium Compounds |
Carboxylic Acids |
Esters |
Ethers |
Phenols
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
Approximating the Electrostatic Contribution to the Entropy Change of Aqueous Phase Lanthanide-Aminocarboxylate Complexation  Thomas J. Manning
A model is presented to approximate the electrostatic contribution to the entropy change of the reaction for aqueous lanthanide-aminocarboxylate complexes. The procedure is outlined using La(3+)-EDTA complexation to predict the entropy change per carboxylate, the entropy change per amine, and the total entropy change.
Thomas J. Manning. J. Chem. Educ. 1996, 73, 661.
Thermodynamics |
Solutions / Solvents |
Reactions |
Coordination Compounds
Examination of a Reaction Mechanism by Polarimetry: An Experiment for the Undergraduate Organic Chemistry Laboratory  Michael D. Mosher, Chad O. Kelly, and Melvyn W. Mosher
The experiment has been shown to be successful with chiral mandelic acid and POCl3 and with chiral lactic acid and HBr. The substitution mechanisms of these reactions proceed with 1% and 38% SN2 character respectively.
Mosher, Michael D.; Kelly, Chad O.; Mosher, Melvyn W. J. Chem. Educ. 1996, 73, 567.
Instrumental Methods |
Mechanisms of Reactions |
Gas Chromatography
A Mixed Aldol Condensation-Michael Addition Experiment  Thomas P. Clausen, Beverly Johnson, and Jim Wood
This article describes the analysis of the recrystallized products of a mixed aldol condensation between symmetrical ketones and aromatic aldehydes.
Clausen, Thomas P.; Johnson, Beverly; Wood, Jim. J. Chem. Educ. 1996, 73, 266.
Aldehydes / Ketones |
NMR Spectroscopy |
Mechanisms of Reactions
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
Diffusion Rates on the Overhead Projector: Amines Compared to HCl  Sally Solomon, Chinhyu Hur, and Alan Lee
Diffusion rates of selected amines are compared to that of HCl using a method very similar to those described for NH3 versus HCl diffusion.
Solomon, Sally; Hur, Chinhyu; Lee, Alan. J. Chem. Educ. 1996, 73, 81.
Amines / Ammonium Compounds |
Transport Properties
Organic Reactions, Volume 45 (Paquette, Leo A.)  
Continuing series.
J. Chem. Educ. 1995, 72, A94.
Synthesis |
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
Redox Challenges: Good Times for Puzzle Fanatics  Roland Stout
Three difficult to balance redox equations.
Stout, Roland. J. Chem. Educ. 1995, 72, 1125.
Reactions |
Stoichiometry |
Oxidation / Reduction |
Enrichment / Review Materials
Photosynthesis: Why Does It Occur?  J. J. MacDonald
Explanation of why photosynthesis occurs; stating that it is merely the reverse of respiration is misleading.
MacDonald, J. J. J. Chem. Educ. 1995, 72, 1113.
Plant Chemistry |
Reactions |
Thermodynamics |
Photochemistry |
Electrochemistry
A Computer Program for Calculating Standard Deviations from Standard Deviations  Edmund R. Malinowski
180. Bits and pieces, 55. A method for visualizing the numerical results of molecular-dynamics simulations using Mathematica.
Malinowski, Edmund R. J. Chem. Educ. 1995, 72, 1077.
Molecular Modeling |
Computational Chemistry |
Mathematics / Symbolic Mathematics |
Reactions
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
Using Copper sulfate as a Classification Test for Amino Acids and Amines  Christine K. F. Hermann
Using copper sulfate to test for amino acids and amines that do not dissolve well in water.
Hermann, Christine K. F. J. Chem. Educ. 1995, 72, 940.
Amino Acids |
Laboratory Management |
Amines / Ammonium Compounds |
Qualitative Analysis
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
A Method to Find the Rate Constants in Chemical Kinetics of a Complex Reaction  Sydney Bluestone and Kin Y. Yan
Method for extracting rate constants for a complex reaction from analytical and simulated data.
Bluestone, Sydney; Yan, Kin Y. J. Chem. Educ. 1995, 72, 884.
Rate Law |
Kinetics |
Reactions |
Chemometrics
Pyrrole: From Dippel to Du Pont   Hugh J. Anderson
Outline of the discovery, isolation, and development of uses for pyrrole.
Anderson, Hugh J. J. Chem. Educ. 1995, 72, 875.
Enrichment / Review Materials |
Amines / Ammonium Compounds
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
Demonstrating a Lack of Reactivity Using a Teflon-Coated Pan  Thomas G. Richmond
Demonstration to illustrate a lack of chemical activity using a Teflon-coated pan.
Richmond, Thomas G.; Krause, Paul F. J. Chem. Educ. 1995, 72, 731.
Reactions |
Covalent Bonding
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
Resistance Measurement as a Tool for Corrosion Studies  Singh, N. P.; Gupta, S. C.; Sood, B. R.
Procedure for determining the rate of corrosion by measuring changes in the resistance of a thin wire or strip of metal; sample data and analysis included.
Singh, N. P.; Gupta, S. C.; Sood, B. R. J. Chem. Educ. 1995, 72, 465.
Oxidation / Reduction |
Metals |
Rate Law |
Reactions |
Electrochemistry
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
"Crack" - A High-Interest Compound Illustrating Important Concepts in General Chemistry  Hoyt, William
Using crack and cocaine as examples of amine acid-base chemistry.
Hoyt, William J. Chem. Educ. 1995, 72, 322.
Acids / Bases |
Enrichment / Review Materials |
Amines / Ammonium Compounds |
Esters
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
Microwave Synthesis of Tetraphenylcyclopentadienone and Dimethyl Tetraphenylphthalate  Elder, John W.
Procedure for using a microwave to synthesize tetraphenylcyclopentadienone and dimethyl tetraphenylphthalate.
Elder, John W. J. Chem. Educ. 1994, 71, A142.
Microscale Lab |
Laboratory Equipment / Apparatus |
Synthesis |
Aromatic Compounds |
Esters |
Amines / Ammonium Compounds
Learning Name Reactions and Name Apparatuses Through Crossword Puzzles  Lee, Albert W. M.; Tse, C. L.
These computer generated crossword puzzles consist of 38 organic name reactions and 13 name apparatuses frequently encountered at the undergraduate level.
Lee, Albert W. M.; Tse, C. L. J. Chem. Educ. 1994, 71, 1071.
Laboratory Equipment / Apparatus |
Reactions
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 Resolution of (+-)-alpha-Methylbenzylamine-A Safer Way  Krause, Josef G.
Preventing boil over during the resolution of (+/-)-alpha-methylbenzylamine.
Krause, Josef G. J. Chem. Educ. 1994, 71, 596.
Amines / Ammonium Compounds |
Laboratory Management
Use of Multimedia in an Introductory Chemistry Course for Student Analysis of Real-Life Situations  Joesten, Melvin D.
Award in the Course and Curriculum Development (CCD) program for FY1994.
Joesten, Melvin D. J. Chem. Educ. 1994, 71, 508.
Addition Reactions
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
An Oscillating Reaction as a Demonstration of Principles Applied in Chemistry and Chemical Engineering  Weimer, Jeffrey J.
Platinum catalyzed decomposition of methanol.
Weimer, Jeffrey J. J. Chem. Educ. 1994, 71, 325.
Thermodynamics |
Catalysis |
Transport Properties |
Kinetics |
Reactions
A WARNING: Explosion Hazards of Reacting Magnesium and Aluminum with Powdered Silver Nitrate  Laing, Michael
Danger of reacting Mg and AgNO3, Al and AgNO3.
Laing, Michael J. Chem. Educ. 1994, 71, 270.
Metals |
Reactions
A Safe and Easy Classroom Demonstration of the Generation of Acetylene Gas  Cox, Marilyn Blagg
Reacting calcium carbide with water to generate ethyne.
Cox, Marilyn Blagg J. Chem. Educ. 1994, 71, 253.
Alkynes |
Reactions
Pyrotechnic Reactions Without Oxygen  Wright, Stephen W.
Reaction of K3FeF6 with Al and poly(tetrafluoroethylene) with Mg.
Wright, Stephen W. J. Chem. Educ. 1994, 71, 251.
Oxidation / Reduction |
Reactions
KineticsLab: The Crystal Violet/Sodium Hydroxide Reaction  Cannon, John F.; Gammon, Steven D.; Hunsberger, Lynn R.
A computer-assisted experiment to collect and analyze data for a kinetic study of the decolorization of crystal violet in basic solution.
Cannon, John F.; Gammon, Steven D.; Hunsberger, Lynn R. J. Chem. Educ. 1994, 71, 238.
Kinetics |
Rate Law |
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
Conversion Reactions in Inorganic Chemistry  Habashi, Fathi.
Liberation of metals from their sulfides through reaction with oxygen.
Habashi, Fathi. J. Chem. Educ. 1994, 71, 130.
Reactions |
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
Selectivity versus reactivity: The safe, efficient metal hydride reduction of a bifunctional organic   Smith, Katrina; Beauvais, Robert; Holman, R. W.
Microscale quantities allow students to perform otherwise dangerous observations of NaBH4 and LiAlH4 reductions.
Smith, Katrina; Beauvais, Robert; Holman, R. W. J. Chem. Educ. 1993, 70, A94.
Microscale Lab |
Reactions |
IR Spectroscopy
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 electrophilic addition to alkynes  Weiss, Hilton M.
Electrophilic additions to alkynes traditionally do not receive as much attention in organic textbooks as electrophilic addition to alkenes.
Weiss, Hilton M. J. Chem. Educ. 1993, 70, 873.
Addition Reactions |
Alkynes
A fast, easy-to-run and safe ene reaction between benzyne and [beta]-pinene  Drouin, Jacques; Jacq, Philippe
A fast, easy-to-run and safe ene reaction between benzyne and [beta]-pinene.
Drouin, Jacques; Jacq, Philippe J. Chem. Educ. 1993, 70, 863.
Alkenes |
Aromatic Compounds |
Alkynes |
Reactions
Products of aldol addition and related reactions: Notation for their prediction  Nwaukwai, Stephen O.
A simple method that can be used to predict products of aldols and aldol-tye addition reactions.
Nwaukwai, Stephen O. J. Chem. Educ. 1993, 70, 626.
Addition Reactions |
Aldehydes / Ketones |
Nomenclature / Units / Symbols
Differential scanning calorimetry study of the cross-linking of styrene and an unsaturated polyester: The chemistry of canoe manufacture.  Vebrel, Joel; Grohens, Yves; Kadmiri, Abderazak; Gowling, Eric W.
An activity geared toward a course where experiments are designed to investigate the preparation of materials, the properties essential to understanding their formation, and the optimization of their application.
Vebrel, Joel; Grohens, Yves; Kadmiri, Abderazak; Gowling, Eric W. J. Chem. Educ. 1993, 70, 501.
Materials Science |
Polymerization |
Reactions |
Calorimetry / Thermochemistry
Kinetics of the reaction of p-nitrobenzyl chloride with cyanide ion: An undergraduate organic chemistry experiment  Hurst, Michael O.; Hill, John W.
The title reaction is used to develop an undergraduate organic kinetics experiment in which the student determines the order and rate constant of the reaction, as well as the effect of solvent upon the rate of the reaction.
Hurst, Michael O.; Hill, John W. J. Chem. Educ. 1993, 70, 429.
Reactions |
Rate Law |
Kinetics |
Aromatic Compounds |
Alcohols |
Solutions / Solvents |
Organosulfur Compounds
The Reaction of Copper(II) with Thiocyanate ions   Tudela, David.
Interesting aspects of a reaction described in this journal by Tykodi in 1991, volume 68, pages 106-109.
Tudela, David. J. Chem. Educ. 1993, 70, 174.
Reactions |
Enrichment / Review Materials
Bleaching with Chlorine: Another Tomato Juice Demonstration   Nemetz, Thomas M.; Ball, David W.
Bubbling chlorine gas through tomato juice produces dramatic color changes. This paper provides safe instructions for the demonstration.
Nemetz, Thomas M.; Ball, David W. J. Chem. Educ. 1993, 70, 154.
Periodicity / Periodic Table |
Reactions
Is This Reaction a Substitution, Oxidation-Reduction, or Transfer?  Imyanitov, Naum S.
Author argues that separation of chemical reaction types based on convention do not always follow objective and consistent rules. This leads to confusion among students and artificial borders within the various sub-disciplines in chemistry.
Imyanitov, Naum S. J. Chem. Educ. 1993, 70, 14.
Reactions |
Oxidation / Reduction
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
Chemical Demonstrations: A Handbook for Teachers of Chemistry, Volume 4 (Shakhashiri, Bassam Z.)  Kauffman, George B.
78 procedures grouped into two chapters, one on clock reactions, the other on electrochemistry, batteries, electrolytic cells, and plating.
Kauffman, George B. J. Chem. Educ. 1992, 69, A187.
Reactions |
Electrochemistry |
Electrolytic / Galvanic Cells / Potentials
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
The synthesis of urea: An undergraduate laboratory experiment   Tanski, Stephanie; Petro, Janeen; Ball, David W.
This paper presents a laboratory experiment for the production of urea from silver cyanate and ammonium chloride.
Tanski, Stephanie; Petro, Janeen; Ball, David W. J. Chem. Educ. 1992, 69, A128.
Synthesis |
Reactions
Ammonia balloon  Mattson, Bruce
Demonstrating ammonia's aqueous solubility using a container whose volume changes.
Mattson, Bruce J. Chem. Educ. 1992, 69, 1029.
Amines / Ammonium Compounds |
Precipitation / Solubility |
Solutions / Solvents |
Aqueous Solution Chemistry
A simple and colorful demonstration of light-catalyzed bromination of an alkane  Stevens, Malcolm P.
Light-catalyzed bromination of an alkane.
Stevens, Malcolm P. J. Chem. Educ. 1992, 69, 1028.
Catalysis |
Alkanes / Cycloalkanes |
Photochemistry |
Reactions
A spontaneous exothermic reaction between two solids: A safe demonstration  Scott, Earle S.
Reaction between equal masses of hydroxylamine hydrochloride and sodium nitrite.
Scott, Earle S. J. Chem. Educ. 1992, 69, 1028.
Solids |
Calorimetry / Thermochemistry |
Reactions
Molecular dynamics of the F + H2 chemical reaction  Kutz, H. Douglas; Copeland, Jonathan H.; Mathai, George T.
Software that presents the F + H2 reaction in terms of the potential energy surface and associated reaction dynamics.
Kutz, H. Douglas; Copeland, Jonathan H.; Mathai, George T. J. Chem. Educ. 1992, 69, 1011.
Molecular Mechanics / Dynamics |
Reactions
Reaction dynamics  Lacks, Daniel
Software that simulates collisions of an atom with a diatomic molecule, allowing students to set the initial conditions and the type of atom or molecule involved.
Lacks, Daniel J. Chem. Educ. 1992, 69, 1010.
Reactions |
Rate Law
A mnemonic for the Krebs cycle: Using letter additions, letter deletions, and anagrams to trace the acylation, decarboxylations, and other changes  Williams, John P.
A mnemonic for the Krebs cycle.
Williams, John P. J. Chem. Educ. 1992, 69, 985.
Reactions
Reactions accelerated by microwave radiation in the undergraduate organic laboratory  Bari, Shamsher S.; Bose, Ajay K.; Chaudhary, Ashok G.; Manhas, Maghar S.; Raju, Vegesna S.; Robb, Ernest W.
The authors have found that with the proper choice of reaction solvent, accelerated reactions can be carried out safely with ordinary glassware in commercial microwave ovens.
Bari, Shamsher S.; Bose, Ajay K.; Chaudhary, Ashok G.; Manhas, Maghar S.; Raju, Vegesna S.; Robb, Ernest W. J. Chem. Educ. 1992, 69, 938.
Laboratory Equipment / Apparatus |
Reactions
Kinetic study of the reaction between ethanol and chloroacetyl chloride in chloroform: A laboratory experiment using Fourier transform infrared spectroscopy  Garcia, M. V.; Tiemblo, P.
Using Fourier transform infrared spectroscopy to study the reaction between ethanol and chloroacetyl chloride in chloroform.
Garcia, M. V.; Tiemblo, P. J. Chem. Educ. 1992, 69, 841.
Kinetics |
Fourier Transform Techniques |
IR Spectroscopy |
Reactions
A walk through snow  Dills, Charles E.
The importance of teaching students the problems of scaling chemical reactions up and down.
Dills, Charles E. J. Chem. Educ. 1992, 69, 784.
Industrial Chemistry |
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
Free-radical polymerization of acrylamide  Silversmith, Ernest F.
A rapid and foolproof thermal polymerization.
Silversmith, Ernest F. J. Chem. Educ. 1992, 69, 763.
Free Radicals |
Polymerization |
Reactions
A simple, continuous-flow stirred-tank reactor for the demonstration and investigation of oscillating reactions  Merino, J. M.
Description and use of a simple, continuous-flow stirred-tank reactor for the demonstration and investigation of oscillating reactions.
Merino, J. M. J. Chem. Educ. 1992, 69, 754.
Laboratory Equipment / Apparatus |
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
Imprecise numbers and incautious safety procedure mar experiment.  Nelson, Robert N.
Problems with significant figures and safety concerns regarding two published experiments.
Nelson, Robert N. J. Chem. Educ. 1992, 69, 688.
Reactions |
Nomenclature / Units / Symbols
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
Schiff base puzzle project.  Todd, David.
Students pick an unknown substituted aniline and a substituted benzaldehyde, produces the corresponding Schiff base from them, and compares its melting point to those of 25 possible Schiff bases (their structures and melting points being given).
Todd, David. J. Chem. Educ. 1992, 69, 584.
Qualitative Analysis |
Aldehydes / Ketones |
Amines / Ammonium Compounds
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
The extent of acid-base reactions (the author replies).  Thompson, Ralph J.
A poor example for calculating the extent of reaction between hydronium ion and aniline was chosen.
Thompson, Ralph J. J. Chem. Educ. 1992, 69, 516.
Acids / Bases |
Reactions
The extent of acid-base reactions.  Tapparo, Andrea.
Several misleading statements can be found in the original article.
Tapparo, Andrea. J. Chem. Educ. 1992, 69, 515.
Acids / Bases |
Reactions
Refrigerated dropping funnel and reflux condenser  Cagle, M. D.; Denton, T.; Eisenbraun, E. J.
This one-piece apparatus has proved useful in controlling the temperature of a reagent during addition to a refluxing reaction mixture.
Cagle, M. D.; Denton, T.; Eisenbraun, E. J. J. Chem. Educ. 1992, 69, 331.
Laboratory Equipment / Apparatus |
Reactions
A kinetic experiment to determine traces of Mo(VI)  Lampard, M.
This experiment deals with the estimation of Mo(VI) on a microchemical scale using visual color end-point detection.
Lampard, M. J. Chem. Educ. 1992, 69, 327.
Microscale Lab |
Kinetics |
Reactions
A graphical solution of the second-reaction rate constant of a two-step consecutive first-order reaction  Marasinghe, P. A. B.; Wirth, L. M.
In this paper, a general unsophisticated method for the determination of the second-reaction rate constant k2 of a two-step consecutive first-order reaction is described.
Marasinghe, P. A. B.; Wirth, L. M. J. Chem. Educ. 1992, 69, 285.
Rate Law |
Reactions
A new twist to an old favorite: The hydrolysis of tert-butyl chloride.  Turner, J.
The author describes a common kinetics experiment in which NMR spectroscopy is used to study the reaction kinetics rather than a titration.
Turner, J. J. Chem. Educ. 1992, 69, 242.
Kinetics |
NMR Spectroscopy |
Reactions
A demonstration of the SN2 reaction and the effects of structure, leaving group, and solvent  Wright, Stephen W.
This demonstration allows the effects of substrate structure, leaving group, and solvent upon the rate of the SN2 reaction to be demonstrated with a visible color change that indicates the completion of the reaction.
Wright, Stephen W. J. Chem. Educ. 1992, 69, 235.
Reactions |
Rate Law
Enzyme activity: The ping-pong ball torture analogy  Helser, Terry L.
The author uses this analogy to help students visualize and understand the effect of reaction conditions on the initial rate of an enzyme-catalyzed reaction.
Helser, Terry L. J. Chem. Educ. 1992, 69, 137.
Enzymes |
Reactions
The conversion of chemical energy: Part 1. Technological examples  Wink, Donald J.
When a chemical reaction occurs, the energy of the chemical species may change and energy can be released or absorbed from the surroundings. This can involve the exchange of chemical energy with another kind of energy or with another chemical system.
Wink, Donald J. J. Chem. Educ. 1992, 69, 108.
Reactions |
Thermodynamics |
Electrochemistry |
Photosynthesis
The bird-scarer (combustion) demo   Battino, Rubin; Arehart, James D.; Foot, Neville W.; Stott, James B.
This is a demonstration version of a device used to scare birds with loud noises occurring at regular intervals.
Battino, Rubin; Arehart, James D.; Foot, Neville W.; Stott, James B. J. Chem. Educ. 1992, 69, 64.
Reactions |
Oxidation / Reduction
An alternative proof that equilibrium concentrations for a chemical reaction are always uniquely determined by the initial concentrations  Glaister, P.
The principle used by the author says that, if a function changes sign in an interval, but its gradient does not change sign in that interval, than the function must vanish once and only once in the interval.
Glaister, P. J. Chem. Educ. 1992, 69, 51.
Equilibrium |
Reactions
Synthesis of trans-2-tert-butylcyclohexanol via hydroboration: A microscale organic experiment demonstrating syn addition  Wigal, Carl T.; Hopkins, William T.; Ronald, Bruce P.
This microscale experiment demonstrates the relative stereochemistry of the titled addition.
Wigal, Carl T.; Hopkins, William T.; Ronald, Bruce P. J. Chem. Educ. 1991, 68, A299.
Synthesis |
Microscale Lab |
Addition Reactions |
Aromatic Compounds |
Stereochemistry
Isomerization of dimethyl maleate to dimethyl fumarate: An undergraduate experiment illustrating amine-catalyzed alkene isomerization, stereochemical principles, sublimation, and product identification by spectroscopic methods  Fryhle, Craig B.; Rybak, Carol M.; Pulley, Kenneth E.
An undergraduate experiment illustrating amine-catalyzed alkene isomerization, stereochemical principles, sublimation, and product identification by spectroscopic methods.
Fryhle, Craig B.; Rybak, Carol M.; Pulley, Kenneth E. J. Chem. Educ. 1991, 68, 1050.
Amines / Ammonium Compounds |
Diastereomers |
Gas Chromatography |
NMR Spectroscopy |
Fourier Transform Techniques |
Catalysis
Spontaneous detonation of a mixture of two odd electron gases   Briggs, Thomas S.
Instructions for safe detonation of ClO2 and NO (the fastest known reaction between two stable molecules at room temperature).
Briggs, Thomas S. J. Chem. Educ. 1991, 68, 938.
Reactions |
Resonance Theory
A quick and effective demonstration of anti-Markovnikov addition to alkenes  Brown, Trevor M.; Dronsfield, Alan T.; Hitchcock, Ian
This reaction can be performed in less then 10 minutes and the product is easily identifiable.
Brown, Trevor M.; Dronsfield, Alan T.; Hitchcock, Ian J. Chem. Educ. 1991, 68, 785.
Alkenes |
Addition Reactions
A puzzle-solving experiment utilizing a Grignard reagent  Silversmith, Ernest F.
Puzzle-solving experiments get away from typical organic laboratories that involve more of a cookbook methodology.
Silversmith, Ernest F. J. Chem. Educ. 1991, 68, 688.
Grignard Reagents |
Addition 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
Recovery of silver from and some uses for waste silver chloride  Murphy, J. A.; Ackerman, A. H.; Heeren, J. K.
Procedures for conversion to silver nitrate, using waste AgCl as an oxidizing agent, and electrodepositon experiments.
Murphy, J. A.; Ackerman, A. H.; Heeren, J. K. J. Chem. Educ. 1991, 68, 602.
Reactions |
Oxidation / Reduction |
Electrochemistry
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
The diverse nature of the C6H6 molecule  Potgeiter, J. H.
The purpose of this discussion is to show that C6H6 describes more than just one kind of benzene.
Potgeiter, J. H. J. Chem. Educ. 1991, 68, 280.
Aromatic Compounds |
Alkenes |
Reactions |
Constitutional Isomers
Reaction Guide for Organic Chemistry (Millam, Michael J.)  Dimoplon, Gloria
Intended to aid students in developing an understanding of organic chemistry reactions.
Dimoplon, Gloria J. Chem. Educ. 1990, 67, A311.
Reactions |
Enrichment / Review Materials
Organic Nomenclature (Lampman, Gary)  Damey, Richard F.
An interactive tutorial / drill for naming organic compounds.
Damey, Richard F. J. Chem. Educ. 1990, 67, A220.
Nomenclature / Units / Symbols |
Enrichment / Review Materials |
Alkanes / Cycloalkanes |
Alkenes |
Alkynes |
Ethers |
Alcohols |
Amines / Ammonium Compounds |
Phenols
Picture biochemistry: A puzzle  Helser, Terry L.
A rebus puzzle of three biochemical equations.
Helser, Terry L. J. Chem. Educ. 1990, 67, 1062.
Reactions
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
Preparation of 1-phenyl-3-phenylaminopyrrolidine-2,5-dione: An organic laboratory experiment on the Michael addition  Ram, Ram N.; Varsha, Kiran
Acylation of aniline with maleic anhydride to give maleanilic acid followed by Michael addition of aniline and cyclization to yield 1-phenyl-3-phenylaminopyrrolidine-2,5-dione.
Ram, Ram N.; Varsha, Kiran J. Chem. Educ. 1990, 67, 985.
Addition Reactions |
Aldehydes / Ketones |
Synthesis
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
Reaction of bromine with hydrocarbons on the overhead, real or simulated  Solomon, Sally; Gregory, Michael; Padmanabhan, Sandeep; Smith, Kurt
A simulation that looks like the addition of bromine to hydrocarbons but is not (the bromine is simulated using a mixture of food colorings).
Solomon, Sally; Gregory, Michael; Padmanabhan, Sandeep; Smith, Kurt J. Chem. Educ. 1990, 67, 961.
Alkanes / Cycloalkanes |
Aromatic Compounds |
Addition Reactions
The H2 + Cl2 explosion as a chemical analogue of the photoelectric effect: A true quantum mechanical demonstration  Knox, Kerro
The photochemical hydrogen-chlorine reaction affords a good example of the quantum aspect of light and its interaction with matter.
Knox, Kerro J. Chem. Educ. 1990, 67, 897.
Reactions |
Quantum Chemistry |
Photochemistry
Effects of "crowding" in protein solutions  Ralston, G. B.
The effects of macromolecular nonideality and crowding on chemical equilibria, association reactions, and enzyme kinetics.
Ralston, G. B. J. Chem. Educ. 1990, 67, 857.
Proteins / Peptides |
Equilibrium |
Reactions |
Enzymes |
Kinetics
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
A catalog of reactions for general chemistry  Tykodi, R. J.
A catalog of chemical reactions intended to help students understand what kinds of chemical reactions commonly occur and why.
Tykodi, R. J. J. Chem. Educ. 1990, 67, 665.
Reactions |
Descriptive Chemistry
Avoid misleading the students  Rich, Ronald L.
Chemists have a long-standing habit, misleading at least to students, of saying that strong bases produce acids in various reactions.
Rich, Ronald L. J. Chem. Educ. 1990, 67, 629.
Acids / Bases |
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
A bromate clock reaction: The formation of purple tris(diphosphato)manganate(III)  Rich, Ronald L.; Noyes, Richard M.
Bromate is used to oxidize nearly colorless Mn(II) to a deep purple complex of Mn(III).
Rich, Ronald L.; Noyes, Richard M. J. Chem. Educ. 1990, 67, 606.
Reactions |
Oxidation / Reduction |
Kinetics
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
Are the equilibrium concentrations for a chemical reaction always uniquely determined by the initial concentrations?  Weltin, E.
A question not often addressed is whether the equilibrium concentrations for a given set of initial concentrations are always unique, or for some complex reaction and initial conditions is it possible for more than one set of chemically meaningful equilibrium concentrations to be satisfied?
Weltin, E. J. Chem. Educ. 1990, 67, 548.
Equilibrium |
Reactions
The cadmium-sodium nitrate reaction  Hill, William D., Jr.
A reaction involving lead and sodium nitrate prompted the idea to try reacting cadmium and sodium nitrate with the anticipation of producing cadmium oxide.
Hill, William D., Jr. J. Chem. Educ. 1990, 67, 529.
Quantitative Analysis |
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
Simple, inexpensive glass reactors for high-temperature aqueous kinetics experiments  Jeffers, Peter M.
The authors have devised methods to make, fill, and seal gas bulbs that have been subsequently heated to 200 degrees Celcius for kinetics studies of hydrolysis reactions.
Jeffers, Peter M. J. Chem. Educ. 1990, 67, 522.
Reactions |
Laboratory Equipment / Apparatus |
Kinetics
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
The kinetics of isotopic exchange reactions  Logan, S. R.
An isotopic exchange reaction progress toward equilibrium follows an equation comparable to that applicable to many reversible isomerization reactions.
Logan, S. R. J. Chem. Educ. 1990, 67, 371.
Kinetics |
Isotopes |
Reactions |
Equilibrium
A small scale equilibrium experiment   Flash, Patrick
An alternative method for the experiment in which the equilibrium constant for the iron-thiocyanate complex is determined.
Flash, Patrick J. Chem. Educ. 1990, 67, 341.
Equilibrium |
Reactions
A chemiluminescent ammonia fountain   Thomas, Nicholas C.
Two popular and dramatic demonstrations offered to student audiences that virtually guarantee their undivided attention are the ammonia fountain and chemiluminescence experiments.
Thomas, Nicholas C. J. Chem. Educ. 1990, 67, 339.
Amines / Ammonium Compounds
The pitfalls of precipitation reactions   Slade, Peter W.; Rayner-Canham, Geoffrey W.
This is an overview of specific equilibria problems in precipitation reactions.
Slade, Peter W.; Rayner-Canham, Geoffrey W. J. Chem. Educ. 1990, 67, 316.
Precipitation / Solubility |
Reactions
Graphic characterization and taxonomy of organic reactions  Fujita, Shinsaku
This paper deals with the substructures of imaginary transition structures as one of the integrated systems for representing organic reactions.
Fujita, Shinsaku J. Chem. Educ. 1990, 67, 290.
Mechanisms of Reactions
An omission   Quellette, Robert J.
Melvin S. Newman's model was overlooked in an article on the SN2 mechanism.
Quellette, Robert J. J. Chem. Educ. 1990, 67, 277.
Mechanisms of Reactions
Photohydration of pyridine: Modification of an undergraduate kinetics experiment  Morine, Gerald H.
In a previous article in this Journal an undergraduate experiment on photochemical kinetics was presented. This author is offering modifications to the original experiment.
Morine, Gerald H. J. Chem. Educ. 1990, 67, 266.
Photochemistry |
Kinetics |
Aromatic Compounds |
Amines / Ammonium Compounds |
Heterocycles
The hydrolysis of salts derived from a weak monoprotic acid and a weak monoprotic base  Cardinali, Mario Emilio; Giomini, Claudio; Marrosu, Giancarlo
The limitations as well as the conditions under which this simplified approach to the hydrolysis of salts from a weak acid and a weak base can yield almost exact results are discussed.
Cardinali, Mario Emilio; Giomini, Claudio; Marrosu, Giancarlo J. Chem. Educ. 1990, 67, 221.
Acids / Bases |
Reactions
The extent of acid-base reactions  Thompson, Ralph J.
How to calculate the equilibrium constant of an acid-base reaction.
Thompson, Ralph J. J. Chem. Educ. 1990, 67, 220.
Acids / Bases |
Reactions |
Equilibrium
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
Chemical Reactions, Reactions in Aqueous Solution, and Oxidation Reduction Reactions, Review II (Weyh, J. A.; Crook, J. R.; Hauge, L. N.)  Coleman, William F.
Programs intended to provide students with drill and practice in equation writing (including formula writing), equation balancing, and reaction predicting.
Coleman, William F. J. Chem. Educ. 1989, 66, A172.
Reactions |
Aqueous Solution Chemistry |
Oxidation / Reduction |
Enrichment / Review Materials
Chemical Reactions, Reactions in Aqueous Solution, and Oxidation Reduction Reactions, Review I (Weyh, J. A.; Crook, J. R.; Hauge, L. N.)  Balahura, Robert J.
Programs intended to provide students with drill and practice in equation writing (including formula writing), equation balancing, and reaction predicting.
Balahura, Robert J. J. Chem. Educ. 1989, 66, A172.
Reactions |
Aqueous Solution Chemistry |
Oxidation / Reduction |
Enrichment / Review Materials
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
The Logichem Organic Inference Program (Burden, F.R.)  Mahaffy, Peter G.
The Logichem Organic Inference Progarm is designed to provide a data base of reactions between organic chemicals.
Mahaffy, Peter G. J. Chem. Educ. 1989, 66, A129.
Reactions
Friedel Crafts acylation and alkylation with acid chlorides  Jarret, Ronald M.; Keil, Nora; Allen, Susan; Cannon, Lisa; Coughlan, Julie; Cusumano, Leonarda; Nolan, Brian
A shortened Friedel-Crafts experiment; the extra time available allows for additional experiments designed to illustrate the finer points of the reaction, such as electrophile rearrangements and decarbonylation of acyl cations.
Jarret, Ronald M.; Keil, Nora; Allen, Susan; Cannon, Lisa; Coughlan, Julie; Cusumano, Leonarda; Nolan, Brian J. Chem. Educ. 1989, 66, 1056.
Electrophilic Substitution |
Aromatic Compounds |
Mechanisms of Reactions |
Microscale Lab
Reaction intermediates in organic chemistry: A colorful demonstration  Novaki, Luzia P.; Brotero, Paula P.; El Seoud, Omar A.
Demonstration in which the reactant, intermediates, and the final product have intense and different colors.
Novaki, Luzia P.; Brotero, Paula P.; El Seoud, Omar A. J. Chem. Educ. 1989, 66, 1040.
Reactive Intermediates |
Mechanisms of Reactions
A study of the E2 reaction for the microscale organic lab  Flash, Patrick; Galle, Fred; Radil, Mark
Students determine the pseudo-first-order rate constant for the elimination of HBr from 2-bromobutane and measure the yield and approximate composition of the alkene products, determine the yield of alkenes from 1-bromobutane under the same conditions, and examine the effect of changing solvent polarity on alkene yields for the two halides.
Flash, Patrick; Galle, Fred; Radil, Mark J. Chem. Educ. 1989, 66, 958.
Elimination Reactions |
Mechanisms of Reactions |
Rate Law |
Kinetics
A Diels-Alder reaction for the overhead projector  Kolb, Kenneth E.
Reacting the strong dienophile tetracyanothylene with anthracene as the diene.
Kolb, Kenneth E. J. Chem. Educ. 1989, 66, 955.
Alkenes |
Mechanisms of Reactions
Oxidation of cyclohexanol - An amoebalike reaction  Kolb, Kenneth E.; Kolb, Doris
Cyclohexanol is oxidized to cyclohexanone.
Kolb, Kenneth E.; Kolb, Doris J. Chem. Educ. 1989, 66, 955.
Oxidation / Reduction |
Alcohols |
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
On a Reaction Involving Oxygen and Metal Sulfides  Hill, William D., Jr.
The role of iron(III) oxide as a catalyst in the production of oxygen by the thermal decomposition of potassium chlorate promoted the idea to use this oxide to repeat the reactions involving oxygen and the metal sulfides described in an earlier article.
Hill, William D., Jr. J. Chem. Educ. 1989, 66, 448.
Catalysis |
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
A classroom demonstration of aliphatic substitution   Perina, Ivo; Mihanovic, Branka
Substitution of an alkane by a halogen can be demonstrated effectively on the stage of an overhead projector using a compartmentalized Petri dish or a transparent Conway dish covered by a glass plate
Perina, Ivo; Mihanovic, Branka J. Chem. Educ. 1989, 66, 257.
Reactions |
Alkanes / Cycloalkanes
Availability of video tape to clarify the method of standard abbreviations  Williams, Kathryn R.
The method of standard addition is recognized as an important calibration technique in instrumental analysis.
Williams, Kathryn R. J. Chem. Educ. 1989, 66, 247.
Calibration |
Addition Reactions |
Instrumental Methods
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
A series of synthetic organic experiments demonstrating physical organic principles  Sayed, Yousry; Ahlmark, Chris A.; Martin, Ned H.
The sequence of reactions described here incorporates several common synthetic organic transformations involving alkenes, alcohols, alkyl halides, and ketones that demonstrate some important principles of physical organic chemistry.
Sayed, Yousry; Ahlmark, Chris A.; Martin, Ned H. J. Chem. Educ. 1989, 66, 174.
Synthesis |
Alkenes |
Alcohols |
Aldehydes / Ketones |
Reactions
In pursuit of chemical literacy: A place for chemical reactions  Bond, Douglas
The author has described one method of implementing a course for nonscience majors in which an early and repeated exposure to chemical reactions in tandem with a set of scientific values is the key to approaching scientific literacy.
Bond, Douglas J. Chem. Educ. 1989, 66, 157.
Nonmajor Courses |
Reactions
Bromination of a hydrocarbon   Deck, Eva; Deck, Charles
The authors have developed a simple one-hour student experiment that demonstrates photochemical halogen substitution in a quantitative way using heptane, bromine, and water.
Deck, Eva; Deck, Charles J. Chem. Educ. 1989, 66, 75.
Reactions |
Photochemistry |
Quantitative Analysis |
Alkanes / Cycloalkanes
Determination of the relative rates of alkaline hydrolysis of esters by the method of competition  Paredes, Rodrigo; Gil, Jimmy; Ocampo, Pamela
A method is presented for further illustration of the electronic and steric factors in the saponification of selected groups of esters.
Paredes, Rodrigo; Gil, Jimmy; Ocampo, Pamela J. Chem. Educ. 1988, 65, 1109.
Esters |
Mechanisms of Reactions |
Kinetics
The synthesis of methyl salicylate: Amine diazotization.  Zanger, Murray; McKee, James R.
Unlike many organic chemistry labs, this experiment does not expose students to carcinogenics, nor does it smell bad.
Zanger, Murray; McKee, James R. J. Chem. Educ. 1988, 65, 1106.
Amines / Ammonium Compounds |
Aromatic Compounds
Shedding a new light on solubility calculations   Stolzberg, Richard J.
Precipitate formation, fractional precipitation and precipitate dissolution can be investigated in a series of lecture demonstrations suitable for general chemistry or quantitative analysis.
Stolzberg, Richard J. J. Chem. Educ. 1988, 65, 621.
Quantitative Analysis |
Amines / Ammonium Compounds |
Aqueous Solution Chemistry
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
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
Preparation of lead compounds: An exercise in applied chemistry  Laing, Michael; Williams-Wynn, David; Suhramoney, Saroj
Uses and synthesis of Pb(NO3)2, PbO2, PbCrO4, PbS, PbO, lead carbonate, lead acetate, and lead metal itself.
Laing, Michael; Williams-Wynn, David; Suhramoney, Saroj J. Chem. Educ. 1987, 64, 811.
Synthesis |
Metals |
Oxidation / Reduction |
Oxidation State |
Reactions |
Descriptive Chemistry
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
A spectacular demonstration: 2H2 + O2 -> 2H2O  Skinner, James F.
Detonating hydrogen in a copper combustion chamber.
Skinner, James F. J. Chem. Educ. 1987, 64, 545.
Reactions |
Free Radicals
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
Spectroscopic analysis using the near-infrared region of the electromagnetic spectrum  Crandall, Elbert W.
Review of the use of near-IR to study simple compounds (amines, hydroxyl, and carbonyl compounds) and polymers.
Crandall, Elbert W. J. Chem. Educ. 1987, 64, 466.
Spectroscopy |
IR Spectroscopy |
Amines / Ammonium Compounds |
Alcohols |
Molecular Properties / Structure
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
A safe, convenient method of generating bromine for qualitative analysis  Slayden, Suzauee W.; Do, Thuy H.; Smiley, Kimberly Y.; Nelson, Donna J.
A safe, convenient method of generating bromine used as a qualitative test for unsaturation, active methylene groups, phenols, and amines.
Slayden, Suzauee W.; Do, Thuy H.; Smiley, Kimberly Y.; Nelson, Donna J. J. Chem. Educ. 1987, 64, 368.
Qualitative Analysis |
Alkenes |
Phenols |
Amines / Ammonium Compounds |
Laboratory Management
Introduction to overhead projector demonstrations  Kolb, Doris
General suggestions for using the overhead projector and 21 demonstrations. [Debut]
Kolb, Doris J. Chem. Educ. 1987, 64, 348.
Rate Law |
Reactions |
Catalysis |
Equilibrium |
Transition Elements |
Metals |
Oxidation / Reduction |
Acids / Bases
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 arsenic(III) sulfide clock reaction  Watkins, Kenneth W.
Two colorless solutions, one containing sodium arsenite and acetic acid and the other containing sodium thiosulfate are mixed in a beaker; after about 20 seconds, the mixture turns a brilliant yellow color. This clock reaction is well suited for determining the order of reaction and the activation energy.
Watkins, Kenneth W. J. Chem. Educ. 1987, 64, 255.
Reactions
An organic synthesis program for allied health chemistry  Flash, Patrick
81. Bits and pieces, 33. Organic Reactions Chemistry was written to aid allied health students in learning and codifying organic reactions.
Flash, Patrick J. Chem. Educ. 1987, 64, 238.
Synthesis |
Medicinal Chemistry |
Nonmajor Courses |
Reactions |
Enrichment / Review Materials
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
Voltammetric monitoring of Br- and Br3- concentrations during the bromination of styrene by Br3-: A laboratory experiment  Desbene Monvernay, Annie; Berthelot, Jacques; Desbene, Paul-Louis
Electrochemical titration of Br- and Br3- and voltammetric monitoring of styrene bromination by TBEBr3.
Desbene Monvernay, Annie; Berthelot, Jacques; Desbene, Paul-Louis J. Chem. Educ. 1987, 64, 86.
Electrochemistry |
Titration / Volumetric Analysis |
Alkenes |
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
Inorganic fireflies - A chemiluminescent clock reaction  Jones, Peter; Frew, Jane E.; Scowen, Nina
Adaptation of a clock reaction to illustrate the application to flow methods in the study of fast reactions and the release of carbon dioxide from the bloodstream in respiration.
Jones, Peter; Frew, Jane E.; Scowen, Nina J. Chem. Educ. 1987, 64, 70.
Photochemistry |
Reactions |
Kinetics
The application of simultaneous electrochemical and spectral data in analyzing complex oscillating reactions  Geckle, David S.; Salmon, James F.
A coupling of the bromide ion and the redox state of cerium ion provides an interesting opportunity to apply simultaneous electrochemical and spectral analysis.
Geckle, David S.; Salmon, James F. J. Chem. Educ. 1986, 63, 908.
Electrochemistry |
Reactions |
Spectroscopy
Introducing plastic in the laboratory: Synthesis of a plasticizer, dioctylphthalate and evaluation of its effects on the physical properties of polystyrenes  Caspar, A.; Gillois, J.; Guillerm, G.; Savignac, M.; Vo-Quang, L.
These authors are proposing a two-stage experimental approach that combines preparative organic chemistry and polymer characterization.
Caspar, A.; Gillois, J.; Guillerm, G.; Savignac, M.; Vo-Quang, L. J. Chem. Educ. 1986, 63, 811.
Esters |
Reactions |
IR Spectroscopy |
UV-Vis Spectroscopy |
NMR Spectroscopy |
Mass Spectrometry |
Thin Layer Chromatography
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
An experiment of homogeneous catalysis  Frugoni, Juan A. Coch; Zepka, Marilene; Figueira, Alvaro Rocha; Campos, Ana Sabina
The experiment described in this article shows, by color changes, the chemical participation of the catalyst and its regeneration when the reaction is complete.
Frugoni, Juan A. Coch; Zepka, Marilene; Figueira, Alvaro Rocha; Campos, Ana Sabina J. Chem. Educ. 1986, 63, 549.
Catalysis |
Reactions
Relative activating ability of various ortho, para-directors  Zaezek, Norbert M.; Tyszkiewicz, Robert B.
The authors saw a need to develop an experiment for students to comprehensively learn about electrophilic aromatic substitution.
Zaezek, Norbert M.; Tyszkiewicz, Robert B. J. Chem. Educ. 1986, 63, 510.
Aromatic Compounds |
Reactions |
Diastereomers |
Stereochemistry
Michael addition and aldol condensation: A simple teaching model for organic laboratory  Garcia-Raso, A.; Garcia-Raso, J.; Sinisterra, J. V.; Mestres, R.
Three experiments are presented in this paper: Michael addition; Michael addition followed by aldol addition; and Michael addition followed by aldol condensation.
Garcia-Raso, A.; Garcia-Raso, J.; Sinisterra, J. V.; Mestres, R. J. Chem. Educ. 1986, 63, 443.
Addition Reactions |
Aldehydes / Ketones |
Alcohols
A multipurpose, dramatic combustion effect  Fenster, Ariel E.; Harpp, David N.; Dore, Marcel; Schwarcz, Joseph A.
A powerful demonstration on combustion that has been used in and out of the classroom is described in this note.
Fenster, Ariel E.; Harpp, David N.; Dore, Marcel; Schwarcz, Joseph A. J. Chem. Educ. 1986, 63, 349.
Reactions
Dangerous demos  Nagel, Miriam C.
The author questions the pedagogical value of demonstrations that pose great danger, such as reacting sodium and water.
Nagel, Miriam C. J. Chem. Educ. 1986, 63, 81.
Reactions
Musical mechanisms  Jones, Peter
Portraying the mechanism of the catalysis of hydrogen peroxide decomposition by catalase using an adaptation of musical notation.
Jones, Peter J. Chem. Educ. 1985, 62, 1093.
Catalysis |
Enzymes |
Mechanisms of Reactions
Doing the dishes: An analogy for use in teaching reaction kinetics  Last, Arthur M.
An analogy between doing dishes and a two-step reaction.
Last, Arthur M. J. Chem. Educ. 1985, 62, 1015.
Kinetics |
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
Uncertainty in establishing a reaction intermediate  Martin, R. Bruce
Shows the difficulty of proving that a compound whose concentration passes through a maximum is necessarily an intermediate on the pathway from initial reactants to products.
Martin, R. Bruce J. Chem. Educ. 1985, 62, 789.
Reactions
New stoichiometry for copper dissolution in nitric acid  El-Cheikh, F. M.; Khalil, S. A.; El-Manguch, M. A.; Omar, Hadi A.
NO2 does not appear to be a primary product in the oxidation of copper metal by nitric acid.
El-Cheikh, F. M.; Khalil, S. A.; El-Manguch, M. A.; Omar, Hadi A. J. Chem. Educ. 1985, 62, 761.
Reactions |
Stoichiometry |
Oxidation / Reduction
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
"Name that product"-A lively organic chemistry review  Mattern, Daniell Lewis
A review activity in which students reveal a hidden reaction on the overhead by answering individual questions regarding various topics; once the hidden reaction is revealed, they must determine its product.
Mattern, Daniell Lewis J. Chem. Educ. 1985, 62, 476.
Reactions |
Enrichment / Review Materials
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
The Fe(II)-Cr(VI) reaction without using mercury  Klett, Lee D.; Black, Arthur H.; Parker, Gordon A.
Procedure that employs titanium rather than mercury in the oxidation-reduction titration of iron(II) with chromium(VI).
Klett, Lee D.; Black, Arthur H.; Parker, Gordon A. J. Chem. Educ. 1984, 61, 1020.
Reactions |
Oxidation State |
Oxidation / Reduction |
Metals
How to get the most from the dichromate volcano demonstration: Aluminothermy  Trogler, William C.
Reducing the green ash produced by the dichromate volcano (Cr2O3) with aluminum in a thermite-like display.
Trogler, William C. J. Chem. Educ. 1984, 61, 908.
Reactions |
Oxidation / Reduction
Synthesis and testing of the insecticide carbaryl  Thadeo, Peter F.; Mowery, Dwight F.
Carbaryl, 1-naphthyl-N-methylcarbamate, is synthesized from alpha-naphthol and triethylamine.
Thadeo, Peter F.; Mowery, Dwight F. J. Chem. Educ. 1984, 61, 742.
Synthesis |
Applications of Chemistry |
Aromatic Compounds |
Amines / Ammonium Compounds
The thermite reaction: A chemical ground breaking  Eastland, George W., Jr.
Technique for initiating the thermite reaction at a safe distance.
Eastland, George W., Jr. J. Chem. Educ. 1984, 61, 723.
Reactions
Photon-initiated hydrogen-chloride reaction: Improvements on a lecture demonstration  Ramette, R. W.
Improvements to the photon-initiated reaction between hydrogen and chlorine gas - the gas mixture is generated by the electrolysis of 8 M HCl.
Ramette, R. W. J. Chem. Educ. 1984, 61, 722.
Photochemistry |
Reactions
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
Teaching of chemical reactions and syntheses  Basolo, Fred
We are obliged to teach students some fundamental reactions that all chemists should know.
Basolo, Fred J. Chem. Educ. 1984, 61, 520.
Reactions |
Synthesis
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
A quick and simple conversion of carboxylic acids into their anilides of heating with phenyl isothiocyanate  Ram, Ram N.; Kumar, Pradeep; Mukerjee, Arya K.
In this article, the authors report a quick and easy procedure using phenyl isothiocyanate, which is ideally suited to students.
Ram, Ram N.; Kumar, Pradeep; Mukerjee, Arya K. J. Chem. Educ. 1983, 60, 508.
Carboxylic Acids |
Aromatic Compounds |
Phenols |
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
Structure elucidation of a natural product  Letcher, Roy M.
This experiment is an attempt to simulate a real-life structure elucidation problem through the isolation, characterization, and chemical transformation of an unknown naturally occurring monoterpene, with extensive use being made of spectroscopy and aided by biogenetic considerations.
Letcher, Roy M. J. Chem. Educ. 1983, 60, 79.
Natural Products |
Separation Science |
NMR Spectroscopy |
UV-Vis Spectroscopy |
Reactions
Organic chemicals from carbon monoxide  Kolb, Kenneth E.; Kolb, Doris
Looking at organic chemicals and their reactions with carbon monoxide has a great pedagogical value.
Kolb, Kenneth E.; Kolb, Doris J. Chem. Educ. 1983, 60, 57.
Synthesis |
Reactions
Spontaneous combustion of familiar substances in chlorine  Briggs, Thomas S.
Reacting chlorine generated from liquid bleach with red phosphorus (from a match book) and iron from steel wool.
Briggs, Thomas S. J. Chem. Educ. 1982, 59, 788.
Reactions |
Oxidation / Reduction
Isobutylene revisited: An experiment introducing both qualitative and quantitative application of NMR spectroscopy  Tremelling, Michael J.; Hammond, Christina N.
The product distribution is a contradiction to the general rule that the more highly substituted alkene is more stable.
Tremelling, Michael J.; Hammond, Christina N. J. Chem. Educ. 1982, 59, 697.
Alkenes |
NMR Spectroscopy |
Addition Reactions |
Molecular Properties / Structure
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
An easily conducted free radical substitution for organic chemistry courses  Pavlis, Robert R.
The photobromination of 1,2-diphenylethane into its dibromo derivative, (2R) (3S) 1,2-dibromo-1,2-diphenylethane.
Pavlis, Robert R. J. Chem. Educ. 1982, 59, 658.
Free Radicals |
Reactions |
Molecular Properties / Structure |
Stereochemistry |
Diastereomers |
Photochemistry |
Alkanes / Cycloalkanes |
Aromatic Compounds
Reactions between chiral molecules: A handy analogy  Richardson, W. S.
Simulating a reaction between R and S structures through the shaking of hands.
Richardson, W. S. J. Chem. Educ. 1982, 59, 649.
Chirality / Optical Activity |
Molecular Properties / Structure |
Enantiomers |
Reactions
Pi bonding without tears  Akeroyd, F. Michael
A non-mathematical treatment of sigma-pi bonding applied to conjugation, hyperconjugation, Markovnikoff addition, aromaticity, and aromatic substitution.
Akeroyd, F. Michael J. Chem. Educ. 1982, 59, 371.
Alkenes |
Mechanisms of Reactions |
Addition Reactions |
Aromatic Compounds
The problem of syn- versus anti-addition: An organic chemistry laboratory experiment  Silversmith, Ernest F.
An experiment that allows a student to determine whether an addition to a carbon-carbon double bond proceeds in syn- or anti-fashion.
Silversmith, Ernest F. J. Chem. Educ. 1982, 59, 346.
Addition Reactions |
Mechanisms of Reactions |
Molecular Properties / Structure |
Stereochemistry |
Synthesis |
Alkenes
The analysis of an amine mixture: An introductory analysis experiment  Williams, T. R.
Analysis of a binary mixture of amines in which students are asked to identify each component and determine the weight percentage of each compound.
Williams, T. R. J. Chem. Educ. 1982, 59, 202.
Amines / Ammonium Compounds |
Qualitative Analysis |
Quantitative Analysis
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
Amperometric determination of phenol bromination kinetics  Cohen, R.; Matzek, C.; Schlosser, S.; Huber, C. O.
A laboratory that allows students to explore bromination substitution reactions as examples of important non-aqueous solution kinetics including the role of a catalyst, the relationship between rate laws and mechanisms, and acid-base properties.
Cohen, R.; Matzek, C.; Schlosser, S.; Huber, C. O. J. Chem. Educ. 1981, 58, 823.
Acids / Bases |
Kinetics |
Catalysis |
Electrochemistry |
Reactions
Conjugate and nonconjugate reduction with LiAlH4 and NaBH4  Meyer, G. Richard
Most organic textbooks present a limited consideration of the action of lithium aluminum hydride and sodium borohydride. This paper explores the topic in greater depth.
Meyer, G. Richard J. Chem. Educ. 1981, 58, 628.
Oxidation / Reduction |
Reactions
Preparation of solid derivatives by differential scanning calorimetry  Crandall, E. W.; Pennington, Maxine
Derivatives of alcohols, amines, phenols, aldehydes, ketones, and haloalkanes are prepared and their phase transitions observed using a differential scanning calorimeter.
Crandall, E. W.; Pennington, Maxine J. Chem. Educ. 1980, 57, 824.
Phases / Phase Transitions / Diagrams |
Aldehydes / Ketones |
Alcohols |
Amines / Ammonium Compounds |
Phenols |
Physical Properties |
Calorimetry / Thermochemistry
Systematic inorganic reaction chemistry: Inorganic reaction types, general methods of synthesis, and the periodic table  Basolo, Fred
It is possible to teach inorganic reactions and syntheses without students having to memorize specific reactions and without the lectures being dull.
Basolo, Fred J. Chem. Educ. 1980, 57, 761.
Reactions |
Synthesis |
Periodicity / Periodic Table |
Descriptive Chemistry
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
The effect of free radical stability on the rate of bromination of hydrocarbons  Doheny, Anthony J.; Loudon, G. Marc
The effect of alkyl free radical stability on the rate of free radical halogenation of hydrocarbons can be convincingly demonstrated by the comparative photobromination of the arenes toluene, ethylbenzene, and cumene.
Doheny, Anthony J.; Loudon, G. Marc J. Chem. Educ. 1980, 57, 507.
Free Radicals |
Reactions |
Alkanes / Cycloalkanes |
Photochemistry |
Molecular Properties / Structure
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
Rossini, William Tell and the iodine clock reaction: A lecture demonstration  Brice, L. K.
The iodine clock reaction is timed to coincide with three portions of the William Tell Overture.
Brice, L. K. J. Chem. Educ. 1980, 57, 152.
Reactions |
Kinetics |
Rate Law
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
Bent thermometer  Smith, Douglas D.
Reducing the breakage of thermometers, using CO2 as an insecticide, and improving the demonstration of the reaction between sodium and water.
Smith, Douglas D. J. Chem. Educ. 1979, 56, 742.
Laboratory Management |
Applications of Chemistry |
Metals |
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 thermite lecture demonstration  Bozzelli, Joseph W.; Barat, Robert B.
Glycerine plus KMnO4 are used to ignite the thermite in a clay flower pot.
Bozzelli, Joseph W.; Barat, Robert B. J. Chem. Educ. 1979, 56, 675.
Reactions |
Oxidation / Reduction
"Invitation to enquiry": The Fe3+/CNS- equilibrium  Driscoll, D. R.
Adding NH4Cl should not affect the position of the reaction equilibrium, but it does. Why?
Driscoll, D. R. J. Chem. Educ. 1979, 56, 603.
Equilibrium |
Reactions |
Aqueous Solution Chemistry
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
Chemical toxicology. Part I. Organic compounds  Carter, D. E.; Fernando, Quintus
General principles of toxicology, and particular consideration of aliphatics, aromatic, and halogenated hydrocarbons; alcohols, aldehydes, esters, ethers, and ketones; sulfides, mercaptans, and carbon disulfide; nitrogen-containing compounds; and carcinogens.
Carter, D. E.; Fernando, Quintus J. Chem. Educ. 1979, 56, 284.
Toxicology |
Alcohols |
Aldehydes / Ketones |
Esters |
Ethers |
Aromatic Compounds |
Amines / Ammonium Compounds |
Lipids
Acid-base half-reactions - A useful formalism for review lessons  Atkinson, G. F.
An effective way to draw analogies between acid-base and redox effects while reviewing both.
Atkinson, G. F. J. Chem. Educ. 1979, 56, 238.
Oxidation / Reduction |
Reactions |
Acids / Bases |
Enrichment / Review Materials
A few chemical magic tricks based on the clock reaction  Shigematsu, Euchi
Three tricks based on the clock reaction involving KIO3 and NaHSO3.
Shigematsu, Euchi J. Chem. Educ. 1979, 56, 184.
Reactions |
Kinetics
Amides and hydrazides from amine and hydrazine hydrochlorides  Shama, Sami A.; Tran, Thuran L.
The Schotten-Baumann procedure is extensively used for the preparation of carboxylic acid derivatives in the undergraduate chemistry laboratory.
Shama, Sami A.; Tran, Thuran L. J. Chem. Educ. 1978, 55, 816.
Amines / Ammonium Compounds |
Carboxylic Acids |
Synthesis
Phase transfer catalysis: An interim project  Reeves, W. Preston
The authors have found that experiments in phase transfer catalysis provide students with a very profitable interim project.
Reeves, W. Preston J. Chem. Educ. 1978, 55, 433.
Catalysis |
Amines / Ammonium Compounds |
Separation Science
Oxidation of primary alcohols to aldehydes with pyridinium chlorochromate. An organic chemistry experiment  Glaros, George
This organic chemistry experiment addresses a common misconception about aldehyde reactions.
Glaros, George J. Chem. Educ. 1978, 55, 410.
Alcohols |
Aldehydes / Ketones |
Reactions
Sodium nitroprusside reagent II-A solvent modification  Dougherty, Charles M.; Baumgarten, Reuben L.; Markowska, Maria; Battey, York C.
The authors report an improvement classification test for aliphatic and aryl amines.
Dougherty, Charles M.; Baumgarten, Reuben L.; Markowska, Maria; Battey, York C. J. Chem. Educ. 1978, 55, 341.
Qualitative Analysis |
Amines / Ammonium Compounds |
Catalysis
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
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
Quarternary ammonia salts: Some recent applications in organic synthesis  Varughese, Pothen
Presents a variety of applications for quarternary ammonia salts, including as reaction media, a reagent for mesylation, catalytic hydrogenation, and micellar and phase-transfer catalysis.
Varughese, Pothen J. Chem. Educ. 1977, 54, 666.
Synthesis |
Amines / Ammonium Compounds |
Micelles |
Catalysis
Selectivity and specificity in organic reactions  Ault, Addison
Distinguishes between various forms of selectivity and specificity (e.g. the us of and differences between stereoselective and stereospecific).
Ault, Addison J. Chem. Educ. 1977, 54, 614.
Reactions |
Stereochemistry |
Diastereomers |
Enantiomers |
Nomenclature / Units / Symbols
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
The Preparation of polyurethane foam: A lecture demonstration  Dirreen, Glen E.; Shakhashiri, Bassam Z.
A polyurethane foam is produced by forming a polyurethane polymer concurrently with a gas evolution process.
Dirreen, Glen E.; Shakhashiri, Bassam Z. J. Chem. Educ. 1977, 54, 431.
Reactions |
Polymerization
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
Experiments with electrophilic aromatic substitution reactions  Cox, B.; Kubler, D. G.; Wilson, C. A.
Comparing the bromination and nitration of benzene.
Cox, B.; Kubler, D. G.; Wilson, C. A. J. Chem. Educ. 1977, 54, 379.
Reactions |
Aromatic Compounds |
Electrophilic Substitution |
Stereochemistry |
Diastereomers
Belousov's oscillating reaction in acid medium other than sulfuric acid  Mishra, H. C.; Singh, C. M.
Reports of the existence of oscillatory phenomenon in the Mn+2 catalyzed reaction between citric acid and potassium bromate in phosphoric and nitric acids.
Mishra, H. C.; Singh, C. M. J. Chem. Educ. 1977, 54, 377.
Acids / Bases |
Reactions |
Catalysis
A Dramatic and relevant demonstration of ring strain  Kelly, T. Ross
Addition of the cyclobutane alpha-pinene to crystalline iodine results in an exceptionally exothermic reaction.
Kelly, T. Ross J. Chem. Educ. 1977, 54, 228.
Molecular Properties / Structure |
Alkanes / Cycloalkanes |
Reactions
The Old Nassau reaction  Alyea, Hubert N.
A description of the chemistry and history of the Old Nassau reactions.
Alyea, Hubert N. J. Chem. Educ. 1977, 54, 167.
Kinetics |
Reactions
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
Teaching aromaticity, conjugation, and enolization  Schambach, Robert A.
An understanding of the delocalization of electrons in organic compounds is central knowledge. In teaching undergraduates about aromaticity, conjugation, and enoliztion, this author has found it useful to present examples of compounds in which delocalization. Effects are sustained in the presence of potentially interfering saturated carbon atoms.
Schambach, Robert A. J. Chem. Educ. 1976, 53, 711.
Aromatic Compounds |
Reactions
Micelle catalysis of an aromatic substitution reaction  Corsaro, Gerald; Smith, J. K.
This article describes an experiment which demonstrates micelle catalysis.
Corsaro, Gerald; Smith, J. K. J. Chem. Educ. 1976, 53, 589.
Micelles |
Aromatic Compounds |
Reactions |
Catalysis
Molecular design of compounds via intermolecular Diels-Alder reactions  Mehta, Goverdhan
The Diels-Alder reaction involving a cycloaddition between a diene and dienophile is one of the most versatile and useful reactions in the armory of the synthetic organic chemists.
Mehta, Goverdhan J. Chem. Educ. 1976, 53, 551.
Synthesis |
Addition Reactions |
Aromatic Compounds
Organoboranes as alkylating agents  Kabalka, George W.; Baker, John D., Jr.; Neal, Gary W.
The authors wish to present two hydroboration-alkylation sequences which clearly demonstrate the synthetic utility of the organoboranes.
Kabalka, George W.; Baker, John D., Jr.; Neal, Gary W. J. Chem. Educ. 1976, 53, 549.
Alkylation |
Reactions
The Friedel-Crafts pathway to diarylcyclopropenones. An undergraduate organic experiment  Agranat, Israel; Tapuhi, Yitzhak
The authors describe a facile entry into the cyclopropenone series which may conveniently be practiced in an undergraduate organic chemistry laboratory.
Agranat, Israel; Tapuhi, Yitzhak J. Chem. Educ. 1976, 53, 531.
Aromatic Compounds |
Reactions
Grignard dehydration reactions. An undergraduate organic experiment.  Duty, Robert C.; Ryder, Bernard L.
In this laboratory, the authors have incorporated the Grignard reaction in a step-wise synthesis that has been successful in demonstrating several experimental and instrumental techniques.
Duty, Robert C.; Ryder, Bernard L. J. Chem. Educ. 1976, 53, 457.
Grignard Reagents |
Reactions |
Synthesis |
Alkenes
Preparation of phenanthridone. A multipurpose experiment for the organic laboratory  Hawbecker, Byron L.; Radovich, David A.; Tillotson, Loyal G.
It is desirable to have a series of multipurpose reactions available which can illustrate a variety of reaction types within a single, three hour lab period.
Hawbecker, Byron L.; Radovich, David A.; Tillotson, Loyal G. J. Chem. Educ. 1976, 53, 398.
Reactions |
Aromatic Compounds |
Aldehydes / Ketones
Two examples of programmed learning in inorganic chemistry  Kaufmann-Goetz, H.; Kaufmann, G.
This paper looks to described a program allowing students in inorganic chemistry to learn individually and requiring them to reflect and participate. They go on to demonstration a simulation of the kinetic study of a chemical reaction.
Kaufmann-Goetz, H.; Kaufmann, G. J. Chem. Educ. 1976, 53, 179.
Kinetics |
Reactions
Free-radical addition of tetrahalomethanes to [beta]-pinene. Experiments in organic chemistry  Kaye, Irving Allan; Odum, Robert A.
This laboratory provides a much needed learning opportunity about free-radicals.
Kaye, Irving Allan; Odum, Robert A. J. Chem. Educ. 1976, 53, 60.
Free Radicals |
Addition Reactions
The hydroboration-oxidation of alkenes. A convenient anti-Markownikoff hydration experiment  Kabalka, George W.; Hedgecock, Herbert C., Jr.
A hydroboration-oxidation sequence that relies on the borane dimethylsulfide complex as the hydroborating agent and trimethylamine-N-oxide dihydrate as the oxidizing agent.
Kabalka, George W.; Hedgecock, Herbert C., Jr. J. Chem. Educ. 1975, 52, 745.
Alkenes |
Oxidation / Reduction |
Addition Reactions
The Gabriel synthesis of benzylamine: An undergraduate organic experiment  Nigh, W. G.
The Gabriel synthesis involves the reaction of the conjugate base of phthalimide and an alkyl halide to give an alkyl phthalimide which is subsequently hydrolyzed to the primary alkyl amine; the reaction is important historically for the synthesis of pure primary amines uncontaminated by secondary or tertiary by-products.
Nigh, W. G. J. Chem. Educ. 1975, 52, 670.
Synthesis |
Aromatic Compounds |
Amines / Ammonium Compounds
Conversion of black and white prints to color in daylight. A demonstration lecture for general and organic courses  Wheeler, Thomas N.
A black and white print is converted to a full color print with the lights on; includes a detailed discussion of the chemical processes involved in the demonstration.
Wheeler, Thomas N. J. Chem. Educ. 1975, 52, 607.
Photochemistry |
Reactions |
Consumer Chemistry |
Dyes / Pigments |
Oxidation / Reduction
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
Aluminothermic reduction. An illustrative experiment  Espelund, A. W.
The thermite reaction can be made into a very illustrative experiment, involving some typical calculations in high-temperature physical chemistry.
Espelund, A. W. J. Chem. Educ. 1975, 52, 400.
Calorimetry / Thermochemistry |
Reactions |
Thermodynamics
Photolysis of a heterocyclic compound. An advanced undergraduate experiment  Jarrar, Adil A.
This experiment is adapted to suit an organic chemistry introduction course and may be introduced near the final stages when the students have acquired the ability to speculate about the mechanisms of the reactions involved. Students appreciated working with small quantities of beautifully crystalline solids.
Jarrar, Adil A. J. Chem. Educ. 1974, 51, 755.
Reactions |
Crystals / Crystallography |
Heterocycles
A novel photochemistry experiment using a Diels-Alder reaction  Nash, E. G.
The authors present a two-step experiment incorporating a novel, but general photochemical reaction that is rapid, does not require special equipment, and which yields an interesting product worthy of further study.
Nash, E. G. J. Chem. Educ. 1974, 51, 619.
Aromatic Compounds |
Reactions |
Photochemistry
Early theories of metal-ammines. A brief historical review from Graham to Claus (1837-1856)  Kauffman, George B.
This article considers the development of some earlier theories of the constitution of the most familiar coordination compounds: the metal-ammines-which led up to the classic paper of Carl Ernst Claus.
Kauffman, George B. J. Chem. Educ. 1974, 51, 522.
Coordination Compounds |
Amines / Ammonium Compounds |
Metals
Conversion of a primary alcohol to an alkyl halide via a tosylate intermediate  Wiseman, Park A.; Betras, Steve; Lindley, Barry
The experiment in this article was designed primarily for and has been performed successfully by sophomore chemistry majors.
Wiseman, Park A.; Betras, Steve; Lindley, Barry J. Chem. Educ. 1974, 51, 348.
Alcohols |
Alkylation |
Reactions |
Aromatic Compounds |
NMR Spectroscopy
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
Stereospecific thermal cycloadditions and catalyzed isomerizations: An organic laboratory project  Pasto, D. J.; Duncan, J. A.; Silversmith, E. F.
The authors have prepared a sequence of experiments for their undergraduate organic chemistry laboratory concerned with the preparation of cis and trans 1,4-diphenyl-2-butene-1,4diones, their cycloadditions reactions with cyclopentandiene, and with related isomerization reactions of both the sequence, which has met with much success experimentally, clearly and collectively demonstrates certain aspects of the concepts of thermodynamics, kinetics, and stereochemistry and photochemistry.
Pasto, D. J.; Duncan, J. A.; Silversmith, E. F. J. Chem. Educ. 1974, 51, 277.
Photochemistry |
Constitutional Isomers |
Addition Reactions
Some reactions of tungsten: A lecture demonstration  Nelson, D. L.; Reeves, R. R.; Richtol, H. H.
Several demonstrations involving reactions of tungsten.
Nelson, D. L.; Reeves, R. R.; Richtol, H. H. J. Chem. Educ. 1973, 50, 810.
Metals |
Reactions |
Oxidation / Reduction
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
Organic mah-jongg  Day, Alan S.
A game to aid the learning of reaction sequences in organic chemistry.
Day, Alan S. J. Chem. Educ. 1973, 50, 687.
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
An oscillating iodine clock  Briggs, Thomas S.; Rauscher, Warren C.
An oscillating iodine clock reaction that gives striking cyclic changes from colorless to gold to blue using simple reagents.
Briggs, Thomas S.; Rauscher, Warren C. J. Chem. Educ. 1973, 50, 496.
Reactions |
Kinetics
Synthesis of a photochromic benzothiazolinic spiropyran  Guglielmetti, R.; Meyer, R.; Dupuy, C.
The purpose of this type of experiment is to elucidate structure of the different compounds gradually prepared starting from reaction mechanisms and chiefly from spectroscopic data given perviously to students.
Guglielmetti, R.; Meyer, R.; Dupuy, C. J. Chem. Educ. 1973, 50, 413.
Photochemistry |
Synthesis |
Mechanisms of Reactions |
Molecular Properties / Structure
The phenomenon of synergism in the field of chemistry  Sunier, Arthur A.
Presents examples of synergism in chemistry and examines its underlying causes.
Sunier, Arthur A. J. Chem. Educ. 1972, 49, 805.
Reactions
A new method for learning organic reactions  Perlmutter, Howard D.; Kristol, David S.
Using wooden cubes in a game to help students learn organic reactions.
Perlmutter, Howard D.; Kristol, David S. J. Chem. Educ. 1972, 49, 793.
Reactions |
Mechanisms of Reactions |
Synthesis
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
Pseudo first-order kinetics  Corbett, John F.
A kinetic study of second-order reactions under first-order conditions can yield accurate second-order rate constants provided an empirical allowance is made for the depletion of the reactant in excess.
Corbett, John F. J. Chem. Educ. 1972, 49, 663.
Kinetics |
Reactions |
Rate Law
The gas phase free radical halogenation of hydrocarbons. An undergraduate experiment  Scala, Alfred A.
Investigates the photochemically initiated gas phase chlorination and bromination of lower hydrocarbons.
Scala, Alfred A. J. Chem. Educ. 1972, 49, 573.
Free Radicals |
Alkylation |
Reactions |
Electrochemistry |
Photochemistry
Passage of fruit flies through a hole. A model for a reversible chemical reaction  Runquist, Elizabeth A.; Runquist, Olaf
The passage of fruit flies through a single orifice provides an excellent model for illustrating the principles of equilibrium and chemical dynamics; the results are found to be temperature dependent and reproducible.
Runquist, Elizabeth A.; Runquist, Olaf J. Chem. Educ. 1972, 49, 534.
Reactions |
Equilibrium |
Kinetics |
Rate Law
Benzenesulfonyl chloride does react with tertiary amines. The Hinsberg test in proper prospective  Gambill, C. R.; Roberts, T. D.; Shechter, H.
Addresses the long standing myths that tertiary amines do not react with nitrous acid or benzylsulfonyl chloride.
Gambill, C. R.; Roberts, T. D.; Shechter, H. J. Chem. Educ. 1972, 49, 287.
Amines / Ammonium Compounds |
Qualitative Analysis
The preparation of 3-phenylanthranil. A sequential experiment for the undergraduate organic laboratory  Kenny, David H.; Strieter, Jeffrey C.
A sequence of reactions that can be completed by the average student over ten weeks and involves a Friedel-Crafts reaction and Hofmann rearrangement.
Kenny, David H.; Strieter, Jeffrey C. J. Chem. Educ. 1972, 49, 130.
Synthesis |
Reactions
Alkylations in organic chemistry  Mundy, Bradford P.
Examines some of the subtle factors involved in alkylations, including alkylations via enolates, alkylations via enamines, and alkylation of enolates derived from reduction of enone systems.
Mundy, Bradford P. J. Chem. Educ. 1972, 49, 91.
Synthesis |
Alkylation |
Aldehydes / Ketones |
Mechanisms of Reactions
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
Relative reactivates in free radical systems. An organic chemistry experiment  Hutchinson, Mary Jane; Mosha, Melvyn W.
An organic chemistry experiment which demonstrates the importance of reaction rates.
Hutchinson, Mary Jane; Mosha, Melvyn W. J. Chem. Educ. 1971, 48, 629.
Free Radicals |
Reactions |
Rate Law
Transannular carbene reactions. An intermediate organic laboratory experiment  Hecht, Stephen S.
The experiment described in this article has been used to integrate physical, organic, and inorganic chemistry and stresses the use of research techniques in understanding the relationship between structure and reactivity.
Hecht, Stephen S. J. Chem. Educ. 1971, 48, 340.
Spectroscopy |
Chromatography |
Aromatic Compounds |
Reactions |
Molecular Properties / Structure
Migratory aptitudes. An organic chemistry experiment  Zaczek, Norbert M.; Ruff, James C.; Jackewitz, Albert H.; Roswell, David F.
The authors share a set of reactions and analysis that illustrates to students not only a rearrangement reaction by also reinforces the concept of migratory aptitude discussed in the classroom.
Zaczek, Norbert M.; Ruff, James C.; Jackewitz, Albert H.; Roswell, David F. J. Chem. Educ. 1971, 48, 257.
Reactions
The stereospecific synthesis of trans-1,4-disubstituted cyclohexanes. An organic chemistry laboratory experiment  Monson, Richard S.
The authors present a synthetic experiment suitable for the introductory organic chemistry laboratory which the introductory organic chemistry laboratory which allows for the unambiguous preparation of trans-1,4-disubstituted cyclohexane derivatives from readily available starting materials.
Monson, Richard S. J. Chem. Educ. 1971, 48, 197.
Alkanes / Cycloalkanes |
Stereochemistry |
Reactions
Organic ion radical chemistry  Maler, Larry L.
This paper will briefly introduce ion radicals as a relatively new class of reactive intermediates.
Maler, Larry L. J. Chem. Educ. 1971, 48, 168.
Free Radicals |
Reactions
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
A color indicating time reaction  Chen, Philip S.
Combining solutions of sodium thoisulfate and ferric chloride produces a dramatic color change.
Chen, Philip S. J. Chem. Educ. 1970, 47, A784.
Reactions |
Oxidation / Reduction |
Aqueous Solution Chemistry
Catalysis demonstrations with Cr2O3  Briggs, Thomas S.
Cr2O3 is used as a catalyst in the oxidation of nonflammable substances such as glycerine and glacial acetic acid.
Briggs, Thomas S. J. Chem. Educ. 1970, 47, A206.
Oxidation / Reduction |
Reactions |
Catalysis
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
Autoxidation of benzoin  Chen, Philip S.
Benzoin in its enediol form undergoes autoxidation in alkaline solution in the presence of air.
Chen, Philip S. J. Chem. Educ. 1970, 47, A67.
Oxidation / Reduction |
Reactions
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
Statistical study of the influence of environment on the decomposition of sodium perborate  Fitzpatrick, Noel J.
Notes the availability of a series of experiments on the decomposition of sodium perborate in solution.
Fitzpatrick, Noel J. J. Chem. Educ. 1970, 47, 764.
Aqueous Solution Chemistry |
Reactions
Fluorine compounds as teaching aids in organic theory  Young, John A.
Fluorine compounds do obey the fundamental tenets of organic theory, but their frequent reversal of polarity, relative to hydrocarbon analogs, and the change in emphasis from a positive hydrogen ion to a negative fluoride ion allow the instructor to frame questions that demand reasoning rather than reiteration on the part of the student.
Young, John A. J. Chem. Educ. 1970, 47, 733.
Aromatic Compounds |
Mechanisms of Reactions
Donor-acceptor interactions in organic chemistry  Sunderwirth, S. G.
The purpose of this article is to aid teachers in making even more effective use of theoretical considerations in teaching organic chemistry; the primary objective is to emphasize the underlying principles that are common to the following four basic types of reactions: substitution, addition, elimination, and rearrangement.
Sunderwirth, S. G. J. Chem. Educ. 1970, 47, 728.
Reactions |
Mechanisms of Reactions |
Addition Reactions |
Elimination Reactions |
Nucleophilic Substitution
Simple method for demonstrating an enzymatic reaction  Tang, Chung-Shih
Uses taste sensations of papaya seeds under varying conditions to demonstrate an enzymatic reaction.
Tang, Chung-Shih J. Chem. Educ. 1970, 47, 692.
Enzymes |
Proteins / Peptides |
Food Science |
Reactions |
Consumer Chemistry |
Applications of Chemistry
The hexaphenylethane landmark falls  Smith, William B.
A reexamination of Gomberg's discovery that the treatment of triphenylmethyl chloride with silver results in hexaphenylethane has demonstrated that the dimer formed is not hexaphenylethane; a new product has been proposed.
Smith, William B. J. Chem. Educ. 1970, 47, 535.
Reactions |
Molecular Properties / Structure |
NMR Spectroscopy
Controlled potential electrolysis: An experiment for elementary quantitative analysis  Kennedy, John H; Adams, Frank
Iron(II), iodide, and arsenic(III) are oxidized and data recorded using the E-cell Data-Stor Unit, a small silver coulometer.
Kennedy, John H; Adams, Frank J. Chem. Educ. 1970, 47, 461.
Quantitative Analysis |
Electrochemistry |
Oxidation / Reduction |
Reactions
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
Demonstration of photochemistry and the dimerization and trapping of free radicals  Silversmith, Ernest F.
This demonstration uses simple equipment and involves a rapid, readily noticeable color change and also illustrates dimerization and the trapping of free radicals.
Silversmith, Ernest F. J. Chem. Educ. 1970, 47, 315.
Photochemistry |
Free Radicals |
Reactions
Preparation of lithium amalgam  Alexander, Jose; Rao, G. S. Krirshna
Lithium amalgam is useful in effecting Wurtz type intramolecular and intermolecular coupling reactions.
Alexander, Jose; Rao, G. S. Krirshna J. Chem. Educ. 1970, 47, 277.
Reactions |
Laboratory Management
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
Definition of reaction rate and the steady state assumption  Rasiel, Yecheskel; Freeman, Wade A.
Clarifies the definition of reaction rate and the steady state assumption.
Rasiel, Yecheskel; Freeman, Wade A. J. Chem. Educ. 1970, 47, 159.
Rate Law |
Reactions
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
Energy of activation  Idoux, John P.
Spinning a half sphere until it comes to a rest on its flat side serves as an analogy to a system of molecules that must acquire a certain amount of energy until they become products.
Idoux, John P. J. Chem. Educ. 1969, 46, A547.
Reactions
The oxidation of hydrazine by basic iodine solutions: A stoichiometric study  Cooper, J. N.; Ramette, R. W.
This experiment relies on an oxidation-reduction reaction for which a variety of products is energetically possible.
Cooper, J. N.; Ramette, R. W. J. Chem. Educ. 1969, 46, 872.
Stoichiometry |
Oxidation / Reduction |
Reactions
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
Group VI. The Sulfur Family D. Sulfur Dioxide  Alyea, Hubert N.
Seven demonstrations involving sulfur dioxide.
Alyea, Hubert N. J. Chem. Educ. 1968, 45, A977.
Phases / Phase Transitions / Diagrams |
Reactions |
Precipitation / Solubility |
Oxidation / Reduction
Nitrogen chemistry. C. Fixation of nitrogen  Mancuso, Carl J.
Demonstrations include air + Al-amalgam; the arc process for NO2; and the Ostwald process: NH3 + O2 and NO to HNO3.
Mancuso, Carl J. J. Chem. Educ. 1968, 45, A567.
Agricultural Chemistry |
Reactions
The kinetics of oxidation-reduction reactions: An alternate derivation of Marcus' cross relation  Newton, T. W.
The purpose of this article is to show how Marcus' cross relation can be derived from a simple, essentially mechanical model.
Newton, T. W. J. Chem. Educ. 1968, 45, 571.
Kinetics |
Oxidation / Reduction |
Reactions
Hofmann elimination  Lyle, Robert E.
Clarification regarding the products of Hofmann elimination reactions.
Lyle, Robert E. J. Chem. Educ. 1968, 45, 547.
Elimination Reactions |
Mechanisms of Reactions |
Receptors
Mechanisms of oxidation-reduction reactions  Taube, Henry
Examines the mechanisms of oxidation-reduction reactions.
Taube, Henry J. Chem. Educ. 1968, 45, 452.
Mechanisms of Reactions |
Oxidation / Reduction |
Reactions |
Oxidation State |
Coordination Compounds
Why does methane burn?  Sanderson, R. T.
A thermodynamic explanation for why methane burns.
Sanderson, R. T. J. Chem. Educ. 1968, 45, 423.
Thermodynamics |
Reactions |
Oxidation / Reduction |
Calorimetry / Thermochemistry |
Covalent Bonding |
Ionic Bonding
Bimolecular nucleophilic displacement reactions  Edwards, John O.
The bimolecular nucleophilic displacement reaction is important and should be included in any detailed discussion of kinetics and mechanism at an early undergraduate level.
Edwards, John O. J. Chem. Educ. 1968, 45, 386.
Reactions |
Nucleophilic Substitution |
Kinetics |
Mechanisms of Reactions
From stoichiometry and rate law to mechanism  Edwards, John O.; Greene, Edward F.; Ross, John
Examines the rules used by chemists as guidelines in developing mechanisms from stoichiometric and rate law observations.
Edwards, John O.; Greene, Edward F.; Ross, John J. Chem. Educ. 1968, 45, 381.
Stoichiometry |
Rate Law |
Kinetics |
Mechanisms of Reactions |
Equilibrium |
Reactive Intermediates
The Eschweiler-Clark methylation of amines: An organic chemistry experiment  Pine, Stanley H.
In this procedure, benzylamine is converted to N,N-dimethylbenzylamine.
Pine, Stanley H. J. Chem. Educ. 1968, 45, 118.
Amines / Ammonium Compounds |
Synthesis
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
Is there a neutral ammonium radical?  Wan, J. K. S.
Examines theoretical considerations and experimental approaches regarding the generation of a neutral NH4 molecule.
Wan, J. K. S. J. Chem. Educ. 1968, 45, 40.
Amines / Ammonium Compounds
Reaction Rates and Equilibria A. Rate of Reaction 1. Effect of concentration  Cooper, Edwin H., Alyea, Hubert N.
Demonstrations of the effect of concentration on the rate of a reaction include H2O2+Cu(NH3)4++, Zn+acid, and the "long delay" iodine clock reaction.
Cooper, Edwin H., Alyea, Hubert N. J. Chem. Educ. 1967, 44, A274.
Reactions |
Rate Law |
Kinetics
Group 1. The Alkali Metals B. The Alkali Metals. Ammonium ion  Young, James A.
Demonstration of the formation of an ammonium amalgam.
Young, James A. J. Chem. Educ. 1967, 44, A1005.
Amines / Ammonium Compounds
Energy C. Electrical Energy  Soule, Dean; Hornbeck, Leroy G.; Jackson, Kenneth V.; Barnard, Robert; Noerdin, Isjrin
Demonstrations include aluminum flashed in oxygen; photo-bromination of cinnamic acid, hexane, tartaric acid, toluene; photochemical H2+Cl2 explosion and the slow photochemical H2+Cl2 into 2HCl.
Soule, Dean; Hornbeck, Leroy G.; Jackson, Kenneth V.; Barnard, Robert; Noerdin, Isjrin J. Chem. Educ. 1967, 44, A83.
Reactions |
Oxidation / Reduction |
Photochemistry
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
Unimolecular gas reactions at low pressures  Perlmutter-Hayman, Berta
Discusses potential student confusion regarding the kinetics of unimolecular gas reactions at low pressures.
Perlmutter-Hayman, Berta J. Chem. Educ. 1967, 44, 605.
Gases |
Reactions |
Kinetics
The stoichiometry of an oxidation-reduction reaction  Latimer, George W., Jr.
A short note on the titration of hydrazine sulfate with standard bromate in the presence of sodium molybdate that requires students to identify the products through the use of some elementary qualitative analysis.
Latimer, George W., Jr. J. Chem. Educ. 1967, 44, 537.
Stoichiometry |
Oxidation / Reduction |
Reactions |
Titration / Volumetric Analysis |
Qualitative Analysis
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
VII - Combustion and flame  Anderson, Robbin C.
Presents and describes an extensive bibliography on the study of combustion and flames.
Anderson, Robbin C. J. Chem. Educ. 1967, 44, 248.
Oxidation / Reduction |
Reactions |
Gases
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
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
Unattended laboratory operations. Part 2. Running laboratory reactions under safe control  Conlon, D. R.
Considers the apparatus and procedures for the safe control of endothermic reactions.
Conlon, D. R. J. Chem. Educ. 1966, 43, A652.
Laboratory Equipment / Apparatus |
Laboratory Management |
Calorimetry / Thermochemistry |
Reactions
Energy B. Heat energy   Klug, Evangeline B.; Hornbeck, Leroy G.; Alyea, Hubert N.
Demonstrations of the heat of crystallization (sodium acetate and Na2S2O3[5H2O]), heat of formation (ZnCl2), heat of hydration (CaO and CuSO4), heat of neutralization, heat of solvation (alcohols), evaporation of ether and methyl chloride, and heat of solution (NH4NO3).
Klug, Evangeline B.; Hornbeck, Leroy G.; Alyea, Hubert N. J. Chem. Educ. 1966, 43, A1079.
Reactions |
Calorimetry / Thermochemistry |
Aqueous Solution Chemistry |
Phases / Phase Transitions / Diagrams |
Crystals / Crystallography |
Precipitation / Solubility
The Investigation of Organic Reactions (Stewart, Ross)  Hiatt, Richard

Hiatt, Richard J. Chem. Educ. 1966, 43, A1004.
Reactions
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
Enamine reactions for the undergraduate organic laboratory: A student water separator  Darling, S. D.
This note describes the design and efficiency of a device that facilitates the removal of water in reactions such as enamine preparation or esterfications.
Darling, S. D. J. Chem. Educ. 1966, 43, 665.
Laboratory Equipment / Apparatus |
Amines / Ammonium Compounds |
Esters |
Synthesis |
Separation Science
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
Fusion reactions under the microscope  Benedetti-Pichler, A. A.; Vikin, Joe
An electrically heated wire is used to identify a variety of cations and anions according to colors observed under a microscope.
Benedetti-Pichler, A. A.; Vikin, Joe J. Chem. Educ. 1966, 43, 421.
Reactions |
Qualitative Analysis |
Atomic Properties / Structure
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
Demonstration of chemical reaction via aerosol spray reagents  Stedman, Earl D.
Demonstrations of chemical reactions via aerosol spray reagents may include acid-base indicators and precipitation reactions.
Stedman, Earl D. J. Chem. Educ. 1966, 43, 377.
Acids / Bases |
Precipitation / Solubility |
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
The use of oxidation potentials in inorganic chemistry  Jolly, William L.
This paper attempts to show, using a minimum of thermodynamics, how oxidation potentials can be used to predict the products and driving forces of oxidation-reduction reactions.
Jolly, William L. J. Chem. Educ. 1966, 43, 198.
Oxidation / Reduction |
Reactions |
Thermodynamics
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
Electronic timer for the study of electron transfer reactions  Stephens, J. F.; Chakrabarty, M. R.
Studies of rapid kinetic processes by a quenching method necessitated the construction of electronic timing devices, capable of pumping reacting solutions into a vessel and introducing a quenching solution at desired time intervals.
Stephens, J. F.; Chakrabarty, M. R. J. Chem. Educ. 1965, 42, 562.
Laboratory Equipment / Apparatus |
Reactions
Device for measuring instantaneous rates of gas-evolving reactions  Steiner, Edwin C.; Hartzell, Gordon E.
Presents a device for measuring instantaneous rates of gas-evolving reactions that relies on a hypodermic syringe capable of responding to extremely small pressure changes.
Steiner, Edwin C.; Hartzell, Gordon E. J. Chem. Educ. 1965, 42, 559.
Laboratory Equipment / Apparatus |
Gases |
Reactions |
Rate Law |
Kinetics
Combustion versus biological oxidation  Asenjo, Conrado F.
Describes a simple toy that can be used to illustrate the difference between combustion and biological oxidation.
Asenjo, Conrado F. J. Chem. Educ. 1965, 42, 558.
Oxidation / Reduction |
Reactions
Effect of amine structure on the relative acidity of conjugate acids  Griswold, Robert E.
the primary objectives of this experiment are to investigate the effect of structure of amines on the relative acidity of their conjugate acids and to study some of the factors affecting equilibrium constants.
Griswold, Robert E. J. Chem. Educ. 1965, 42, 483.
Acids / Bases |
Molecular Properties / Structure |
Amines / Ammonium Compounds |
Equilibrium |
pH
Resolution of D,L-alpha-phenylethylamine: An introductory organic chemistry experiment  Ault, Addison
This experiment clarifies several of the concepts of optical isomerism and introduces the techniques of recrystallization, extraction, and distillation.
Ault, Addison J. Chem. Educ. 1965, 42, 269.
Amines / Ammonium Compounds |
Enantiomers |
Chirality / Optical Activity
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
Continuous process for catalytic oxidation of ammonia  Olmsted, Michael P.
A heated platinum coil catalyzes the oxidation of ammonia.
Olmsted, Michael P. J. Chem. Educ. 1964, 41, A973.
Catalysis |
Oxidation / Reduction |
Reactions
A new clock reaction preparation of dicinnamalacetone  King, L. Carroll; Ostrum, G. Kenneth
Presents a new clock reaction preparation of dicinnamalacetone.
King, L. Carroll; Ostrum, G. Kenneth J. Chem. Educ. 1964, 41, A139.
Reactions |
Kinetics |
Rate Law
Constitutional Problems in Organic Chemistry (Watson, M. B.; Youngson, G. W.)  Haynes, LeRoy W.

Haynes, LeRoy W. J. Chem. Educ. 1964, 41, 691.
Reactions |
Synthesis
Infrared spectrometry to study second order reaction kinetics  Gastambide, B.; Blanc, J.; Allamagny, Y.
The change studied is a synthesis reaction between menthol and phenyl isocyanate.
Gastambide, B.; Blanc, J.; Allamagny, Y. J. Chem. Educ. 1964, 41, 613.
Spectroscopy |
IR Spectroscopy |
Reactions |
Kinetics |
Synthesis
The hydration of carbon dioxide: A double clock experiment  Jones, P.; Haggett, Max L.; Longridge, Jethro L.
This extension of the "Soda Water Clock" experiment provides a quantitative kinetics investigation.
Jones, P.; Haggett, Max L.; Longridge, Jethro L. J. Chem. Educ. 1964, 41, 610.
Reactions |
Rate Law |
Kinetics |
pH |
Acids / Bases |
Aqueous Solution Chemistry
Letters  Helliwell, G. P.
The author seeks to clarify certain facts in an earlier published article.
Helliwell, G. P. J. Chem. Educ. 1964, 41, 575.
Microscale Lab |
Reactions |
Laboratory Equipment / Apparatus |
Laboratory Management
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
The amine catalyzed Perkin condensation: A class project  Ketcham, Roger
In this exercise students carry out the amine catalyzed Perkin condensations of substituted benzaldehydes with substituted phenylacetic acids to give alpha-phenyl-cis- and trans-cinnamic acids.
Ketcham, Roger J. Chem. Educ. 1964, 41, 565.
Amines / Ammonium Compounds |
Catalysis |
Reactions |
Synthesis
The oxidation of iodide ion by persulfate ion  Moews, P. C., Jr.; Petrucci, R. H.
Presents the oxidation of iodide ion by persulfate ion as an ideal reaction to study as part of an experiment on kinetics.
Moews, P. C., Jr.; Petrucci, R. H. J. Chem. Educ. 1964, 41, 549.
Oxidation / Reduction |
Reactions |
Kinetics |
Rate Law
The quinhydrone test for amines  Meek, Willoughby F.; Entrikin, John B.
Proposes modifications to the quinhydrone test for amines that allows for accurate classification.
Meek, Willoughby F.; Entrikin, John B. J. Chem. Educ. 1964, 41, 420.
Amines / Ammonium Compounds |
Qualitative Analysis
Nucleophlic substitution at a saturated carbon atom; Elimination reactions (Bunton, C. A.; Banthorpe, D. V.)  Bunnett, Joseph F.

Bunnett, Joseph F. J. Chem. Educ. 1964, 41, 406.
Nucleophilic Substitution |
Elimination Reactions |
Mechanisms of Reactions
The Friedel-Crafts alkylation of benzene: A first year organic laboratory experiment  Dunathan, H. C.
This experiment involves the alkylation of benzene with each of the four butyl chlorides and aluminum chloride; the monobutylbenzenes from each reaction are then analyzed by vapor phase chromatography and IR spectroscopy.
Dunathan, H. C. J. Chem. Educ. 1964, 41, 278.
Aromatic Compounds |
Reactions |
Mechanisms of Reactions |
IR Spectroscopy
Nucleophilic reactions at trigonally bonded carbon  Cash, R. Vincent
Examines the mechanisms of nucleophilic displacement reactions, nucleophilic addition reactions, and nucleophilic addition with elimination, all at trigonally bonded carbon.
Cash, R. Vincent J. Chem. Educ. 1964, 41, 108.
Nucleophilic Substitution |
Reactions |
Mechanisms of Reactions |
Addition Reactions |
Elimination Reactions
Three-dimensional effects in biochemistry  Ingraham, Lloyd L.
Explores stereospecificity and stereoselectivity; rigidity requirements; steric effects; and stereospecificity when not required mechanistically.
Ingraham, Lloyd L. J. Chem. Educ. 1964, 41, 66.
Molecular Properties / Structure |
Catalysis |
Enzymes |
Molecular Recognition |
Mechanisms of Reactions |
Stereochemistry |
Chirality / Optical Activity |
Enantiomers
Rocket propulsion: The chemical challenge  Dafler, James R.
Examines the chemistry of rocket fuels and engines.
Dafler, James R. J. Chem. Educ. 1964, 41, 58.
Reactions |
Applications of Chemistry |
Oxidation / Reduction
Colorimetric chemical kinetics experiment  Corsaro, Gerald
This article describes an experiment in which a photocolorimetric technique is employed to follow a bimolecular reaction rate; the reactants are crystal violet and the hydroxide ion.
Corsaro, Gerald J. Chem. Educ. 1964, 41, 48.
Kinetics |
Rate Law |
Reactions
The direct esterification of phenols  Offenhauer, Robert D.
It is not true that phenols cannot be esterfied by the direct action of an organic acid; includes an experiment demonstrating the fallacy of this common textbook error.
Offenhauer, Robert D. J. Chem. Educ. 1964, 41, 39.
Phenols |
Esters |
Reactions
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
PolystyreneA multistep synthesis  Wilen, S. H.
Suggestions for research to accompany a previously published article.
Wilen, S. H. J. Chem. Educ. 1963, 40, A463.
Undergraduate Research |
Reactions |
Polymerization |
Synthesis
The pyrolytic decomposition of carboxylate salts to ketones  Schultz, H. P.; Sichels, J. P.
Suggestions for research to accompany a previously published article.
Schultz, H. P.; Sichels, J. P. J. Chem. Educ. 1963, 40, A463.
Undergraduate Research |
Reactions |
Aldehydes / Ketones
Apparatus for the Friedel-Crafts reaction  Kremer, C. B.
Suggestions for research to accompany a previously published article.
Kremer, C. B. J. Chem. Educ. 1963, 40, A463.
Undergraduate Research |
Reactions |
Synthesis
Solvolytic displacement reactions (Streitwieser, Andrew, Jr.)  Kreevoy, Maurice M.

Kreevoy, Maurice M. J. Chem. Educ. 1963, 40, A407.
Reactions
A guidebook to mechanism in organic chemistry (Sykes, Peter)  Detar, D. F.

Detar, D. F. J. Chem. Educ. 1963, 40, A224.
Reactions |
Mechanisms of Reactions
The use of the Perkin reaction in organic chemistry classes  Buckles, R. E.
Provides suggestions for student research based on an earlier article published in the Journal.
Buckles, R. E. J. Chem. Educ. 1963, 40, A139.
Undergraduate Research |
Reactions |
Aromatic Compounds |
Aldehydes / Ketones |
Amines / Ammonium Compounds
Structures and reactions of organic compounds: An introduction (Grundon, M. F.; Henbest, H. B.)  James, Floyd L.

James, Floyd L. J. Chem. Educ. 1963, 40, 670.
Molecular Properties / Structure |
Reactions
Alkali metal-water reactions  Markowitz, Meyer M.
The typical open-air demonstration of sodium reacting with water does not in reality represent the typical reaction of an alkali metal with liquid water; the article goes on to consider other factors that may influence these reactions.
Markowitz, Meyer M. J. Chem. Educ. 1963, 40, 633.
Reactions |
Metals |
Water / Water Chemistry
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
Flowing clock reactions  Haggett, M. L.; Jones, Peter; Oldham, K. B.
Describes an apparatus and its application to the study of the iodine and formaldehyde clock reactions.
Haggett, M. L.; Jones, Peter; Oldham, K. B. J. Chem. Educ. 1963, 40, 367.
Reactions |
Kinetics |
Rate Law
The theory of the formaldehyde clock reaction  Jones, P.; Oldham, K. B.
Presents a theory for the formaldehyde clock reaction.
Jones, P.; Oldham, K. B. J. Chem. Educ. 1963, 40, 366.
Reactions |
Kinetics |
Rate Law |
Aldehydes / Ketones
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
Friedel-Crafts alkylation  Marsi, Kenneth L.; Wilen, Samuel H.
Some organic textbooks state that n-alkyl derivatives cannot be synthesized by the Friedel-Crafts reaction, or that they are formed in only minor amounts, though this is not the case.
Marsi, Kenneth L.; Wilen, Samuel H. J. Chem. Educ. 1963, 40, 214.
Reactions |
Synthesis
The decarboxylation of organic acid  March, Jerry
Simple aliphatic acids (except for acetic) do not give good yields of the corresponding alkanes through decarboxylation, although many organic chemistry textbooks cite this as a general method for the preparation of alkanes.
March, Jerry J. Chem. Educ. 1963, 40, 212.
Acids / Bases |
Reactions |
Synthesis |
Alkanes / Cycloalkanes |
Carboxylic Acids
Multicenter and assisted mechanistic pathways in the reactions of organometallic compounds  Dessy, Raymond E.; Paulik, Frank
Examines a variety of nucleophilic and electrophilic, multicenter and assisted mechanistic pathways in the reactions of organometallic compounds.
Dessy, Raymond E.; Paulik, Frank J. Chem. Educ. 1963, 40, 185.
Organometallics |
Mechanisms of Reactions |
Nucleophilic Substitution |
Electrophilic Substitution
The reaction of tertiary amines with nitrous acid  Hein, George E.
Examines the history of investigation into the reaction of tertiary amines with nitrous acid as an example of the inherently conservative nature of science and resistance to new concepts.
Hein, George E. J. Chem. Educ. 1963, 40, 181.
Amines / Ammonium Compounds |
Reactions |
Mechanisms of Reactions
Chemistry of diphosphorus compounds  Huheey, James E.
Examines diphosphorus chemistry, including tri- and tetra- covalent diphosphorus compounds; optical activity in diphosphines; unsaturated diphosphorus compounds, cyclic compounds, and higher phosphines; reactions producing and destroying P-P bonds; and diphosphorus compounds as ligands.
Huheey, James E. J. Chem. Educ. 1963, 40, 153.
Molecular Properties / Structure |
Reactions |
Covalent Bonding |
Coordination Compounds
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 catalyzed decomposition of potassium chlorate  Rochow; Eugene G.; Gaidis, James M.
Research into why manganese dioxide acts as a catalyst in the decomposition of potassium chlorate.
Rochow; Eugene G.; Gaidis, James M. J. Chem. Educ. 1963, 40, 78.
Catalysis |
Reactions
Theoretical titration error: In potentiometric, asymmetrical precipitation titrations  Christopherson, Howard L.
Derives and presents a table of theoretical potentiometric titration error for asymmetrical precipitation reactions.
Christopherson, Howard L. J. Chem. Educ. 1963, 40, 63.
Chemometrics |
Titration / Volumetric Analysis |
Precipitation / Solubility |
Reactions |
Quantitative Analysis
A Diels-Alder reaction experiment  Sheppard, William J.
The original method of Diels and Alder for the reaction of cyclopentadiene with maleic anhydride is modified for use in the elementary organic laboratory.
Sheppard, William J. J. Chem. Educ. 1963, 40, 40.
Reactions
The formation of acetone from acetates  Young, Jay A.; Taylor, John K.
Suggests some research activities based on an article published previously in the Journal.
Young, Jay A.; Taylor, John K. J. Chem. Educ. 1962, 39, A962.
Undergraduate Research |
Aldehydes / Ketones |
Reactions
Demonstration notes: Spontaneous combustion of H2S  Thomas, P. M.
Hydrogen sulfide passed over lead(IV) oxide bursts into flame.
Thomas, P. M. J. Chem. Educ. 1962, 39, A839.
Oxidation / Reduction |
Reactions
Name Reactions in Organic Chemistry (Surrey, Alexander R.)  Burgstahler, Albert W.

Burgstahler, Albert W. J. Chem. Educ. 1962, 39, 326.
Reactions
Reactions of functional groups: An approach for the basic course in organic chemistry  Bauer, Ludwig; Daniels, Ralph
Outlines an introductory organic chemistry curriculum based on the reactions of functional groups.
Bauer, Ludwig; Daniels, Ralph J. Chem. Educ. 1962, 39, 303.
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
A rotating tubular reactor  Markowitz, Meyer M.; Boryta, Daniel A.
Presents a simple design for a rotating tubular reactor to achieve efficient interaction between a solid and a gas.
Markowitz, Meyer M.; Boryta, Daniel A. J. Chem. Educ. 1962, 39, 122.
Laboratory Equipment / Apparatus |
Reactions |
Solids |
Gases
Periodate cleavage of glycols: A quantitative organic analysis experiment  Schenk, George H.
This reaction is much used by organic chemists and uses the familiar standard solutions of iodine and sodium arsenite, common buffers, and stable organic glycols, such as ethylene glycol and pinacol.
Schenk, George H. J. Chem. Educ. 1962, 39, 32.
Quantitative Analysis |
Alcohols |
Reactions
A qualitative elemental analysis system correlated with the periodic table  Swift, Ernest H.; Schaefer, William P.
This article describes a new system of qualitative analysis developed especially for instructional purposes as a means of teaching descriptive inorganic chemistry and the principles of chemical reactions.
Swift, Ernest H.; Schaefer, William P. J. Chem. Educ. 1961, 38, 607.
Periodicity / Periodic Table |
Qualitative Analysis |
Descriptive Chemistry |
Reactions
Name index of organic reactions (Gowan, J. E.; Wheeler, T. S.)  Smith, L. Oliver, Jr.

Smith, L. Oliver, Jr. J. Chem. Educ. 1961, 38, 588.
Reactions
Organic Reactions. Volume II (Cope, Arthur C., ed.)  

J. Chem. Educ. 1961, 38, 431.
Reactions
The reactive intermediates of organic chemistry  Stewart, Ross
The purpose of this paper is to outline a logical presentation of the more important reactive intermediates the student is likely to encounter in organic chemistry.
Stewart, Ross J. Chem. Educ. 1961, 38, 308.
Reactive Intermediates |
Free Radicals |
Mechanisms of Reactions
A convenient method for demonstration of stable carbanions  Landsbury, Peter T.
Highly colored pyridine solutions of carbanions are used as a convenient demonstration illustrating reactive intermediates.
Landsbury, Peter T. J. Chem. Educ. 1961, 38, 307.
Reactive Intermediates |
Reactions |
Free Radicals
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 side-chain halogenation of n-alkyl benzenes  Goldwhite, H.
A number of textbooks state that in the halogenation of the side-chains of normal alkyl benzenes with elemental halogens there is a strong tendency for halogenation to take place preferentially at the carbon atom next to the aromatic nucleus; the literature does not support this conclusion.
Goldwhite, H. J. Chem. Educ. 1960, 37, 295.
Aromatic Compounds |
Alkylation |
Reactions
A separation and identification experiment for elementary organic chemistry laboratory  Laughton, Paul M.
The student selects a test tube containing two unknowns and is told only that they have been selected from two of three possible groups: a primary or tertiary amine, an aldehyde or ketone, and an acid or phenol. The components are to be separated, their physical properties determined, their categories assigned, and one specific derivative prepared for each.
Laughton, Paul M. J. Chem. Educ. 1960, 37, 133.
Separation Science |
Qualitative Analysis |
Amines / Ammonium Compounds |
Aldehydes / Ketones |
Acids / Bases |
Phenols |
Physical Properties |
Synthesis
The stability of solutions for the iodine clock reaction  Kauffman, George B.; Hall, Charles R.
The results of attempts to stabilize solutions needed for the iodine clock reaction to allow long-term storage.
Kauffman, George B.; Hall, Charles R. J. Chem. Educ. 1958, 35, 577.
Reactions |
Kinetics |
Oxidation / Reduction |
Aqueous Solution 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
The reduction of carbon dioxide  Hollander, Jerome; Spialter, Leonard
Examines the reduction of carbon through a variety of processes, including catalytic hydrogenation, reduction by metals and complex metal hydrides, electrochemical reduction, and reduction under the influence of radiation.
Hollander, Jerome; Spialter, Leonard J. Chem. Educ. 1958, 35, 446.
Reactions |
Oxidation / Reduction |
Catalysis |
Metals |
Electrochemistry |
Nuclear / Radiochemistry
Textbook errors: Guest column- XIX. The relative reactivity of acetylenes and olefins toward bromine  Mysels, Karol J.; Daniels, Ralph; Bauer, Ludwig
Many contemporary textbooks and laboratory manuals in organic chemistry either state explicitly or imply that bromine ass much faster to acetylenes than to olefins.
Mysels, Karol J.; Daniels, Ralph; Bauer, Ludwig J. Chem. Educ. 1958, 35, 444.
Reactions |
Addition Reactions |
Alkylation |
Alkynes
Polymerization of ethylene at atmospheric pressure: A demonstration using a "Ziegler" type catalyst  Zilkha, Albert; Calderon, Nissim; Rabani, Joseph; Frankel, Max
A simple experiment on the polymerization of ethylene at atmospheric pressure is described using a "Ziegler" type catalyst prepared from amyl lithium and titanium tetrachloride.
Zilkha, Albert; Calderon, Nissim; Rabani, Joseph; Frankel, Max J. Chem. Educ. 1958, 35, 344.
Polymerization |
Reactions |
Catalysis |
Alkenes
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
Spot reaction experiments (Tr. by Ralph E. Oesper)  Feigl, Fritz
The development of new spot tests for organic analysis led to the discovery of reaction modes of organic compounds, which are of interest as spot tests for teaching purposes.
Feigl, Fritz J. Chem. Educ. 1957, 34, 457.
Reactions
Reduction with complex metal hydrides  Gaylord, Norman G.
Focusses on the use of lithium aluminum hydride, aluminum hydride, magnesium aluminum hydride, sodium aluminum hydride, sodium borohydride, potassium borohydride, lithium borohydride, and lithium gallium hydride as analytical reducing reagents.
Gaylord, Norman G. J. Chem. Educ. 1957, 34, 367.
Oxidation / Reduction |
Metals |
Reactions
Some aspects of organic molecules and their behavior. II. Bond energies  Reinmuth, Otto
Examines bond and dissociation energies, the "constancy" of C-H and C-C dissociation energies, and some common types of organochemical reactions.
Reinmuth, Otto J. Chem. Educ. 1957, 34, 318.
Covalent Bonding |
Molecular Properties / Structure |
Reactions
An efficient chemiluminescent system and a chemiluminescent clock reaction  White, Emil H.
Presents the investigation of two chemiluminescent systems - the first is particularly brilliant and the second acts as a clock reaction.
White, Emil H. J. Chem. Educ. 1957, 34, 275.
Photochemistry |
Reactions
Model of a potential energy surface  Dye, J. L.
Describes a physical, three-dimensional model of the potential energy surface for HBr.
Dye, J. L. J. Chem. Educ. 1957, 34, 215.
Kinetics |
Reactive Intermediates |
Reactions
A phosphine fire flask  Dillard, Clyde R.
Presents a flask and demonstration that relies on the spontaneous combustion of phosphine gas.
Dillard, Clyde R. J. Chem. Educ. 1956, 33, 137.
Reactions
Textbook errors: V. The reaction of the Leclanche dry cell  Mysels, Karol J.
Most textbooks do not completely and accurately describe the chemistry of the Leclanche dry cell.
Mysels, Karol J. J. Chem. Educ. 1955, 32, 638.
Electrochemistry |
Electrolytic / Galvanic Cells / Potentials |
Reactions |
Oxidation / Reduction
Aromatic substitution by free radicals  Nelson, Peter F.
This article summarizes recent investigations upon orientation and reaction rates with respect to homolytic substitution.
Nelson, Peter F. J. Chem. Educ. 1955, 32, 606.
Free Radicals |
Aromatic Compounds |
Reactions |
Rate Law |
Molecular Properties / Structure
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
Lecture demonstrations of incendiaries. II  Antelman, Marvin
Demonstrations described involve gunpowder, the combustion of sulfur dioxide, zirconium, nitric acid, sodium peroxide, hot iron, ammonium nitrate, organic chlorates and nitrates, and zinc stearate.
Antelman, Marvin J. Chem. Educ. 1955, 32, 273.
Reactions |
Oxidation / Reduction
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
A sequence of synthesis in the general organic laboratory class  Lange, Erwin F.; Teranishi, Roy; Christensen, Bert E.
This synthesis involves the oxidation of p-xylene, nitration and esterfication of terephthalic acid, reduction of nitroterephthalic acid, and the preparation of 4-quinazolone-7-carboxylic acid.
Lange, Erwin F.; Teranishi, Roy; Christensen, Bert E. J. Chem. Educ. 1955, 32, 40.
Synthesis |
Aromatic Compounds |
Reactions |
Oxidation / Reduction
Le Châtelier's principle and the equilibrium constant  Miller, Arild J.
Many students of chemistry have difficulty in understanding how the position of equilibrium in a gaseous reaction can change when the pressure is altered, in accordance with Le Châtelier's principle, without causing a corresponding variation in the equilibrium constant.
Miller, Arild J. J. Chem. Educ. 1954, 31, 455.
Equilibrium |
Reactions |
Gases
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 action of nitric acid on metals  Tillu, Mahadeo M.
A general equation for the action of nitric acid on metals has been computed.
Tillu, Mahadeo M. J. Chem. Educ. 1953, 30, 290.
Acids / Bases |
Metals |
Reactions
Letters  Miranda, Bienvenido T.
Commmentary on two earlier Journal articles.
Miranda, Bienvenido T. J. Chem. Educ. 1953, 30, 264.
Oxidation State |
Oxidation / Reduction |
Reactions
Silver trees  Gleim, David I.
Describes the classic silver tree and the examination of its crystals under the microscope.
Gleim, David I. J. Chem. Educ. 1953, 30, 151.
Reactions |
Aqueous Solution Chemistry
The Friedel-Crafts reaction in elementary organic laboratories  Wright, Oscar L.; Fuhlhage, Donald; Sheridan, Earl
Presents a modification of the Perrier ketone synthesis.
Wright, Oscar L.; Fuhlhage, Donald; Sheridan, Earl J. Chem. Educ. 1952, 29, 620.
Reactions |
Aldehydes / Ketones |
Synthesis
The Versene complexes  Pecsok, Robert L.
Examines some of the analytical applications of ethylenediaminetetraacetic acid, with particular reference to polarography.
Pecsok, Robert L. J. Chem. Educ. 1952, 29, 597.
Amines / Ammonium Compounds
Thermite ignition assured  Brockett, Clyde P.
Offers a suggestion for igniting course mixtures of commercial grade thermite.
Brockett, Clyde P. J. Chem. Educ. 1952, 29, 525.
Reactions
Modified Hinsberg procedure  Ritter, Frank O.
Improves the Hinsberg method for differentiating between primary, secondary, and tertiary amines.
Ritter, Frank O. J. Chem. Educ. 1952, 29, 506.
Amines / Ammonium Compounds |
Qualitative Analysis
Fragments of Chemistry. 3. Silicon, germanium, and tin  Kraus, Charles A.
Examines the chemistry of silicon, germanium, and tin.
Kraus, Charles A. J. Chem. Educ. 1952, 29, 488.
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
A clock reaction  Suryaraman, M. G.; Viswanathan, Arcot
Ferrous ions in an alkaline solution of a tartrate form of a soluble chelate complex that reacts sluggishly with iodine.
Suryaraman, M. G.; Viswanathan, Arcot J. Chem. Educ. 1951, 28, 386.
Reactions |
Kinetics |
Aqueous Solution Chemistry