| Journal Articles: 55 results |
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"As Simple as Possible, but Not Simpler"—The Case of Dehydroascorbic Acid Robert C. Kerber Textbooks routinely assign dehydroascorbic acid a tricarbonyl structure that is highly improbable in aqueous solution and inconsistent with its colorless appearance. Studies of oxidized forms of ascorbic acid are summarized here, and a plea is entered for accurate descriptions of chemical structures in this and other cases, even at the cost of some simplicity. Kerber, Robert C. J. Chem. Educ. 2008, 85, 1237.
Bioorganic Chemistry |
Free Radicals |
Natural Products |
NMR Spectroscopy |
Vitamins
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Radical Quenching of 1,1-Diphenyl-2-picrylhydrazyl: A Spectrometric Determination of Antioxidant Behavior John M. Berger, Roshniben J. Rana, Hira Javeed, Iqra Javeed, and Sandi L. Schulien Describes a colorimetric assay using the persistent radical 1,1-diphenyl-2-picrylhydrazyl to measure the activity of common antioxidants. This exercise is particularly appropriate for a course geared for nutrition or food science majors. Berger, John M.; Rana, Roshniben J.; Javeed, Hira; Javeed, Iqra; Schulien, Sandi L. J. Chem. Educ. 2008, 85, 408.
Food Science |
Free Radicals |
UV-Vis Spectroscopy |
Vitamins
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The Chemistry of Paper Preservation Henry A. Carter This article examines the applications of chemistry to paper preservation. The acid-catalyzed hydrolysis of cellulose accounts for the deterioration of paper in library books and other written records. To combat this threat to our written heritage, new permanent papers have been developed that are relatively chemically stable and undergo a very slow rate of deterioration. Carter, Henry A. J. Chem. Educ. 2007, 84, 1937.
Acids / Bases |
Applications of Chemistry |
Aqueous Solution Chemistry |
Free Radicals |
Gas Chromatography |
HPLC |
pH |
Kinetics |
Rate Law
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The Quantitative Determination of Butylated Hydroxytoluene in Chewing Gum Using GC–MS A. E. Witter An undergraduate experiment for the quantitative determination of the synthetic antioxidant butylated hydroxytoluene (BHT) in chewing gum is described. A simple extraction procedure was used that did not require sample derivatization for analysis. Witter, A. E. J. Chem. Educ. 2005, 82, 1538.
Food Science |
Free Radicals |
Instrumental Methods |
Mass Spectrometry |
Quantitative Analysis |
Aromatic Compounds |
Chromatography |
Consumer Chemistry |
Gas Chromatography
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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
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Small Scale Reactor for Ultraviolet Photochemistry James E. Gano, Andrew J. Gano, Patricia Garry, and Padmanabhan Sekher Apparatus for performing photochemical reactions at a variety of wavelengths. Gano, James E.; Gano, Andrew J.; Garry, Patricia; Sekher, Padmanabhan. J. Chem. Educ. 2002, 79, 1361.
Free Radicals |
Laboratory Equipment / Apparatus |
Synthesis |
Photochemistry |
Undergraduate Research |
Laboratory Management
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Radioactivity, Radiation, and the Chemistry of Nuclear Waste Nick Zevos A course that emphasizes an understanding of the nuclear waste generated from the production of plutonium at sites such as Hanford, WA, and Savannah River, GA. Zevos, Nick. J. Chem. Educ. 2002, 79, 692.
Aqueous Solution Chemistry |
Free Radicals |
Nuclear / Radiochemistry |
Nonmajor Courses
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Solar Photocatalytic Destruction of p-Nitrophenol: A Pedagogical Use of Lab Wastes J. A. Herrera-Melián, J. M. Doña-Rodríguez, E. Tello Rendón, A. Soler Vila, M. Brunet Quetglas, A. Alvera Azcárate, and L. Pascual Pariente Using lab wastes to develop new chemistry experiments. Herrera-Melián, J. A.; Doña-Rodríguez, J. M.; Rendón, E. Tello; Soler Vila, A.; Brunet Quetglas, M.; Azcárate, A. Alvera; Pascual Pariente, L. J. Chem. Educ. 2001, 78, 775.
Catalysis |
Free Radicals |
Photochemistry |
Water / Water Chemistry
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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
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Bromination, Elimination, and Polymerization: A 3-Step Sequence for the Preparation of Polystyrene from Ethylbenzene Elizabeth M. Sanford and Heather L. Hermann An organic chemistry lab that introduces students to polymer chemistry is presented. Students complete a radical bromination of ethylbenzene, which is followed by elimination to give styrene. A radical polymerization is then completed to produce polystyrene. Sanford, Elizabeth M.; Hermann, Heather L. J. Chem. Educ. 2000, 77, 1343.
Free Radicals |
Synthesis |
Polymerization
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Correction Word error in original article. J. Chem. Educ. 2000, 77, 830.
Nutrition |
Free Radicals |
Learning Theories
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The Preparation of a UV-Light-Absorbing Polymer: A Project-Oriented Laboratory Experiment for the Introductory Organic Chemistry Curriculum Thomas Poon, Jean P. McIntyre, Andrea Dorigo, Drew J. Davis, Matthew A. Davis, Crystal F. Eller, Leah R. Eller, Heather K. Izumi, Kenya M. Jones, Kurt H. Kelley, William Massello, Megan L. Melamed, Cynthia M. Norris, Jeffrey A. Oelrich, Thomas A. Pluim, Sarah E. Poplawski, Jason M. St. Clair, Matthew P. Stokes, Wells C. Wheeler, and Erin E. Wilkes A laboratory experiment is described that combines organic synthesis, spectroscopy, and polymer chemistry and is suitable for the sophomore organic chemistry curriculum. In this three-week sequence, students synthesize and characterize the UV-absorber 2-(2',4'-dimethylbenzoyl)benzoic acid and incorporate it into films of polymethylmethacrylate. Poon, Thomas; McIntyre, Jean P.; Dorigo, Andrea; Davis, Drew J.; Davis, Matthew A.; Eller, Crystal F.; Eller, Leah R.; Izumi, Heather K.; Jones, Kenya M.; Kelley, Kurt H.; Massello, William; Melamed, Megan L.; Norris, Cynthia M.; Oelrich, Jeffrey A.; Pluim, Thomas A.; Poplawski, Sarah E.; St. Clair, Jason M.; Stokes, Matthew P.; Wheeler, Wells C.; Wilkes, Erin E. J. Chem. Educ. 1999, 76, 1523.
Synthesis |
UV-Vis Spectroscopy |
NMR Spectroscopy |
IR Spectroscopy |
Free Radicals
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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
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Homogeneous Immunoassays: Historical Perspective and Future Promise Edwin F. Ullman The founding and growth of Syva Company is examined in the context of its leadership role in the development of homogeneous immunoassays. The simple mix and read protocols of these methods offer advantages in routine analytical and clinical applications. Ullman, Edwin F. J. Chem. Educ. 1999, 76, 781.
Biotechnology |
Enzymes |
Atomic Properties / Structure |
Free Radicals |
Photochemistry |
Medicinal Chemistry |
Proteins / Peptides
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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
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Free Radical Reactions in Aqueous Solutions: Examples from Advanced Oxidation Processes for Wastewater from the Chemistry in Airborne Water Droplets N. Colin Baird A common free radical reaction in aqueous solution is electron transfer, especially to the hydroxyl radical and to ozone. Hydrogen peroxide and free radicals related to it act as weak acids, so both their neutral and deprotonated forms must be considered in reactions. Free radical reactions also play an important role in the chemistry of water droplets suspended in air in clouds and fogs. Baird, N. Colin. J. Chem. Educ. 1997, 74, 817.
Aqueous Solution Chemistry |
Free Radicals |
Reactive Intermediates |
Atmospheric Chemistry |
Acids / Bases |
Oxidation / Reduction
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Environmental Laboratory Exercise: Analysis of Hydrogen Peroxide by Fluorescence Spectroscopy Judith Weinstein--Lloyd and Jai H. Lee Procedure in which students analyze precipitation samples for trace concentrations of hydrogen peroxide (a deleterious air pollutant) using fluorescence spectroscopy. Weinstein-Lloyd, Judith; Lee, Jai H. J. Chem. Educ. 1995, 72, 1053.
Fluorescence Spectroscopy |
Free Radicals |
Photochemistry |
Acids / Bases |
Atmospheric Chemistry
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Introducing Atmospheric Reactions: A Systematic Approach for Students Baird, N. Colin Outline of the dominant reactions that occur in air, particularly with regard to atmospheric pollutants. Baird, N. Colin J. Chem. Educ. 1995, 72, 153.
Photochemistry |
Free Radicals |
Atmospheric Chemistry
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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
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Free radical halogenation of hydrocarbons: Experiments for organic chemistry using the small-scale approach Gilow, Helmuth M. Better understanding of free radical halogenation can be gained by doing a laboratory experiment. The challenge, however, is that these experiments pose safety threats. Gilow, Helmuth M. J. Chem. Educ. 1991, 68, A122.
Free Radicals |
Microscale Lab
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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
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Undergraduate experiments with a long-lived radical (Fremy's salt): Synthesis of 1,4-benzoquinones by degradative oxidation of p-hydroxybenzyl alcohols Morey, J. The long-lived, stable radical described in this article can be prepared and stored for several months and therefore is an excellent basis for a series of experiments that the author designed for his class. Morey, J. J. Chem. Educ. 1988, 65, 627.
Aqueous Solution Chemistry |
Free Radicals |
Alcohols |
Aromatic Compounds
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Consumer chemistry in an organic course Miller, John A. This paper looks at the main functional groups in organic chemistry and points out their appearance in consumer chemistry. These suggestions are especially useful for courses geared toward health science majors. Miller, John A. J. Chem. Educ. 1988, 65, 210.
Aromatic Compounds |
Free Radicals |
Hormones |
Medicinal Chemistry |
Consumer Chemistry |
Applications of Chemistry
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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
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Stereoisomerism as a result of free radical chlorination of a nonstereoisomeric substance Fulkroad, John E. Examples of questions and solutions regarding stereoisomerism as a result of free radical chlorination of a nonstereoisomeric substance. Fulkroad, John E. J. Chem. Educ. 1987, 64, 533.
Stereochemistry |
Free Radicals
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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
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Thioxanthone sulfone radical anion: A relatively stable ketyl Castrillon, Jose Thioxanthone sulfone is induced to produce a deep blue color upon standing that disappears on shaking. Castrillon, Jose J. Chem. Educ. 1987, 64, 352.
Free Radicals |
Oxidation / Reduction
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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
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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
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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
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Aromatic substitution reactions: when you've said ortho, meta, and para you haven't said it all Traynham, James G. The author presents a range of examples for nucleophilic, electrophilic, and free-radical reactions where the ipso is an important, predominant, or even exclusive site of reaction. Traynham, James G. J. Chem. Educ. 1983, 60, 937.
Nucleophilic Substitution |
Electrophilic Substitution |
Free Radicals |
Diastereomers |
Stereochemistry |
Reactions
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Molecular formulas of organic compounds: the nitrogen rule and degree of unsaturation Pellegrin, Valdo This article wishes to demonstrate the nitrogen rule and the formula for calculating the number of rings plus double bonds of any common organic compound. Pellegrin, Valdo J. Chem. Educ. 1983, 60, 626.
Heterocycles |
Aromatic Compounds |
Free Radicals
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Free radical chlorination of methane: A demonstration Conklin, Alfred R.; Kramme, Alan Free radical reactions are very important and often discussed in chemistry. One of the first such reactions encountered by students of organic chemistry is the free radical chlorination of methane. This reaction serves to introduce the student to free radical reactions and chain reaction. In spite of its common occurrence, demonstrations of this reaction are uncommon. Conklin, Alfred R.; Kramme, Alan J. Chem. Educ. 1983, 60, 597.
Alkanes / Cycloalkanes |
Free Radicals
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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
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A versatile chemical system for instruction in ESR spectroscopy Darcy, Raphael A radical precursor is sued to generate a number of interconvertible, long-lived free radicals whose spectra are observed at room temperature and show variations in detail that illustrate spectroscopic principles. Darcy, Raphael J. Chem. Educ. 1980, 57, 907.
Spectroscopy |
EPR / ESR Spectroscopy |
Reactive Intermediates |
Magnetic Properties |
Free Radicals
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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
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A modification of the free radical bromination of p-toluic acid Olson, Edwin S. The bromination of p-toluic acid proceeds well using less toxic chlorobenzene rather than carbon tetrachloride. Olson, Edwin S. J. Chem. Educ. 1980, 57, 157.
Free Radicals
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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
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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
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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
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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
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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
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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
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Free-radical bromination of p-toluic acid. An experiment in organic chemistry Tuleen, D. L.; Hess, B. A., Jr. This paper describes the synthesis of a-bromo-p-toluic acid (II) and the subsequent displacement of bromide ion by three nucleophiles. Tuleen, D. L.; Hess, B. A., Jr. J. Chem. Educ. 1971, 48, 476.
Free Radicals |
Nucleophilic Substitution
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Free radical chlorination Adduci, Jerry M.; Dayton, Joseph H.; Eaton, David C. The authors describe an experiment on free radical chlorination which is simple, nonhazardous, and well suited for a beginning student. Adduci, Jerry M.; Dayton, Joseph H.; Eaton, David C. J. Chem. Educ. 1971, 48, 313.
Free Radicals
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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
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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
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Chlorination of 2,3-dimethylbutane: A quantitative organic chemistry experiment Markgraf, J. Hodge This paper describes the quantitative study of a free radical chlorination in which the student determines the relative reactivity of selected hydrogens. Markgraf, J. Hodge J. Chem. Educ. 1969, 46, 610.
Quantitative Analysis |
Alkylation |
Alkanes / Cycloalkanes |
Free Radicals
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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
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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
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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
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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
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Balancing organic redox equations Burrell, Harold P. C. This paper presents a method for balancing organic redox equations based on the study of structural formulas and an artificial device - the use of hypothetical free radicals. Burrell, Harold P. C. J. Chem. Educ. 1959, 36, 77.
Stoichiometry |
Oxidation / Reduction |
Free Radicals
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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
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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
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