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Journal Articles: 25 results
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
Free Radical Halogenation, Selectivity, and Thermodynamics: The Polanyi Principle and Hammond's Postulate  Alfred A. Scala
Free radical halogenation reactions are examined in the contexts of the Polanyi principle and Hammond's postulate and used as a vehicle for examination of the concept of selectivity in chemical reactions. The origin of selectivity is related to the thermodynamics of the competing reactions and their chemical dynamics.
Scala, Alfred A. J. Chem. Educ. 2004, 81, 1661.
Free Radicals |
Molecular Mechanics / Dynamics |
Computational Chemistry |
Kinetics |
Thermodynamics
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
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
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
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
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
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
Alkane activation with mercury vapor   Brown, Steven B.; Crabtree, Robert H.
This paper explores the progress made by chemists in activating small molecules (CO,CO2,CH4,C2H4, etc.) with metals or metal compounds.
Brown, Steven B.; Crabtree, Robert H. J. Chem. Educ. 1988, 65, 290.
Metals |
Organometallics |
Reactions |
Catalysis |
Alkanes / Cycloalkanes
The reactivity selectivity principle: Should it ever be used?  Buncel, Erwin; Wilson, Harold
Applications and failures of the reactivity selectivity principle; quantitative aspects of the reactivity selectivity principle; and rationalization of reactivity selectivity principle failures.
Buncel, Erwin; Wilson, Harold J. Chem. Educ. 1987, 64, 475.
Mechanisms of Reactions |
Free Radicals |
Carbocations |
Nucleophilic Substitution
The development of free radical chemistry   Walling, Cheves
A historical look at the development of this branch of chemistry understanding.
Walling, Cheves J. Chem. Educ. 1986, 63, 99.
Free Radicals |
Enrichment / Review Materials
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
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
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
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
Two organic laboratory experiments with benzylic hydrocarbons  Kolb, Kenneth E.; Helmer, Bradley J.
Closely related experiments to illustrate the selective susceptibility toward free radical attack of benzyl hydrogens.
Kolb, Kenneth E.; Helmer, Bradley J. J. Chem. Educ. 1979, 56, 201.
Free Radicals
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
Inductive effects in the chlorination of 1-chlorobutane. An organic laboratory experiment  Reeves, Perry C.
The present paper describes the quantitative study of the directive effect of chlorine already present in the molecule on the orientation of incoming chlorine in the free radical halogenation of 1-chlorobutane.
Reeves, Perry C. J. Chem. Educ. 1971, 48, 636.
Alkanes / Cycloalkanes |
Molecular Properties / Structure
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
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
Halogenation and olefinic nature of cyclopropane  Gordon, Arnold J.
A brief discussion of evidence for the double-bond nature of the cyclopropane ring is presented, followed by a summary of representative studies of cyclopropane halogenations and related reactions.
Gordon, Arnold J. J. Chem. Educ. 1967, 44, 461.
Alkanes / Cycloalkanes |
Molecular Properties / Structure
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
Activation of small molecules by coordination  Jones, Mark M.
Examines the general principles behind and numerous examples of the coordination process as a means of activating molecules for further reaction.
Jones, Mark M. J. Chem. Educ. 1964, 41, 493.
Catalysis |
Coordination Compounds |
Crystal Field / Ligand Field Theory |
Mechanisms of Reactions |
Free Radicals |
Lewis Acids / Bases |
Reactions
Free radical chemistry in solution  Gritter, Roy J.
Considers the general characteristics of free radical reactions in solution, types of free radical reactions, and the effect of structure on bond dissociation energies.
Gritter, Roy J. J. Chem. Educ. 1958, 35, 475.
Free Radicals |
Aqueous Solution Chemistry |
Reactions |
Molecular Properties / Structure |
Covalent Bonding
Chemistry of organic free radicals in the vapor phase. I. Detection and reactions of free alkyl radicals  De La Mare, Harold E.; Vaughan, William E.
Examines the detection of free radicals, the thermal production and reactions of free alkyl radicals, alkyl radical/olefin interactions, the nitration of alkanes, halogenation, and miscellaneous pyrolyses.
De La Mare, Harold E.; Vaughan, William E. J. Chem. Educ. 1957, 34, 10.
Free Radicals |
Reactions |
Alkylation