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Journal Articles: 38 results
Frank Westheimer's Early Demonstration of Enzymatic Specificity  Addison Ault
Reviews one of the most significant accomplishments of one of the most respected chemists of the 20th centurya series of stereospecific enzymatic oxidation and reduction experiments that led chemists to recognize enantiotopic and diastereotopic relationships of atoms, or groups of atoms, within molecules.
Ault, Addison. J. Chem. Educ. 2008, 85, 1246.
Asymmetric Synthesis |
Bioorganic Chemistry |
Catalysis |
Chirality / Optical Activity |
Enantiomers |
Enzymes |
Isotopes |
Nucleophilic Substitution |
Oxidation / Reduction |
Stereochemistry
Polymer-Supported Reagents and 1H–19F NMR Couplings: The Synthesis of 2-Fluoroacetophenone  Nicola Pohl and Kimberly Schwarz
Describes an experiment in which 2-bromoacetophenone is converted to 2-fluoroacetophenone using a solid-phase nucleophilic fluorine source. The experiment introduces students to the utility of solid-phase reagents in organic synthesis, to NMR-active nuclei other than 1H without the requirement of a special NMR probe, and to the unique uses of fluorine in molecular design.
Pohl, Nicola; Schwarz, Kimberly. J. Chem. Educ. 2008, 85, 834.
Aldehydes / Ketones |
NMR Spectroscopy |
Nucleophilic Substitution |
Synthesis
pHantastic Fluorescence  Mark Muyskens
Students easily extract a fluorescent substance from shavings of a wood called narra. The fluorescence is dramatically pH dependent and can be turned on and off repeatedly using commonly available acid and base solutions.
Muyskens, Mark. J. Chem. Educ. 2006, 83, 768A.
Fluorescence Spectroscopy |
Natural Products |
Nucleophilic Substitution |
pH |
Solutions / Solvents |
UV-Vis Spectroscopy
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
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
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
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
An Introduction to the Understanding of Solubility  Trevor M. Letcher and Rubin Battino
This paper explores the solubility process from a number of perspectives, including the second law of thermodynamics and ideal solubility, real solutions and activity coefficients, intermolecular forces, and theories of gases or liquids or solids dissolving in liquids.
Letcher, Trevor M.; Battino, Rubin. J. Chem. Educ. 2001, 78, 103.
Solutions / Solvents |
Learning Theories |
Thermodynamics |
Precipitation / Solubility |
Noncovalent Interactions
Microscale Synthesis of Hexaamminechromium(III) Nitrate Using Liquid Ammonia Generated in the Laboratory  Edward Maslowsky Jr.
The previously published synthesis of hexaamminechromium(III) nitrate using liquid ammonia as the solvent is simplified by performing this experiment on a microscale level and generating the small amount of ammonia needed directly in the laboratory at the time of the experiment. The ammonia is generated by heating concentrated ammonium hydroxide and condensing the ammonia vapors into the reaction vessel.
Maslowsky, Edward, Jr. J. Chem. Educ. 2000, 77, 760.
Coordination Compounds |
Synthesis |
Microscale Lab |
Solutions / Solvents
The Use of Erythrosin B in Undergraduate Spectrophotometry Experiments   L. James Stock III
Substitution of a nontoxic food color for an originally used toxic chromium(VI) salt in a general chemistry, spectrophotometry experiment.
Stock, L. James, III. J. Chem. Educ. 1995, 72, 926.
Toxicology |
Solutions / Solvents |
Spectroscopy |
Laboratory Management
Avoiding the Downstream Hazard in an Ionic Solubility Study  McSwiney, H. D.
Using potassium chlorate rather than potassium dichromate in an ionic solubility experiment for improved waste disposal.
McSwiney, H. D. J. Chem. Educ. 1994, 71, 329.
Precipitation / Solubility |
Solutions / Solvents |
Laboratory Management
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
Nucleophilic aromatic substitution: A microscale organic experiment  Avila, Walter B.; Crow, Jeffrey L.; Utermoehlen, Clifford M.
This experiment demonstrates one feasible route in preparing ortho-substituted benzoic acids and is also an example of nucleophilic aromatic substitution chemistry.
Avila, Walter B.; Crow, Jeffrey L.; Utermoehlen, Clifford M. J. Chem. Educ. 1990, 67, 350.
Nucleophilic Substitution |
Aromatic Compounds |
Microscale Lab |
Carboxylic Acids
The solvation of halide ions and its chemical significance  Sharpe, Alan G.
Most of this article is concerned with structural and thermodynamic aspects of halide ion solvation, first by water and the by other solvents.
Sharpe, Alan G. J. Chem. Educ. 1990, 67, 309.
Solutions / Solvents |
Thermodynamics |
Ionic Bonding
Critical behavior in the solubility of ionic compounds  Gillispie, Gregory D.
The process of an ionic compound dissolving in a pure solvent is a convenient way to introduce Debye-Huckel activity coefficients.
Gillispie, Gregory D. J. Chem. Educ. 1990, 67, 143.
Solutions / Solvents |
Ionic Bonding |
Electrolytic / Galvanic Cells / Potentials
Organic lecture demonstrations  Silversmith, Ernest F.
Organic chemistry may not be known for its spectacular, attention getting chemical reactions. Nevertheless, this author describes a few organic chemistry reactions that put points across and generate interest. This article provides a convenient sources of demonstrations and urges others to add to the collection. Demonstrations concerning: carbohydrates, spectroscopy, proteins, amines, carbohydrates, carboxylic acids, and much more.
Silversmith, Ernest F. J. Chem. Educ. 1988, 65, 70.
Molecular Properties / Structure |
Nucleophilic Substitution |
Acids / Bases |
Physical Properties |
Alkenes |
Stereochemistry |
Enantiomers |
Chirality / Optical Activity |
Aldehydes / Ketones |
Alcohols
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
TLC of organic dyes in undergraduate labs  Sciam, Allen J.
Investigation into the effectiveness of varying the solvent composition in terms of resolving the components of a mixture of dyes using thin layer chromatography.
Sciam, Allen J. J. Chem. Educ. 1985, 62, 361.
Thin Layer Chromatography |
Dyes / Pigments |
Solutions / Solvents
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
Organic lecture demonstrations of common-ion effect, ionizing power of solvents, and first-order reaction kinetics  Danen, Wayne C.; Blecha, Sr. M. Therese
The hydrolysis of tert-butyl chloride is the basis of three demonstrations which each illustrate an important principle of organic chemistry: the common-ion or mass law effect, the effect of changing the ionizing power of a solvent on a solvolysis reaction, and the collecting and plotting of data to illustrate a first-order reaction.
Danen, Wayne C.; Blecha, Sr. M. Therese J. Chem. Educ. 1982, 59, 659.
Aqueous Solution Chemistry |
Solutions / Solvents |
Nucleophilic Substitution |
Kinetics |
Rate Law
Phase transfer catalysis. Part II: Synthetic applications  Gokel, George W.; Weber, William P.
In this month's continuation of an article, the authors have catalogued a number of illustrative examples so that the range of applicability of phase transfer catalysis will be.
Gokel, George W.; Weber, William P. J. Chem. Educ. 1978, 55, 429.
Phases / Phase Transitions / Diagrams |
Catalysis |
Aromatic Compounds |
Organometallics |
Nucleophilic Substitution |
Synthesis |
Esters |
Oxidation / Reduction |
Alkylation
Phase-transfer catalysis using quaternary 'Onium salts  Mclntosh, J. M.
This article is intended to focus attention on the preparative applications of the catalytic phase-transfer technique.
Mclntosh, J. M. J. Chem. Educ. 1978, 55, 235.
Catalysis |
Ethers |
Solutions / Solvents
On mole fractions in equilibrium constants  Delaney, C. M.; Nash, Leonard K.
Proposes a hybrid equilibrium constant for use in introductory chemistry courses.
Delaney, C. M.; Nash, Leonard K. J. Chem. Educ. 1977, 54, 151.
Equilibrium |
Stoichiometry |
Aqueous Solution Chemistry |
Solutions / Solvents
Molar solubility calculations and the control equilibrium  Chaston, S. H. H.
The Control-Equilibrium method uses as its starting point a precise procedure for obtaining the equilibrium that accounts for the bulk of the decomposition of starting materials.
Chaston, S. H. H. J. Chem. Educ. 1975, 52, 206.
Solutions / Solvents |
Chemometrics |
Equilibrium
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
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
Nucleophilic reactivities of the halide anions  Puar, Mohindar S.
Ranks the nucleophilic reactivities of free halide ions in various solvents.
Puar, Mohindar S. J. Chem. Educ. 1970, 47, 473.
Nucleophilic Substitution
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
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
Hard and soft acids and bases, HSAB, part II: Underlying theories  Pearson, Ralph G.
Explores possible explanations for and presents applications of the principles of hard and soft acids and bases.
Pearson, Ralph G. J. Chem. Educ. 1968, 45, 643.
Acids / Bases |
Lewis Acids / Bases |
Aqueous Solution Chemistry |
Solutions / Solvents |
Ionic Bonding |
Covalent 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
Teaching aromatic substitution: A molecular orbital approach  Meislich, Herbert
This paper presents a way of teaching aromatic substitution using the concepts of alternate polarity and electron delocalization through extended pi-bonding.
Meislich, Herbert J. Chem. Educ. 1967, 44, 153.
Aromatic Compounds |
MO Theory |
Nucleophilic Substitution |
Covalent Bonding |
Molecular Properties / Structure
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
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
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 determination of stability constants of complex inorganic species in aqueous solutions  Tobias, R. Stuart
The purpose of this paper is to discuss the presently accepted methods for the determination of stability constants, i.e. the methods that are deemed to be the most reliable for indicating just what ionic species exist in solutions of "salts" of multivalent metal ions with various ligands.
Tobias, R. Stuart J. Chem. Educ. 1958, 35, 592.
Aqueous Solution Chemistry |
Solutions / Solvents |
Metals |
Coordination Compounds