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Journal Articles: 25 results
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
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
Precision in Stereochemical Terminology  LeRoy G. Wade, Jr.
This article recommends that instructors use the precise terms asymmetric carbon atom and chirality center when they apply, and use the broader term stereocenter only when there is a need to include stereogenic atoms that are not chirality centers.
Wade, LeRoy G., Jr. J. Chem. Educ. 2006, 83, 1793.
Chemical Technicians |
Diastereomers |
Enantiomers |
Stereochemistry |
Nomenclature / Units / Symbols |
Chirality / Optical Activity
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
Ozonolysis Problems That Promote Student Reasoning  Ray A. Gross Jr.
The structural features inherent in acyclic monoterpenes that follow the isoprene rule often lead to unique sets of ozonolysis products from which their structures, excluding stereochemistry, can be determined from molecular formulas only. This article shows how students may elucidate the structures of these compounds by analysis of the oxidative and reductive workup products.
Gross, Ray A., Jr. J. Chem. Educ. 2006, 83, 604.
Aldehydes / Ketones |
Alkenes |
Alkynes |
Carboxylic Acids |
Oxidation / Reduction |
Student-Centered Learning
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
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
Regioselective Synthesis of a Stereodefined Heterocyclic Push–Pull Alkene. 1H NMR Studies and Two-Dimensional TLC Illustrating Z/E Isomerization  Rade Markovi, Marija Baranac, Vesna Jovanovi, and Zdravko Dambaski
Facile and direct regioselective synthesis of the 4-oxothiazolidine derivative from inexpensive chemicals as an example of kinetic versus thermodynamic control is described.
Markovi, Rade; Baranac, Marija; Jovanovi, Vesna; Dambaski, Zdravko. J. Chem. Educ. 2004, 81, 1026.
Heterocycles |
Alkenes |
Stereochemistry |
Synthesis |
NMR Spectroscopy
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
Models and Molecules - A Workshop on Stereoisomers  Robert W. Baker, Adrian V. George, and Margaret M. Harding
A molecular model workshop aimed at first year university undergraduates has been devised to illustrate the concepts of organic stereochemistry. The students build models to teach the relationship within, and between, conformational isomers, enantiomers, and diastereomers.
Baker, Robert W.; George, Adrian V.; Harding, Margaret M. J. Chem. Educ. 1998, 75, 853.
Molecular Properties / Structure |
Stereochemistry |
Molecular Modeling |
Enantiomers |
Diastereomers
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
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
The Wittig synthesis of alkenes by phase-transfer catalysis: The syntheses of 4,4'-dichlorostilbenes and of E, E-1,4 -diphenylbutadiene   Breuer, Stephen W.
The syntheses of 4,4'-dichlorostilbenes and of E, E-1,4 -diphenylbutadiene.
Breuer, Stephen W. J. Chem. Educ. 1991, 68, A58.
Synthesis |
Microscale Lab |
Alkenes |
Aromatic Compounds
Chiral crackers: A palatable approach to optical isomerism  Griffin, Susan F.
Crackers obtained from the grocery store can be used to help students understand enantiomers.
Griffin, Susan F. J. Chem. Educ. 1991, 68, 1029.
Chirality / Optical Activity |
Stereochemistry |
Enantiomers
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
Flow chart determination of isomeric relationships  Black, Kersey A.
This flow chart presentation is particularly effective in helping the student to distinguish between the different types of stereochemical relationships.
Black, Kersey A. J. Chem. Educ. 1990, 67, 141.
Stereochemistry
An easily constructed bicapped trigonal prism model  Yamana, Shukichi
Using a two sealed envelopes to construct a bicapped trigonal prism model.
Yamana, Shukichi J. Chem. Educ. 1989, 66, 1021.
Molecular Modeling |
Molecular Properties / Structure |
Stereochemistry
Stereochemistry of cyclic hydrocarbons   Perkins, Robert R.
The topic of stereochemistry always poses great difficulties for many students in introductory organic chemistry. The following problems can be used as a tutorial question after having introduced the various terms associated with stereochemistry. The question requires skills at the applications level in the Bloom taxonomy.
Perkins, Robert R. J. Chem. Educ. 1988, 65, 860.
Alkanes / Cycloalkanes |
Chirality / Optical Activity |
Stereochemistry |
Diastereomers |
Constitutional Isomers
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
Confusion over D and L Nomenclature  Yuan, Sun-Shine
The use of the (R,S) convention will eliminate (D,L) confusion.
Yuan, Sun-Shine J. Chem. Educ. 1980, 57, 528.
Amino Acids |
Stereochemistry |
Nomenclature / Units / Symbols
Facile assignment of R,S designations to Fischer projections  Price, Howard C.
Suggests a method of assigning R,S designations to Fischer projections that easier than that described in the cited article.
Price, Howard C. J. Chem. Educ. 1980, 57, 528.
Stereochemistry |
Molecular Properties / Structure |
Chirality / Optical Activity |
Enantiomers
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
Diphenylbutadienes syntheses by means of the Wittig reaction: Experimental introduction to the use of phase transfer catalysis  Gillois, J.; Guillerm, G.; Stephen, E.; Vo-Quang, L.
Intended as a project carried out by students at the end of introductory organic chemistry.
Gillois, J.; Guillerm, G.; Stephen, E.; Vo-Quang, L. J. Chem. Educ. 1980, 57, 161.
Synthesis |
Catalysis |
Alkenes |
Aldehydes / Ketones |
Stereochemistry
Glutamic acid in pheromone synthesis: A useful chiral synthon  Smith, Leverett R.; Williams, Howard J.
Outlines synthetic routes for the formation of various pheromones from glutamic acid.
Smith, Leverett R.; Williams, Howard J. J. Chem. Educ. 1979, 56, 696.
Synthesis |
Chirality / Optical Activity |
Natural Products |
Stereochemistry |
Enantiomers |
Amino Acids
Z- and E-stereoisomerism: An experiment using photochemistry  Bourelle-Wargnier, F.; Feigenbaum, A.; Muzart, J.
The authors' report on the preparation of 2-benzylidenecyclohexanone E(I).
Bourelle-Wargnier, F.; Feigenbaum, A.; Muzart, J. J. Chem. Educ. 1978, 55, 339.
Stereochemistry |
Photochemistry |
Aromatic Compounds |
Thin Layer Chromatography |
IR Spectroscopy |
Enantiomers