| Journal Articles: 52 results |
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Borohydride Reduction of Estrone Animesh Aditya, David E. Nichols, and G. Marc Loudon This experiment presents a guided-inquiry approach to the demonstration of diastereoselectivity using chiral hindered ketones that undergo facile reduction with sodium borohydride. The resulting diastereomeric estradiols can be analyzed and differentiated by thin-layer chromatography and melting point. Aditya, Animesh; Nichols, David E.; Loudon, G. Marc. J. Chem. Educ. 2008, 85, 1535.
Aldehydes / Ketones |
Diastereomers |
IR Spectroscopy |
Microscale Lab |
Stereochemistry |
Steroids |
Thin Layer Chromatography
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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
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Mosher Amides: Determining the Absolute Stereochemistry of Optically-Active Amines Damian A. Allen, Anthony E. Tomaso, Jr., Owen P. Priest, David F. Hindson, and Jamie L. Hurlburt In this experiment, teams of students are given an optically-pure amine of known structure but unknown stereochemistry. Different teams derivatize samples of the amine with (R) and (S) conformations of Mosher's acid chloride. The resulting diastereomers are analyzed by NMR to determine the absolute configuration of the initial, unknown amine. Allen, Damian A.; Tomaso, Anthony E., Jr.; Priest, Owen P.; Hindson, David F.; Hurlburt, Jamie L. J. Chem. Educ. 2008, 85, 698.
Amides |
Chirality / Optical Activity |
Chromatography |
Diastereomers |
Microscale Lab |
NMR Spectroscopy |
Stereochemistry
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A Simple Method for Drawing Chiral Mononuclear Octahedral Metal Complexes Aminou Mohamadou and Arnaud Haudrechy This article presents a simple and progressive method to draw all of the octahedral complexes of coordination units with at least two different monodentate ligands and show their chiral properties. Mohamadou, Aminou; Haudrechy, Arnaud. J. Chem. Educ. 2008, 85, 436.
Asymmetric Synthesis |
Chirality / Optical Activity |
Coordination Compounds |
Diastereomers |
Enantiomers |
Molecular Properties / Structure |
Stereochemistry |
Transition Elements
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Dynamic Stereochemistry: A Simple Approach To Delineating Relative Configuration Dipak K. Mandal A simple approach is presented for delineating relative stereochemistry of the product in reactions involving stereogenic center(s). Mandal, Dipak K. J. Chem. Educ. 2007, 84, 274.
Chirality / Optical Activity |
Diastereomers |
Enantiomers |
Molecular Properties / Structure |
Stereochemistry
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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
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The Step-by-Step Robinson Annulation of Chalcone and Ethyl Acetoacetate. An Advanced Undergraduate Project in Organic Synthesis and Structural Analysis Lionel Delaude, Jean Grandjean, and Alfred F. Noels The Robinson annulation is a three-step process involving a Michael addition followed by an internal aldol condensation and a dehydration. It is possible to stop the reaction after every step and to isolate the three products, allowing students to confirm the validity of the stepwise mechanism and develop a more thorough understanding of the whole process. Delaude, Lionel; Grandjean, Jean; Noels, Alfred F. J. Chem. Educ. 2006, 83, 1225.
Catalysis |
Chirality / Optical Activity |
Conformational Analysis |
Diastereomers |
IR Spectroscopy |
Synthesis |
NMR Spectroscopy |
Stereochemistry
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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
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An Engaging Illustration of the Physical Differences among Menthol Stereoisomers Edward M. Treadwell and T. Howard Black The differences and similarities in the physical behavior of enantiomers and diastereomers can easily be demonstrated using the commercial stereoisomers (-)-menthol, (+)-menthol, (+)-isomenthol, and (+)-neomenthol. Thin-layer chromatography and melting point determinations clearly show that diastereomers have different physical properties from enantiomers and each other, but that enantiomers have identical physical properties in achiral environments. By obtaining a mixed melting point and optical rotations the difference in enantiomers can be observed. Treadwell, Edward M.; Black, T. Howard. J. Chem. Educ. 2005, 82, 1046.
Chirality / Optical Activity |
Stereochemistry |
Thin Layer Chromatography |
Diastereomers |
Enantiomers |
Physical Properties
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Enantiomeric Resolution of (±)-Mandelic Acid by (1R,2S)-(–)-Ephedrine. An Organic Chemistry Laboratory Experiment Illustrating Stereoisomerism Marsha R. Baar and Andrea L. Cerrone-Szakal There has been an increasing need, particularly in the pharmaceutical industry, to prepare chiral substances in single-isomer form. A chiral technique that makes an excellent introductory organic chemistry experiment is enantiomeric resolution. The classical resolution of ()-mandelic acid using the chiral amine, (1R,2S)-()-ephedrine, was adapted for use in introductory organic chemistry lab curricula. Baar, Marsha R.; Cerrone-Szakal, Andrea L. J. Chem. Educ. 2005, 82, 1040.
Acids / Bases |
Chirality / Optical Activity |
Separation Science |
Stereochemistry |
Diastereomers |
Enantiomers
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Enantiomeric and Diastereoisomeric Relationships: A Practical Approach V. Durieu, G. Martiat, M. Ch. Vandergeten, F. Pirsoul, F. Toubeau, and Agnès Van Camp An experiment in organic chemistry in which the students prepare, purify, and characterize optical isomers. The three optical isomers of the bisoxalamides obtained by the reaction of racemic 1-phenylethylamine with diethyloxalate are separable by flash chromatography into the racemic mixture of (R,R) + (S,S) oxalamides and the (R,S) meso compound. Durieu, V.; Martiat, G.; Vandergeten, M. Ch.; Pirsoul, F.; Toubeau, F.; Van Camp, Agnès. J. Chem. Educ. 2000, 77, 752.
Molecular Properties / Structure |
Stereochemistry |
Separation Science |
Enantiomers |
Diastereomers |
Chirality / Optical Activity |
Synthesis
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Synthesis and Separation of a Diastereomeric Sulfonium Ion by Capillary Zone Electrophoresis Francisco A. Valenzuela, Thomas K. Green, and Darwin B. Dahl An undergraduate laboratory exercise utilizing capillary zone electrophoresis in the analysis of the student-synthesized sulfonium ion sec-butylmethyl-p-tolylsulfonium tetrafluoroborate is presented. The sulfonium ion contains two stereogenic centers and thereby yields four optical isomers. Valenzuela, Francisco A.; Green, Thomas K.; Dahl, Darwin B. J. Chem. Educ. 1998, 75, 1590.
Electrophoresis |
Stereochemistry |
NMR Spectroscopy |
Diastereomers |
Separation Science |
Synthesis
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Stereowordimers-Minding Your P's and Q's Edward G. Neeland The use of words having different colored sides is a excellent way to introduce stereochemical concepts that might not be easily grasped when using molecular examples. We have found that concepts such as enantiomers, diastereomers, identical molecules, chirality, achirality, mirror planes of symmetry, and internal planes of symmetry are readily understood by students when using stereowordimer examples. Neeland, Edward G. J. Chem. Educ. 1998, 75, 1573.
Stereochemistry |
Diastereomers |
Enantiomers |
Molecular Properties / Structure
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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
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1H NMR Analysis of R/S Ibuprofen by the Formation of Diasteriomeric Pairs: Microscale Stereochemistry Experiment for the Undergraduate Organic Laboratory Stephanie E. Sen and Keith S. Anliker A multicomponent experiment is described which elucidates the chirality of the commercially available analgesic, ibuprofen. Stephanie E. Sen and Keith S. Anliker. J. Chem. Educ. 1996, 73, 569.
Stereochemistry |
Enantiomers |
Drugs / Pharmaceuticals |
Diastereomers |
Gas Chromatography |
NMR Spectroscopy
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The stereochemistry of commercial 2,6-dimethylcyclohexanone: An application of capillary gas chromatography Garner, Charles M. One example of how capillary gas chromatography can be employed in undergraduate organic laboratories. Garner, Charles M. J. Chem. Educ. 1993, 70, A310.
Gas Chromatography |
Microscale Lab |
Laboratory Equipment / Apparatus |
Aldehydes / Ketones |
Diastereomers |
Stereochemistry
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The enumeration of isomers-With special reference to the stereoisomers of decane Whyte, J. R. C.; Clugston, M. J. Structural isomers predicted through algorithms. Whyte, J. R. C.; Clugston, M. J. J. Chem. Educ. 1993, 70, 874.
Alkanes / Cycloalkanes |
Stereochemistry |
Diastereomers
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The square knot and the granny knot: An analogy for diastereomers. Tavernier, Dirk. Few of the diastereomorphs generated by joining two man-made chiral objects have different names; the author is aware of just one example - the square knot and the granny knot. Tavernier, Dirk. J. Chem. Educ. 1992, 69, 627.
Diastereomers |
Molecular Properties / Structure |
Stereochemistry |
Chirality / Optical Activity
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An introduction to fullerene structures: Geometry and symmetry. Boo, W. O. J. The formidable task of organizing the fullerenes can be simplified greatly by categorizing them by their symmetries. Boo, W. O. J. J. Chem. Educ. 1992, 69, 605.
Alkenes |
Molecular Properties / Structure |
Group Theory / Symmetry |
Stereochemistry |
Diastereomers
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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
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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
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Photochemical and thermal isomerization of trans- and cis-1,2-dibenzoylethylene: A microscale approach Klemm, Dennis V; Tuncay, Atilla Both conversions are analyzed through thin layer chromatography. Klemm, Dennis V; Tuncay, Atilla J. Chem. Educ. 1989, 66, 519.
Photochemistry |
Stereochemistry |
Microscale Lab |
Thin Layer Chromatography |
Diastereomers
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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
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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
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A synthesis of chrysanthemic ester: An undergraduate experiment Kelly, Lawrence F. Procedure for producing a mixture of cis- and trans-ethyl chrysanthemates. Kelly, Lawrence F. J. Chem. Educ. 1987, 64, 1061.
Esters |
Synthesis |
Catalysis |
Diastereomers |
Stereochemistry
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A Wittig reaction that gives only one stereoisomer Silversmith, Ernest F. This popular experiment can be extended to illustrate the use of spectroscopy to elucidate stereochemistry. Silversmith, Ernest F. J. Chem. Educ. 1986, 63, 645.
Stereochemistry |
Diastereomers |
Separation Science
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Stress the twofold axis of the threo isomer Tavernier, D. The author weighs in on the the controversy of the threo and erythro nomenclature. Tavernier, D. J. Chem. Educ. 1986, 63, 511.
Nomenclature / Units / Symbols |
Molecular Properties / Structure |
Stereochemistry |
Enantiomers |
Diastereomers
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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
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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
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Determination of stereochemical relationships Ayorinde, Folahan O. A sequence of steps to enable students to arrive with relative ease at correct stereochemical relationships. Ayorinde, Folahan O. J. Chem. Educ. 1985, 62, 297.
Stereochemistry |
Molecular Properties / Structure |
Chirality / Optical Activity |
Enantiomers |
Diastereomers
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Structural isomer identification via NMR: A nuclear magnetic resonance experiment for organic, analytical, or physical chemistry Szafran, Zvi This experiment examines the ability of NMR to distinguish between structural isomers via resonance multiplicities and chemical shifts. Szafran, Zvi J. Chem. Educ. 1985, 62, 260.
NMR Spectroscopy |
Stereochemistry |
Diastereomers
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Models for illustrating chirality at two centers Feldman, Martin R. This note suggests common objects that can be used as models to illustrate chirality at two centers, and to introduce the concepts of diastereomers and the meso configuration. Feldman, Martin R. J. Chem. Educ. 1984, 61, 1050.
Molecular Properties / Structure |
Molecular Modeling |
Chirality / Optical Activity |
Diastereomers |
Stereochemistry |
Enantiomers
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Examples of diastereomers Bell, William Using right- and left-handed doors as examples of familiar objects that exhibit enantiomerism. Bell, William J. Chem. Educ. 1984, 61, 901.
Stereochemistry |
Diastereomers |
Molecular Properties / Structure |
Chirality / Optical Activity
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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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An experiment on isomerism in metal-amino acid complexes: Preparation and characterization of cobalt(III) complexes containing N-bonded monodentate, O-bonded monodentate and N,O-chelated glycine ligands Harrison, R. Graeme; Nolan, Kevin B. Synthesis of three cobalt(III) complexes that illustrate three possible modes of bonding of glycine to a metal ion, as well as methods for distinguishing among the products. Harrison, R. Graeme; Nolan, Kevin B. J. Chem. Educ. 1982, 59, 1054.
Stereochemistry |
Amino Acids |
Coordination Compounds |
Synthesis |
Diastereomers |
IR Spectroscopy |
Crystal Field / Ligand Field Theory
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The preparation and characterization of the geometric isomers of a coordination complex: cis- and trans-bis-glycinato copper(II) monohydrates O'Brien, Paul The preparation of the cis and trans isomers of the kinetically labile bis glycinato copper(II) has a number of advantages including its facility, economy, ready theoretical interpretation, and biological relevance. O'Brien, Paul J. Chem. Educ. 1982, 59, 1052.
Synthesis |
Stereochemistry |
Diastereomers |
IR Spectroscopy |
Coordination Compounds |
Crystal Field / Ligand Field Theory
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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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Diastereomers, geometric isomers, and rotation about bonds McCullough, John J. A simple and consistent introduction to the stereochemistry of carbon, diastereomers, and geometric isomers. McCullough, John J. J. Chem. Educ. 1982, 59, 37.
Stereochemistry |
Diastereomers |
Molecular Properties / Structure
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A helpful stereochemical instructional tool England, Don The figure found in this note has been helpful in aiding student understanding of stereochemistry. England, Don J. Chem. Educ. 1981, 58, 31.
Stereochemistry |
Molecular Modeling |
Molecular Properties / Structure |
Chirality / Optical Activity |
Diastereomers |
Enantiomers
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Stereochemical nonequivalence of ligands and faces (heterotopicity) Eliel, Ernest L. Reviews the concepts associated with stereochemical non-equivalence (heterotopicity). Eliel, Ernest L. J. Chem. Educ. 1980, 57, 52.
Stereochemistry |
Enantiomers |
Diastereomers |
Constitutional Isomers |
Group Theory / Symmetry
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Optical illusions in drawings of cyclohexane derivatives Feldman, Martin R. An optical illusion in the representation of chair cyclohexanes. Feldman, Martin R. J. Chem. Educ. 1979, 56, 659.
Molecular Properties / Structure |
Stereochemistry |
Enantiomers |
Diastereomers |
Alkanes / Cycloalkanes
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Computation of the number of isomers of coordination compounds containing different monodentate ligands Chung, Chung-Sun
Chung, Chung-Sun J. Chem. Educ. 1979, 56, 398.
Chemometrics |
Molecular Properties / Structure |
Coordination Compounds |
Stereochemistry |
Diastereomers
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Identification of geometrical isomers of the cobalt(III)-iminodiacetate system: An inorganic experiment Lawrance, Geoffrey A.; Rix, Colin J. Procedure for the preparation and isolation of two differently colored geometric isomers of Co(IDA)2- and their characterization using pmr and visible spectroscopy. Lawrance, Geoffrey A.; Rix, Colin J. J. Chem. Educ. 1979, 56, 211.
Stereochemistry |
Diastereomers |
Coordination Compounds |
Spectroscopy |
UV-Vis Spectroscopy
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Schemes and transformations in the (CH)8 series. The "valence isomers" of cyclooctatetraene Smith, Leverett R. The authors provide a scheme for deriving valence isomers. Smith, Leverett R. J. Chem. Educ. 1978, 55, 569.
Aromatic Compounds |
Enantiomers |
Stereochemistry |
Diastereomers
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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
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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
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Calculation of the number of cis-trans isomers in a "symmetric" polyene Har-zvi, Ron; Wittes, Janet Turk A problem in which students are to derive a general expression for the number of cis-trans isomers in a "symmetric" straight chain polyene when there are n double bonds. Har-zvi, Ron; Wittes, Janet Turk J. Chem. Educ. 1975, 52, 545.
Stereochemistry |
Molecular Properties / Structure |
Diastereomers |
Alkenes
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Photochemical and thermal interconversion of cis and trans isomers. An organic laboratory experiment Silversmith, Ernest F.; Dunson, Fay C. The photoisomerization of trans-1,4-diphenyl-2-butene-1,4-dione to the cis isomer. Silversmith, Ernest F.; Dunson, Fay C. J. Chem. Educ. 1973, 50, 568.
Photochemistry |
Molecular Properties / Structure |
Diastereomers |
Stereochemistry
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On diastereomeric meso compounds Andrist, A. Harry A table of the number of diastereomeric meso diacids possible from the oxidation of carbohydrates containing different numbers of asymmetric carbon atoms. Andrist, A. Harry J. Chem. Educ. 1972, 49, 551.
Oxidation State |
Stereochemistry |
Diastereomers |
Carbohydrates
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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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Conformational analysis and chemical reactivity Idoux, John P. Uses acyclic chemistry to illustrate important concepts regarding conformational analysis and chemical reactivity. Idoux, John P. J. Chem. Educ. 1967, 44, 495.
Conformational Analysis |
Stereochemistry |
Diastereomers
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The unraveling of geometric isomerism and tautomerism Ihde, Aaron J. Examines the work of Van't Hoff in unraveling isomerism due to carbon-carbon double bonds using fumaric and maleic acids as exemplars. Ihde, Aaron J. J. Chem. Educ. 1959, 36, 330.
Molecular Properties / Structure |
Stereochemistry |
Diastereomers
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