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Journal Articles: 516 results
The Way of Synthesis. Evolution of Design and Methods for Natural Products (Tomás Hudlicky and Josephine W. Reed)  David G. J. Young
The Way of Synthesis is a 1000-page book on the progress of synthetic organic chemistry spanning its apparent inception in 1828 (Wohlers preparation of urea) to the state of the art in 2007.
Young, David G. J. J. Chem. Educ. 2008, 85, 1626.
Diastereomers |
Enantiomers |
Natural Products |
Reactions |
Stereochemistry |
Synthesis
The Synthesis of N-Benzyl-2-azanorbornene via Aqueous Hetero Diels–Alder Reaction  Xavier Sauvage and Lionel Delaude
Characterization of the product of this organic synthesis through IR and NMR data analysis provides valuable material to familiarize students with different types of protonproton coupling patterns and their typical ranges, serves to illustrate the concepts of green chemistry and atom efficiency, and can be used to exemplify structural analysis and computational studies.
Sauvage, Xavier; Delaude, Lionel. J. Chem. Educ. 2008, 85, 1538.
Alkenes |
Aqueous Solution Chemistry |
Conformational Analysis |
Green Chemistry |
IR Spectroscopy |
Molecular Modeling |
NMR Spectroscopy |
Stereochemistry |
Synthesis
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
Percy Julian, Robert Robinson, and the Identity of Eserethole  Addison Ault
The Nova production Percy JulianForgotten Genius, which included the very public disagreement over the identity of "eserethole," the key intermediate for the synthesis of the alkaloid physostigmine, left three important chemical questions unanswered.
Ault, Addison. J. Chem. Educ. 2008, 85, 1524.
Constitutional Isomers |
Enantiomers |
Natural Products |
Stereochemistry |
Synthesis
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
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
The Same and Not the Same: Chirality, Topicity, and Memory of Chirality  Wolfgang H. Kramer and Axel G. Griesbeck
Describes a simple molecular approach that aids students in learning stereochemical terms, definitions, and concepts, particularly when chemical structures are drawn in two dimensions.
Kramer, Wolfgang H.; Griesbeck, Axel G. J. Chem. Educ. 2008, 85, 701.
Chirality / Optical Activity |
Stereochemistry
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
Acylation, Diastereoselective Alkylation, and Cleavage of an Oxazolidinone Chiral Auxiliary  Thomas E. Smith, David P. Richardson, George A. Truran, Katherine Belecki, and Megumi Onishi
Describes an introduction to the concepts and experimental techniques of diastereoselective synthesis using a chiral auxiliary that gives students the opportunity to gain proficiency with the techniques of modern organic synthesis, including the manipulation of moisture-sensitive reagents, low temperature reactions, column chromatography, TLC, and NMR analysis.
Smith, Thomas E.; Richardson, David P.; Truran, George A.; Belecki, Katherine; Onishi, Megumi. J. Chem. Educ. 2008, 85, 695.
Alkylation |
Asymmetric Synthesis |
Chromatography |
Diastereomers |
Enantiomers |
Mechanisms of Reactions |
NMR Spectroscopy |
Stereochemistry
Use of the Chemical Literature as a Template To Probe Stereoselective Reactions by NMR  Thomas P. Clausen, Thomas K. Green, and Benjamin Steiner
The approach to the organic laboratory described here presents students with literature studies that form the basis of developing new unpublished experiments to answer specific questions. As a result, students are better exposed to the chemical literature, gain experience in experimental design, and are forced to interpret rather than simply match spectra.
Clausen, Thomas P.; Green, Thomas K.; Steiner, Benjamin. J. Chem. Educ. 2008, 85, 692.
Grignard Reagents |
NMR Spectroscopy |
Stereochemistry |
Undergraduate Research
Stereochemical Control in Carbohydrate Chemistry  Rhys Batchelor, Peter T. Northcote, Joanne E. Harvey, Emma M. Dangerfield, and Bridget L. Stocker
Describes a sequence of experiments that leads students from the derivatization of naturally occurring D-glucose through to the formation of simple alkyl and aryl glycosides. In doing so, this experiment provides an overview of glycoside synthesis with a focus on the control of stereochemistry at the anomeric center and structural elucidation through NMR spectroscopy.
Batchelor, Rhys; Northcote, Peter T.; Harvey, Joanne E.; Dangerfield, Emma M.; Stocker, Bridget L. J. Chem. Educ. 2008, 85, 689.
Carbohydrates |
NMR Spectroscopy |
Stereochemistry |
Synthesis
A Simple Laboratory Experiment To Determine the Kinetics of Mutarotation of D-Glucose Using a Blood Glucose Meter  Carlos E. Perles and Pedro L. O. Volpe
A simple commercial blood glucose meter is used to follow the kinetics of mutarotation of D-glucose in aqueous solution. The results may be compared with those obtained using an automatic polarimeter.
Perles, Carlos E.; Volpe, Pedro L. O. J. Chem. Educ. 2008, 85, 686.
Aqueous Solution Chemistry |
Bioanalytical Chemistry |
Carbohydrates |
Chirality / Optical Activity |
Enzymes |
Kinetics |
Solutions / Solvents |
Stereochemistry
Pyrolysis of Aryl Sulfonate Esters in the Absence of Solvent: E1 or E2? A Puzzle for the Organic Laboratory  John J. Nash, Marnie A. Leininger, and Kurt Keyes
An aryl sulfonate ester is synthesized and then pyrolyzed at reduced pressure. The volatile products are analyzed using gas chromatography to determine whether the thermal decomposition occurs via an E1 or E2 mechanism.
Nash, John J.; Leininger, Marnie A.; Keyes, Kurt . J. Chem. Educ. 2008, 85, 552.
Alkenes |
Carbocations |
Elimination Reactions |
Gas Chromatography |
Mechanisms of Reactions |
Synthesis
The Meaning of Meso  Addison Ault
The original use of the prefix "meso" was to refer to an optically inactive, non-resolvable member of a set of stereoisomers, some of which were optically active.
Ault, Addison. J. Chem. Educ. 2008, 85, 441.
Chirality / Optical Activity |
Stereochemistry
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
Can a Non-Chiral Object Be Made of Two Identical Chiral Moieties?  Jean François LeMaréchal
Uses the cut of an apple to show that the association of identical chiral moieties can form a non-chiral object.
LeMaréchal, Jean François. J. Chem. Educ. 2008, 85, 433.
Chirality / Optical Activity |
Coordination Compounds |
Enantiomers |
Group Theory / Symmetry |
Stereochemistry |
Transition Elements
Ring-Opening Polymerization of Lactide To Form a Biodegradable Polymer  Jennifer L. Robert and Katherine B. Aubrecht
In this laboratory, students carry out the tin(II) bis(2-ethylhexanoate)/benzyl alcohol mediated ring-opening polymerization of lactide to form the biodegradable polymer polylactide. As the mechanism of the polymerization is analogous to that of a transesterification reaction, the experiment can be used to demonstrate reactions of carboxylic acid derivatives.
Robert, Jennifer L.; Aubrecht, Katherine B. J. Chem. Educ. 2008, 85, 258.
Esters |
Green Chemistry |
NMR Spectroscopy |
Polymerization |
Stereochemistry
Unequal Activities of Enantiomers via Biological Receptors: Examples of Chiral Drug, Pesticide, and Fragrance Molecules  Albrecht Mannschreck, Roland Kiesswetter, and Erwin von Angerer
Proposes a two-hour lecture intended for medicinal chemistry students that emphasizes the similarity between the different types of receptor-mediated actions of enantiomers which serve as the basis for the actions of chiral drug, pesticide, and fragrance molecules.
Mannschreck, Albrecht; Kiesswetter, Roland; von Angerer, Erwin. J. Chem. Educ. 2007, 84, 2012.
Agricultural Chemistry |
Bioorganic Chemistry |
Chirality / Optical Activity |
Drugs / Pharmaceuticals |
Enantiomers |
Medicinal Chemistry |
Receptors |
Stereochemistry
Showing Enantiomorphous Crystals of Tartaric Acid  Julio Andrade-Gamboa
Most drawings of enantiomorphous crystals are inadequate to demonstrate that they are non-superimposable mirror images. This article examines the classic case of tartaric acid and the use of an alternative graphical representation and a paper model to facilitate the conceptualization of this subject.
Andrade-Gamboa, Julio. J. Chem. Educ. 2007, 84, 1783.
Chirality / Optical Activity |
Crystals / Crystallography |
Enantiomers |
Stereochemistry
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
A Knoevenagel Initiated Annulation Reaction Using Room Temperature or Microwave Conditions  A. Gilbert Cook
The product of a Knoevenagel initiated annulation reaction is identified through a guided prelab exercise of the synthesis of the Hagemann ester, and then through the analysis of GCMS, NMR, and IR spectra. The stereochemistry of the product is determined through the NMR spectrum and Karplus curve, and the student is required to write a mechanism for the reaction.
Cook, A. Gilbert. J. Chem. Educ. 2007, 84, 1477.
Aldehydes / Ketones |
Conformational Analysis |
Gas Chromatography |
IR Spectroscopy |
Mass Spectrometry |
Mechanisms of Reactions |
NMR Spectroscopy |
Stereochemistry |
Synthesis
Reaction-Map of Organic Chemistry  Steven Murov
The Reaction-Map of Organic Chemistry has been designed to provide an overview of most of the reactions needed for the organic chemistry course and should help students develop synthetic routes from one functional group to another.
Murov, Steven. J. Chem. Educ. 2007, 84, 1224.
Addition Reactions |
Electrophilic Substitution |
Elimination Reactions |
Nucleophilic Substitution |
Oxidation / Reduction |
Periodicity / Periodic Table |
Reactions |
Synthesis |
Enrichment / Review Materials
Synthesis and NMR Spectral Analysis of Amine Heterocycles: The Effect of Asymmetry on the 1H and 13C NMR Spectra of N,O-Acetals  Shahrokh Saba, James A. Ciaccio, Jennifer Espinal, and Courtney E. Aman
Describe an undergraduate organic laboratory experiment in which students prepare two N,O-acetals that differ only in a single ring substituent that introduces asymmetry, giving each compound a distinct 1H and 13C NMR spectral pattern that must be explained by students.
Saba, Shahrokh; Ciaccio, James A.; Espinal, Jennifer; Aman, Courtney E. J. Chem. Educ. 2007, 84, 1011.
Amines / Ammonium Compounds |
Chirality / Optical Activity |
Green Chemistry |
Heterocycles |
NMR Spectroscopy |
Stereochemistry |
Synthesis
CARBOHYDECK: A Card Game To Teach the Stereochemistry of Carbohydrates  Manuel João Costa
This paper describes CARBOHYDECK, a card game that may replace or complement lectures identifying and differentiating monosaccharide isomers.
Costa, Manuel João. J. Chem. Educ. 2007, 84, 977.
Aldehydes / Ketones |
Carbohydrates |
Molecular Properties / Structure |
Stereochemistry |
Enrichment / Review Materials |
Student-Centered Learning
Nuclear Overhauser Effect Spectroscopy. An Advanced Undergraduate Experiment  Michael T. Huggins and Freida Billimoria
Describes an advanced laboratory experiment in which students prepare a set of compounds to study both the configuration of a newly formed double bond (E or Z) and the conformation of the molecule.
Huggins, Michael T.; Billimoria, Freida. J. Chem. Educ. 2007, 84, 471.
Alkenes |
Conformational Analysis |
Molecular Modeling |
NMR Spectroscopy |
Stereochemistry |
Synthesis |
Molecular Properties / Structure |
Chirality / Optical Activity
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
A Green Enantioselective Aldol Condensation for the Undergraduate Organic Laboratory  George D. Bennett
The proline-catalyzed aldol condensation between acetone and isobutyraldehyde proceeds in good yield and with high enantioselectivity at room temperature. This multi-week experiment also illustrates a number of principles and trade-offs of green chemistry.
Bennett, George D. J. Chem. Educ. 2006, 83, 1871.
Addition Reactions |
Aldehydes / Ketones |
Asymmetric Synthesis |
Catalysis |
Chirality / Optical Activity |
Green Chemistry |
Mechanisms of Reactions |
Stereochemistry
Keeping Your Students Awake: Facile Microscale Synthesis of Modafinil, a Modern Anti-Narcoleptic Drug  Evangelos Aktoudianakis, Rui Jun Lin, and Andrew P. Dicks
Describes the microscale preparation of modafinil, a pharmaceutical recently approved for the treatment of narcolepsy, by a sulfide oxidation reaction. An unusual feature of modafinil is the presence of a chiral sulfoxide functionality where a sulfur atom acts as a stereocenter, demonstrating that atoms other than carbon can act as centers of chirality.
Aktoudianakis, Evangelos; Lin, Rui Jun; Dicks, Andrew P. J. Chem. Educ. 2006, 83, 1832.
Chirality / Optical Activity |
Drugs / Pharmaceuticals |
Synthesis |
Mechanisms of Reactions |
IR Spectroscopy |
NMR Spectroscopy |
Microscale Lab |
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
Asymmetric Aldol Reaction Induced by Chiral Auxiliary  Jorge Pereira and Carlos A. M. Afonso
Describes an asymmetric aldol reaction based on the use of (4R,5S)-1,5-dimethyl-4-phenylimidazolidin- 2-one as a chiral auxiliary in a three-step procedure.
Pereira, Jorge; Afonso, Carlos A. M. J. Chem. Educ. 2006, 83, 1333.
Aldehydes / Ketones |
Asymmetric Synthesis |
Chirality / Optical Activity |
Diastereomers |
NMR Spectroscopy |
Chromatography |
Synthesis |
Stereochemistry
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
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
Stereospecific Synthesis of the Geometrical Isomers of a Natural Product  T. Grove, D. DiLella, and E. Volker
Presents an experiment for the synthesis of (Z) and (E) isomers that is presented to students as a puzzle in which they must determine the identity of the major component in anise oil. A necessary part of the analysis is the preparation the (E) and (Z) isomers of anethole. Molecular modeling is used to explore the conformation of and energy difference between isomers.
Grove, T.; DiLella, D.; Volker, E. J. Chem. Educ. 2006, 83, 1055.
Alkenes |
Computational Chemistry |
Gas Chromatography |
IR Spectroscopy |
NMR Spectroscopy |
Stereochemistry |
Synthesis
Enantioselective Reduction by Crude Plant Parts: Reduction of Benzofuran-2-yl Methyl Ketone with Carrot (Daucus carota) Bits  Silvana Ravía, Daniela Gamenara, Valeria Schapiro, Ana Bellomo, Jorge Adum, Gustavo Seoane, and David Gonzalez
Presents the enantioselective reduction of a ketone by crude plant parts, using carrot (Daucus carota) as the reducing agent.
Ravía, Silvana; Gamenara, Daniela; Schapiro, Valeria; Bellomo, Ana; Adum, Jorge; Seoane, Gustavo; Gonzalez, David. J. Chem. Educ. 2006, 83, 1049.
Aldehydes / Ketones |
Biotechnology |
Catalysis |
Chromatography |
Green Chemistry |
Oxidation / Reduction |
Stereochemistry |
Separation Science
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
Mannich Reactions in Room Temperature Ionic Liquids (RTILs): An Advanced Undergraduate Project of Green Chemistry and Structural Elucidation  Kendrew K. W. Mak, Jane Siu, Y. M. Lai, and Pak-kei Chan
This experiment describes the synthesis of a commonly used ionic liquid, 1-butyl-3-methylimidazolium tetrafluoroborate, and the application of this ionic liquid as a recyclable medium for Mannich reactions.
Mak, Kendrew K. W.; Siu, Jane; Lai, Y. M.; Chan, Pak-kei. J. Chem. Educ. 2006, 83, 943.
Aldehydes / Ketones |
Amines / Ammonium Compounds |
Green Chemistry |
Mechanisms of Reactions |
NMR Spectroscopy |
Stereochemistry |
Synthesis |
Undergraduate Research
Synthesis and Characterization of (σ2-terpyridyl)Re(CO)3Cl with Determination of Chemical Ring Exchange Constant  Andrea Freyer, Alan Freyer, and Christine DiMeglio
A coordination complex is synthesized according to a straight-forward literature preparation and then purified by re-crystallization. The solid-state properties of the complex produced are characterized by means of X-ray crystallography.
Freyer, Andrea; Freyer, Alan; DiMeglio, Christine. J. Chem. Educ. 2006, 83, 788.
Coordination Compounds |
Crystals / Crystallography |
Enantiomers |
Kinetics |
NMR Spectroscopy |
Stereochemistry |
Synthesis |
X-ray Crystallography
Use of 1H NMR in Assigning Carbohydrate Configuration in the Organic Laboratory  John L. Sorensen, Ross Witherell, and Lois M. Browne
This article describes a laboratory experiment suitable for an advanced undergraduate organic laboratory class that combines synthetic organic chemistry and 1H NMR in the determination of the identity of a simple carbohydrate.
Sorensen, John L.; Witherell, Ross; Browne, Lois M. J. Chem. Educ. 2006, 83, 785.
Carbohydrates |
Chromatography |
Conformational Analysis |
NMR Spectroscopy |
Stereochemistry
Synthesis of Unsymmetrical Alkynes via the Alkylation of Sodium Acetylides. An Introduction to Synthetic Design for Organic Chemistry Students  Jennifer N. Shepherd and Jason R. Stenzel
Teams of students design a microscale synthesis of an unsymmetrical alkyne using commercially available terminal alkynes and alkyl halides and characterize the resulting products using TLC, IR, and 1H NMR spectroscopy. Depending on the chosen reactants, students observe both substitution and elimination products, or in some cases, no reaction at all.
Shepherd, Jennifer N.; Stenzel, Jason R. J. Chem. Educ. 2006, 83, 425.
Alkylation |
Alkynes |
Elimination Reactions |
IR Spectroscopy |
Microscale Lab |
NMR Spectroscopy |
Nucleophilic Substitution |
Synthesis
Grubbs's Cross Metathesis of Eugenol with cis-2-Butene-1,4-diol To Make a Natural Product. An Organometallic Experiment for the Undergraduate Lab   Douglass F. Taber and Kevin J. Frankowski
Describes the ruthenium catalyzed cross metathesis of eugenol with cis-1,4-butenediol. The experiment is an excellent example of the powerful selectivity possible with the Grubbs' catalyst, demonstrating the preference for trans over cis alkene formation and for cross metathesis over homodimerization.
Taber, Douglass F.; Frankowski, Kevin J. J. Chem. Educ. 2006, 83, 283.
Alkenes |
Catalysis |
IR Spectroscopy |
Mass Spectrometry |
Mechanisms of Reactions |
Microscale Lab |
Natural Products |
NMR Spectroscopy |
Organometallics |
Stereochemistry |
Synthesis |
Thin Layer Chromatography |
Transition Elements
Diastereoselectivity in the Reduction of α-Hydroxyketones. An Experiment for the Chemistry Major Organic Laboratory  David B. Ball
Describes a research type, inquiry-based project where students synthesize racemic ahydroxyketones using umpolung, a polarity-reversal approach; investigate chelating versus non-chelating reducing agents; and determine the diastereoselectivity of these reducing processes by NMR spectroscopy.
Ball, David B. J. Chem. Educ. 2006, 83, 101.
Addition Reactions |
Aldehydes / Ketones |
Chirality / Optical Activity |
Chromatography |
Conferences |
Constitutional Isomers |
Enantiomers |
NMR Spectroscopy |
Stereochemistry |
Synthesis |
Conformational Analysis
A New Exploration of the Torsional Energy Surface of n-Pentane Using Molecular Models and Molecular Modeling Software  Sérgio E. Galembeck, Giovanni F. Caramori, and José Ricardo Romero
Presents a computational experiment involving the conformational analysis of n-pentane that can be performed by advanced undergraduate or beginning graduate students.
Galembeck, Sérgio E.; Caramori, Giovanni F.; Romero, José Ricardo. J. Chem. Educ. 2005, 82, 1800.
Computational Chemistry |
Molecular Mechanics / Dynamics |
Molecular Modeling |
Noncovalent Interactions |
Stereochemistry |
Theoretical Chemistry
Cotton Effect in Copper–Proline Complexes in the Visible Region  Victor Volkov and Rolf Pfister
This article suggests taking advantage of the visible dd electronic transition of Cu2+, which allows one to contrast the normal optical rotatory dispersion response of d- and l-proline in aqueous solution with the strong Cotton effect observed when these amino acids are complexed with a metal cation.
Volkov, Victor; Pfister, Rolf. J. Chem. Educ. 2005, 82, 1663.
Chirality / Optical Activity |
IR Spectroscopy |
Molecular Properties / Structure |
Spectroscopy |
Stereochemistry |
UV-Vis Spectroscopy |
Amino Acids |
Coordination Compounds |
Crystal Field / Ligand Field Theory
Diels–Alder Synthesis of endo-cis-N-Phenylbicyclo[2.2.2]oct-5-en-2,3-dicarboximide  Marsha R. Baar and Kristin Wustholz
endo-cis-N-Phenylbicyclo[2.2.2]oct-5-en-2,3-dicarboximide was synthesized by a DielsAlder cycloaddition of 1,3-cyclohexadiene and N-phenylmaleimide in ethyl acetate. 1,3-Cyclohexadiene and N-phenylmaleimide were selected to illustrate the Alder rule, which reflects a preference for endo products and to overcome the difficulties associated with the traditional combination of 1,3-cyclopentadiene and maleic anhydride.
Baar, Marsha R.; Wustholz, Kristin. J. Chem. Educ. 2005, 82, 1393.
Asymmetric Synthesis |
Microscale Lab |
Stereochemistry |
Addition Reactions |
Alkenes |
IR Spectroscopy |
NMR Spectroscopy
The Chemistry of Coffee  William F. Coleman
The paper by Marino Petracco provides a hearty blend of molecules for this month. The author deals with coffee at a number of different levels ranging from the economic and social to the still perplexing questions of flavor and aroma. The associated molecules demonstrate a range of structural features that students will benefit from examining in three dimensions.
Coleman, William F. J. Chem. Educ. 2005, 82, 1167.
Molecular Modeling |
Molecular Properties / Structure |
Stereochemistry
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
Use of Enzymes in Organic Synthesis: Reduction of Ketones by Baker's Yeast Revisited  James Patterson and Snorri Th. Sigurdsson
The undergraduate organic laboratory Bakers Yeast Reduction of Ethyl Acetoacetate has been improved in two different ways. First, the addition of small quantities of hexane to the aqueous yeast system along with an improved workup protocol has dramatically increased the yield and reproducibility of the ketone conversion to the corresponding alcohol with a high enantiomeric excess. Second, the enantiomeric excess of the alcohol product was ascertained by coupling the alcohol mixture with a chiral acid and analyzing the resulting mixture of diastereomeric esters by proton NMR.
Patterson, James; Sigurdsson, Snorri Th. J. Chem. Educ. 2005, 82, 1049.
Enzymes |
NMR Spectroscopy |
Stereochemistry |
Gas Chromatography |
Synthesis
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
Chiral Crystallization of Ethylenediamine Sulfate  Lawrence Koby, Jyothi B. Ningappa, Maria Dakessian, and Louis A. Cuccia
Optimized conditions for the chiral crystallization of ethylenediamine sulfate, which can serve as an ideal undergraduate experiment, are described. Large, flat, colorless crystals of ethylenediamine sulfate are obtained in an undisturbed evaporation dish within a period of approximately five to seven days. The crystals are ideal for polarimetry studies and observation using Polaroid sheets. Students become familiar with polarizing filters and how they can be used to distinguish between dextrorotatory and levorotatory crystals.
Koby, Lawrence; Ningappa, Jyothi B.; Dakessian, Maria; Cuccia, Louis A. J. Chem. Educ. 2005, 82, 1043.
Chirality / Optical Activity |
Crystals / Crystallography |
Stereochemistry |
Physical Properties
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
Differentiations of Enantiomers via Their Diastereomeric Association Complexes—There Are Two Ways of Shaking Hands  Albrecht Mannschreck and Roland Kiesswetter
The following practical applications of the formation of two diastereomeric association complexes that may differ with respect to their physical and chemical properties are briefly described: the small- and large-scale preparation of the enantiomers of organic compounds; the analysis of chiral nonracemic mixtures by chromatography and by NMR spectroscopy; and the growing use of drugs in the form of one of the enantiomers. It is proposed to emphasize the similarity of the association-based differentiations.
Mannschreck, Albrecht; Kiesswetter, Roland. J. Chem. Educ. 2005, 82, 1034.
Chirality / Optical Activity |
Noncovalent Interactions |
Stereochemistry |
Bioorganic Chemistry |
Chromatography |
Enantiomers |
Medicinal Chemistry |
NMR Spectroscopy |
Precipitation / Solubility |
Receptors |
Molecular Properties / Structure
Stereogenic Centers and Axes: A Comparison of the Chiral Topologies Available to Cabcd and abC=C=Ccd  Paul Lloyd-Williams and Ernest Giralt
In this article we provide a comparative analysis of molecular chirality as a consequence of the presence of stereogenic centers and axes. We have found this to be a useful and informative classroom exercise that helps to put some of the most important stereochemical principles on a firmer footing. Chirality in molecules incorporating a stereogenic center can be fully explained using the regular tetrahedron as a model. Analysis of chirality in molecules incorporating a stereogenic axis, on the other hand, requires the use of a less regular, stretched or extended, tetrahedron. The key difference between the two types of molecule is the number of chiral topologies available to each.
Lloyd-Williams, Paul; Giralt, Ernest. J. Chem. Educ. 2005, 82, 1031.
Chirality / Optical Activity |
Molecular Properties / Structure |
Stereochemistry
Chirality Made Simple: A 1- and 2-Dimensional Introduction to Stereochemistry  Robert E. Gawley
Using internal and external reflection elements in one-, two-, and three-dimensional space, the concept of chirality can be introduced in simple terms that are readily understood. Illustrations of 2-D chirality include block letters of the alphabet and the popular video game Tetris. The concepts of 3-D chirality follow logically and can be simplified by projection back to 2-D. Several examples are given, and a PowerPoint presentation of the concepts is available in the Supplemental Material.
Gawley, Robert E. J. Chem. Educ. 2005, 82, 1009.
Chirality / Optical Activity |
Group Theory / Symmetry |
Stereochemistry |
Enantiomers
Multi-Choice Enzymatic Resolutions of Racemic Secondary Alcohols Using Candida antarctica Lipase B. A Collaborative Experiment for Advanced Undergraduates  Francisca Rebolledo and Ramón Liz
An advanced bioorganic chemistry laboratory set of experiments is described in which the lipase B from Candida antarctica is used for the kinetic resolution of four racemic secondary alcohols. The biotransformations are transesterification reactions of these alcohols, as well as hydrolyses and aminolyses of ()-1-phenylethyl acetate. Independent work is assigned to each student, and the overall results are analyzed at the end of the laboratory course. Moshers method and the so-called modified Moshers method are used to determine the enantiomeric excesses and absolute configurations, respectively, of products and remaining substrates.
Rebolledo, Francisca; Liz, Ramón. J. Chem. Educ. 2005, 82, 930.
Bioorganic Chemistry |
Catalysis |
Enzymes |
NMR Spectroscopy |
Stereochemistry |
Chromatography |
Microscale Lab
Quantitative Determination of the Rotameric Energy Differences of 1,2-Dihaloethanes Using Raman Spectroscopy. An Experimental Project for the Physical Chemistry Laboratory  Mark D. Young, Natalia C. Borjemscaia, and Brian D. Wladkowski
The effects of structure and environment on the rotameric energy difference between gauche and trans conformations of 1,2-disubtitutedethanes are determined quantitatively through the use of Raman spectroscopy. Two 1,2-dihaloethanes (chloro- and bromo-) were analyzed in the condensed phase (pure liquid, carbon tetrachloride, and acetonitrile solutions). Since the gauche conformation of these molecules has a nonzero dipole, dissolving the compounds in solvents with increasing dielectric constant causes a stabilization of the gauche conformation, thus decreasing the absolute energy difference between the rotamers. The major factor governing the intrinsic stability is that of steric hindrance.
Young, Mark D.; Borjemscaia, Natalia C.; Wladkowski, Brian D. J. Chem. Educ. 2005, 82, 912.
Instrumental Methods |
IR Spectroscopy |
Quantitative Analysis |
Raman Spectroscopy |
Alkanes / Cycloalkanes |
Conformational Analysis |
Stereochemistry
A Literature Exercise Using SciFinder Scholar for the Sophomore-Level Organic Chemistry Course  Ian J. Rosenstein
This report details an exercise for the sophomore-level organic course using SciFinder Scholar to search the Chemical Abstracts database. Students each research the synthesis and use of a chiral auxiliary then present their findings to their classmates in a short oral presentation.
Rosenstein, Ian J. J. Chem. Educ. 2005, 82, 652.
Stereochemistry |
Molecular Properties / Structure
The Stereochemistry of Biochemical Molecules: A Subject to Revisit  Josep J. Centelles and Santiago Imperial
This article reports on errors in stereochemistry of complex hydrosoluble vitamin B12 molecule. Twenty-five popular biochemistry textbooks were examined for their treatment of the stereoisomery of vitamin B12. Mistakes, discrepancies, and oddities reported in vitamin B12 are just an example of this problem. Biochemistry textbook authors and teachers should pay more attention to the stereoisomery of biochemical molecules to avoid students confusion.
Centelles, Josep J.; Imperial, Santiago. J. Chem. Educ. 2005, 82, 75.
Stereochemistry |
Vitamins
A Set of Hands-On Exercises on Conformational Analysis  Silvina C. Pellegrinet and Ernesto G. Mata
This article describes a set of comprehensive exercises on conformational analysis that employs a hands-on approach by the use of molecular modeling kits. In addition, the exercises provide illustrations of other topics such as nomenclature, functional groups, and isomerism, and introduce some notions of chirality.
Pellegrinet, Silvina C.; Mata, Ernesto G. J. Chem. Educ. 2005, 82, 73.
Alkanes / Cycloalkanes |
Conformational Analysis |
Constitutional Isomers |
Molecular Properties / Structure |
Stereochemistry
Synthesis and Resolution of the Atropisomeric 1,1'-Bi-2-naphthol: An Experiment in Organic Synthesis and 2-D NMR Spectroscopy  Kendrew K. W. Mak
The synthesis and resolution of the atropisomeric 1,1'-bi-2-naphthol illustrates several important concepts in organic chemistry and serves as a good experiment for organic chemistry laboratory course of intermediate to advanced levels. Racemic 1,1'-bi-2-naphthol is synthesized by the oxidative coupling of 2-naphthol and is resolved into the enantiopure form by the selective inclusion compound formation of the R enantiomer with (-)-N-benzylcinchonidinium chloride. The enantiomeric excess of the products are determined by chiral HPLC.
Mak, Kendrew K. W. J. Chem. Educ. 2004, 81, 1636.
Chromatography |
NMR Spectroscopy |
Synthesis |
Stereochemistry |
Chirality / Optical Activity |
Enantiomers
A Simple Illustration of Hemihedral Faces  Addison Ault
A pair of blocks is described that illustrate exactly the enantiomeric relationship that led Pasteur to the concept of molecular chirality. The blocks are enantiomeric and have C2 symmetry.
Ault, Addison. J. Chem. Educ. 2004, 81, 1605.
Chirality / Optical Activity |
Stereochemistry |
Enantiomers
The Molecular Structure of Penicillin  Ronald Bentley
The chemical structure of penicillin was determined between 1942 and 1945 under conditions of secrecy established by the U.S. and U.K. governments. The evidence was not published in the open literature but as a monograph. This complex volume does not present a structure proof that can be readily comprehended by a student. In this article, a basic structural proof for the penicillin molecule is provided, emphasizing the chemical work.
Bentley, Ronald. J. Chem. Educ. 2004, 81, 1462.
Drugs / Pharmaceuticals |
Applications of Chemistry |
Natural Products |
Molecular Properties / Structure |
Mechanisms of Reactions |
Stereochemistry
Wittig Reaction Using a Stabilized Phosphorus Ylid: An Efficient and Stereoselective Synthesis of Ethyl trans-Cinnamate  Traci J. Speed, Jean P. McIntyre, and Dasan M. Thamattoor
The synthesis of ethyl trans-cinnamate, by the reaction of benzaldehyde with the stabilized phosphorus ylid (carbethoxymethylene)triphenylphosphorane, serves as a useful experiment to illustrate the Wittig reaction in the introductory organic chemistry laboratory. The reaction is highly stereoselective and affords the product in excellent yield and purity. The stereochemistry of the product is established by examining the coupling constants displayed by the olefinic protons in the 1H NMR spectrum. The experiment highlights several important aspects of organic chemistry such as synthesis, stereochemistry, instrumental analysis, and molecular modeling.
Speed, Traci J.; McIntyre, Jean P.; Thamattoor, Dasan M. J. Chem. Educ. 2004, 81, 1355.
Chromatography |
Computational Chemistry |
IR Spectroscopy |
Mass Spectrometry |
NMR Spectroscopy |
Synthesis |
Stereochemistry
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 Darzens Condensation: Structure Determination through Spectral Analysis and Understanding Substrate Reactivity  R. David Crouch, Michael S. Holden, and Candice A. Romany
The Darzens condensation involves two steps that are typically included in the sophomore organic curriculum: an aldol reaction followed by an intramolecular nucleophilic substitution.
Crouch, R. David; Holden, Michael S.; Romany, Candice A. J. Chem. Educ. 2004, 81, 711.
NMR Spectroscopy |
Synthesis |
Stereochemistry |
Mechanisms of Reactions |
Aldehydes / Ketones
Use of Optical Rotation and NMR Signal Counting To Identify Common Aldoses  John Almy
An inexpensive, small scale experiment for second semester organic students describes the unambiguous identification of a common aldose "unknown" from five possible candidates: glucose, mannose, galactose, arabinose, or xylose
Almy, John. J. Chem. Educ. 2004, 81, 708.
NMR Spectroscopy |
Carbohydrates |
Microscale Lab |
Molecular Properties / Structure |
Stereochemistry
The Tragedy of Hamlet, Son of an Organic Chemist of Denmark  Ronald G. Brisbois
Herein, Hamlet (the son of an organic chemist of Denmark) is the surrogate of any and every student as he uses a thoroughly Shakespearean approach to sorting out some of the key distinguishing features of SN2 versus SN1 reactions.
Brisbois, Ronald G. J. Chem. Educ. 2004, 81, 502.
Kinetics |
Mechanisms of Reactions |
Stereochemistry |
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
The Monosodium Glutamate Story: The Commercial Production of MSG and Other Amino Acids  Addison Ault
Examples of the industrial synthesis of pure amino acids are presented. The emphasis is on the synthesis of (S)-glutamic acid and, to a lesser extent, (S)-lysine and (R,S)-methionine. These amino acids account for about 90% of the total world production of amino acids.
Ault, Addison. J. Chem. Educ. 2004, 81, 347.
Amino Acids |
Biotechnology |
Chirality / Optical Activity |
Consumer Chemistry |
Enzymes |
Natural Products |
Stereochemistry |
Synthesis |
Food Science
Conformational Analysis in an Advanced Integrated Laboratory Course  David B. Ball and Randy M. Miller
An interdisciplinary project is described that requires students to synthesize conformationally mobile and static a-bromocyclohexanones and to assess, qualitatively and quantitatively, and validate, using several spectroscopic tools, solvent effects on the conformational preferences of these molecules. The project exposes students to a variety of experimental and theoretical techniques that include organic synthesis, product purification, 1H and 13C NMR spectrometry, GCMS, molecular modeling, and IR and UV spectroscopy.
Ball, David B.; Miller, Randy M. J. Chem. Educ. 2004, 81, 121.
Equilibrium |
IR Spectroscopy |
Molecular Modeling |
Molecular Properties / Structure |
NMR Spectroscopy |
Synthesis |
Stereochemistry |
UV-Vis Spectroscopy |
Conformational Analysis |
Gas Chromatography |
Mass Spectrometry |
Aldehydes / Ketones
An NMR-Smell Module for the First-Semester General Chemistry Laboratory  Erich S. Uffelman, Elizabeth H. Cox, J. Brown Goehring, Tyler S. Lorig, and C. Michele Davis
The series of experiments involves an exploration of organic stereochemistry via hands-on model building, several chemosensory smell tests, and hands-on use of 13C NMR, thus serving as a powerful interdisciplinary lab involving chemistry, physics, and neuroscience. Similarities and differences between NMR and MRI methods are emphasized.
Uffelman, Erich S.; Cox, Elizabeth H.; Goehring, J. Brown; Lorig, Tyler S.; Davis, C. Michele. J. Chem. Educ. 2003, 80, 1368.
NMR Spectroscopy |
Stereochemistry |
Molecular Modeling |
Medicinal Chemistry
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
Desymmetrization of the Tetrahedron: Stereogenic Centers  Paul Lloyd-Williams and Ernest Giralt
While the regular tetrahedron is the more straightforward model and is preferable for rationalizing stereochemistry at the undergraduate level for molecules containing stereogenic centers , it is important that both the instructor and students be fully aware that the tetrahedral model represents a simplification and that the use of irregular tetrahedra would be physically more realistic.
Lloyd-Williams, Paul; Giralt, Ernest. J. Chem. Educ. 2003, 80, 1178.
Chirality / Optical Activity |
Molecular Properties / Structure |
Stereochemistry
Synthesis, Kinetics, and Thermodynamics: An Advanced Laboratory Investigation of the Cis–Trans Isomerization of Mo(CO)4(PR3)2   Ashfaq A. Bengali and Kim E. Mooney
The students synthesize the cis complex and then study its conversion to the trans isomer. This experiment illustrates the important relationship between kinetics and thermodynamics and the results emphasize the selfconsistency of the data.
Bengali, Ashfaq A.; Mooney, Kim E. J. Chem. Educ. 2003, 80, 1044.
Kinetics |
Metals |
Organometallics |
Thermodynamics |
Stereochemistry |
Synthesis |
Coordination Compounds
Orgo Cards: Organic Chemistry Review (Steven Q. Wang, Babak Razani, Edward J. K. Lee, Jennifer Wu, and William Berkowitz)  Eugene Gooch
The major strength of this product lies in coverage of the reaction mechanisms. Mechanisms are written out using curved arrow notation, steps are numbered, and a sentence describes the details of each step. Efforts are made to describe both ionic and radical mechanisms accurately. Stereochemical details are integrated into the descriptions of reactions and their mechanisms.
Gooch, Eugene. J. Chem. Educ. 2003, 80, 1009.
Enrichment / Review Materials |
Reactions |
Mechanisms of Reactions |
Stereochemistry
Bromination and Debromination of Cholesterol: An Inquiry-Based Lab Involving Structure Elucidation, Reaction Mechanism, and 1H NMR  Andrew Grant and Devin Latimer
An experiment designed to examine a reaction mechanism and its stereochemical consequences; students propose the product and a mechanism for its production before conducting the experiment and analyzing the product with 1H NMR.
Grant, Andrew S.; Latimer, Devin. J. Chem. Educ. 2003, 80, 670.
Mechanisms of Reactions |
NMR Spectroscopy |
Stereochemistry |
Natural Products |
Synthesis |
Steroids
Spiral Puzzle for Organic Chemistry Students  Ender Erdik
Puzzle to review organic reactions and their reagents.
Erdik, Ender. J. Chem. Educ. 2003, 80, 428.
Synthesis |
Learning Theories |
Enrichment / Review Materials |
Addition Reactions |
Alkylation |
Electrophilic Substitution |
Elimination Reactions |
Reactions |
Nucleophilic Substitution |
Mechanisms of Reactions |
Grignard Reagents
"Chiral Acetate": The Preparation, Analysis, and Applications of Chiral Acetic Acid  Addison Ault
Production of chiral acetic acid using deuterium and tritium and its application to understanding stereochemistry and the specificity of enzymatic reactions.
Ault, Addison. J. Chem. Educ. 2003, 80, 333.
Chirality / Optical Activity |
Enzymes |
Isotopes |
Synthesis |
Stereochemistry |
Enrichment / Review Materials |
Carboxylic Acids |
Enantiomers |
Reactions |
Mechanisms of Reactions
Semi-Microscale Williamson Ether Synthesis and Simultaneous Isolation of an Expectorant from Cough Tablets  Ryan G. Stabile and Andrew P. Dicks
Procedure for synthesis of the active ingredient in many well-known, over-the-counter cough syrups - 3-(2-methoxyphenoxy)-1,2-propanediol, an aromaric ether.
Stabile, Ryan G.; Dicks, Andrew P. J. Chem. Educ. 2003, 80, 313.
Chirality / Optical Activity |
Drugs / Pharmaceuticals |
Mathematics / Symbolic Mathematics |
Microscale Lab |
Synthesis |
Stereochemistry |
Applications of Chemistry |
Ethers |
Aromatic Compounds |
Medicinal Chemistry
The Professorial Career of Clifford R. Haymaker: A Life of Chemistry Imagined and Bequeathed  John J. Eisch and Daniel T. Haworth
Biography of Clifford R. Haymaker, a blind professor of chemistry at Marquette University for 35 years.
Eisch, John J.; Haworth, Daniel T. J. Chem. Educ. 2003, 80, 275.
Quantitative Analysis |
Stereochemistry |
Learning Theories |
Undergraduate Research |
Minorities in Chemistry
The World's First "Pastarimeter": An Analogous Demonstration of Polarimetry Using Pasta Fusilli  Claire Saxon, Scott Brindley, Nic Jervis, Graeme R. Jones, E. David Morgan, and Christopher A. Ramsden
Demonstration in which clockwise pasta in one glass tube causes exiting water to rotate in that direction while counter clockwise pasta in a second tube has the opposite effect.
Saxon, Claire; Brindley, Scott; Jervis, Nic; Jones, Graeme R.; Morgan, E. David; Ramsden, Christopher A. J. Chem. Educ. 2002, 79, 1214.
Chirality / Optical Activity |
Stereochemistry
Generating Closed Shapes from Regular Tilings  William O. J. Boo and Daniell L. Mattern
Rules for generating closed shapes from hexagonal, tetragonal, and trigonal tiles
Boo, William O. J.; Mattern, Daniell L. J. Chem. Educ. 2002, 79, 1017.
Group Theory / Symmetry |
Molecular Properties / Structure |
Solid State Chemistry |
Stereochemistry
1H NMR Measurement of the Trans–Cis Photoisomerization of Cinnamic Acid Derivatives  Basil Danylec and Magdy N. Iskander
Procedure that illustrates trans-cis photoisomerization.
Danylec, Basil; Iskander, Magdy N. J. Chem. Educ. 2002, 79, 1000.
NMR Spectroscopy |
Photochemistry |
Stereochemistry |
Aromatic Compounds |
Alcohols |
Esters |
Alkenes |
Molecular Properties / Structure
The Nobel Prize in Chemistry for 2001  Addison Ault

Ault, Addison. J. Chem. Educ. 2002, 79, 572.
Drugs / Pharmaceuticals |
Stereochemistry
On the Stereochemistry of 'Natural' a-Amino Acids (re J. Chem. Educ. 2000, 77, 48-49)  Sam H. Leung

Leung, Sam H. J. Chem. Educ. 2002, 79, 559.
Amino Acids |
Nomenclature / Units / Symbols |
Stereochemistry
On the Stereochemistry of 'Natural' a-Amino Acids (re J. Chem. Educ. 2000, 77, 48-49)  Giovanni Lentini

Lentini, Giovanni. J. Chem. Educ. 2002, 79, 558.
Amino Acids |
Nomenclature / Units / Symbols |
Stereochemistry
The Cis-Trans Equilibrium of N-Acetyl-L-Proline. An Experiment for the Biophysical Chemistry Laboratory  Kathryn R. Williams, Bhavin Adhyaru, Igor German, and Eric Alvarez
A cis-trans equilibrium system that demonstrates the effect of solvent polarity and aqueous pH.
Williams, Kathryn R.; Adhyaru, Bhavin; German, Igor; Alvarez, Eric. J. Chem. Educ. 2002, 79, 372.
Amino Acids |
Biophysical Chemistry |
NMR Spectroscopy |
Proteins / Peptides |
NMR Spectroscopy |
Amines / Ammonium Compounds |
Carboxylic Acids |
Equilibrium |
Stereochemistry |
Diastereomers
Stereochemistry (by David G. Morris)  R. David Crouch
Supplement to organic chemistry texts.
Crouch, R. David. J. Chem. Educ. 2002, 79, 167.
Stereochemistry
Diastereoselective Synthesis of a Strawberry Flavoring Agent by Epoxidation of Ethyl trans-b-Methylcinnamate  Gayle J. Pageau, Rodwell Mabaera, Kathryn M. Kosuda, Tamara A. Sebelius, Ali H. Ghaffari, Kenneth A. Kearns, Jean P. McIntyre, Tina M. Beachy, and Dasan M. Thamattoor
Synthesis of the "strawberry aldehyde" epoxide, a well-known food and perfume additive.
Pageau, Gayle J.; Mabaera, Rodwell; Kosuda, Kathryn M.; Sebelius, Tamara A.; Ghaffari, Ali H.; Kearns, Kenneth A.; McIntyre, Jean P.; Beachy, Tina M.; Thamattoor, Dasan M. J. Chem. Educ. 2002, 79, 96.
Molecular Modeling |
NMR Spectroscopy |
Synthesis |
Stereochemistry |
Epoxides |
Consumer Chemistry |
Food Science
Preparation of a D-Glucose-Derived Alkene. An E2 Reaction for the Undergraduate Organic Chemistry Laboratory  Peter Norris and Andrew Fluxe
Synthesis of four carbohydrate derivatives that highlight techniques such as inert atmosphere work, rotary evaporators, and flash column chromatography.
Norris, Peter; Fluxe, Andrew. J. Chem. Educ. 2001, 78, 1676.
Carbohydrates |
NMR Spectroscopy |
Synthesis |
Alkenes |
Elimination Reactions |
Chromatography
"Dishing Out" Stereochemical Principles  Harold Hart
Demonstrating the concepts of chiral centers and enantiomers using plastic dishes.
Hart, Harold. J. Chem. Educ. 2001, 78, 1632.
Chirality / Optical Activity |
Molecular Modeling |
Stereochemistry |
Molecular Properties / Structure |
Enantiomers
Using Guided Inquiry to Study Optical Activity and Optical Rotatory Dispersion in a Cross-Disciplinary Chemistry Lab  Michael A. Vaksman and James W. Lane
Procedure in which students are challenged to measure the angle optical rotation at a particular wavelength for an optically active sample.
Vaksman, Michael A.; Lane, James W. J. Chem. Educ. 2001, 78, 1507.
Chirality / Optical Activity |
Lasers |
Spectroscopy |
Stereochemistry
The Use of Stick Figures to Visualize Fischer Projections  Laurie S. Starkey
Using stick figures to help students visualize the three-dimensional orientations represented by Fischer projections.
Starkey, Laurie S. J. Chem. Educ. 2001, 78, 1486.
Molecular Properties / Structure |
Stereochemistry |
Molecular Modeling
The Importance of Non-Bonds in Coordination Compounds  Michael Laing
Significance of noncovalent interactions in determining the structure and behavior of coordination compounds.
Laing, Michael. J. Chem. Educ. 2001, 78, 1400.
Noncovalent Interactions |
Coordination Compounds |
Kinetics |
Stereochemistry |
Molecular Properties / Structure
Synthesis and Use of Jacobsen's Catalyst: Enantioselective Epoxidation in the Introductory Organic Laboratory  John Hanson
Laboratory series to introduce students to an important synthetic method and many common techniques used in running reactions, purifying products, and characterizing compounds.
Hanson, John. J. Chem. Educ. 2001, 78, 1266.
Catalysis |
Chirality / Optical Activity |
Synthesis |
Organometallics |
Stereochemistry |
Epoxides |
Enantiomers |
Aromatic Compounds
Discovery-Oriented Approach To Organic Synthesis: Tandem Aldol Condensation-Michael Addition Reactions. Identifying Diastereotopic Hydrogens in an Achiral Molecule by NMR Spectroscopy  Nanette Wachter-Jurcsak and Kendra Reddin
Procedure illustrating aldol condensation and Michael addition reactions.
Wachter-Jurcsak, Nanette; Reddin, Kendra. J. Chem. Educ. 2001, 78, 1264.
NMR Spectroscopy |
Synthesis |
Stereochemistry |
Aromatic Compounds |
Aldehydes / Ketones |
Addition Reactions |
Mechanisms of Reactions
Looking beyond the endo Rule in a Diels-Alder Discovery Lab  Ronald M. Jarret, Jamie New, Rebecca Hurley, and Laura Gillooly
Procedure to introduce preference for generation of the endo product and the stereochemistry of alkene addition of the Diels-Alder reaction.
Jarret, Ronald M.; New, Jamie; Hurley, Rebecca; Gillooly, Laura. J. Chem. Educ. 2001, 78, 1262.
NMR Spectroscopy |
Synthesis |
Stereochemistry |
Alkenes
From the Wood-Shop to Crystal Engineering: Teaching Three-Dimensional Chemistry  James D. Martin
Teaching students an understanding of the three-dimensionality of chemistry and developing skills in 2-D to 3-D translation through a drafting exercise.
Martin, James D. J. Chem. Educ. 2001, 78, 1195.
Crystals / Crystallography |
Molecular Properties / Structure |
Stereochemistry
On Chirality in Substituted Metallocenes Bearing Identical Substituents  Daisy de Brito Rezende and Ivan P. de Arruda Campos
Analysis of planar chirality in substituted metallocenes.
Rezende, Daisy de Brito; Campos, Ivan P. de Arruda. J. Chem. Educ. 2001, 78, 1130.
Chirality / Optical Activity |
Organometallics |
Stereochemistry |
Molecular Properties / Structure
Simple Preparation and NMR Analysis of mer and fac Isomers of Tris(1,1,1-trifluoro-2,4-pentanedionato)cobalt(III). An Experiment for the Inorganic Chemistry Laboratory  Ashley W. Jensen and Brian A. O'Brien
A one-step procedure for the preparation of tris(1,1,1-trifluoro-2,4-pentanedionato)cobalt(III) from hydrated cobalt(II) carbonate and 10% hydrogen peroxide, in which tert-butyl alcohol is used as a component of the solvent.
Jensen, Ashley W.; O'Brien, Brian A. J. Chem. Educ. 2001, 78, 954.
Chromatography |
Coordination Compounds |
Synthesis |
NMR Spectroscopy |
Stereochemistry
A Method for Drawing the Cyclohexane Ring and Its Substituents  Veljko Dragojlovic
A simple method for drawing cyclohexanes.
Dragojlovic, Veljko. J. Chem. Educ. 2001, 78, 923.
Molecular Properties / Structure |
Stereochemistry |
Alkanes / Cycloalkanes
Mechanisms of Pentacoordinate Pseudorotation. A Molecular Modeling Study of PF5  Craig D. Montgomery
This exercise in molecular modeling allows students to compare the two commonly suggested mechanisms for pseudorotation in pentacoordinate compounds--the Berry and turnstile mechanisms.
Montgomery, Craig D. J. Chem. Educ. 2001, 78, 844.
Computational Chemistry |
Mechanisms of Reactions |
Molecular Modeling |
Stereochemistry
Build a Simple Polarimeter  Frank E. Stary and Norman Woldow
Details of the construction of a durable, inexpensive portable polarimeter with a self-contained 585-nm light source are given, combining the best features of several polarimeters; may easily be scaled up in size for increased sensitivity.
Stary, Frank E.; Woldow, Norman. J. Chem. Educ. 2001, 78, 644.
Instrumental Methods |
Kinetics |
Laboratory Equipment / Apparatus |
Stereochemistry
Diastereoselective Synthesis of (+/-)-1,2-Diphenyl-1,2-propanediol. A Discovery-Based Grignard Reaction Suitable for a Large Organic Lab Course  James A. Ciaccio, Roxana P. Bravo, Antoinette L. Drahus, John B. Biggins, Rosalyn V. Concepcion, and David Cabrera
An experiment that probes the diastereoselectivity of the reaction between a Grignard reagent and a common, inexpensive alpha-chiral ketone; introduces students to pi-facial discrimination by having them establish the stereochemical course of kinetically controlled nucleophilic addition to a carbonyl.
Ciaccio, James A.; Bravo, Roxana P.; Drahus, Antoinette L.; Biggins, John B.; Concepcion, Rosalyn V.; Cabrera, David. J. Chem. Educ. 2001, 78, 531.
Mechanisms of Reactions |
Synthesis |
Organometallics |
Stereochemistry |
Grignard Reagents |
Aldehydes / Ketones
Introducing Stereochemistry to Non-science Majors  Hannia Luján-Upton
Two exercises to introduce concepts associated with stereochemistry such as "sameness", superimposability, chirality, enantiomers, optical activity, polarimetry, and racemic mixtures; one compares chirality in hands with the achiral nature of two textbooks, the other involves a murder mystery.
Luján-Upton, Hannia. J. Chem. Educ. 2001, 78, 475.
Chirality / Optical Activity |
Stereochemistry |
Nonmajor Courses |
Molecular Properties / Structure
Determination of the Position of the Conformational Equilibrium of a Trans 1,2-Disubstituted Cyclohexane by NMR Spectroscopy. An Experiment in Physical Organic Chemistry for Undergraduate Students  Andrei G. Kutateladze and Joseph M. Hornback
An experiment using NMR spectroscopy to determine the relative amounts of the two chair conformations of trans-1-chloro-2-(2-nitrophenythio)cyclohexane is described. The coupling constants for the hydrogens adjacent to the chlorine and sulfur are used to calculate the percentage of each conformer in the equilibrium mixture.
Kutateladze, Andrei G.; Hornback, Joseph M. J. Chem. Educ. 2001, 78, 81.
Equilibrium |
NMR Spectroscopy |
Stereochemistry |
Conformational Analysis |
Molecular Properties / Structure |
Diastereomers
The Discovery-Oriented Approach to Organic Chemistry. 5. Stereochemistry of E2 Elimination: Elimination of cis- and trans-2-Methylcyclohexyl Tosylate  Marcus E. Cabay, Brad J. Ettlie, Adam J. Tuite, Kurt A. Welday, and Ram S. Mohan
A discovery-oriented lab that illustrates the stereochemistry of the E2 elimination reaction and is a good exercise in 1H NMR spectroscopy. The added element of discovery insures that student interest and enthusiasm are retained.
Cabay, Marcus E.; Ettlie, Brad J.; Tuite, Adam J.; Welday, Kurt A.; Mohan, Ram S. J. Chem. Educ. 2001, 78, 79.
IR Spectroscopy |
Mechanisms of Reactions |
NMR Spectroscopy |
Stereochemistry |
Elimination Reactions |
Reactions |
Alkenes
The Energy Profile for Rotation about the C-C Bond in Substituted Ethanes
(re
J. Chem. Educ. 1998, 75, 900-906)  Victor M. S. Gil
Encouraging students to appreciate the approximations involved in using the rotational isomeric state approximation and the conditions under which they can be acceptable.
Gil, Victor M. S. J. Chem. Educ. 2001, 78, 32.
Computational Chemistry |
Laboratory Computing / Interfacing |
Stereochemistry
Periplanar or Coplanar?  Saul Kane and William H. Hersh
The prefix peri, derived from the Greek for "near", was chosen to make the meaning "approximately planar". However, the current common usage of syn and antiperiplanar is planar, which is incorrect. In the interests of proper language, we suggest that future authors instead use "syn-coplanar" and "anti-coplanar".
Kane, Saul; Hersh, William H. J. Chem. Educ. 2000, 77, 1366.
Mechanisms of Reactions |
Nomenclature / Units / Symbols |
Stereochemistry |
Molecular Properties / Structure
The Other Double Helix--The Fascinating Chemistry of Starch  Robert D. Hancock and Bryon J. Tarbet
The chemistry of starch, particularly the structure of starch and starch granules.
Hancock, Robert D.; Tarbet, Bryon J. J. Chem. Educ. 2000, 77, 988.
Bioorganic Chemistry |
Carbohydrates |
Food Science |
Stereochemistry |
Applications of Chemistry |
Molecular Properties / Structure
The R/S System: A New and Simple Approach to Determining Ligand Priority and a Unified Method for the Assignment and Correlation of Stereogenic Center Configuration in Diverse Stereoformulas  Dipak K. Mandal
A new approach providing an "at-a-glance" priority order of ligands attached to a stereogenic center in organic molecules and a unified method for assigning and correlating stereogenic center absolute configuration in diverse stereochemical representations is presented.
Mandal, Dipak Kumar. J. Chem. Educ. 2000, 77, 866.
Molecular Properties / Structure |
Stereochemistry |
Nomenclature / Units / Symbols
A Simple Method of Drawing Stereoisomers from Complicated Symmetrical Structures  A. Haudrechy
A practical and systematic method to establish the number and relationships of stereoisomers in cases of complex molecular symmetry is described.
Haudrechy, Arnaud. J. Chem. Educ. 2000, 77, 864.
Stereochemistry |
Molecular Properties / Structure
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
SOS: A Mnemonic for the Stereochemistry of Glucose  Ronald Starkey
The mnemonic SOS (Same, Opposite, Same) can be helpful to recall the stereochemistry in either D-glucose or L-glucose. It refers to the configurations of C-2, C-3, and C-4 relative to that of C-5 in an aldohexose.
Starkey, Ronald. J. Chem. Educ. 2000, 77, 734.
Carbohydrates |
Stereochemistry |
Molecular Properties / Structure
Complete Analysis of a Biologically Active Tetrapeptide: A Project Utilizing Thin-Layer Chromatography and Tandem Quadrupole Mass Spectrometry  Joseph W. LeFevre and David W. Dodsworth
The biologically active tetrapeptide d-Ala-Gly-l-Phe-d-Leu ([des-Tyr1-d-Ala2-d-Leu5]enkephalin) is analyzed for its amino acid content and stereochemistry by normal and reversed-phase thin-layer chromatography (TLC), and its sequence is determined by tandem quadrupole mass spectrometry.
LeFevre, Joseph W. ; Dodsworth, David W. J. Chem. Educ. 2000, 77, 503.
Proteins / Peptides |
Amino Acids |
Stereochemistry |
Mass Spectrometry |
Microscale Lab
Using Computer Assisted Learning to Teach Molecular Reaction Dynamics  Katharine L. Reid, Richard J. Wheatley, Stephen W. Brydges, and John C. Horton
A Computer Assisted Learning program to aid in the teaching of molecular reaction dynamics to undergraduate students. Dynamic and steric factors affecting reaction outcomes are investigated by observing individual molecular collisions. Students control the reactions by experimenting with the initial trajectories of the molecules.
Reid, Katharine L.; Wheatley, Richard J.; Brydges, Stephen W.; Horton, John C. J. Chem. Educ. 2000, 77, 407.
Kinetics |
Molecular Modeling |
Molecular Mechanics / Dynamics |
Stereochemistry |
Mechanisms of Reactions
Probing the Active Site of Yeast Alcohol Dehydrogenase through Microscale Yeast-Mediated Reductions of Acetophenone and Acetylpyridines. A Collaborative and Research-Based Advanced Bioorganic Chemistry Laboratory Project  Moses Lee, Jennifer Azbell, Michael Carnahan, Kari Cox, Joey Espinosa, Ray Feaster, Robert Hirsch, Andrew Lam, Shane Roller, Brent Steadman, and James Toth
The project involves microscale and stereoselective reductions of acetophenone and 2-, 3-, and 4-acetylpyridines by yeast. Each pair of students is assigned two substrates to ensure duplication of each individual experiment, and the results are combined. At the end of the project, each student prepares a detailed report based on the entire set of results.
Lee, Moses; Azbell, Jennifer; Carnahan, Michael; Cox, Kari; Espinosa, Joey; Feaster, Ray; Hirsch, Robert; Lam, Andrew; Roller, Shane; Steadman, Brent; Toth, James. J. Chem. Educ. 2000, 77, 363.
Bioorganic Chemistry |
Enzymes |
Microscale Lab |
Molecular Recognition |
Undergraduate Research |
Stereochemistry
Introducing Chiroscience into the Organic Laboratory Curriculum  Kenny B. Lipkowitz, Tim Naylor, and Keith S. Anliker
"Chiroscience" is a young but robust industry linking science and technology with chemistry and biology; includes description of an asymmetric reduction of a ketone followed by an assessment of the enantiomeric excess by GC using a chiral stationary phase.
Lipkowitz, Kenny B.; Naylor, Tim; Anliker, Keith S. J. Chem. Educ. 2000, 77, 305.
Chirality / Optical Activity |
Chromatography |
Mechanisms of Reactions |
Synthesis |
Separation Science |
Stereochemistry |
Gas Chromatography |
Aldehydes / Ketones
Catalytic Asymmetric Epoxidation Using a Fructose-Derived Catalyst  Andy Burke, Patrick Dillon, Kyle Martin, and T. W. Hanks
Modern epoxidation methods are able to create two adjacent stereocenters with very high enantioselectivity. Opening of the epoxides with nucleophiles permits rapid entry into complex organic systems, making this powerful synthetic methodology one of the fundamental reactions in organic synthesis.
Burke, Andy; Dillon, Patrick; Martin, Kyle; Hanks, Timothy W. J. Chem. Educ. 2000, 77, 271.
Catalysis |
NMR Spectroscopy |
Stereochemistry |
Enantiomers
Conformer Hunting: An Open-Ended Computational Chemistry Exercise That Expresses Real-World Complexity and Student Forethought  Kenny B. Lipkowitz and Daniel Robertson
In this project we ask students the following simple question: "Which conformer searching strategy in Spartan is the best?" To answer this question the students need to develop a working definition of what "best" means within the context of the project, design their own experiments that can address that question most suitably, carry out the calculations to derive a compelling answer, and then write their results in the form of a research paper.
Lipkowitz, Kenny B.; Robertson, Daniel. J. Chem. Educ. 2000, 77, 206.
Computational Chemistry |
Stereochemistry |
Molecular Modeling |
Molecular Properties / Structure |
Stereochemistry
Trigonometric Basis Set Functions: Their Application to the C-H Stretching and Deformation Motions of Benzene and to Orbital Symmetry  G. Bor and Sidney F. A. Kettle
The unifying power of the use of trigonometric basis functions in group character tables is demonstrated. Additionally, these functions provide a simple way of generating pictures of symmetry coordinates. This is illustrated for the in-plane stretch and out-of-plane deformation motions of the C-H bonds in benzene. Their application to orbital symmetry applications is also indicated.
Bor, G.; Kettle, Sidney F. A. J. Chem. Educ. 1999, 76, 1723.
Group Theory / Symmetry |
Molecular Modeling |
Stereochemistry |
Molecular Properties / Structure |
Aromatic Compounds |
Spectroscopy |
IR Spectroscopy |
Raman Spectroscopy |
UV-Vis Spectroscopy
Synthesis of Derivatives of (1R)-(-)- and (1S)-(+)-10-Camphorsulfonic Acid  Steven C. Cermak and David F. Wiemer
The preparation of optically active (camphorsulfonyl)oxaziridines from commercially available (1R)-(-) and/or (1S)-(+)10-camphorsulfonic acid provides a clear demonstration of the lack of relationship between absolute configuration and optical rotation. The parent sulfonic acid can be converted to the corresponding acid chloride and then to the sulfonamide, sulfonylimine, and finally to an oxaziridine in a series of practical organic laboratory experiments.
Cermak, Steven C.; Wiemer, David F. J. Chem. Educ. 1999, 76, 1715.
Stereochemistry |
Synthesis |
Aromatic Compounds |
Ethers |
Alcohols |
Aldehydes / Ketones |
Acids / Bases
trans-Cyclohexane-1,2-diamine  Treptow, Richard S.
First successful resolution of the diamine.
Treptow, Richard S. J. Chem. Educ. 1999, 76, 1484.
Chromatography |
Separation Science |
Synthesis |
Stereochemistry
Organic Chemistry Course Development in a Forensic Science Program: Use of FT-NMR  Ronald Callahan, Lawrence Kobilinsky, and Robert Rothchild
The acquisition of a modern, multinuclear, medium-field (7 tesla) FT-NMR, with partial support from NSF-ILI, has made possible the introduction of a major special project for second-semester organic chemistry laboratory, within a forensic science program.
Callahan, Ronald; Kobilinsky, Lawrence; Rothchild, Robert. J. Chem. Educ. 1999, 76, 1332.
Forensic Chemistry |
NMR Spectroscopy |
Synthesis |
Microscale Lab |
Molecular Modeling |
Stereochemistry
Molecular Modeling as an Aid to Understanding Stereoselectivity  John B. Klassen, Kate J. Graham, and William P. Muldoon
Students use a molecular mechanics calculation program within Spartan to determine the Boltzmann distribution of conformers of 2-, 3-, and 4-methylcyclohexanone. On the basis of these data, they predict the face of the carbonyl most susceptible to attack by hydride.
Klassen, John B.; Graham, Kate J.; Muldoon, William P. J. Chem. Educ. 1999, 76, 985.
Computational Chemistry |
Mechanisms of Reactions |
Quantum Chemistry |
Stereochemistry |
MO Theory |
Molecular Modeling
A New Method To Convert the Fischer Projection of Monosaccharide to the Haworth Projection  Qing-zhi Zhang and Shen-song Zhang
The D,L-configuration of a sugar in Haworth projection can be directly determined by designating the R,S-configuration of the highest-numbered asymmetric carbon; that is, the most distant carbon from the anomeric carbon. The R-configuration at this carbon corresponds to the D-family, and S- to the L-family.
Zhang, Qing-zhi; Zhang, Shen-song. J. Chem. Educ. 1999, 76, 799.
Carbohydrates |
Stereochemistry |
Molecular Properties / Structure |
Molecular Modeling
Bird-in-the-Hand Method for Determination of Absolute Configuration in Fischer Projections  Edward Siloac
The bird-in-the-hand technique allows for easy visualization and identification of stereogenic centers on Fischer projections. It uses the student's hand as a molecular model to simplify the stereochemistry of Fischer projections.
Siloac, Edward. J. Chem. Educ. 1999, 76, 798.
Stereochemistry |
Molecular Properties / Structure |
Molecular Modeling
Modified Stereographic Projections of Point Groups and Diagrams of Their Irreducible Representations  Sidney F. A. Kettle
Modified versions of the stereographic projections of the point groups of classical crystallography are presented. They show the consequences of symmetry operations rather than emphasizing the existence of symmetry elements. These projections may be used to give pictures of the irreducible representations of point groups and several examples are given.
Kettle, Sidney F. A. J. Chem. Educ. 1999, 76, 675.
Stereochemistry |
Group Theory / Symmetry |
Quantum Chemistry |
Theoretical Chemistry |
Molecular Properties / Structure
Sharpless Asymmetric Dihydroxylation: Effect of Alkene Structure on Rates and Selectivity  Alan C. Spivey, R. Hanson, N. Scorah, and S. J. Thorpe
Each student is assigned an alkene and performs three dihydroxylation reactions: one racemic and two enantioselective variants. The products are characterized by 1H NMR, IR, MS, [a]D20, and chiral chromatography (HPLC or GC). Comparison by the students of their results with those reported in the literature, particularly the extensive work of Sharpless, allows an exploration of the validity of Sharpless's mnemonic for predicting the stereochemical outcome of these reactions.
Spivey, Alan C.; Hanson, R.; Scorah, N.; Thorpe, S. J. J. Chem. Educ. 1999, 76, 655.
Synthesis |
Catalysis |
Stereochemistry |
Organometallics |
Molecular Properties / Structure
Illustrating Newman Projections by Using Overhead Transparencies  L. Phillip Silverman and John Barbaro
A method of illustrating the Newman projection of a molecule using an overhead projector is described. This method, which uses two overhead transparencies linked by a thumbtack, provides both an easy and a clear way to present this type of conformational analysis to large lecture classes.
Silverman, L. Phillip; Barbaro, John. J. Chem. Educ. 1999, 76, 630.
Learning Theories |
Stereochemistry |
Molecular Properties / Structure
Solving the Mathematics of a Kinetic and Regiochemical Problem: The Dehydration Reaction of a cis-trans Mixture of 2-Methylcycloalkanols  John J. Cawley
A take-home exam is presented. It is based on an experiment that studied the dehydration of a cis-trans mixture of 2-methylcyclohexanols. The "givens" are the idealized kinetic and regiochemical data. The focus is strictly on the mathematics, not the experimental details. The goal is to calculate six specific rate constants using a little ingenuity and some fundamental mathematics, to show that the Saytzeff elimination rule is followed for the dehydration of each of the two reactant isomeric alcohols.
Cawley, John J. J. Chem. Educ. 1999, 76, 58.
Kinetics |
Stereochemistry
Conformation Interchange in Nuclear Magnetic Resonance Spectroscopy  Keith C. Brown, Randy L. Tyson, and John A. Weil
Intramolecular dynamics are readily discernible by use of nuclear magnetic resonance spectrometry. A relatively simple laboratory tutorial experiment demonstrating such motion, an internal interchange of conformations, in a readily available nitroaromatic hydrazine (2,2-diphenyl-1-picrylhydrazine in liquid solution) is presented and discussed.
Brown, Keith C.; Tyson, Randy L.; Weil, John A. J. Chem. Educ. 1998, 75, 1632.
Magnetic Properties |
Molecular Properties / Structure |
NMR Spectroscopy |
Stereochemistry |
Aromatic Compounds
Reduction of 2,6-Dimethylcyclohexanone with Sodium Borohydride Revisited: A Correction on the Structural Assignments of the Products, and the Discovery of a Solvent Effect  Bruce A. Hathaway
Changing the solvent from methanol to ethanol produced a different ratio of cis-cis to trans-trans than was reported in the original work. Therefore, a short series of solvents was investigated to determine if there was a solvent effect. The results indicate that as the size and bulk of the solvent increase, the proportion of the trans alcohol product increases.
Hathaway, Bruce A. J. Chem. Educ. 1998, 75, 1623.
Stereochemistry |
NMR Spectroscopy |
Aldehydes / Ketones |
Alcohols
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
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
Photodimerization of Maleic Anhydride  Zhang, Zhijun
Why the photodimerization of maleic anhydride produces the cis, tans, cis product.
Zhang, Zhijun J. Chem. Educ. 1998, 75, 1515.
Photochemistry |
Stereochemistry |
Molecular Properties / Structure |
Alkenes
Resolution of trans-Cyclohexane-1,2-diamine and Determination of the Enantiopurity Using Chiral Solid-Phase HPLC Techniques and Polarimetry  Patrick J. Walsh, Diane K. Smith, and Chris Castello
The experiment is designed to reinforce and broaden the students' understanding of the relationship between enantiomers and diasteriomers and of diasteriomeric interactions. Additionally, it illustrates the differences in physical properties (solubility and melting range) between a racemic mixture and the same compound in highly resolved form.
Walsh, Patrick J.; Smith, Diane K.; Castello, Chris. J. Chem. Educ. 1998, 75, 1459.
Chromatography |
Synthesis |
Separation Science |
Stereochemistry |
HPLC |
Alkanes / Cycloalkanes |
Amines / Ammonium Compounds |
Chirality / Optical Activity
Bis(dicarbonyl-p-cyclopentadienyliron)-A Solid-State Vibrational Spectroscopic Lesson  S. F. A. Kettle, E. Diana, R. Rossetti, and P. L. Stanghellini
Despite a general increase in the study of crystalline materials, the vibrational spectroscopy of molecular solids is covered in few chemistry courses, perhaps because of perceived theoretical difficulties. The present paper shows how easy it is to cover the subject by detailing a discussion of the spectral characteristics of the terminal n(CO) modes of the crystalline forms of the cis and trans isomers of (h5-C5H5)2Fe2(CO)4.
Kettle, S. F. A.; Diana, E.; Rossetti, R.; Stanghellini, P. L. J. Chem. Educ. 1998, 75, 1333.
IR Spectroscopy |
Raman Spectroscopy |
Group Theory / Symmetry |
Stereochemistry
A Very Simple Method Way to Convert Haworth Representation to Zigzag Representation  Janine Cossy and Véronique Bellosta
A very simple method to convert Haworth representation of hexoses and pentoses to zigzag representation is proposed
Cossy, Janine; Bellosta, Véronique. J. Chem. Educ. 1998, 75, 1307.
Carbohydrates |
Nomenclature / Units / Symbols |
Stereochemistry |
Molecular Properties / Structure
Organic Reactions Involving Bromine: Puzzles for the Organic Laboratory  Sarita I. McGowens and Ernest F. Silversmith
Five puzzles for the organic chemistry laboratory are described. All involve bromine, which is generated in a safe, convenient way that makes it possible to control the amount of bromine precisely. Three of the puzzles involve orientation in electrophilic aromatic substitution, one is a determination of the stereochemistry of addition to alkenes, and the other one looks at the possibility of dehydrohalogenation following addition.
McGowens, Sarita I.; Silversmith, Ernest F. J. Chem. Educ. 1998, 75, 1293.
NMR Spectroscopy |
Synthesis |
Stereochemistry |
Mechanisms of Reactions
Determination of the Enantiomeric Purity of Commercial L-[U-14C] Valine: An Experiment Utilizing Reversed-Phase Thin-Layer Chromatography and Liquid Scintillation Counting  Joseph W. LeFevre
The enantiomeric purity of commercial L-[U-14C]valine was determined. The process involved sequential dilution with nonradioactive DL-valine, N-dansylation using dansyl chloride, and resolution using reversed-phase thin-layer chromatography in the presence of b-cyclodextrin, a chiral mobile phase additive.
LeFevre, Joseph W. . J. Chem. Educ. 1998, 75, 1287.
Chromatography |
Isotopes |
Microscale Lab |
Nuclear / Radiochemistry |
Stereochemistry |
Amino Acids |
Thin Layer Chromatography |
Enantiomers
Circular Dichroism and Linear Dichroism (by Alison Rodger and Bengt Norden)  Richard Pagni
Deals specifically with two powerful, independent but often complementary, topics: circular dichroism (CD), which deals with the differential absorption of left-handed and right-handed circularly polarized light by optically active molecules, usually involving electronic transitions in the visible and ultraviolet regions of the electromagnetic spectrum; and linear dichroism (LD), which deals with the differential absorption of linearly polarized light (really a superposition of left-handed and right-handed circularly polarized light) of oriented molecules, not necessarily optically active, parallel and perpendicular to the orienting axes.
Pagni, Richard. J. Chem. Educ. 1998, 75, 1095.
Stereochemistry |
Photochemistry |
Molecular Properties / Structure
A Simple Molecular Orbital Treatment of the Barrier to Internal Rotation in the Ethane Molecule  Derek W. Smith
The origin of the barrier to internal rotation in the ethane molecule is explored in terms of elementary molecular orbital (MO) considerations. Emphasis is placed on the antibonding effect, i.e. the result that an antibonding MO is more destabilized than its bonding counterpart is stabilized, relative to the parent atomic orbitals (AOs). It is shown that, in the case of two equivalent AOs, this effect is approximately proportional to the square of the overlap integral.
Smith, Derek W. J. Chem. Educ. 1998, 75, 907.
Covalent Bonding |
MO Theory |
Stereochemistry |
Theoretical Chemistry |
Alkanes / Cycloalkanes
The Energy Profile for Rotation about the C-C Bond in Substituted Ethanes: A Multi-Part Experimental Computational Project for the Physical Chemistry Laboratory  Luther E. Erickson and Kevin F. Morris
This paper describes a multi-part project for the physical chemistry lab that includes both experimental and computational approaches to the investigation of the energy profile for internal rotation in substituted ethanes. Experimental approaches include dipole moment determinations, high-resolution nmr spectroscopy (including coupling constant determinations from the analysis of C-13 satellites), and infrared spectral analysis, all directed toward the goal of determining the relative populations - and thereby the relative energies - of low energy rotamers of a substituted ethane as a function of substituent, temperature and solvent composition.
Erickson, Luther E.; Morris, Kevin F. J. Chem. Educ. 1998, 75, 900.
Theoretical Chemistry |
Computational Chemistry |
Stereochemistry |
Alkanes / Cycloalkanes
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
The Baker's Yeast Reduction of Keto-Esters in Organic Solvents: A One Week Research Project for Undergraduate Students   Michael North
An experiment has been designed which allows final year undergraduate students to carry out a mini-research project in one week and thus get a flavor of the joys and tribulations of conducting chemical research before they undertake a major research project. The experiment is an investigation into the reduction of alpha- or beta-keto esters using non-fermenting Baker's yeast in petroleum ether.
North, Michael. J. Chem. Educ. 1998, 75, 630.
Bioinorganic Chemistry |
Bioorganic Chemistry |
Enzymes |
Synthesis |
Stereochemistry |
Aldehydes / Ketones |
Esters |
Undergraduate Research
Enzymatic Synthesis of (S)-(-)-gamma-Methyl-gamma-butyrolactone from Racemic Methyl gamma-hydroxypentanoate Using Porcine Pancreatic Lipase: A Microscale Advanced Bioorganic Chemistry Laboratory Project  Moses Lee
An advanced lab project utilizing a chiral auxiliary to induce asymmetry into organic reactions. The project includes many chemical and spectroscopic techniques - extraction, filtration, rotavaporation, infrared, proton-NMR, polarity, and circular dichroism.
Lee, Moses. J. Chem. Educ. 1998, 75, 217.
Bioorganic Chemistry |
Chromatography |
Enzymes |
NMR Spectroscopy |
Microscale Lab |
Stereochemistry
Thermodynamic and Kinetic Controlled Enolates: A Project for a Problem-Oriented Laboratory Course  Augustine Silveira Jr., Michael A. Knopp, and Jhong Kim
A microscale preparation of thermodynamic and kinetic enolates is given as an undergraduate research laboratory. This experiment provides student involvement and discussion.
Silveira, Augustine, Jr.; Knopp, Michael A.; Kim, Jhong. J. Chem. Educ. 1998, 75, 78.
Equilibrium |
Microscale Lab |
Stereochemistry |
Acids / Bases |
Kinetics |
Thermodynamics
Investigation of Atropisomerism in ortho-Substituted Tetraphenylporphyrins: An Experimental Module Involving Synthesis, Chromatography, and NMR Spectroscopy  Ruth Freitag Beeston, Shannon E. Stitzel , and Mitchell A. Rhea
It is shown that as the number of cofacial methyl neighbors for a particular methyl group decreases, the chemical shift of the methyl protons increases. This experiment leads to a greater understanding of chromatography and NMR spectroscopy in addition to introducing students to porphyrin synthesis and the concepts of atropisomerism and statistical distributions.
Beeston, Ruth Freitag; Stitzel, Shannon E.; Rhea, Mitchell A. J. Chem. Educ. 1997, 74, 1468.
Instrumental Methods |
NMR Spectroscopy |
Synthesis |
Stereochemistry
Epoxidation of Geraniol: An Advanced Organic Experiment that Illustrates Asymmetric Synthesis  Lynn M. Bradley, Joseph W. Springer, Gregory M. Delate, and Andrew Goodman
The experiment described in this paper illustrates the principle of asymmetric epoxidation and enables students to determine enantiomeric product ratios using chiral shift reagents and NMR spectroscopy.
Bradley, Lynn M.; Springer, Joseph W.; Delate, Gregory M.; Goodman, Andrew. J. Chem. Educ. 1997, 74, 1336.
Chromatography |
NMR Spectroscopy |
Synthesis |
Stereochemistry
Resolution of Racemic Phenylsuccinic Acid Using (-)-Proline as a Resolving Agent: An Introductory Organic Chemistry Experiment  Victor Cesare and Ralph Stephani
Isolation of the (+)-enantiomer can be completed in about two hours and this procedure can also be used to introduce the reflux and recrystallization techniques.
Cesare, Victor; Stephani, Ralph. J. Chem. Educ. 1997, 74, 1226.
Stereochemistry |
Chirality / Optical Activity |
Enantiomers
Separation of Enantiomeric Barbiturates by Capillary Electrophoresis Using a Cyclodextrin Containing Run Buffer  S. Contradi, Carla Vogt, and E. Rohde
This article is intended to demonstrate the potential of CE for the determination of enantiomers. The separation is based on the addition of a suitable chiral selector to the buffer. Cyclodextrins perform as excellent selectors forming diastereomeric complexes of different stability with the enantiomeric forms of the analyte.
Contradi, S.; Vogt, Carla; Rohde E. J. Chem. Educ. 1997, 74, 1122.
Drugs / Pharmaceuticals |
Electrophoresis |
Separation Science |
Stereochemistry |
Enantiomers |
Medicinal Chemistry
A Thermostable Microbial Enzyme for Fast Preparative Organic Chemistry: The Preparation of (R)-(+)-1-Phenylethanol from (+)-1-Phenylethyl Pentanoate and n-Butanol  Jacques Drouin, Jeanne Costante, Eryk Guibe-Jampel
Enantiopure (+)-1-phenylethanol is conveniently obtained from (+)-1-phenylethyl pentanoate in a fast enzymatic transesterification reaction using n-butanol and an immobilized thermostable enzyme. The enantiomeric excess and the absolute configuration of the alcohol are ascertained.
Drouin, Jacques; Costante, Jeanne; Guibe-Jampel, Eryk. J. Chem. Educ. 1997, 74, 992.
Biotechnology |
Enzymes |
NMR Spectroscopy |
Separation Science |
Enantiomers |
Stereochemistry
Extraction and Assay of Ornithine Decarboxylase: A Laboratory Experiment that Introduces Principles of Radiochemical Enzymatic Assay  William H. Voige
A laboratory experiment involving preparation of an Escherichia coli extract in which ornithine decarboxylase (ODC) is quantitated by radiochemical assay has been developed. The assay is based on the ODC-catalyzed decarboxylation of [1-14C]ornithine to yield 14CO2.
Voige, William H. J. Chem. Educ. 1997, 74, 988.
Enzymes |
Nuclear / Radiochemistry |
Stereochemistry
A Three-Dimensional Energy Surface for the Conformational Inversion of Cyclohexane  Nicholas Leventis*, Samir B. Hanna, Chariklia Sotiriou-Leventis
While it is well known that chair forms of cyclohexane can interconvert without passing through the boat conformation, the same statement frequently comprises a source of confusion regarding the location of the boat conformation on the energy surface of the conformational inversion of cyclohexane. To alleviate this problem, a novel three-dimensional energy diagram has been introduced showing explicitly how the chair forms of cyclohexane interconvert.
Leventis, Nicholas; Hanna , Samir B. ; Sotiriou-Leventis, Chariklia . J. Chem. Educ. 1997, 74, 813.
Learning Theories |
Mechanisms of Reactions |
Stereochemistry |
Alkanes / Cycloalkanes |
Conformational Analysis |
Molecular Properties / Structure
Molecules, Crystals, and Chirality  Il-Hwan Suh, Koon Ha Park, William P. Jensen, David E. Lewis*
The development of the concept of chirality from the early work of Pasteur, van't Hoff and Le Bel to the work of Cahn, Ingold and Prelog is presented, and the constraints that chirality imposes on the symmetry of molecules - that chiral molecules may not possess an improper axis of rotation - is discussed.
Suh, Il-Hwan; Park, Koon Ha ; Jensen, William P.; Lewis, David E. J. Chem. Educ. 1997, 74, 800.
Crystals / Crystallography |
Molecular Properties / Structure |
Stereochemistry |
X-ray Crystallography
Determination of the Enantiomeric Purity of Naproxen: An Organic Chemistry Laboratory Experiment  Thomas D. Walsh and Curtis S. Koontz
Recent availability of and publicity surrounding the antiinflammatory drug naproxen presents an opportunity for an organic chemistry laboratory experiment of great up-to-the-minute interest.
Walsh, Thomas D.; Koontz, Curtis S. . J. Chem. Educ. 1997, 74, 585.
Stereochemistry |
Drugs / Pharmaceuticals |
Molecular Properties / Structure |
Aromatic Compounds |
Carboxylic Acids
endo- and exo-Stereochemistry in the Diels-Alder Reaction: Kinetic versus Thermodynamic Control  James H. Cooley and Richard Vaughan Williams
In these experiments, which were used in the problem-solving mode, the stereoselectivity of the Diels-Alder cycloaddition of N-phenylmaleimide to furan is deduced by the characteristic splitting patterns in the proton-NMR spectra. The relationship of coupling constants to dihedral angle, as described by the Karplus equation, is illustrated.
Cooley, James H.; Williams, Richard Vaughan. J. Chem. Educ. 1997, 74, 582.
Kinetics |
Molecular Modeling |
NMR Spectroscopy |
Stereochemistry |
Thermodynamics
An Example of a Human Topological Rubber Glove Act  Yock Chai Toong and Shih Yung Wang
A hitherto unreported human body narcissistic inversion which is an example of the rubber glove act has been uncovered from a Chinese acrobatic performance. This inversion is related to the unimolecular enantiomerizations of chiral molecules, a topological figure and a rubber glove via chiral pathway.
Toong, Yock Chai; Wang, Shih Yung. J. Chem. Educ. 1997, 74, 403.
Chirality / Optical Activity |
Enantiomers |
Stereochemistry |
Aromatic Compounds
Discovery-Based Stereochemistry Tutorials Available on the World Wide Web  Abby L. Parrill and Jacquelyn Gervay
The WWW offers the ability to develop interactive, discovery-based tutorials for use as study tools, and multimedia offers significant improvements in the display of three-dimensional objects. As part of a chemical education research program, three stereochemistry tutorials were developed to capitalize on these advantages.
Parrill, Abby L.; Gervay, Jacquelyn. J. Chem. Educ. 1997, 74, 329.
Stereochemistry |
Molecular Properties / Structure |
Molecular Modeling
An Experiment to Demonstrate Magnetic Nonequivalence in Proton NMR  Christopher J. Welch
The bicyclic compound, 3a,6a-diethoxycarbonyl-2,5-dimethyl-1,4-dioxo-octahydropyrrolo[3,4-c]pyrrole, prepared by a literature procedure is used to demonstrate magnetic nonequivalence for methylene protons in the proton NMR experiment.
Welch, Christopher J. J. Chem. Educ. 1997, 74, 247.
Spectroscopy |
NMR Spectroscopy |
Stereochemistry |
Aldehydes / Ketones
The Acid Catalyzed Dehydration of an Isomeric 2-Methylcyclohexanol Mixture: A Kinetic and Regiochemical Study of the Evelyn Effect  John J. Cawley and Patrick E. Linder
This paper details an experiment which serves as an introduction to organic laboratory research. The reaction is the dehydration of a cis, trans mixture of 2-methylcyclohexanols. At intervals of times the reactant mixture is sampled for the cis and trans reactants. At those same intervals of times the receiver flasks of product cyclohexanes being collected are changed, such that sequential fractions of material are obtained.
Cawley, John J.; Linder, Patrick E. J. Chem. Educ. 1997, 74, 102.
Catalysis |
Kinetics |
Alcohols |
Stereochemistry
Stereochemistry of Organic Compounds  reviewed by Ronald D. McKelvey
Organic stereochemistry text.
McKelvey, Ronald D. J. Chem. Educ. 1996, 73, A174.
Stereochemistry
Symmetry Elements and Operations  Albert W.M. Lee, K.M. Leung, W.J Daniel, C.L. Chan
Symmetry Elements and Operations is a multimedia presentation that illustrates the basics of symmetry with three dimensional molecular models and simple text explanations.
Lee, Albert W.M.; Leung, K.M.; Kwong, Daniel W.J.; Chan, C.L. . J. Chem. Educ. 1996, 73, 924.
Molecular Modeling |
Spectroscopy |
Stereochemistry |
Mechanisms of Reactions |
Group Theory / Symmetry |
Quantum Chemistry |
Enrichment / Review Materials
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
When Drug Molecules Look in the Mirror  Edwin Thall
Enantiomers possess virtually identical physical properties but often display very different biological activities. Stereochemical non-equivalence, chiral recognition, enantiomer uniqueness, and the preparation of optically active drugs are reviewed.
Thall, Edwin. J. Chem. Educ. 1996, 73, 481.
Enantiomers |
Stereochemistry |
Drugs / Pharmaceuticals |
Chirality / Optical Activity
Stereoisomer Bubbles  Melanie J. Lesko
Undergraduate organic chemistry students are given a simple method to determine the stereochemical relationships between several molecules with more than one chiral center.
Lesko, Melanie J. J. Chem. Educ. 1996, 73, 429.
Stereochemistry
Steric Attraction: The Far Side  Ronald R. Sauers
The concept of steric attractions is discussed in terms of the individual contributions of repulsive and attractive terms.
Sauers, Ronald R. J. Chem. Educ. 1996, 73, 114.
Stereochemistry |
Molecular Modeling
A Straightforward Method for Assigning Stereochemical Lambda/Delta Descriptors to Octahedral Coordination Compounds  Santiago Herrero and Miguel Angel Usón
A straightforward method for assigning stereochemical ?/? descriptors to octahedral coordination compounds.
Herrero, Santiago; Uson, Miguel Angel. J. Chem. Educ. 1995, 72, 1065.
Stereochemistry |
Molecular Properties / Structure |
Coordination Compounds |
Chirality / Optical Activity
Chemical Topology: The Ins and Outs of Molecular Structure  Dennis K. Mitchell and Jean-Claude Chambron
Using models of macromolecules to develop and broaden an understanding of bonding and structure; includes many examples of molecules of topological interest.
Mitchell, Dennis K.; Chambron, Jean-Claude. J. Chem. Educ. 1995, 72, 1059.
Molecular Properties / Structure |
Molecular Modeling |
Stereochemistry |
Molecular Mechanics / Dynamics |
Covalent Bonding
Diastereospecific Synthesis of an Epoxide: An Introductory Experiment in Organic Synthetic and Mechanistic Chemistry  James A. Ciaccio
A two-step epoxide synthesis that can be presented to students in the form of two mechanistic "puzzles" that probe the stereoselectivity of two important reactions: halohydrin formation from alkenes and epoxide formation via intramolecular Williamson ether synthesis.
Ciaccio, James A. J. Chem. Educ. 1995, 72, 1037.
Stereochemistry |
Molecular Properties / Structure |
Mechanisms of Reactions |
Synthesis |
Epoxides |
Alkenes
NMR Spectroscopy Using a Chiral Lanthanide Shift Reagent to Assess the Optical Purity of 1-Phenylethylamine  Tito Viswanathan and Alan Toland
An experiment to exemplify the use of NMR in determining the resolution of a racemic mixture separation.
Viswanathan, Tito; Toland, Alan. J. Chem. Educ. 1995, 72, 945.
NMR Spectroscopy |
Chirality / Optical Activity |
Stereochemistry |
Separation Science |
Amines / Ammonium Compounds
Chiroptical Spectroscopy  Jerome E. Gurst
Use of chiroptical spectroscopy to assign absolute or relative configurations and in conformational analysis.
Gurst, Jerome E. J. Chem. Educ. 1995, 72, 827.
Chirality / Optical Activity |
Stereochemistry |
Conformational Analysis
Animation of Imaginary Frequencies at the Transition State  Robert H. Higgins
176. Software tutorial for strengthening spatial skills and an understanding of stereochemistry in exploring molecular structures.
Higgins, Robert H. J. Chem. Educ. 1995, 72, 699.
Molecular Properties / Structure |
Stereochemistry |
Molecular Modeling
"Double Unknown " Microscale Preparation and COSY Analysis of an Unknown Ester:
An Introductory 2D-NMR Experiment
  Stephen E. Branz, Robert G. Miele, Roy K. Okuda, and Daniel A. Straus
Proton NMR activity designed to highlight the power of the technique to analyze structures and not merely confirm the identity of known substances.
Branz, Stephen E.; Miele, Robert G.; Okuda, Roy K.; Straus, Daniel A. J. Chem. Educ. 1995, 72, 659.
NMR Spectroscopy |
Stereochemistry |
Alcohols |
Carboxylic Acids |
Esters
Steric Hindrance by Bromination of Alkylbenzenes: Experimental Demonstration  Cooley, James H.; Abobaker, Nagib M.
Procedure to illustrate the influence of steric hindrance on organic chemistry in which students must decide what data to collect and how to interpret it.
Cooley, James H.; Abobaker, Nagib M. J. Chem. Educ. 1995, 72, 463.
Molecular Properties / Structure |
Synthesis |
Chirality / Optical Activity |
Aromatic Compounds |
Stereochemistry
Chemical Education via MOLGEN  Benecke, C.; Grund, R.; Kerber, A.; Laue, R.; Wieland, T.
173. Bits and pieces, 53. Software used to produce all the isomers for a given chemical formula.
Benecke, C.; Grund, R.; Kerber, A.; Laue, R.; Wieland, T. J. Chem. Educ. 1995, 72, 403.
Molecular Properties / Structure |
Chirality / Optical Activity |
Stereochemistry |
Molecular Modeling
A More Affordable Undergraduate Experiment on the Reduction of Acetophenone by Yeast  Lee, Moses; Huntington, Martha
Preparation of Mosher's esters through the reduction of acetophenone with baker's yeast.
Lee, Moses; Huntington, Martha J. Chem. Educ. 1994, 71, A62.
Microscale Lab |
Aromatic Compounds |
Aldehydes / Ketones |
Oxidation / Reduction |
Stereochemistry |
Chirality / Optical Activity |
Esters |
Synthesis
The Molecule and Its Double (Jacques, Jean)  Wilen, Samuel H.
Louis Pasteur's seminal discoveries that laid the groundwork for the development of stereochemistry are the centerpiece of this engaging little book written for the layman.
Wilen, Samuel H. J. Chem. Educ. 1994, 71, A53.
Stereochemistry |
Molecular Properties / Structure
Incorporating Heterotopicity into Organic Chemistry  Thall, Edwin
This paper reviews topological relationships and suggests how to incorporate heterotopic concepts into the contemporary chemistry curriculum.
Thall, Edwin J. Chem. Educ. 1994, 71, 1034.
Stereochemistry |
Crystal Field / Ligand Field Theory
A Spreadsheet Approach to Determining the Degree of Distortion in Five-Coordinate Compounds  Montgomery, Craig D.
166. Calculating the distortion of five-coordinate compounds using Holmes' method of dihedral angles adapted to a spreadsheet.
Montgomery, Craig D. J. Chem. Educ. 1994, 71, 885.
Coordination Compounds |
Stereochemistry |
Molecular Properties / Structure |
Metals
Molecular Modelling in the Undergraduate Chemistry Curriculum: The Use of beta-Lactams as a Case Study  Ringan, Neil S.; Grayson, Lisa
A case study to give students an opportunity for hands-on use of a molecular modelling package to construct a model of the D-ALA-D-ALA portion of the penta-peptide of the peptidoglycan and to compare this model to the crystal structure of a biologically active penicillin.
Ringan, Neil S.; Grayson, Lisa J. Chem. Educ. 1994, 71, 856.
Molecular Modeling |
Stereochemistry |
Molecular Properties / Structure |
Proteins / Peptides
Molecular Models Constructed in an Easy Way: Part 3. Models Constructed by Using Octahedral Units as Building Blocks  He, Fu-cheng; Liu, Lu-bin; Li, Xiang-yuan
Using octahedral units to construct paper models that are useful for teaching stereo- and coordination chemistry.
He, Fu-cheng; Liu, Lu-bin; Li, Xiang-yuan J. Chem. Educ. 1994, 71, 734.
Molecular Modeling |
Molecular Properties / Structure |
Stereochemistry |
Coordination Compounds
Angular Overlap Model Approach To Explain the Trans Effect in d8 Square Planar Metal Complexes  Lee, Liangshiu
The idea of structure preference energy and ligand field stabilization energy expressed in terms of angular overlap model parameters can be extended to treat the substitution behavior of d8 square planar metal complexes.
Lee, Liangshiu J. Chem. Educ. 1994, 71, 644.
Coordination Compounds |
Crystal Field / Ligand Field Theory |
Molecular Properties / Structure |
Stereochemistry |
Transition Elements |
Metals
Molecular Modeling and Chemical Activity: An Experiment for the Introductory Organic Course  Simpson, John
Students are asked to determine minimum steric energies for a series of compounds and to perform a subsequent correlation analysis of these ground state values with relative reaction rates from the literature.
Simpson, John J. Chem. Educ. 1994, 71, 607.
Molecular Modeling |
Stereochemistry |
Rate Law
Haloallenes: Chiral Compounds without Chiral Carbon Atoms  Novak, Igor
Four questions regarding the structure, stereochemistry, and symmetry of haloallenes.
Novak, Igor J. Chem. Educ. 1994, 71, 579.
Chirality / Optical Activity |
Group Theory / Symmetry |
Stereochemistry |
Molecular Properties / Structure |
Alkenes
Inverse Problem of Isomer Enumeration  Novak, Igor
How an isomeric enumeration can be performed on a small molecule generating a vast number of possibilities from a few structural and chemical elements.
Novak, Igor J. Chem. Educ. 1994, 71, 512.
Stereochemistry |
Molecular Properties / Structure
Nevil Vincent Sidgwick, 1873-1952: One of the Unsung Truly Greats  Laing, Michael
Students of chemistry usually get to hear of G. N. Lewis and Linus Pauling, but few appreciate the enormous contributions of great men like Sidgwick.
Laing, Michael J. Chem. Educ. 1994, 71, 472.
VSEPR Theory |
Stereochemistry |
Coordination Compounds |
Organometallics
The Dehydration of 2-Methylcyclohexanol Revisited: The Evelyn Effect  Todd, David
Modification to an earlier procedure that allows students to observe the results of a hydride shift mechanism.
Todd, David J. Chem. Educ. 1994, 71, 440.
Alcohols |
Mechanisms of Reactions |
Gas Chromatography |
Alkenes |
Elimination Reactions
Models of 2-Butanone: Using Graphics To Illustrate Complementary Approaches to Molecular Structure and Reactivity  Hanks, T. W.
157. Ways in which a graphics workstation can be used to illustrate various concepts of molecular structure.
Hanks, T. W. J. Chem. Educ. 1994, 71, 62.
Aldehydes / Ketones |
Molecular Properties / Structure |
Molecular Modeling |
Molecular Mechanics / Dynamics |
Stereochemistry |
Quantum Chemistry |
MO Theory
Grasping the Concepts of Stereochemistry  Barta, Nancy S.; Stille, John R.
An alternative procedure for the determination of R or S configuration for chiral molecules.
Barta, Nancy S.; Stille, John R. J. Chem. Educ. 1994, 71, 20.
Stereochemistry |
Molecular Properties / Structure |
Nomenclature / Units / Symbols |
Chirality / Optical Activity
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
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
GC/MS experiments for the organic chemistry laboratory: I. E2 elimination of 2-bromo-2-methyloctane   Novak, Michael; Heinrich, Julie; Martin, Kristy A.; Green, John; Lytle, Scott
Two capillary GC/MS experiments that were designed for and tested in a sophomore organic laboratory course.
Novak, Michael; Heinrich, Julie; Martin, Kristy A.; Green, John; Lytle, Scott J. Chem. Educ. 1993, 70, A103.
Gas Chromatography |
Alkenes |
Alkanes / Cycloalkanes |
Alcohols |
Elimination Reactions |
Synthesis
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
Optical activity can be created from "nothing"  Caswell, Lesley; Garcia-Garibay, Miguel A.; Scheffer, John R.; Trotter, James
Optically active products can be generated from achiral reactants.
Caswell, Lesley; Garcia-Garibay, Miguel A.; Scheffer, John R.; Trotter, James J. Chem. Educ. 1993, 70, 785.
Enantiomers |
Stereochemistry
The Caltech chemistry animation project   Lewis, Nathan S.
Animations are being produced on subjects such as: atomic and molecular orbitals, lattices, VSPER, nucleophilic substitution, stereochemistry, sigma and pi bonding, and many more.
Lewis, Nathan S. J. Chem. Educ. 1993, 70, 739.
Stereochemistry |
Atomic Properties / Structure |
Molecular Modeling |
MO Theory |
Crystals / Crystallography
Stereochemistry and the "ether" in the evolution of molecular structure theory: The musings of a chemist on Moller's supplanted "screw-theory", beginning with a view of the obnoxious and equally outdated cod-liver oil  Greenberg, Arthur
A look at a chemist's attempt to explain optical rotation of plane-polarized light by enantiomers documented in a text published in 1895 that the author of this article had stumbled upon.
Greenberg, Arthur J. Chem. Educ. 1993, 70, 284.
Stereochemistry |
Enrichment / Review Materials
Microscale elimination reactions: Experiments for organic chemistry using the small scale approach  Gilow, Helmuth M.
Procedure illustrating E1 and E2 reactions.
Gilow, Helmuth M. J. Chem. Educ. 1992, 69, A265.
Microscale Lab |
Reactions |
Elimination Reactions |
Alcohols |
Alkenes |
Catalysis
Meso and dl diastereomers: Synthesis and 1H NMR study of the 1,3-diphenylpropane-1,3-diols: An advanced undergraduate project in physical organic chemistry  Depres, Jean-Pierre; Morat, Claude
An integrated laboratory project that gives students an experimental approach to diastereomerism in molecular structure and to first- and second-order NMR spectroscopic analysis.
Depres, Jean-Pierre; Morat, Claude J. Chem. Educ. 1992, 69, A232.
Synthesis |
NMR Spectroscopy |
Diastereomers |
Stereochemistry |
Group Theory / Symmetry |
Molecular Properties / Structure
The dehydrohalogenation of 2-bromobutane: A simple illustration of anti-Saytzeff elimination as a laboratory experiment for organic chemistry.  Leone, Stephen A.; Davis, J. David.
A quantitative microscale experiment of the dehydrohalogenation of 2-bromobutane to explore how increasing the base size affects the distribution of products.
Leone, Stephen A.; Davis, J. David. J. Chem. Educ. 1992, 69, A175.
Microscale Lab |
Elimination Reactions |
Mechanisms of Reactions
An easily constructed model: The boat form of a six-membered ring composed of six distorted tetrahedral penetrating each other  Yamana, Shukichi
Instructions for constructing a model of the boat form of a six-membered ring using six empty envelopes.
Yamana, Shukichi J. Chem. Educ. 1992, 69, 964.
Molecular Modeling |
Molecular Properties / Structure |
Alkanes / Cycloalkanes |
Stereochemistry
Isomerism in adamantane-like inorganic compounds  Vittal, Jagadese J.
Analysis of the structure and isomerism of adamantane-like inorganic compounds.
Vittal, Jagadese J. J. Chem. Educ. 1992, 69, 955.
Stereochemistry |
Group Theory / Symmetry |
Molecular Properties / Structure
Structure, chirality, and FT-NMR in sophomore organic chemistry  Chapman, Orville L.; Russell, Arlene A.
An experimental approach (NMR) to teaching organic structure.
Chapman, Orville L.; Russell, Arlene A. J. Chem. Educ. 1992, 69, 779.
NMR Spectroscopy |
Fourier Transform Techniques |
Molecular Properties / Structure |
Chirality / Optical Activity |
Stereochemistry |
Elimination Reactions
Of men and marigolds: Counting the quaterthienyls  Perrine, Daniel M.; VandeVelde, J. Richard
Description of branched quaterthienyls and their isomers.
Perrine, Daniel M.; VandeVelde, J. Richard J. Chem. Educ. 1992, 69, 719.
Alkenes |
Molecular Properties / Structure |
Stereochemistry |
Diastereomers
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
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
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
A source of isomer-drawing assignments  Kjonaas, Richard A.
A comprehensive source from which instructors can choose a wide variety of good isomer drawing examples to use as homework assignments and exam questions.
Kjonaas, Richard A. J. Chem. Educ. 1992, 69, 452.
Stereochemistry |
Alcohols |
Alkanes / Cycloalkanes |
Alkenes |
Aldehydes / Ketones |
Ethers |
Esters |
Alkynes
Toward the consistent use of regiochemical and stereochemical terms in introductory organic chemistry.  Adams, David L.
Proposes consistency and clarity in the use of definitions for regioselective, stereoselective, and stereospecific in introductory organic chemistry.
Adams, David L. J. Chem. Educ. 1992, 69, 451.
Stereochemistry |
Nomenclature / Units / Symbols
Representing isomeric structures: Five applications.  Thall, Edwin.
Five applications of a new method that the author calls Representing Isomeric Structures, in which arrows are used to point to unique sites on the carbon skeleton to represent functional groups.
Thall, Edwin. J. Chem. Educ. 1992, 69, 447.
Stereochemistry |
Molecular Properties / Structure |
Chirality / Optical Activity |
Enantiomers
Determining a chiral molecule's R/S configuration using the rule of multiplication  Wang, Jin-Xian; Yang, Chi
The authors have developed a simple, rapid, and general method for specifying the R/S configuration of a stereogenic center.
Wang, Jin-Xian; Yang, Chi J. Chem. Educ. 1992, 69, 373.
Chirality / Optical Activity |
Stereochemistry |
Chemometrics
An easily constructed helix model  Yamana, Shukichi.
A simple type helix model for teaching stereochemistry can be made by using several sealed, empty envelopes.
Yamana, Shukichi. J. Chem. Educ. 1992, 69, 275.
Molecular Modeling |
Stereochemistry
The new method of rapid determination of chiral molecule configuration: The triangle method  Yongsheng, Han; Cailan, Wang
This paper describes a new method for applying the Cahn-Ingold-Prelog rules to determine the configuration of a chiral molecule directly from its Fischer projection formula.
Yongsheng, Han; Cailan, Wang J. Chem. Educ. 1992, 69, 273.
Chirality / Optical Activity |
Enantiomers |
Stereochemistry |
Molecular Properties / Structure
An easily constructed model of the chair form of a six-membered ring composed of six distorted tetrahedra penetrating each other.  Yamana, Shukichi.
A model of the chair form of a six-membered ring composed of six distorted tetrahedra penetrating each other is useful for teaching stereorchemistry of organic compounds.
Yamana, Shukichi. J. Chem. Educ. 1992, 69, 216.
Molecular Modeling |
Stereochemistry
Synthesis of trans-2-tert-butylcyclohexanol via hydroboration: A microscale organic experiment demonstrating syn addition  Wigal, Carl T.; Hopkins, William T.; Ronald, Bruce P.
This microscale experiment demonstrates the relative stereochemistry of the titled addition.
Wigal, Carl T.; Hopkins, William T.; Ronald, Bruce P. J. Chem. Educ. 1991, 68, A299.
Synthesis |
Microscale Lab |
Addition Reactions |
Aromatic Compounds |
Stereochemistry
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
Natural and unnatural models for illustrating chirality at two centers  Nave, Paul M.
Some clever suggestions for models that will help students understand chirality better. Puppies and a two-headed goat are involved.
Nave, Paul M. J. Chem. Educ. 1991, 68, 1028.
Stereochemistry |
Chirality / Optical Activity |
Enantiomers
Discovering stereoselectivity: Synthesis of exo- and endobrevicomin using a tunable hydride reduction: A program of organic synthesis experiments for advanced undergraduate students  Richardson, David P.; Wilson, Whitney; Mattson, Rebecca J.; Powers, Dawn M.; Dolan, Brian T.
With their low molecular weights and modest structural complexity, insect pheromones have proven to be especially fruitful for advanced undergraduate organic synthesis laboratory exercises.
Richardson, David P.; Wilson, Whitney; Mattson, Rebecca J.; Powers, Dawn M.; Dolan, Brian T. J. Chem. Educ. 1991, 68, 951.
Natural Products |
Diastereomers |
Enantiomers |
Stereochemistry |
Aldehydes / Ketones |
Alcohols |
Gas Chromatography |
Alkanes / Cycloalkanes
Cyclic ketals of 9-fluorenone: Advanced organic laboratory exercise in synthesis and stereochemical analysis using 13C NMR  Rablen, Paul R.; Deuber, Mark A.; Lim, Ai Ching; Dickson, Robert M.; Wintner, Claude E.
A set of examples that vividly demonstrate the power of 13C NMR spectroscopy to solve stereochemical problems unambiguously and to differentiate pairs of carbon atoms that are homotopic or enantiotopic from pairs which are diastereotopic.
Rablen, Paul R.; Deuber, Mark A.; Lim, Ai Ching; Dickson, Robert M.; Wintner, Claude E. J. Chem. Educ. 1991, 68, 796.
Diastereomers |
Enantiomers |
Stereochemistry |
NMR Spectroscopy
The use of the Desktop Molecular Modeller software in the teaching of structural chemistry  Aduldecha, S.; Akhter, P.; Field, P.; Nagle, P.; O'Sullivan, E.; O'Connor, K.; Hathaway, B. J.
127. A review of a molecular modeling program that can be used for the computer graphic display of molecules, their construction from smaller molecules or fragments, and for the manipulation of molecular structure.
Aduldecha, S.; Akhter, P.; Field, P.; Nagle, P.; O'Sullivan, E.; O'Connor, K.; Hathaway, B. J. J. Chem. Educ. 1991, 68, 576.
Molecular Modeling |
Molecular Properties / Structure |
Crystals / Crystallography |
Stereochemistry
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
An easily constructed model of a distorted tetrahedron penetrated by two trigonal pyramids  Yamana, Shukichi
Step-by-step diagrams and descriptions.
Yamana, Shukichi J. Chem. Educ. 1991, 68, 464.
Stereochemistry
Identification and rectification of student difficulties concerning three-dimensional structures, rotation, and reflection  Tuckey, Helen; Selvaratnam, Mailoo; Bradley, John
A study was conducted to reveal that even at university level, many students have difficulties with three-dimensional thinking. This is a skill that needs to be emphasized more than current treatment at the pre-college level.
Tuckey, Helen; Selvaratnam, Mailoo; Bradley, John J. Chem. Educ. 1991, 68, 460.
Molecular Modeling |
Enantiomers |
Stereochemistry
The synthesis of 2'-bromostyrene  Corvari, Linda; McKee, James R.; Zanger, Murray
Organic chemistry laboratories need not be the repositories of foul smells. This synthesis produces an aroma akin to hyacinth.
Corvari, Linda; McKee, James R.; Zanger, Murray J. Chem. Educ. 1991, 68, 161.
Synthesis |
NMR Spectroscopy |
IR Spectroscopy |
Stereochemistry |
Alkenes
An easily constructed model of twin trigonal pyramids penetrating each other  Yamana, Shukichi
A model of twin trigonal pyramids penetrating each other made from two sealed envelopes.
Yamana, Shukichi J. Chem. Educ. 1990, 67, 1029.
Molecular Modeling |
Molecular Properties / Structure |
Stereochemistry
Binary representation in carbohydrate nomenclature  McGinn, Clifford J.; Wheatley, William B.
A binary notation is used to indicate the structure of carbohydrates.
McGinn, Clifford J.; Wheatley, William B. J. Chem. Educ. 1990, 67, 747.
Carbohydrates |
Nomenclature / Units / Symbols |
Stereochemistry
Saccharin alkylation: O vs. N substitution  Greenberg, Fred H.
Illustrates charge delocalization of an ambident anion in an SN2 reaction, the comparative deshielding of oxygen and nitrogen in proton NMR, and the use of the NMR integral in assessing isomer distribution.
Greenberg, Fred H. J. Chem. Educ. 1990, 67, 611.
Nucleophilic Substitution |
Mechanisms of Reactions |
Aromatic Compounds |
Heterocycles |
NMR Spectroscopy |
Stereochemistry
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
A mnemonic scheme for interconverting Fischer projections of open-chain monosaccharides and Haworth projections of corresponding alpha- and beta-anomeric forms  Mitschele, Jonathan
Rules that make it easy for students to recognize alpha- and beta-anomers and the D and L forms of monosaccharides in their Hawthorn projections.
Mitschele, Jonathan J. Chem. Educ. 1990, 67, 553.
Carbohydrates |
Molecular Properties / Structure |
Stereochemistry
Three easy puzzles based on the Diels-Alder reaction  Pickering, Miles.
This paper recasts some classic systems so that they can be done at room temperature on a small scale in a large lab course without sophisticated instrumentation. Furthermore, they start the student using experimental results to solve mechanistic problems.
Pickering, Miles. J. Chem. Educ. 1990, 67, 524.
Mechanisms of Reactions |
Stereochemistry
Magnetic nonequivalence in 1,2-disubstituted ethanes: An organic experiment in NMR spectroscopy  Colborn, Robert E.
The main purpose of this experiment is to help students consider the various couplings available in organic molecules and determine whether specific groups will have identical chemical shifts or not.
Colborn, Robert E. J. Chem. Educ. 1990, 67, 438.
NMR Spectroscopy |
Stereochemistry
Steric course of lactonization in the deamination of glutamic acid: An organic mechanism experiment  Markgraf, J. Hodge; Davis, Howard A.
The stereochemical consequences of a reaction at a chiral center offer a unique way to distinguish among mechanistic hypothesis.
Markgraf, J. Hodge; Davis, Howard A. J. Chem. Educ. 1990, 67, 173.
Mechanisms of Reactions |
Stereochemistry |
Alcohols
Molecular mechanics as an organic chemistry laboratory exercise  Jarret, Ronald M.; Sin, Ny
Molecular mechanics calculations can be used in conjunction with hand-held models for a more complete approach to the instruction of stereochemistry.
Jarret, Ronald M.; Sin, Ny J. Chem. Educ. 1990, 67, 153.
Stereochemistry |
Molecular Modeling |
Molecular Mechanics / Dynamics
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
Making stereo pair views with Molecular Editor  Robinson, Trevor
This program is useful for building, rotating, and observing molecular structures.
Robinson, Trevor J. Chem. Educ. 1989, 66, A62.
Molecular Properties / Structure |
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
An easily constructed triangulated dodecahedron model  Yamana, Shukichi
Using a sealed envelope to construct a triangulated dodecahedron model.
Yamana, Shukichi J. Chem. Educ. 1989, 66, 1019.
Molecular Modeling |
Molecular Properties / Structure |
Stereochemistry
A new philosophy for teaching advanced organic chemistry: Representative laboratory experiment: Stereoselective reduction of a chiral iminium ion  Polniaszek, Richard P.
Students are introduced to lithium diisopropylamide (LDA), enolate chemistry, and the field of assymetric synthesis.
Polniaszek, Richard P. J. Chem. Educ. 1989, 66, 970.
Chirality / Optical Activity |
Stereochemistry
A study of the E2 reaction for the microscale organic lab  Flash, Patrick; Galle, Fred; Radil, Mark
Students determine the pseudo-first-order rate constant for the elimination of HBr from 2-bromobutane and measure the yield and approximate composition of the alkene products, determine the yield of alkenes from 1-bromobutane under the same conditions, and examine the effect of changing solvent polarity on alkene yields for the two halides.
Flash, Patrick; Galle, Fred; Radil, Mark J. Chem. Educ. 1989, 66, 958.
Elimination Reactions |
Mechanisms of Reactions |
Rate Law |
Kinetics
Concerning orientations of certain syn-elimination reactions  Ho, Tse-Lok
Explanation of an interesting aspect of the orientation of unsymmetrically substituted oxides.
Ho, Tse-Lok J. Chem. Educ. 1989, 66, 785.
Elimination Reactions |
Mechanisms of Reactions
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
Viewing stereo drawings  Srinivasan, A. R.; Olson, Wilma K.
Using stereo triptych representations in place of conventional stereo diagrams.
Srinivasan, A. R.; Olson, Wilma K. J. Chem. Educ. 1989, 66, 664.
Molecular Properties / Structure |
Stereochemistry
Polymer tacticity in simulated NMR spectra  Ober, Christopher K.
105. Bits and pieces, 41. A subroutine that has been used to simulate the 1H-NMR spectra of poly(methylacrylate) with different tacticities.
Ober, Christopher K. J. Chem. Educ. 1989, 66, 645.
NMR Spectroscopy |
Physical Properties |
Molecular Properties / Structure |
Stereochemistry
An easily constructed monocapped antiprism model  Yamana, Shukichi
An monocapped antiprism model easily constructed from a sealed, empty envelope and useful for teaching stereochemistry.
Yamana, Shukichi J. Chem. Educ. 1989, 66, 576.
Molecular Modeling |
Molecular Properties / Structure |
Stereochemistry
A query on the etymology of the symbols, R and S  Koga, Gen
Confusion regarding the etymology of the stereochemical symbols, R and S.
Koga, Gen J. Chem. Educ. 1989, 66, 534.
Nomenclature / Units / Symbols |
Stereochemistry
A tandem Michael-aldol reaction sequence: An undergraduate research organic experiment  Coutlangus, Marilyin L.; Filla, Sandra A.; Rowland, Alex T.
A short reaction sequence that allows students to determine by spectroscopic methods the constitutions of and stereochemistry in the reaction products.
Coutlangus, Marilyin L.; Filla, Sandra A.; Rowland, Alex T. J. Chem. Educ. 1989, 66, 520.
Mechanisms of Reactions |
Spectroscopy |
Stereochemistry |
IR Spectroscopy |
UV-Vis Spectroscopy |
NMR Spectroscopy
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
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
A mnemonic device for assignment of pro-R and pro-S descriptors to stereoheterotopic ligands  Nasipuri, Dhanonjoy
A simple mnemonic device for assigning configurational descriptors to appropriate ligands in molecules with a prochiral center or centers written in Fischer projection formulas and in molecules with a prochiral axis.
Nasipuri, Dhanonjoy J. Chem. Educ. 1989, 66, 483.
Chirality / Optical Activity |
Stereochemistry |
Molecular Properties / Structure
Absolutely "simple" configuration in Fischer projection formula  Reddy, K. R. N.
A table from which one can easily assign the absolute configuration in Fischer projection formula after designating priorities of the substituents directly bonded to the chiral center.
Reddy, K. R. N. J. Chem. Educ. 1989, 66, 480.
Molecular Properties / Structure |
Chirality / Optical Activity |
Stereochemistry
Drawing different views of the chair form of substituted cyclohexanes  Richardson, W. S.
A set of rules to instruct students in a method for drawing chair structures of cyclohexane after rotation about the central axis.
Richardson, W. S. J. Chem. Educ. 1989, 66, 478.
Alkanes / Cycloalkanes |
Molecular Properties / Structure |
Stereochemistry
Rotation of polarized light by stereoisomers of limonene   Solomon, Sally
Neat samples of limonene stereoisomers are used to demonstrate the rotation of polarized light on an overhead projector.
Solomon, Sally J. Chem. Educ. 1989, 66, 436.
Stereochemistry
An easily constructed bicapped pentagonal prism model  Yamana, Shukichi
A model of a bicapped pentagonal prism, which is useful for teaching stereochemistry can be made easily by using a sealed empty envelope.
Yamana, Shukichi J. Chem. Educ. 1989, 66, 302.
Molecular Modeling |
Stereochemistry
An easily constructed pentagonal pyramid model  Yamana, Shukichi
A model of a pentagonal pyramid, which is useful for teaching stereochemistry can be made easily by using a sealed empty envelope.
Yamana, Shukichi J. Chem. Educ. 1989, 66, 301.
Molecular Modeling |
Stereochemistry
Overlooked opportunities in stereochemistry: Part II. The neglected connection between metal-ammines (Alfred Werner) and organic onium compounds (William Jackson Pope)  Kauffman, George B.; Bernal, Ivan
The authors have shown how the work of each of two great stereochemists could have mutually enriched, reinforced, and accelerated the contributions of the other.
Kauffman, George B.; Bernal, Ivan J. Chem. Educ. 1989, 66, 293.
Coordination Compounds |
Stereochemistry
C167H336 is the smallest alkane with more realizable isomers than the observed universe has "particles"  Davies, Robert E.; Freyd, Peter J.
The number of stereoisomers of C167H336 that can exist, though not all at the same time, is greater than the classical figure for the number of particles in the observed universe.
Davies, Robert E.; Freyd, Peter J. J. Chem. Educ. 1989, 66, 278.
Alkanes / Cycloalkanes |
Stereochemistry
Stereochemistry Makes the World Go "Round"  
Everywhere we look we can find examples of stereochemistry making our lives possible - or just more enjoyable.
J. Chem. Educ. 1989, 66, 274.
Stereochemistry
An easily constructed bicapped tetrahedron model  Yamana, Shukichi
A model of a bicapped tetrahedron which is useful for teaching stereochemistry can be made easily using two sealed, empty envelopes.
Yamana, Shukichi J. Chem. Educ. 1989, 66, 250.
Molecular Modeling |
Stereochemistry
Carbohydrate stereochemistry  Shallenberger, Robert S.; Wienen, Wanda J.
A progress in the development of general stereochemical principles has been significantly influenced by studies that led to determination of the crystalline and solution structures of sugars, the subject of carbohydrate chemistry is developed here in historical fashion.
Shallenberger, Robert S.; Wienen, Wanda J. J. Chem. Educ. 1989, 66, 67.
Carbohydrates |
Stereochemistry
Van't Hoff, Le Bel, and the development of stereochemistry: A reassessment  Grossman, Robert B.
The author gives a review of and possible explanations for Van't Hoff's inconsistencies.
Grossman, Robert B. J. Chem. Educ. 1989, 66, 30.
Stereochemistry |
Group Theory / Symmetry
A molecular model for the quaternary structure of ferritin  Smith, John M. A.; Stansfield, Robert F.; Ford, Geoffrey C.; White, Jan L.; Harrison, Pauline M.
A template that can be photocopied and assembled to model ferritin.
Smith, John M. A.; Stansfield, Robert F.; Ford, Geoffrey C.; White, Jan L.; Harrison, Pauline M. J. Chem. Educ. 1988, 65, 1083.
Stereochemistry |
Molecular Modeling |
Proteins / Peptides |
Crystals / Crystallography
An easily constructed trigonal pyramid model  Yamana, Shukichi
A diagram and instructions for constructing a trigonal pyramid model.
Yamana, Shukichi J. Chem. Educ. 1988, 65, 1074.
Molecular Modeling |
Stereochemistry
An easily constructed tetragonal pyramid model  Yamana, Shukichi
A diagram and instructions for constructing a tetragonal pyramid model.
Yamana, Shukichi J. Chem. Educ. 1988, 65, 1072.
Stereochemistry |
Molecular Modeling
An easily constructed monocapped trigonal prism model  Yamana, Shukichi
A diagram and instructions for constructing a monocapped trigonal prism model.
Yamana, Shukichi J. Chem. Educ. 1988, 65, 1071.
Molecular Modeling |
Stereochemistry
Stereoisomerism in coordination chemistry: A laboratory experiment for undergraduate students  Gargallo, Maria Fe; Lechuga, Laura; Puerta, M. Carmen; Gonzalez-Vilchez, Francisco; Vilaplana, Rosario
This experiment makes students become acquainted with stereochemical concepts and several techniques used in this field and incorporate in the learning some of the recent research tasks.
Gargallo, Maria Fe; Lechuga, Laura; Puerta, M. Carmen; Gonzalez-Vilchez, Francisco; Vilaplana, Rosario J. Chem. Educ. 1988, 65, 1018.
Stereochemistry |
Diastereomers |
Coordination Compounds
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
Rules for determining d,l configurations in Haworth structures  Wilson, Jerry L.
This article provides a set of rules for determining the proper stereochemistry of carbohydrates when using Haworth projections that are simple enough for use in a basic biochemistry course.
Wilson, Jerry L. J. Chem. Educ. 1988, 65, 783.
Carbohydrates |
Stereochemistry |
Enantiomers |
Chirality / Optical Activity
Flow charting leaving group reactions  Hagen, James P.
The authors present a handy way of organizing information for organic chemistry learners.
Hagen, James P. J. Chem. Educ. 1988, 65, 620.
Mechanisms of Reactions |
Elimination Reactions
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
Organic Stereochemistry, Review I (Bays, J. Philip)  Finzel, Rodney B.
Software intended to cover the concepts of stereochemistry as they are applied to organic molecules.
Finzel, Rodney B. J. Chem. Educ. 1987, 64, A116.
Stereochemistry |
Chirality / Optical Activity |
Enrichment / Review Materials
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
Drawing enantiomers the easy way  Dunn, Howard E.
Drawing mirror images simultaneously using both hands.
Dunn, Howard E. J. Chem. Educ. 1987, 64, 1042.
Stereochemistry |
Enantiomers
Molecular structure and chirality  Brand, David J.; Fisher, Jed
Clarification of the meaning of the term chiral and its application to both chiral and achiral molecules.
Brand, David J.; Fisher, Jed J. Chem. Educ. 1987, 64, 1035.
Molecular Properties / Structure |
Chirality / Optical Activity |
Stereochemistry |
Enantiomers
An astonishingly easy method for determining R and S for Fischer projections  Ruekberg, Benjamin P.
Identifying the absolute configuration of Fischer projections once students have mastered the concept of Cahn-Ingold-Prelog sequencing.
Ruekberg, Benjamin P. J. Chem. Educ. 1987, 64, 1034.
Stereochemistry |
Chirality / Optical Activity
A quiz on stereochemistry  Ghosh, Abhik
Five open-book questions on organic stereochemistry for senior undergraduates and graduate students.
Ghosh, Abhik J. Chem. Educ. 1987, 64, 1015.
Stereochemistry
Structural theories applied to taste chemistry  Kuang-chih, Tseng; Hua-zhong, He
Explaining various tastes from viewpoints of structural theories in chemistry.
Kuang-chih, Tseng; Hua-zhong, He J. Chem. Educ. 1987, 64, 1003.
Molecular Properties / Structure |
Stereochemistry
Chiral shift reagent analysis of enantioselectivity in baker's yeast reductions of ethyl acetoacetate: An NMR experiment  Lipkowitz, K. B.; Mooney, J. L.
A laboratory exercise in which NMR is used to monitor enantiometric excess in assymetric reductions.
Lipkowitz, K. B.; Mooney, J. L. J. Chem. Educ. 1987, 64, 985.
Chirality / Optical Activity |
Enantiomers |
NMR Spectroscopy |
Stereochemistry
Polymer glass transition temperatures  Burfield, David R.
Correction and clarification of polymer glass transition temperatures.
Burfield, David R. J. Chem. Educ. 1987, 64, 875.
Stereochemistry
From shadows to three dimensions: Stereographic images using Dreiding models and the Macintosh  Strauss, Michael J.; Gribble, Gordon
Printing stereographic images using ChemDraw.
Strauss, Michael J.; Gribble, Gordon J. Chem. Educ. 1987, 64, 850.
Alkanes / Cycloalkanes |
Stereochemistry |
Molecular Modeling |
Molecular Properties / Structure
Assigning absolute configuration: Another view  Hambly, Gordon F.
Should we be teaching a two-dimensional gimmick when stereochemistry is so vital to organic chemistry?
Hambly, Gordon F. J. Chem. Educ. 1987, 64, 732.
Molecular Properties / Structure |
Stereochemistry |
Chirality / Optical Activity
Assigning absolute configuration  Bunting, John W.
Ayorinde's method has a feature that has the potential for creating considerable confusion among students.
Bunting, John W. J. Chem. Educ. 1987, 64, 731.
Chirality / Optical Activity |
Stereochemistry |
Molecular Properties / Structure
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
Electronic spectra of cis and trans disubstituted octahedral chromium(III) complexes: An advanced inorganic chemistry experiment  Teixidor, Francesc; Casabo, Jaume; Solans, Andreu
Among the most dramatic examples that show the power of electronic spectra to elucidate stereochemistry are the spectra of cis and trans distributed octahedral complexes of Cr(III) or Co(III).
Teixidor, Francesc; Casabo, Jaume; Solans, Andreu J. Chem. Educ. 1987, 64, 461.
Stereochemistry |
Diastereomers |
Coordination Compounds |
Spectroscopy |
Group Theory / Symmetry |
Quantum Chemistry |
Synthesis
Concerning dehydration of 2-methycyclohexanol  Feigenbaum, A.
One half of class dehydrates 2-methycyclohexanol, the other half dehydrates 1-methycyclohexanol; gas chromatography retention times are then compared for the two product mixtures.
Feigenbaum, A. J. Chem. Educ. 1987, 64, 273.
Alcohols |
Alkenes |
Stereochemistry |
Constitutional Isomers |
Gas Chromatography
The nomenclature of relative stereochemistry: Choosing between likes and preferences  Brook, Michael A.
The commonly used descriptors for relative stereochemistry are introduced and compared.
Brook, Michael A. J. Chem. Educ. 1987, 64, 218.
Nomenclature / Units / Symbols |
Stereochemistry |
Molecular Properties / Structure |
Chirality / Optical Activity
Configurations of glucose and other aldoses: New twists and reflections an old problems  Bentley, Ronald; Popp, Janet L.
Develops a comprehensive treatment of the configurations of aldoses in terms of the concept of rotational symmetry.
Bentley, Ronald; Popp, Janet L. J. Chem. Educ. 1987, 64, 15.
Carbohydrates |
Stereochemistry |
Molecular Properties / Structure
The ultraviolet spectra of benzene derivatives: A physical chemistry experiment  DiBenedetto, John S.; Joens, Jeffrey A.
This paper describes an experiment that can be carried out using only a standard UV-visible scanning spectrophotometer and commonly available chemicals that make use of the fundamental concepts in symmetry and spectroscopy.
DiBenedetto, John S.; Joens, Jeffrey A. J. Chem. Educ. 1986, 63, 1095.
Aromatic Compounds |
Spectroscopy |
Stereochemistry
A BASIC program for the calculation of elemental compositions from structural formulas  Smith, Roger A.; Spencer, Robin W.
78. Bits and pieces, 32. The authors have written a computer program in BASIC that will calculate the molecular weights and elemental compositions from a structural formula.
Smith, Roger A.; Spencer, Robin W. J. Chem. Educ. 1986, 63, 1076.
Molecular Properties / Structure |
Stereochemistry
A novel method of viewing stereo drawings  Graham, D. M.
The author explores drawbacks of typical stereo-pair drawings and presents an alternative that overcomes these drawbacks while presenting some advantages to be found in the novel method.
Graham, D. M. J. Chem. Educ. 1986, 63, 872.
Stereochemistry |
Molecular Modeling
Study of conformational equilibrium by dipole moment measurements: A source of experiments in physical organic chemistry  Conde, Joao P.; Moura-Ramos, Joaquim, J.
The purpose of the experiment described in this paper is to demonstrate the interdependence of the various areas of chemistry.
Conde, Joao P.; Moura-Ramos, Joaquim, J. J. Chem. Educ. 1986, 63, 823.
Covalent Bonding |
Stereochemistry |
Thermodynamics |
Equilibrium |
Diastereomers
Stereochemistry and the origins of life  Brewster, James H.
Does the monochirality of life indicate supernatural creation? Let us give science a chance, as philosophy and religion have had thousands of years to come up with their answers.
Brewster, James H. J. Chem. Educ. 1986, 63, 667.
Chirality / Optical Activity |
Stereochemistry |
Enantiomers
The enzymatic resolution of aromatic amino acids  Sheardy, Riehard; Liotta, L.; Steinhart, E.; Champion, R.; Rinker, J.; Planutis, M.; Salinkas, J.; Boyer, T.; Carcanague, D.
This article presents an experiment that can demonstrate as many principles of steroisomersim as possible and is also efficient in terms of time and preparation.
Sheardy, Riehard; Liotta, L.; Steinhart, E.; Champion, R.; Rinker, J.; Planutis, M.; Salinkas, J.; Boyer, T.; Carcanague, D. J. Chem. Educ. 1986, 63, 646.
Stereochemistry |
Chirality / Optical Activity |
Enantiomers |
Aromatic Compounds |
Amino Acids |
Enzymes
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
A simple hand method for Cahn-Ingold-Prelog assignment of R and S configuration to chiral carbons  Aalund, Martin P.; Pincock, James A.
A description of a simple hand method for Cahn-Ingold-Prelog assignment of R and S configuration to chiral carbons.
Aalund, Martin P.; Pincock, James A. J. Chem. Educ. 1986, 63, 600.
Enantiomers |
Stereochemistry
A novel method for assigning R, S labels to enantiomers  Huheey, James E.
A procedure is suggested to provide students with greater insight into the properties of dissymmetrical molecules.
Huheey, James E. J. Chem. Educ. 1986, 63, 598.
Enantiomers |
Stereochemistry
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
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
Illustration of plane-polarized light  Elakovich, Stella D.
A simple illustration of the effect of polarizing lenses.
Elakovich, Stella D. J. Chem. Educ. 1986, 63, 268.
Stereochemistry |
Spectroscopy |
Instrumental Methods
Application of organometallic catalysis to the commercial production of L-DOPA  Knowles, W. S.
This paper describes the application of a novel technology to the commercial preparation of L-DOPA.
Knowles, W. S. J. Chem. Educ. 1986, 63, 222.
Industrial Chemistry |
Enantiomers |
Stereochemistry |
Aromatic Compounds |
Alkenes |
Heterocycles |
Mechanisms of Reactions |
Catalysis |
Organometallics |
Alcohols
Stereochemistry (Ramsay, O. Bertrand)  Kauffman, George B.
Provides a survey of stereochemistry from its inception to the 1960s.
Kauffman, George B. J. Chem. Educ. 1985, 62, A189.
Stereochemistry |
Molecular Properties / Structure
An easily constructed cuboctahedron model  Yamana, Shukichi
A model constructed from a single, sealed envelope.
Yamana, Shukichi J. Chem. Educ. 1985, 62, 1088.
Molecular Modeling |
Crystals / Crystallography |
Stereochemistry
The molecular structure conundrum  Woolley, R. G.
Further discussion on two key points made in the original, referenced article.
Woolley, R. G. J. Chem. Educ. 1985, 62, 1082.
Molecular Properties / Structure |
Theoretical Chemistry |
Quantum Chemistry |
Stereochemistry
An aldol condensation-photochemical bromination sequence with emphasis on spectroscopic interpretations: An undergraduate organic experiment  Rowland, Alex T.; Brechbiel, Martin W.; Gerelus, Anne Sykes
The focus in these procedures is to extend students' abilities in the interpretation of spectral data in order to reach sound conclusions regarding the constitution and stereochemistry of reaction products.
Rowland, Alex T.; Brechbiel, Martin W.; Gerelus, Anne Sykes J. Chem. Educ. 1985, 62, 908.
Photochemistry |
Mechanisms of Reactions |
IR Spectroscopy |
UV-Vis Spectroscopy |
NMR Spectroscopy |
Stereochemistry
Computer-assisted quantitative infrared conformational analysis of alpha, beta-unsaturated ketones  Tisnes, P.; Perry, M.
Investigates the s-cis <> s-trans conformational equilibrium of alpha, beta-unsaturated ketones.
Tisnes, P.; Perry, M. J. Chem. Educ. 1985, 62, 903.
Aldehydes / Ketones |
Conformational Analysis |
IR Spectroscopy |
Stereochemistry |
Molecular Properties / Structure |
Quantitative Analysis
Identification of the stable conformer of cyclohexane by vibrational spectroscopy  Garcia, M. V.; Redondo, M. I.
A laboratory experiment that uses group theory to help interpret infrared and Raman spectra of cyclohexane.
Garcia, M. V.; Redondo, M. I. J. Chem. Educ. 1985, 62, 887.
Alkanes / Cycloalkanes |
Spectroscopy |
Stereochemistry |
IR Spectroscopy |
Raman Spectroscopy |
Conformational Analysis |
Molecular Properties / Structure |
Group Theory / Symmetry
mer- and fac-[Co(NH3)3(NO2)3] Do they exist? A laboratory project with poster session  Laing, Michael
Students attempt the preparation of [Co(NH3)3(NO2)3] by three published methods, two for the mer and one for the fac isomers and find that none of the published recipes gives either pure compounds or reproducible results.
Laing, Michael J. Chem. Educ. 1985, 62, 707.
Coordination Compounds |
Stereochemistry |
IR Spectroscopy |
Separation Science
A critical point  Gonzalez, Orestes J.
Some troublesome gaps in the theory of evolution have been overlooked.
Gonzalez, Orestes J. J. Chem. Educ. 1985, 62, 503.
Synthesis |
Chirality / Optical Activity |
Stereochemistry
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
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
A course on macromolecules  Horta, Arturo
Description of a course intended to be a comprehensive treatment of macromolecules.
Horta, Arturo J. Chem. Educ. 1985, 62, 286.
Molecular Properties / Structure |
Stereochemistry |
Proteins / Peptides |
Carbohydrates
Electrocyclic ring opening of halocyclopropanes  Markgraf, J. Hodge; Finkelstein, Manuel; Leonard, Kathryn J.; Lusskin, Shari I.
An experiment that demonstrates the stereospecific rearrangement of cyclopropyl halides to allylic halides.
Markgraf, J. Hodge; Finkelstein, Manuel; Leonard, Kathryn J.; Lusskin, Shari I. J. Chem. Educ. 1985, 62, 265.
Synthesis |
Stereochemistry
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
The R/S system: A method for assignment and some recent modifications  Eliel, Ernest L.
A method that can be applied to all three-dimensional formulas.
Eliel, Ernest L. J. Chem. Educ. 1985, 62, 223.
Molecular Properties / Structure |
Stereochemistry |
Chirality / Optical Activity
Fingertip assignment of absolute configuration  Mattern, Daniell Lewis
Modification of an earlier procedure using the arm and first three fingers to aid in the assignment of R or S absolute configuration to chiral centers.
Mattern, Daniell Lewis J. Chem. Educ. 1985, 62, 191.
Stereochemistry |
Chirality / Optical Activity
A proposed new convention for graphic presentation of molecular geometry and topography  Maehr, Hubert
A review of the popular conventions for drawing molecular structures and a proposal to define strictly graphic symbols in terms of topographic and geometric descriptor properties.
Maehr, Hubert J. Chem. Educ. 1985, 62, 114.
Molecular Modeling |
Molecular Properties / Structure |
Stereochemistry |
Chirality / Optical Activity
Chain Structure and Conformation of Macromolecules (Bovey, Frank A.; Jelinski, Lynn W.)  Carraher, Charles E., Jr.
The first seven chapters are based on lectures delivered in 1981 at MIT.
Carraher, Charles E., Jr. J. Chem. Educ. 1984, 61, A209.
Molecular Properties / Structure |
Stereochemistry |
Conformational Analysis |
NMR Spectroscopy
A simple polarimeter and experiments utilizing an overhead projector  Dorn, H. C.; Bell, H.; Birkett, T.
Design and application of an overhead polarimeter that relies on small amounts of chiral solution and provides a "dual beam" light source for direct comparison of plane-polarized light emerging from chiral and achiral media.
Dorn, H. C.; Bell, H.; Birkett, T. J. Chem. Educ. 1984, 61, 1106.
Laboratory Equipment / Apparatus |
Chirality / Optical Activity |
Stereochemistry |
Molecular Properties / Structure
An easily constructed dodecahedron model  Yamana, Shukichi
A model of a dodecahedron made from a sealed envelope.
Yamana, Shukichi J. Chem. Educ. 1984, 61, 1058.
Crystals / Crystallography |
Solids |
Stereochemistry |
Molecular Modeling
An easily constructed model of a square antiprism  Yamana, Shukichi
A model of a square antiprism made from a sealed envelope.
Yamana, Shukichi J. Chem. Educ. 1984, 61, 1056.
Crystals / Crystallography |
Solids |
Stereochemistry |
Molecular Modeling
An easily constructed trigonal prism model  Yamana, Shukichi
A model of a trigonal prism made from a sealed envelope.
Yamana, Shukichi J. Chem. Educ. 1984, 61, 1055.
Crystals / Crystallography |
Solids |
Stereochemistry |
Molecular Modeling
An easily constructed cube model  Yamana, Shukichi; Kawaguchi, Makoto
A model of a cube made from a sealed envelope.
Yamana, Shukichi; Kawaguchi, Makoto J. Chem. Educ. 1984, 61, 1054.
Crystal Field / Ligand Field Theory |
Solids |
Stereochemistry |
Molecular Modeling
Easily constructed model of twin octahedrons having a common line  Yamana, Shukichi; Kawaguchi, Makoto
A model of twin octahedrons made from a sealed envelope.
Yamana, Shukichi; Kawaguchi, Makoto J. Chem. Educ. 1984, 61, 1053.
Crystals / Crystallography |
Solids |
Molecular Modeling |
Stereochemistry
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
The possible chirality of tetrahedral carbon atoms with two substituents of identical constitution  Schafer, Lothar; Van Alsenoy, C.; Van Den Enden, L.
Because of differences in bond angles, species of the form Cabc2 may in fact be chiral.
Schafer, Lothar; Van Alsenoy, C.; Van Den Enden, L. J. Chem. Educ. 1984, 61, 945.
Chirality / Optical Activity |
Molecular Properties / Structure |
Stereochemistry |
Enantiomers
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
"Absolutely" simple stereochemistry  Beauchamp, Philip S.
Using the arm and fingers to determine the stereochemistry of chiral centers.
Beauchamp, Philip S. J. Chem. Educ. 1984, 61, 666.
Stereochemistry |
Molecular Properties / Structure |
Chirality / Optical Activity
R/S: Apple stereochemistry program  Barone, Rene; Meyer, Roger; Arbelot, Michel
51. Bits and pieces, 20. Computer program for helping students to learn R/S conventions.
Barone, Rene; Meyer, Roger; Arbelot, Michel J. Chem. Educ. 1984, 61, 524.
Stereochemistry |
Molecular Properties / Structure |
Chirality / Optical Activity |
Enantiomers |
Enrichment / Review Materials
An easily constructed model of twin pentahedral cones having a common pentagonal plane  Yamana, Shukichi
A model that can be made from a sealed, empty envelope.
Yamana, Shukichi J. Chem. Educ. 1984, 61, 449.
Crystals / Crystallography |
Molecular Modeling |
Stereochemistry
Specification of R/S in a multichiral molecule (3)  Aronson, John N.
Any system, simple or complex, cannot be used successfully to relate the R, S designations to Fischer projections if an incorrect two-dimensional projection is made of the three-dimensional model of the structure.
Aronson, John N. J. Chem. Educ. 1984, 61, 90.
Stereochemistry |
Molecular Properties / Structure |
Chirality / Optical Activity
Specification of R/S in a multichiral molecule (2)  Milakofsky, Louis
Suggested method has been presented before.
Milakofsky, Louis J. Chem. Educ. 1984, 61, 90.
Stereochemistry |
Molecular Properties / Structure |
Chirality / Optical Activity
Specification of R/S in a multichiral molecule (1)  Diehl, Justin W.
Suggested method becomes extremely difficult for a multichiral molecule.
Diehl, Justin W. J. Chem. Educ. 1984, 61, 90.
Stereochemistry |
Molecular Properties / Structure |
Chirality / Optical Activity
The determination of the stereochemistry of erythro-1,2-diphenyl-1,2-ethanediol: an undergraduate organic experiment  Rowland, Alex T.
The author describes a successful experiment that has been conducted by first-year organic chemistry students which illustrates the power of H NMR spectroscopy in a configuration determination.
Rowland, Alex T. J. Chem. Educ. 1983, 60, 1084.
Phenols |
Alcohols |
NMR Spectroscopy |
Stereochemistry |
Chirality / Optical Activity |
Enantiomers
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
A new gimmick for assigning absolute configuration  Ayorinde, F. O.
One of the most challenging aspects of stereochemistry for students is the assignment of configurational symbol (R or S). To solve this problem, a recommendation is illustrated in this article.
Ayorinde, F. O. J. Chem. Educ. 1983, 60, 928.
Stereochemistry |
Chirality / Optical Activity
Chromium ammines and acidoammines: A case study  Kirk, A. D.
The objectives of this article are to contrast the thermal and photochemical processes of these compounds, to describe their behavior on irradiation, the influences of solvent, temperature, and wavelength, to expand on their interesting stereochemistry and finally, to address the question of the photophysical pathways and the nature of the excited states that participate in reaction as far as they are known. From the State-of-the-Art Symposium: Inorganic Photochemistry, held at the ACS meeting, Seattle, 1983.
Kirk, A. D. J. Chem. Educ. 1983, 60, 843.
Amines / Ammonium Compounds |
Photochemistry |
Stereochemistry |
Coordination Compounds |
Diastereomers
Cyclohexane stereochemistry   Dauphinee, G. A.; Forrest, T. P .
44. Bits and pieces, 16. The authors report on a graphic program for cyclohexane stereochemistry which has proven to be highly successful in developing both visualization aptitude and drawing skills.
Dauphinee, G. A.; Forrest, T. P . J. Chem. Educ. 1983, 60, 732.
Stereochemistry |
Enantiomers |
Chirality / Optical Activity |
Molecular Modeling
Two-dimensional chirality in three-dimensional chemistry  Wintner, Claude E.
The author points out a valuable way to enhance students' understanding of 3-dimensional stereochemistry: through the concept of 2-dimensional chirality.
Wintner, Claude E. J. Chem. Educ. 1983, 60, 550.
Stereochemistry |
Chirality / Optical Activity |
Molecular Properties / Structure
An easily constructed hexagonal prism model  Yamana, Shukichi; Kawaguchi, Makoto
A model of a hexagonal prism, which is necessary for teaching stereochemistry (especially of inorganic compounds) can be made easily by using a sealed, empty envelope. The steps are illustrated and described in this article.
Yamana, Shukichi; Kawaguchi, Makoto J. Chem. Educ. 1983, 60, 548.
Stereochemistry |
Molecular Properties / Structure
A study of stereospecificity: the Beckmann rearrangement  Stradling, S. S.; Hornick, D.; Lee, J.; Riley, J.
These authors have developed a Beckmann rearrangement which explores the concept of stereospecificity, and concurrently exposes the student to synthetic, spectrometric, and chromatographic processes for an advanced laboratory.
Stradling, S. S.; Hornick, D.; Lee, J.; Riley, J. J. Chem. Educ. 1983, 60, 502.
Synthesis |
Chromatography |
Spectroscopy |
Stereochemistry |
Aldehydes / Ketones |
NMR Spectroscopy |
Alkenes |
Phenols
The flat and direct way to R and S configurations: two-dimensional designation of absolute configuration  Brun, Y.; Leblanc, P.
Teaching stereochemistry poses a challenge to teachers when representations are two-dimensional. These authors suggest a method where students convert wedge representations into Fischer projections. This offers some pedagogical advantages.
Brun, Y.; Leblanc, P. J. Chem. Educ. 1983, 60, 403.
Molecular Properties / Structure |
Molecular Modeling |
Stereochemistry |
Chirality / Optical Activity |
Enantiomers
Resolvability and the tetrahedral configuration of carbon  Kauffman, George B.
A popular explanation about the tetrahedral configuration of carbon is not entirely accurate.
Kauffman, George B. J. Chem. Educ. 1983, 60, 402.
Molecular Properties / Structure |
Alkanes / Cycloalkanes |
Enantiomers |
X-ray Crystallography |
Stereochemistry |
Chirality / Optical Activity
Julius Bredt and the structure of camphor: On the threshold of modern stereochemistry  Kauffman, George B.
Bredt's pioneering work on camphor and its derivatives allowed stereochemistry to be one of the most thoroughly investigated and understood fields of organic chemistry.
Kauffman, George B. J. Chem. Educ. 1983, 60, 341.
Stereochemistry |
Natural Products
Highly stereoselective synthesis and rearrangement of beta-amino alpha-bromo chalcones  Arnould, J. C.; Feigenbaum, A.; Henin, F.
The authors propose an experiment for advanced students which involves a sequence of easy steps illustrating important reactions and concepts of organic chemistry.
Arnould, J. C.; Feigenbaum, A.; Henin, F. J. Chem. Educ. 1983, 60, 82.
Synthesis |
Stereochemistry |
Amino Acids |
Phenols |
Synthesis |
Aromatic Compounds
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
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
Richard Anschutz (1852-1937), Kekule's forgotten successor Part II: The work  Kauffman, George B.
In his mistaken attempt to prove that maleic and fumaric acids are structural rather than geometric isomers, Anschutz carried out much useful work not only on these compounds but also on many polybasic acids and their derivatives.
Kauffman, George B. J. Chem. Educ. 1982, 59, 745.
Carboxylic Acids |
Stereochemistry |
Diastereomers |
Acids / Bases |
Molecular Properties / Structure
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
A resource file for chemical stereoviews  Jensen, William B.
Putting stereoimages on 4 x 6 in. index cards.
Jensen, William B. J. Chem. Educ. 1982, 59, 385.
Molecular Properties / Structure |
Stereochemistry
The problem of syn- versus anti-addition: An organic chemistry laboratory experiment  Silversmith, Ernest F.
An experiment that allows a student to determine whether an addition to a carbon-carbon double bond proceeds in syn- or anti-fashion.
Silversmith, Ernest F. J. Chem. Educ. 1982, 59, 346.
Addition Reactions |
Mechanisms of Reactions |
Molecular Properties / Structure |
Stereochemistry |
Synthesis |
Alkenes
An easily constructed rhombohedron model  Yamana, Shukichi; Kawaguchi, Makoto
A model of a rhombohedron constructed from a single sealed envelope.
Yamana, Shukichi; Kawaguchi, Makoto J. Chem. Educ. 1982, 59, 197.
Molecular Modeling |
Crystals / Crystallography |
Stereochemistry
Easily constructed model of twin octahedrons having a common plane  Yamana, Shukichi
A model of twin octahedrons constructed from a single sealed envelope.
Yamana, Shukichi J. Chem. Educ. 1982, 59, 196.
Molecular Modeling |
Crystals / Crystallography |
Stereochemistry
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
Molecular weight and molecular weight distributions in synthetic polymers  Ward, Thomas Carl
In this introductory treatment an attempt is made to provide sufficient educational material on MWD's for students interested in polymers without engaging in extensive derivations.
Ward, Thomas Carl J. Chem. Educ. 1981, 58, 867.
Physical Properties |
Polymerization |
Diastereomers |
Stereochemistry |
Chemometrics
Sulfur, stereochemistry and the Reverend William Archibald Spooner  Davenport, Derek A.
An amusing note on the history of chemistry.
Davenport, Derek A. J. Chem. Educ. 1981, 58, 682.
Stereochemistry
Some developments in the stereochemistry of coordination compounds in the last fifty years  Bailar, John C., Jr.
This article is taken from the author's Perspective Lecture and begins with a description of how the author had to successfully narrow his topic in order to fit it into the allotted time, a testimony to the diversity of a "specialist."
Bailar, John C., Jr. J. Chem. Educ. 1981, 58, 674.
Stereochemistry |
Coordination Compounds |
Enantiomers |
Chirality / Optical Activity
The driving force of addition and elimination reactions clarified through the Hellmann-Feynman theorem  Blaise, Paul; Pujol, Phillippe; Henri-Rousseau, Olivier
The energy involved in the transition state is explored in this article.
Blaise, Paul; Pujol, Phillippe; Henri-Rousseau, Olivier J. Chem. Educ. 1981, 58, 615.
Thermodynamics |
Addition Reactions |
Elimination Reactions |
Reactions
Calculation and specification of the multiple chirality displayed by sugar pyranoid ring structures  Shallenberger, Robert S.; Wrolstad, Ronald E.; Kerschner, Laurie E.
Calculation and specification of the multiple chirality displayed by sugar pyranoid ring structures.
Shallenberger, Robert S.; Wrolstad, Ronald E.; Kerschner, Laurie E. J. Chem. Educ. 1981, 58, 599.
Chemometrics |
Chirality / Optical Activity |
Stereochemistry |
Enantiomers |
Carbohydrates
Stereochemistry and macromolecules: Principles and applications  Quirk, Roderic P.
This article was written to provide an introduction to the basic concepts of polymer stereochemistry and their applications.
Quirk, Roderic P. J. Chem. Educ. 1981, 58, 540.
Stereochemistry |
Chirality / Optical Activity |
Enantiomers
Organic stereochemistry: An undergraduate exercise with molecular models  Murphy, William S.
Textbooks alone are not sufficient in aiding students in the understanding of stereochemistry. This exercise enables students to take an active role in better understanding this often challenging topic.
Murphy, William S. J. Chem. Educ. 1981, 58, 504.
Molecular Modeling |
Stereochemistry
Lagormorphs and enantiomorphs-simple stereomodels   Garrett, James M.; Henry, Bruce A.; Cates, Charles R.
Rabbits can help us understand stereochemistry.
Garrett, James M.; Henry, Bruce A.; Cates, Charles R. J. Chem. Educ. 1981, 58, 448.
Stereochemistry |
Enantiomers |
Chirality / Optical Activity
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
Determination of the absolute stereochemistry of secondary alcohols: An advanced organic chemistry experiment for undergraduate students  Bandaranayake, Wickramasinghe M.
Introduces students to the Ingold, Prelog, and Cahn R and S sequence rules.
Bandaranayake, Wickramasinghe M. J. Chem. Educ. 1980, 57, 828.
Alcohols |
Molecular Properties / Structure |
Stereochemistry
Conversion of (+)-Limonene to (-)-Carvone: An organic laboratory sequence of local interest  Rothenberger, Otis S.; Krasnoff, Stuart B.; Rollins, Ronald B.
Orange oil is converted to one of the components of spearmint oil; the detectable odor difference is due to stereochemical factors.
Rothenberger, Otis S.; Krasnoff, Stuart B.; Rollins, Ronald B. J. Chem. Educ. 1980, 57, 741.
Stereochemistry |
Molecular Properties / Structure |
Synthesis |
Separation Science |
Industrial Chemistry |
Applications of Chemistry |
Enantiomers
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
Optical Activity  Mickey, Charles D.
Historical background of stereoisomerism, the properties of light, the principles of a polarimeter, and optically active compounds.
Mickey, Charles D. J. Chem. Educ. 1980, 57, 442.
Stereochemistry |
Chirality / Optical Activity |
Molecular Properties / Structure |
Enantiomers
An easily constructed octahedron model  Yamana, Shukichi; Kawaguchi, Makoto
An octahedral model constructed from a single, sealed envelope.
Yamana, Shukichi; Kawaguchi, Makoto J. Chem. Educ. 1980, 57, 434.
Crystals / Crystallography |
Molecular Modeling |
Stereochemistry
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
Rotation of plane-polarized light: A simple model  Hill, Roger R.; Whatley, Barrie G.
A simple model that explains why enantiomers of a chiral compound rotate light in different directions.
Hill, Roger R.; Whatley, Barrie G. J. Chem. Educ. 1980, 57, 306.
Photochemistry |
Molecular Modeling |
Chirality / Optical Activity |
Stereochemistry |
Enantiomers |
Molecular Properties / Structure
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
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
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
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
Prochirality and the English beer glass  Sanders, J. K. M.
The English beer glass represents an ideal model for illustrating the concepts of prochirality and assymetric induction.
Sanders, J. K. M. J. Chem. Educ. 1979, 56, 594.
Molecular Properties / Structure |
Chirality / Optical Activity |
Stereochemistry |
Enantiomers
Determination of chiral molecule configuration using the 1,2,5 Rule  Dietzel, Richard Adams
Determining R / S configurations using the 1,2,5 rule.
Dietzel, Richard Adams J. Chem. Educ. 1979, 56, 451.
Molecular Properties / Structure |
Chirality / Optical Activity |
Stereochemistry |
Enantiomers
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
A dynamic carbon model capable of showing changes in hybridization  Fountain, K. R.
It is possible to construct a simple dynamic model of a carbon atom that demonstrates the Walden inversion, the SN1 reaction, and when joined with another units like itself demonstrates the full spectrum of elimination reactions.
Fountain, K. R. J. Chem. Educ. 1979, 56, 379.
Molecular Modeling |
Nucleophilic Substitution |
Elimination Reactions
Computer-assisted instruction in stereochemical configuration analysis  Bishop, Marvin; Nowak, Maria

Bishop, Marvin; Nowak, Maria J. Chem. Educ. 1979, 56, 318.
Molecular Properties / Structure |
Stereochemistry |
Conformational Analysis |
Nomenclature / Units / Symbols
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
From molecular point group symmetry to space group symmetry: An undergraduate experiment in model building  Hathaway, Brian
A timetable for learning molecular symmetry through the sophomore to senior year and a space group model building experiment.
Hathaway, Brian J. Chem. Educ. 1979, 56, 166.
Group Theory / Symmetry |
Crystals / Crystallography |
Molecular Modeling |
Molecular Properties / Structure |
Stereochemistry
The reaction between a vinylic ether and 2,4-dinitrobenzenesulfenyl chloride  Silversmith, Ernest F.
Interpretation of the experiment involves Markovnikov's rule, including resonance stabilization of the intermediate carbocation; students are also exposed to the chemical literature by reading key references and being asked to predict possible products.
Silversmith, Ernest F. J. Chem. Educ. 1979, 56, 127.
Stereochemistry |
Spectroscopy |
NMR Spectroscopy
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
An inexpensive model for illustrating stereochemistry of SN1 and SN2 reactions (old music stands never die - they just invert away)  Garrett, James M.; Griffin, E. L.
An inexpensive model for illustrating stereochemistry of SN1 and SN2 reactions .
Garrett, James M.; Griffin, E. L. J. Chem. Educ. 1978, 55, 516.
Reactions |
Stereochemistry
Use of hand models for assigning configurational nomenclature  Garrett, James M.
A subject which often produces consternation in a beginning student in organic chemistry is that of sequential nomenclature involving chiral centers. After having studied the Cahn-Ingold-Prelog rules of nomenclature a student may be asked to examine a structure as shown in this article.
Garrett, James M. J. Chem. Educ. 1978, 55, 493.
Nomenclature / Units / Symbols |
Chirality / Optical Activity |
Stereochemistry |
Enantiomers
Synthesis of chrysanthemic acid: A multistep organic synthesis for undergraduate students  Schatz, Paul F.
This laboratory is geared toward intermediate organic chemistry laboratory courses that will acquaint students, predominantly chemistry majors, with the strategies and techniques in carrying out a multistep synthesis.
Schatz, Paul F. J. Chem. Educ. 1978, 55, 468.
Synthesis |
Acids / Bases |
Aldehydes / Ketones |
Stereochemistry
Enumeration of permutational isomers: The porphyrins  Tapscott, R. E.; Marcovich, D.
The use of combinatorial methods permits the counting of permutational isomers in systems that are sufficiently complex that direct counting is tedious and/ or likely to be in error. The use of Polya's theorem has been illustrated for the porphyrin system, here the isomers for all possible ligand partitions have been counted.
Tapscott, R. E.; Marcovich, D. J. Chem. Educ. 1978, 55, 446.
Diastereomers |
Stereochemistry |
Enantiomers |
Constitutional Isomers |
Chemometrics |
Coordination Compounds
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
Project for problem-oriented undergraduate organic or integrated undergraduate laboratory  Silveira, Augustine, Jr.
This paper reports on an open-ended project which allows a great degree of flexibility in the laboratory. The project provided about a 6-week study for groups of 24 students each.
Silveira, Augustine, Jr. J. Chem. Educ. 1978, 55, 57.
Synthesis |
Undergraduate Research |
Spectroscopy |
Diastereomers |
Addition Reactions |
MO Theory |
Elimination Reactions |
Thermodynamics |
Kinetics
Molecular models based on Petri dishes  Yeadon, A.
The construction and use of several models of Petri dishes that can be used to model stereochemistry are presented in this paper.
Yeadon, A. J. Chem. Educ. 1978, 55, 39.
Molecular Modeling |
Stereochemistry |
Molecular Properties / Structure |
Chirality / Optical Activity |
Group Theory / Symmetry
Synthesis and properties of an optically active complex: A polarimeter experiment for general chemistry  Hunt, Harold R., Jr.
Synthesizing and determining the optical rotation of d-Co(phen)3(ClO4)3.2H2O.
Hunt, Harold R., Jr. J. Chem. Educ. 1977, 54, 710.
Chirality / Optical Activity |
Molecular Properties / Structure |
Stereochemistry |
Synthesis |
Coordination Compounds
Pharmacological projects/case studies for teaching molecular structure and reactivity  Webb, John; Rasmussen, Malcolm
Using pharmacological agents to provide projects that develop and illustrate concepts of molecular stereochemistry, functional groups, and types of reactions and reactivity.
Webb, John; Rasmussen, Malcolm J. Chem. Educ. 1977, 54, 677.
Drugs / Pharmaceuticals |
Stereochemistry |
Reactions |
Mechanisms of Reactions
From the concept of relative configuration to the definition of erythro and threo  Gielen, Marcel
Defines the relative configuration of two chiral centers and uses this concept to define erythro and threo.
Gielen, Marcel J. Chem. Educ. 1977, 54, 673.
Molecular Properties / Structure |
Stereochemistry |
Chirality / Optical Activity |
Enantiomers
Chirality of the disulfide bond in biomolecules  Panijpan, Bhinyo
Draws attention to the chirality of the disulfide bond and its significance in the structure and activity of biomolecules.
Panijpan, Bhinyo J. Chem. Educ. 1977, 54, 670.
Chirality / Optical Activity |
Molecular Properties / Structure |
Stereochemistry |
Enantiomers
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
Synthesis of 4-methyl-3-heptanol and 4-methyl-3-heptanone. Two easily synthesized insect pheromones  Einterz, Robert M.; Ponder, Jay W.; Lenox, Ronald S.
A two step reaction sequence involving the Grignard synthesis of an alcohol followed by oxidation of this alcohol to the corresponding ketone.
Einterz, Robert M.; Ponder, Jay W.; Lenox, Ronald S. J. Chem. Educ. 1977, 54, 382.
Natural Products |
Synthesis |
Applications of Chemistry |
Grignard Reagents |
Mechanisms of Reactions |
Stereochemistry |
Alcohols |
Aldehydes / Ketones
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
Infrared spectroscopy of tetrahedral ligands. An advanced experiment in inorganic chemistry  Ribas, J. Casabo; Coronas, J. M.
This study lets the student familiarize himself with the important role played by IR spectroscopy in the determination of the stereochemistry of coordination compounds; this example involves complexes of Cr(III) and NH3.
Ribas, J. Casabo; Coronas, J. M. J. Chem. Educ. 1977, 54, 321.
Spectroscopy |
IR Spectroscopy |
Crystal Field / Ligand Field Theory |
Coordination Compounds |
Stereochemistry
Pathway of minimum steps for the bullvalene automerization  Bennett, Karl E.; Fisher, Allan
The minimum Cope rearrangements necessary for interconversion among various structures of bullvalene.
Bennett, Karl E.; Fisher, Allan J. Chem. Educ. 1977, 54, 166.
Alkenes |
Molecular Properties / Structure |
Stereochemistry
Application of nmr to biochemical kinetics. A laboratory experiment in physical biochemistry  Drake, Evelyn Nobles; Brown, Charles Eric
This procedure teaches students how to perform an nmr experiment and allows them to compare in a laboratory setting the capabilities of nmr spectrometry with those of another technique used routinely in biochemistry.
Drake, Evelyn Nobles; Brown, Charles Eric J. Chem. Educ. 1977, 54, 124.
Spectroscopy |
Biophysical Chemistry |
Kinetics |
Conformational Analysis |
Carbohydrates |
Molecular Properties / Structure |
Stereochemistry |
Enzymes
Nuclear magnetic resonance studies of the stereochemistry and non-rigidity of titanium-[beta]-diketonate complexes. An interpretive NMR experiment applied to metal complexes  Kranbuehl, David E.; Metzger, Patricia M.; Thompson, David W.; Fay, Robert C.
An interpretative experiment involving the application of symmetry and temperature dependent proton and fluorine nmr spectroscopy to the solution of structural and kinetic problems in coordination chemistry.
Kranbuehl, David E.; Metzger, Patricia M.; Thompson, David W.; Fay, Robert C. J. Chem. Educ. 1977, 54, 119.
Spectroscopy |
NMR Spectroscopy |
Stereochemistry |
Coordination Compounds |
Metals |
Kinetics
Mechanistic study of a reaction. An experimental course offering  Fisher, Robert D.
Brief description of an integrated chemistry course, the first half of which regards reaction parameters, the second half of which focusses on nucleophilic substitution reactions.
Fisher, Robert D. J. Chem. Educ. 1977, 54, 118.
Reactions |
Mechanisms of Reactions |
Kinetics |
Stereochemistry |
Nucleophilic Substitution
Microbial hydroxylation of progesterone. An organic-biological experiment involving a reaction important to the pharmaceutical industry  Volker, Eugene J.
Illustrates the use of microorganisms to produce materials that serve as a crucial step in the sequence that allows the conversion of the plant-derived steroid diogenin to cortisone and its derivatives.
Volker, Eugene J. J. Chem. Educ. 1977, 54, 65.
Bioorganic Chemistry |
Drugs / Pharmaceuticals |
Industrial Chemistry |
Stereochemistry |
Natural Products
How to see molecules in 3-D: A low cost device for stereoscopic views  Gelbard, C.
Students may find some difficulties in visualizing in space the molecules drawn in their handbook. Teaching stereochemistry and reaction mechanism is made easier by the aid of stereoscopic devices such as the one described in this note.
Gelbard, C. J. Chem. Educ. 1976, 53, 792.
Stereochemistry |
Spectroscopy |
Molecular Properties / Structure |
Molecular Modeling
Ketene cycloadditions  Holder, Richard W.
Mechanisms of ketene cycloadditions.
Holder, Richard W. J. Chem. Educ. 1976, 53, 81.
Aldehydes / Ketones |
Mechanisms of Reactions |
Stereochemistry |
Reactions
Conformational analysis, 1869  Brescia, Frank; Mangiaracina, Pietro
This paper examines historical inaccuracies resulting from an inquiry into the conformational analysis of C2HCl5.
Brescia, Frank; Mangiaracina, Pietro J. Chem. Educ. 1976, 53, 32.
Constitutional Isomers |
Stereochemistry
Vibrational spectra of iron carbonyl complexes  Montemayor, R. G.
The experiment described here distinguishes between cis and trans-isomers of Mo(CO)4L2 complexes on the basis of the observed infrared bands in the CO-stretching region and the expected number of infrared active CO-stretching vibrations as derived from group theoretical considerations.
Montemayor, R. G. J. Chem. Educ. 1976, 53, 16.
IR Spectroscopy |
Stereochemistry |
Atomic Properties / Structure |
Diastereomers |
Group Theory / Symmetry |
Chemometrics
The resolution of racemic acid: A classic stereochemical experiment for the undergraduate laboratory  Kauffman, George B.; Myers, Robin D.
Includes historical background of Pasteur's work and a procedure for investigating the relations between the tartaric acids, racemic acid, and their sodium ammonium salts.
Kauffman, George B.; Myers, Robin D. J. Chem. Educ. 1975, 52, 777.
Stereochemistry |
Molecular Properties / Structure |
Chirality / Optical Activity |
Enantiomers
The octant rule: Its place in organic stereochemistry  Murphy, William S.
Considers optical rotatory dispersion and circular dichroism, the Cotton effect and the octant rule, and applications of the octant rule.
Murphy, William S. J. Chem. Educ. 1975, 52, 774.
Stereochemistry |
Molecular Properties / Structure |
Conformational Analysis
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
The determination of a mechanism of isomerization of maleic acid to fumaric acid  Meek, John S.
Procedure in which students attempt to determine the mechanism for the isomerization of maleic acid to fumaric acid by heating with hydrochloric acid.
Meek, John S. J. Chem. Educ. 1975, 52, 541.
Mechanisms of Reactions |
Molecular Properties / Structure |
Stereochemistry |
Carboxylic Acids
Accident, suicide, or murder? A question of stereochemistry  Hart, Harold
A murder mystery by Dorothy Sayers in which the resolution of the crime depends entirely on stereochemistry.
Hart, Harold J. Chem. Educ. 1975, 52, 444.
Stereochemistry |
Molecular Properties / Structure
Easily constructed models for demonstrating stereochemical nonrigidity in four- and six-coordinate complexes  Levenson, Robert A.
Availability of templates and instructions for paper models that demonstrate stereochemical nonrigidity in four- and six-coordinate complexes.
Levenson, Robert A. J. Chem. Educ. 1975, 52, 386.
Stereochemistry |
Molecular Properties / Structure |
Molecular Modeling |
Coordination Compounds |
Transition Elements |
Metals
Stereoisomerism about a double bond (1-3)  Fernelius, W. C.; Loening, Kurt; Adams, Roy M.
Rules for specifying E and Z configurations.
Fernelius, W. C.; Loening, Kurt; Adams, Roy M. J. Chem. Educ. 1975, 52, 60.
Stereochemistry |
Diastereomers |
Molecular Properties / Structure |
Alkenes |
Nomenclature / Units / Symbols
Infrared determination of stereochemistry in metal complexes. The determination of symmetry coordinates  Darensbourg, Donald J.; Darensbourg, Marcetta York
The authors work through some examples of the determination of symmetry coordinates that are pedagogically helpful.
Darensbourg, Donald J.; Darensbourg, Marcetta York J. Chem. Educ. 1974, 51, 787.
Stereochemistry |
Group Theory / Symmetry |
Metals
The sequence rules  Fernelius, W. C.; Loening, Kurt; Adams, Roy M.
The authors explain the usefulness of the sequence rules in learning about chirality.
Fernelius, W. C.; Loening, Kurt; Adams, Roy M. J. Chem. Educ. 1974, 51, 735.
Nomenclature / Units / Symbols |
Chirality / Optical Activity |
Stereochemistry |
Enantiomers |
Coordination Compounds
The significance of a methyl group in the stereoselectivity of cobalt(lII) complexes  Brubaker, George R.
This paper represents the first attempt to apply methods of conformational analysis to problems of stereochemistry in metal complexes.
Brubaker, George R. J. Chem. Educ. 1974, 51, 608.
Coordination Compounds |
Molecular Mechanics / Dynamics |
Organometallics |
Stereochemistry |
Metals
Optical rotation and the DNA helix-to-coil transition. An undergraduate project  Baker, Gregory L.; Alden, Mark E.
The experiment described in this paper is a relatively inexpensive experiment that can be executed by an undergraduate student over the course of a semester.
Baker, Gregory L.; Alden, Mark E. J. Chem. Educ. 1974, 51, 591.
Enantiomers |
Stereochemistry |
Undergraduate Research
A demonstration of stereoselectivity  Tapscott, Robert E.
The author contributes a demonstration in stereoselectivity to fill a need: there are few good demonstrations on this topic.
Tapscott, Robert E. J. Chem. Educ. 1974, 51, 586.
Stereochemistry
A simple algorithmic method for the recognition of theoretically chiral octahedral complexes  Richardson, Robert T.
A simple algorithmic procedure is available which allows the student to unambiguously determine whether a particular octahedral configuration is chiral or achiral without recourse to drawing mirror-images or knowingly applying symmetry theory.
Richardson, Robert T. J. Chem. Educ. 1974, 51, 347.
Enantiomers |
Coordination Compounds |
Stereochemistry |
Group Theory / Symmetry
Stereochemistry of carbonyl addition reactions  Goller, Edwin J.
This article is a brief summary of some of the more important unifying concepts that have been proposed in the study of the stereo chemistry of carbonyl addition reactions.
Goller, Edwin J. J. Chem. Educ. 1974, 51, 182.
Addition Reactions |
Stereochemistry |
Aldehydes / Ketones |
Aromatic Compounds
A simple dynamic stereomodel for the interconversion of enantiomers via a high-energy achiral intermediate  Stirling, C. J. M.
A simple dynamic stereomodel for the interconversion of enantiomers via a high-energy achiral intermediate because introduction of molecular chirality to the elementary students is often effectively made by the comparison of familiar chiral and achiral objects.
Stirling, C. J. M. J. Chem. Educ. 1974, 51, 50.
Chirality / Optical Activity |
Enantiomers |
Stereochemistry |
Molecular Modeling
A stereochemical model for illustrating pseudorotation of five-coordinate atoms  Riess, Jean G.
Design of an inexpensive, articulated model that simulates intramolecular isomerization or fluxional behavior on five-coordinate atoms.
Riess, Jean G. J. Chem. Educ. 1973, 50, 850.
Stereochemistry |
Molecular Properties / Structure |
Molecular Modeling
Some stereochemical principles from polymers. Molecular symmetry and molecular flexibility  Price, Charles C.
The properties of polymers from ethylene, propylene, isobutylene, and the three related epoxides, can be used to illustrate several important basic principles relating chemical structure to properties.
Price, Charles C. J. Chem. Educ. 1973, 50, 744.
Conferences |
Professional Development |
Molecular Properties / Structure |
Stereochemistry |
Chirality / Optical Activity |
Enantiomers
Attractive steric effects  Liberles, A.; Greenberg, A.; Eilers, J. E.
Attractive steric effects cause some organic structures to be more stable when bulky side-groups are closer together.
Liberles, A.; Greenberg, A.; Eilers, J. E. J. Chem. Educ. 1973, 50, 676.
Molecular Properties / Structure |
Alkenes |
Stereochemistry |
Diastereomers
A simple demonstration of enantiomerism  Richards, K. E.
Design for a wooden box containing a mirror that uses a molecular model to demonstrate enantiomerism.
Richards, K. E. J. Chem. Educ. 1973, 50, 632.
Molecular Properties / Structure |
Molecular Modeling |
Stereochemistry |
Enantiomers |
Chirality / Optical Activity
An overhead projection demonstration of optical activity  Hill, John W.
An overhead projection demonstration of optical activity the makes use of two polarizing lenses and an optically active compound.
Hill, John W. J. Chem. Educ. 1973, 50, 574.
Chirality / Optical Activity |
Molecular Properties / Structure |
Stereochemistry |
Carbohydrates
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
Spontaneous generation of optical activity  Pincock, Richard E.; Wilson, Keith R.
Reviews the background that has led to the attitude that spontaneous generation of optical activity is not possible, and identifies those published examples of this phenomenon.
Pincock, Richard E.; Wilson, Keith R. J. Chem. Educ. 1973, 50, 455.
Chirality / Optical Activity |
Molecular Properties / Structure |
Stereochemistry
Films of rotating molecular models. The stereoscopic effect  McGrew, LeRoy; Kitzman, Kathy
A method of motion picture photography that offers a three-dimensional effect useful for the illustration of molecular structure with less effort than previous methods of stereo photography.
McGrew, LeRoy; Kitzman, Kathy J. Chem. Educ. 1973, 50, 407.
Molecular Properties / Structure |
Molecular Modeling |
Stereochemistry
Overhead projection of stereographic images  Crozat, Madeleine M.; Watkins, Steven F.
A simple technique that employs an overhead projector, colored filters, and colored transparent overlays to create three-dimensional images of molecules for viewing by up to thirty students simultaneously.
Crozat, Madeleine M.; Watkins, Steven F. J. Chem. Educ. 1973, 50, 374.
Stereochemistry |
Molecular Properties / Structure |
Molecular Modeling
The preparation and dehydration of 1-benzylcycloalkanols  Newkome, George R.; Allen, J. W.; Anderson, G. M.
This reaction sequence sheds light on carbocation intermediates, steric effects, conjugation, and elimination mechanisms.
Newkome, George R.; Allen, J. W.; Anderson, G. M. J. Chem. Educ. 1973, 50, 372.
Synthesis |
Alcohols |
Mechanisms of Reactions |
Elimination Reactions
Factors involved in the stereochemistry of AX6E systems of the heavy main group elements  Wynne, Kenneth J.
Despite the prediction of the VSEPR theory, many AX6E molecules exhibit octahedral symmetry.
Wynne, Kenneth J. J. Chem. Educ. 1973, 50, 328.
Stereochemistry |
Molecular Properties / Structure |
Main-Group Elements |
Coordination Compounds |
VSEPR Theory
Spectral comparison of geometrical isomers  Haworth, D. T.; Elsen, K. M.
The synthesis of transition metal complexes and the distinction between cis and trans isomers through the interpretation of spectra.
Haworth, D. T.; Elsen, K. M. J. Chem. Educ. 1973, 50, 300.
Stereochemistry |
Diastereomers |
Synthesis |
Molecular Properties / Structure |
Coordination Compounds |
Crystal Field / Ligand Field Theory |
Transition Elements |
Spectroscopy
Determination of the relative and absolute configurations of (-)menthol and (+)neomenthol. An introductory stereochemistry experiment  Barry, J.
This activity serves to familiarize students with stereochemistry and the conformational analysis of cyclohexane systems.
Barry, J. J. Chem. Educ. 1973, 50, 292.
Stereochemistry |
Molecular Properties / Structure |
Alcohols |
Conformational Analysis
Isomers of the porphyrins  Blackman, David
Demonstrates the possibility of more positional isomers of the porphyrins than usually indicated by textbooks.
Blackman, David J. Chem. Educ. 1973, 50, 258.
Enzymes |
Molecular Properties / Structure |
Stereochemistry
Sterospecificity in the palm of your hand  Treptow, Richard S.
A simple demonstration to illustrate the reaction between two optically active agents.
Treptow, Richard S. J. Chem. Educ. 1973, 50, 131.
Stereochemistry |
Chirality / Optical Activity |
Enantiomers |
Molecular Properties / Structure
The odor of optical isomers. An experiment in organic chemistry  Murov, Steven L.; Pickering, Miles
The experiment described involves the separation and characterization of l-carvone from spearmint oil and d-carvone from caraway seed oil.
Murov, Steven L.; Pickering, Miles J. Chem. Educ. 1973, 50, 74.
Molecular Properties / Structure |
Chirality / Optical Activity |
Enantiomers |
Stereochemistry |
Separation Science
Lanthanide nmr shift reagents. A powerful new stereochemical tool  Peterson, Max R., Jr.; Wahl, George H., Jr.
Examines the effect of adding certain lanthanide complexes to an nmr solution of a compound possessing an appropriate lone pair of electrons.
Peterson, Max R., Jr.; Wahl, George H., Jr. J. Chem. Educ. 1972, 49, 790.
Transition Elements |
NMR Spectroscopy |
Stereochemistry |
Magnetic Properties |
Molecular Properties / Structure
The synthesis and characterization of tin complexes using inert atmosphere techniques. An advanced laboratory experiment  Thompson, David W.; Kranbuehl, David E.; Schiavelli, Melvyn D.
This study of the tin tetrachloride-acetyl-acetone system is a good introduction for upper division students to techniques used in handling air-sensitive compounds.
Thompson, David W.; Kranbuehl, David E.; Schiavelli, Melvyn D. J. Chem. Educ. 1972, 49, 569.
Synthesis |
Coordination Compounds |
IR Spectroscopy |
NMR Spectroscopy |
Molecular Properties / Structure |
Stereochemistry
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
Complementary rules to define R or S configuration. Viewing molecules from any side  Cori, O.
Reviews the rules to specify the configuration of a chiral center.
Cori, O. J. Chem. Educ. 1972, 49, 461.
Chirality / Optical Activity |
Enantiomers |
Stereochemistry |
Molecular Properties / Structure
The concept of dissymmetric worlds. A utilization of the power of optical isomerism  Abernethy, John L.
Elaborates on the concept of dissymmetric worlds and the dependence of life on dissymmetric compounds.
Abernethy, John L. J. Chem. Educ. 1972, 49, 455.
Chirality / Optical Activity |
Molecular Properties / Structure |
Enantiomers |
Stereochemistry
The natural origin of optically active compounds  Elias, W. E.
There are plausible explanations, based on natural processes, by which organic compounds mat have been produced and then converted into structures of unique chirality.
Elias, W. E. J. Chem. Educ. 1972, 49, 448.
Natural Products |
Chirality / Optical Activity |
Molecular Properties / Structure |
Enantiomers |
Stereochemistry
A model for demonstrating helical dissymmetry  Magliulo, Anthony R.
Ordinary pipe cleaners can be used to illustrate the concept of helical dissymmetry.
Magliulo, Anthony R. J. Chem. Educ. 1972, 49, 391.
Molecular Properties / Structure |
Molecular Modeling |
Stereochemistry |
Enantiomers |
Chirality / Optical Activity
Chirality in Sea Shells  Plumb, Robert C.; Martin, Dean F.
Gastropods exhibit a preference for either right- or left-handed spirals.
Plumb, Robert C.; Martin, Dean F. J. Chem. Educ. 1972, 49, 330.
Chirality / Optical Activity |
Stereochemistry |
Enantiomers
Preparation and resolution of N,N-dimethyl-o-ferrocenylethylamine. An advanced organic experiment  Gokel, George W.; Ugi, Ivar K.
A reaction series selected to simulate an actual research level synthetic sequence.
Gokel, George W.; Ugi, Ivar K. J. Chem. Educ. 1972, 49, 294.
Synthesis |
Thin Layer Chromatography |
IR Spectroscopy |
UV-Vis Spectroscopy |
NMR Spectroscopy |
Stereochemistry
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
Easily constructed paper stereomodels  Freeland, B. H.; O'Brien, R. J.
A system of low cost paper stereomodels for personal use by students of organic chemistry has been outlined in this journal. The student of coordination chemistry has a similar need for the dimensional models of the standard "solid" geometrical figures. These authors extend on previous described models of tetrahedron by a simple construction from a sealed empty envelope.
Freeland, B. H.; O'Brien, R. J. J. Chem. Educ. 1971, 48, 771.
Solid State Chemistry |
Molecular Modeling |
Stereochemistry |
Coordination Compounds
Computer calculation of alkane isomers  Davis, Charles C.; Ebel, Michael
A FORTRAN IV computer program has been written which calculates the number of possible isomers of the saturated aliphatic hydrocarbons.
Davis, Charles C.; Ebel, Michael J. Chem. Educ. 1971, 48, 675.
Alkanes / Cycloalkanes |
Stereochemistry |
Diastereomers |
Constitutional Isomers
The two faces of D and L nomenclature  Slocum, D. W.; Surgarman, D.; Tucker, S. P.
This paper reviews the conflicts and ambiguities in two older nomenclature methods.
Slocum, D. W.; Surgarman, D.; Tucker, S. P. J. Chem. Educ. 1971, 48, 597.
Stereochemistry |
Nomenclature / Units / Symbols
Stereochemical course of the pinacol rearrangement  Mundy, Bradford P.; Otzenberger, Rodney D.
The authors bring to our attention some common misunderstandings about stereochemical paths that are often found in textbooks.
Mundy, Bradford P.; Otzenberger, Rodney D. J. Chem. Educ. 1971, 48, 431.
Stereochemistry |
Mechanisms of Reactions
The stereospecific synthesis of trans-1,4-disubstituted cyclohexanes. An organic chemistry laboratory experiment  Monson, Richard S.
The authors present a synthetic experiment suitable for the introductory organic chemistry laboratory which the introductory organic chemistry laboratory which allows for the unambiguous preparation of trans-1,4-disubstituted cyclohexane derivatives from readily available starting materials.
Monson, Richard S. J. Chem. Educ. 1971, 48, 197.
Alkanes / Cycloalkanes |
Stereochemistry |
Reactions
Recent advances in stereochemical nomenclature  Eliel, Ernest L.
It is the purpose of this brief article to deal with the most significant of the recent nomenclature changes and additions.
Eliel, Ernest L. J. Chem. Educ. 1971, 48, 163.
Nomenclature / Units / Symbols |
Stereochemistry
Elements of stereochemistry (Eliel, Ernest; Baslo, F.)  Chittum, John W.

Chittum, John W. J. Chem. Educ. 1970, 47, A62.
Stereochemistry |
Molecular Properties / Structure
Donor-acceptor interactions in organic chemistry  Sunderwirth, S. G.
The purpose of this article is to aid teachers in making even more effective use of theoretical considerations in teaching organic chemistry; the primary objective is to emphasize the underlying principles that are common to the following four basic types of reactions: substitution, addition, elimination, and rearrangement.
Sunderwirth, S. G. J. Chem. Educ. 1970, 47, 728.
Reactions |
Mechanisms of Reactions |
Addition Reactions |
Elimination Reactions |
Nucleophilic Substitution
Stereochemical correlations in the norbornane system  Markgraf, J. Hodge; Leung, Pak-Tong
In this experiment 2-norbornanone is converted to the epimeric 2-methyl-2-norbornanols by two routes; the structural assignments of the products are not specified, but must be determined from comparisons of various physical properties.
Markgraf, J. Hodge; Leung, Pak-Tong J. Chem. Educ. 1970, 47, 707.
Stereochemistry |
Molecular Properties / Structure |
Synthesis
Stereochemistry of the citric acid cycle  Smith, W. Grady; York, J. Lyndal
A large percentage of biochemistry texts show the trans structure for aconitate but label it cis.
Smith, W. Grady; York, J. Lyndal J. Chem. Educ. 1970, 47, 588.
Stereochemistry |
Molecular Properties / Structure |
Diastereomers |
Carboxylic Acids
The rearrangement of diazotized 4-bromobenzophenone hydrazone: A stereospecific reaction  Hawbeker, Byron L.
This procedure involves the synthesis of hydrazone and its subsequent diazotization / rearrangement to produce an anilide.
Hawbeker, Byron L. J. Chem. Educ. 1970, 47, 218.
Reactions |
Stereochemistry |
Molecular Properties / Structure |
Aromatic Compounds |
Mechanisms of Reactions |
Synthesis
Organic chemistry: Neighboring group participation  Dolbier, William R., Jr.
This paper is intended to be an introduction to neighboring group participation appropriate for undergraduate instruction.
Dolbier, William R., Jr. J. Chem. Educ. 1970, 47, 42.
Kinetics |
Stereochemistry |
Mechanisms of Reactions |
Reactions |
Molecular Properties / Structure
Infrared determination of stereochemistry in metal complexes: An application of group theory  Darensbourg, Donald J.; Darensbourg, Marcetta Y.
This paper is designed to introduce the reader to the uses (and limitations) of group theory in conjunction with infrared spectroscopy in assigning stereochemistry to transition metal carbonyl complexes.
Darensbourg, Donald J.; Darensbourg, Marcetta Y. J. Chem. Educ. 1970, 47, 33.
Spectroscopy |
IR Spectroscopy |
Molecular Properties / Structure |
Stereochemistry |
Metals |
Coordination Compounds |
Group Theory / Symmetry |
Synthesis
LTE. Rule of thumb for predicting optical activity  Mowery, Dwight F., Jr.
The author clarifies a point made in his earlier article.
Mowery, Dwight F., Jr. J. Chem. Educ. 1969, 46, 700.
Chirality / Optical Activity |
Molecular Properties / Structure |
Enantiomers |
Stereochemistry
Resolution and stereochemistry of asymmetric silicon, germanium, tin, and lead compounds  Belloli, Robert
It is the purpose of this review to summarize the results of stereochemical studies on compounds containing an asymmetric group IVA atom.
Belloli, Robert J. Chem. Educ. 1969, 46, 640.
Stereochemistry |
Organometallics |
Enantiomers |
Mechanisms of Reactions |
Nucleophilic Substitution
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
Simplified molecular orbital approach to inorganic stereochemistry  Gavin, R. M., Jr.
The purpose of this paper is to outline the simplest of the Huckel-type molecular orbital models for inorganic molecules and to explore the information on molecular geometry implicit in this model.
Gavin, R. M., Jr. J. Chem. Educ. 1969, 46, 413.
MO Theory |
Stereochemistry |
Molecular Properties / Structure |
VSEPR Theory
An NMR determination of optical purity: An advanced undergraduate laboratory experiment  Jacobus, John; Raban, Morton
Presents an advanced organic laboratory applying NMR spectroscopy to the determination of optical purity that illustrates several important stereochemical concepts.
Jacobus, John; Raban, Morton J. Chem. Educ. 1969, 46, 351.
NMR Spectroscopy |
Stereochemistry |
Chirality / Optical Activity |
Enantiomers |
Diastereomers |
Molecular Properties / Structure
Organic chemistry  Dolbier, William R., Jr.
Presents an explanation that encompasses all electrophilic additions to alkenes within a single, unifying picture.
Dolbier, William R., Jr. J. Chem. Educ. 1969, 46, 342.
Addition Reactions |
Alkenes |
Mechanisms of Reactions |
Stereochemistry
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
Hofmann elimination  Lyle, Robert E.
Clarification regarding the products of Hofmann elimination reactions.
Lyle, Robert E. J. Chem. Educ. 1968, 45, 547.
Elimination Reactions |
Mechanisms of Reactions |
Receptors
The construction of solid tetrahedral and octahedral models  Sheppard, William J.
Describes the construction of solid tetrahedral and octahedral models from wooden blocks.
Sheppard, William J. J. Chem. Educ. 1967, 44, 683.
Stereochemistry |
Molecular Modeling |
Molecular Properties / Structure
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
Stereochemical correlations in the camphor series  Markgraf, J. Hodge
This paper presents a series of experiments that require the student to interpret the effect of structure on the steric course of an oxidation and a reduction in a bicyclic system.
Markgraf, J. Hodge J. Chem. Educ. 1967, 44, 36.
Stereochemistry |
Reactions |
Oxidation / Reduction |
Mechanisms of Reactions |
Molecular Properties / Structure
Introduction to stereochemistry (Mislow, Kurt)  Petersen, Quentin R.

Petersen, Quentin R. J. Chem. Educ. 1966, 43, A272.
Stereochemistry
A useful metallocene stereomodel  Goldberg, Stanley I.
Presents a useful metallocene stereomodel.
Goldberg, Stanley I. J. Chem. Educ. 1966, 43, 554.
Stereochemistry |
Molecular Modeling |
Organometallics
Student laboratory preparation of cis- and trans-4-t-butylcyclohexanols  Kaye, I. A.
These experiments were designed to prepare students for research in organic chemistry by introducing them to laboratory techniques that are not usually taught in the introductory organic chemistry course.
Kaye, I. A. J. Chem. Educ. 1966, 43, 535.
Synthesis |
Alcohols |
Molecular Properties / Structure |
Stereochemistry |
Conformational Analysis
On the spatial arrangement of atoms in nitrogen-containing molecules  Hantzsch, A.; Werner, A.
Reprint of Alfred Werner's inaugural dissertation on the one hundredth anniversary of his winning of the first Nobel Prize in chemistry.
Hantzsch, A.; Werner, A. J. Chem. Educ. 1966, 43, 156.
Stereochemistry
Foundation of nitrogen stereochemistry: Alfred Werner's inaugural dissertation  Kauffman, George B.
Reviews Alfred Werner's inaugural dissertation on the one hundredth anniversary of his winning of the first Nobel Prize in chemistry.
Kauffman, George B. J. Chem. Educ. 1966, 43, 155.
Stereochemistry
Optical studies in organophosphorus chemistry  Cammarata, Arthur
This paper examines those organophosphorus reactions that have been studied using optically active phosphines and phosphonium salts.
Cammarata, Arthur J. Chem. Educ. 1966, 43, 64.
Stereochemistry |
Mechanisms of Reactions
Stereochemistry: The static principles (Grundy, J.)  Petersen, Quentin R.

Petersen, Quentin R. J. Chem. Educ. 1965, 42, A494.
Stereochemistry |
Molecular Properties / Structure
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
Paper stereomodels  Larson, G. Olof
Describes the use of folded paper models to illustrate stereochemical concepts.
Larson, G. Olof J. Chem. Educ. 1965, 42, 274.
Molecular Modeling |
Stereochemistry
Nucleophlic substitution at a saturated carbon atom; Elimination reactions (Bunton, C. A.; Banthorpe, D. V.)  Bunnett, Joseph F.

Bunnett, Joseph F. J. Chem. Educ. 1964, 41, 406.
Nucleophilic Substitution |
Elimination Reactions |
Mechanisms of Reactions
Nucleophilic reactions at trigonally bonded carbon  Cash, R. Vincent
Examines the mechanisms of nucleophilic displacement reactions, nucleophilic addition reactions, and nucleophilic addition with elimination, all at trigonally bonded carbon.
Cash, R. Vincent J. Chem. Educ. 1964, 41, 108.
Nucleophilic Substitution |
Reactions |
Mechanisms of Reactions |
Addition Reactions |
Elimination Reactions
The stereochemistry of complex inorganic compounds  Busch, Daryle H.
Examines optical activity, absolute configuration, stereospecificity, linkage isomers, electronic isomers, and template reactions.
Busch, Daryle H. J. Chem. Educ. 1964, 41, 77.
Stereochemistry |
Coordination Compounds |
Crystal Field / Ligand Field Theory |
Chirality / Optical Activity |
Stereochemistry |
Molecular Properties / Structure
Teaching organic stereochemistry  Eliel, Ernest L.
Focusses on suggestions for the teaching of stereochemistry in general chemistry.
Eliel, Ernest L. J. Chem. Educ. 1964, 41, 73.
Molecular Properties / Structure |
Stereochemistry
Tetrahedral and octahedral models  Larson, G. Olof
This short note describes simple models constructed from heavy paper and styrofoam balls used to facilitate discussions in stereochemistry.
Larson, G. Olof J. Chem. Educ. 1964, 41, 69.
Molecular Modeling |
Molecular Properties / Structure |
Stereochemistry
Three-dimensional effects in biochemistry  Ingraham, Lloyd L.
Explores stereospecificity and stereoselectivity; rigidity requirements; steric effects; and stereospecificity when not required mechanistically.
Ingraham, Lloyd L. J. Chem. Educ. 1964, 41, 66.
Molecular Properties / Structure |
Catalysis |
Enzymes |
Molecular Recognition |
Mechanisms of Reactions |
Stereochemistry |
Chirality / Optical Activity |
Enantiomers
Stereochemistry in the terminal course  Evans, Gordon G.
Discusses the role of stereochemistry in the terminal course of students who are not majoring in chemistry.
Evans, Gordon G. J. Chem. Educ. 1963, 40, 438.
Stereochemistry |
Nonmajor Courses
alpha-Pinene, a starting material for a sequence of organic experiments  Dominguez, X. A.; Leal, G.
This paper presents a unified sequence of experiments that illustrates the unit operations and unit processes of organic chemistry and includes rearrangements and stereoisomerism exemplified by the chemistry of the terpenes.
Dominguez, X. A.; Leal, G. J. Chem. Educ. 1963, 40, 347.
Synthesis |
Reactions |
Mechanisms of Reactions |
Stereochemistry |
Molecular Properties / Structure
The stereochemistry of (-) menthol: An organic laboratory experiment  Dunathan, H. C.
This experiment determines the relative configuration of (-) menthol in which students measure optical rotations, follows the rate of a mutarotation, evaluates rate constants, and carries out a reaction involving asymmetric induction.
Dunathan, H. C. J. Chem. Educ. 1963, 40, 205.
Stereochemistry |
Molecular Properties / Structure |
Oxidation / Reduction
Stereochemistry of carbon compounds (Eliel, Ernest L.)  Beringer, F. Marshall

Beringer, F. Marshall J. Chem. Educ. 1962, 39, 543.
Stereochemistry
Experiments with photoconductive cadmium sulfide  Sheehan, William F.
The objectives of this experiment are to prepare photoconductive CdS containing deliberately added traces of chlorine and copper; to determine the influence of copper content upon the electrical properties of the photoconductor; and to characterize the photoconductor by measuring certain physical properties.
Sheehan, William F. J. Chem. Educ. 1962, 39, 540.
Conductivity |
Elimination Reactions
The electronic structures and stereochemistry of NO2+, NO2, and NO2-  Panckhurst, M. H.
A comparison of the electronic structures and stereochemistry of NO2+, NO2, and NO2-.
Panckhurst, M. H. J. Chem. Educ. 1962, 39, 270.
Stereochemistry |
Molecular Properties / Structure |
Resonance Theory
Stereoisomerism of carbon compounds  Noyce, William K.
The purpose of this article is to suggest a different setting for the classification of the various types of stereoisomerism commonly encountered in organic chemistry, with the view to providing a better correlation with contemporary concepts of atomic and molecular structure.
Noyce, William K. J. Chem. Educ. 1961, 38, 23.
Stereochemistry |
Molecular Properties / Structure
Organic chemistry. Volume 2: Stereochemistry and the chemistry of natural products (Finar, I. L.)  Abernethy, John Leo

Abernethy, John Leo J. Chem. Educ. 1960, 37, A562.
Stereochemistry |
Natural Products
Inorganic chemistry taught as a requirement for all professional chemists  Sisler, Harry H.
The author argues that inorganic chemistry is an essential part of the training of every professional chemist, identifies several specific, theoretical concepts that inorganic courses develop, and provides an outline of a course in structural inorganic chemistry.
Sisler, Harry H. J. Chem. Educ. 1959, 36, 515.
Covalent Bonding |
Stereochemistry |
Acids / Bases
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
Simplified models of inorganic stereoisomers  Kauffman, George B.
The purpose of the proposed models is to demonstrate stereoisomerism as simply as possible.
Kauffman, George B. J. Chem. Educ. 1959, 36, 82.
Molecular Properties / Structure |
Molecular Modeling |
Stereochemistry |
Coordination Compounds
The principle of minimum bending of orbitals  Stewart, George H.; Eyring, Henry
The authors present a theory of valency that accounts for a variety of organic and inorganic structures in a clear and easily understood manner.
Stewart, George H.; Eyring, Henry J. Chem. Educ. 1958, 35, 550.
Atomic Properties / Structure |
Molecular Properties / Structure |
Elimination Reactions
Structure of synthetic high polymers  McGrew, Frank C.
Reviews the determination of the size, structure, composition, and stereochemistry of synthetic high polymers.
McGrew, Frank C. J. Chem. Educ. 1958, 35, 178.
Molecular Properties / Structure |
Physical Properties |
Covalent Bonding |
Stereochemistry
Letters to the editor  Mayper, Stuart A.
The author analyzes more closely a dismissed method for representing hexacovalent complexes with specific configurations.
Mayper, Stuart A. J. Chem. Educ. 1957, 34, 623.
Molecular Properties / Structure |
Stereochemistry |
Enantiomers |
Chirality / Optical Activity
Comparative organic chemistry: Carbon and silicon  Wilk, I. J.
Contrasts silicone chemistry with that of regular organic compounds.
Wilk, I. J. J. Chem. Educ. 1957, 34, 463.
Covalent Bonding |
Ionic Bonding |
Mechanisms of Reactions |
Stereochemistry
Letters to the editor  Freedman, Jules
Commentary on the D and L convention as applied to tartaric acid.
Freedman, Jules J. Chem. Educ. 1957, 34, 362.
Acids / Bases |
Stereochemistry |
Nomenclature / Units / Symbols |
Molecular Properties / Structure |
Enrichment / Review Materials |
Chirality / Optical Activity
Letters to the editor  Pickering, Roger A.
Commentary on the D and L convention as applied to tartaric acid.
Pickering, Roger A. J. Chem. Educ. 1957, 34, 362.
Stereochemistry |
Nomenclature / Units / Symbols |
Acids / Bases |
Molecular Properties / Structure |
Enantiomers |
Chirality / Optical Activity
Aids in teaching stereochemistry: Plastic sheets for plane projection diagrams  Shine, H. J.
The use of plane projection diagrams on cards which can be rotated is helpful as an aids in teaching stereochemistry.
Shine, H. J. J. Chem. Educ. 1957, 34, 355.
Stereochemistry
Assignment of D and L prefixes to the tartaric acids  Vickery, Hubert Bradford
Discusses conventions regarding the assignment of D and L prefixes to the tartaric acids.
Vickery, Hubert Bradford J. Chem. Educ. 1957, 34, 339.
Molecular Properties / Structure |
Enantiomers |
Stereochemistry |
Chirality / Optical Activity |
Nomenclature / Units / Symbols
The numbers and structures of isomers of hexacovalent complexes  Bailar, John C., Jr.
The purpose of this article is to outline a simple method of counting the stereoisomers that can be theoretically formed by monodentate or polydentate ligands and of showing their structures.
Bailar, John C., Jr. J. Chem. Educ. 1957, 34, 334.
Coordination Compounds |
Stereochemistry |
Molecular Properties / Structure
A chart of the stereochemical relationships of the aldoses  Nelson, Peter F.
Provides a chart of the stereochemical relationships of the aldoses that allows students to review and visualize the Rosanoff classification by comparing the D and L enantiomeric forms.
Nelson, Peter F. J. Chem. Educ. 1957, 34, 179.
Stereochemistry |
Molecular Properties / Structure |
Carbohydrates |
Enantiomers |
Chirality / Optical Activity
Assignment of D and L prefixes to the tartaric acids: The Wohl conventions  Abernethy, John Leo
Examines the Wohl system for designating dextro- and levorotatory tartaric acids.
Abernethy, John Leo J. Chem. Educ. 1957, 34, 150.
Nomenclature / Units / Symbols |
Molecular Properties / Structure |
Enantiomers |
Stereochemistry |
Chirality / Optical Activity |
Acids / Bases
Assignment of D and L prefixes to the tartaric acids: An unsettled stereochemical question  Nenitzescu, Costin D.
Examines the Wohl and Freudenberg systems of designating dextro- and levorotatory tartaric acids.
Nenitzescu, Costin D. J. Chem. Educ. 1957, 34, 147.
Molecular Properties / Structure |
Nomenclature / Units / Symbols |
Acids / Bases |
Stereochemistry |
Enantiomers |
Chirality / Optical Activity
Letters to the editor  Gorin, George
Amplifies the discussion of proper configurational prefixes for the tartaric acids.
Gorin, George J. Chem. Educ. 1956, 33, 478.
Nomenclature / Units / Symbols |
Molecular Properties / Structure |
Stereochemistry |
Enantiomers |
Chirality / Optical Activity
Hydrogen bonding and physical properties of substances  Ferguson, Lloyd N.
Physical properties influenced by hydrogen bonding considered in this paper include transition temperatures, vapor pressure, water solubility, the ionization of carboxylic acids, stereoisomerism, adsorption, and infrared spectra.
Ferguson, Lloyd N. J. Chem. Educ. 1956, 33, 267.
Hydrogen Bonding |
Noncovalent Interactions |
Physical Properties |
Aqueous Solution Chemistry |
Carboxylic Acids |
Stereochemistry |
IR Spectroscopy
Some difficulties and common errors related to the designation of sugar configurations  Abernethy, John Leo
Examines some difficulties and common errors related to the designation of sugar configurations.
Abernethy, John Leo J. Chem. Educ. 1956, 33, 88.
Carbohydrates |
Nomenclature / Units / Symbols |
Molecular Properties / Structure |
Stereochemistry |
Chirality / Optical Activity |
Enantiomers
A notation for the study of certain stereochemical problems  Newman, Melvin S.
Newman introduces the projections of compounds containing two adjacent asymmetric carbons that would later bear his name.
Newman, Melvin S. J. Chem. Educ. 1955, 32, 344.
Nomenclature / Units / Symbols |
Stereochemistry |
Molecular Properties / Structure |
Conformational Analysis |
Chirality / Optical Activity
Introducing stereoisomerism  Schreiber, Kurt C.
Criticizes the traditional presentation of stereochemistry in isolation and offers a more integrated approach.
Schreiber, Kurt C. J. Chem. Educ. 1955, 32, 83.
Stereochemistry |
Molecular Properties / Structure |
Nucleophilic Substitution
van't Hoff (1852-1911) in retrospect  van Klooster, H. S.
Examines the life and accomplishments of van't Hoff, particularly his ground-breaking suggestions regarding the tetrahedral structure of carbon and stereochemistry.
van Klooster, H. S. J. Chem. Educ. 1952, 29, 376.
Stereochemistry |
Molecular Properties / Structure
Stereochemistry of simple ring systems  Figueras, John, Jr.
This paper introduces a procedure for examining the stereochemistry of simple carbocyclic and heterocyclic rings, which is essentially a generalization of Fieser's earlier notation.
Figueras, John, Jr. J. Chem. Educ. 1951, 28, 134.
Molecular Properties / Structure |
Stereochemistry