TIGER

Journal Articles: 192 results
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 Resolution of Ibuprofen, 2-(4′-Isobutylphenyl)propionic Acid  James V. McCullagh
In this experiment the over-the-counter pain reliever ibuprofen is resolved using (S)-(-)-a-phenethylamine as the resolving agent. This procedure has several key advantages over previous resolution experiments.
McCullagh, James V. J. Chem. Educ. 2008, 85, 941.
Chirality / Optical Activity |
Drugs / Pharmaceuticals |
Enantiomers |
Quantitative Analysis |
Separation Science
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
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
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
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
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
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
Mechanisms That Interchange Axial and Equatorial Atoms in Fluxional Processes: Illustration of the Berry Pseudorotation, the Turnstile, and the Lever Mechanisms via Animation of Transition State Normal Vibrational Modes  Marion E. Cass, King Kuok Hii, and Henry S. Rzepa
Teaching the Berry pseudorotation mechanism presents particular pedagogic problems due to both its dynamic and three dimensional character. The approach described here illustrates these processes using interactive animations embedded in a Web page.
Cass, Marion E.; Hii, King Kuok; Rzepa, Henry S. J. Chem. Educ. 2006, 83, 336.
Computational Chemistry |
Enantiomers |
Molecular Mechanics / Dynamics |
Molecular Properties / Structure |
Mechanisms of Reactions |
NMR Spectroscopy |
Nonmetals
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
Monoterpene Unknowns Identified Using IR, 1H-NMR, 13C-NMR, DEPT, COSY, and HETCOR  Lisa T. Alty
This set of NMR experiments can be a capstone experience for a spectroscopy or advanced laboratory course following organic chemistry. Students are given a monoterpene to identify using IR, 1H-NMR, 13C-NMR, and DEPT data. Once the unknown is identified, they can fully interpret and assign each carbon and each proton signal to the structure using COSY and HETCOR along with the one-dimensional NMR data. The rigidity of the ring systems and the chiral centers in all of the compounds present diastereotopic hydrogens and, in some cases, diastereotopic methyl groups.
Alty, Lisa T. J. Chem. Educ. 2005, 82, 1387.
Natural Products |
NMR Spectroscopy |
Diastereomers |
Chirality / Optical Activity |
IR Spectroscopy |
Undergraduate Research
Cis and Trans Isomers of Cycloalkenes  Susan E. Barrows and Thomas H. Eberlein
The purpose of this article is to provide that analysis. In order for a cycloalkene to accommodate a trans double bond one or more of the following nonideal geometries must occur: a twisted p bond; pyramidal sp2-carbon atoms; nonideal sp3 bond angles; or longer than normal CC single and double bonds. This article provides a list of experimentally determined relative energies of the cis and trans isomers within the series cycloheptenecycloundecene, along with computationally derived energies at several levels of theory. It also examines the geometric distortions through which cycloalkenes relieve the strain introduced by a trans double bond.
Barrows, Susan E.; Eberlein, Thomas H. J. Chem. Educ. 2005, 82, 1334.
Computational Chemistry |
Molecular Modeling |
Alkenes |
Diastereomers
Circular Dichroism Investigation of Dess–Martin Periodinane Oxidation in the Organic Chemistry Laboratory  Nicole A. Reed, Robert D. Rapp, Christian S. Hamann, and Pamela G. Artz
Using circular dichroism, organic laboratory students investigated the change in absolute stereochemistry upon oxidation of menthol to menthone. In the first laboratory period, the oxidation was performed with DessMartin periodinane, which is a facile and less toxic oxidizing agent. Half the laboratory group performed the oxidation with ()-menthol and the other half used (+)-menthol to produce ()-menthone and (+)-menthone, respectively. The products were analyzed in the second laboratory period using infrared spectroscopy and gas chromatography/mass spectrometry to determine the fraction of starting alcohol converted to ketone. Comparison was made between CD spectra both for the menthol reactant and menthone product and for the (+)- and ()-menthone enantiomers.
Reed, Nicole A.; Rapp, Robert D.; Hamann, Christian S.; Artz, Pamela G. J. Chem. Educ. 2005, 82, 1053.
Instrumental Methods |
Molecular Properties / Structure |
Oxidation / Reduction |
Reactions |
Enantiomers
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
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
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
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
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
"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
Effect of Anisotropy on the Chemical Shift of Vinyl Protons in trans- and cis-1,2-Dibenzoylethylenes. A Small-Group or Recitation Activity  Roosevelt Shaw, David Roane, and Sean Nedd
Procedure to help students explain chemical shift differences for vinyl protons in alkene diastereomers.
Shaw, Roosevelt; Roane, David; Nedd, Sean. J. Chem. Educ. 2002, 79, 67.
Magnetic Properties |
NMR Spectroscopy |
Undergraduate Research |
Diastereomers |
Aromatic Compounds |
Alkenes |
Photochemistry |
Molecular Properties / Structure
"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
Demonstrating Chirality: Using a Mirror with Physical Models to Show Non-superimposability of Chiral Molecules with Their Mirror Images  Michael J. Collins
Using a mirror with physical models to show non-superimposability of chiral molecules with their mirror images.
Collins, Michael J. J. Chem. Educ. 2001, 78, 1484.
Chirality / Optical Activity |
Enantiomers |
Molecular Modeling |
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
Pólya's Isomer Enumeration Method: A Unique Exercise in Group Theory and Combinatorial Analysis for Undergraduates  S. Pevac and G. Crundwell
The use of Plya's isomer enumeration method (IEM) to determine the number of deuterated isomers of boat cyclohexane, C6H12-xDx, is explained in detail. Determining the total number of deuterated chair cyclohexanes is left as a supplemental exercise.
Pevac, S; Crundwell, Guy. J. Chem. Educ. 2000, 77, 1358.
Group Theory / Symmetry |
Enantiomers |
Molecular Properties / Structure
Trisethylenediaminecobalt(III) Chloride Sulfate as a Subject Material for Widely Different Chemistry Lab Courses  Yoshiki Moriguchi
A new unified lab curriculum, expanded to include an organic chemistry or stereochemistry lab course using rac-tris(ethylenediamine)cobalt(III)chloridesulfate (rac-[Co(en)3]ClSO4).
Moriguchi, Yoshiki. J. Chem. Educ. 2000, 77, 1045.
Coordination Compounds |
Synthesis |
Quantitative Analysis |
Enantiomers
Elucidation of Molecular Structure Using NMR Long-Range Coupling: Determination of the Single Isomer Formed in a Regiospecific Reaction  Samuel Delagrange and Françoise Nepveu
The experiment presented in this article introduces students to the main concepts of two essential NMR techniques for investigating molecular structure. Heteronuclear multiple bond connectivity (HMBC) and proton-coupled 13C NMR are used to determine which isomer, from a possible two, is formed by a regiospecific reaction. The demonstration, based on long-range coupling between quaternary carbons and protons on neighboring carbons, is presented step by step.
Delagrange, Samuel; Nepveu, Françoise. J. Chem. Educ. 2000, 77, 895.
Molecular Properties / Structure |
NMR Spectroscopy |
Synthesis |
Carboxylic Acids |
Reactions |
Diastereomers
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
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
A Way To Predict the Relative Stabilities of Structural Isomers  John M. Lyon
This paper discusses a method to evaluate the relative stabilities of structural isomers of inorganic and organic compounds. The method uses a simple set of rules that can be applied with only a knowledge of the electron configuration of the atoms and the periodic trends in atomic size.
Lyon, John M. J. Chem. Educ. 1999, 76, 364.
Covalent Bonding |
Diastereomers |
Molecular Properties / Structure
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
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
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
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
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
Put the Body to Them!  Perkins, Robert R.
Examples of chemistry demonstrations involving student participation, including quantized states and systems, boiling point trends, intermolecular vs. intramolecular changes, polar/nonpolar molecules, enantiomers and diastereomers, and chromatography.
Perkins, Robert R. J. Chem. Educ. 1995, 72, 151.
Chromatography |
Physical Properties |
Phases / Phase Transitions / Diagrams |
Molecular Properties / Structure |
Chirality / Optical Activity |
Quantum Chemistry |
Diastereomers |
Enantiomers
Which Organic Molecule Should I Pick?  Perkins, Robert
Examples of questions requiring students to demonstrate their understanding of organic structures, nomenclature, isomerism, and chemical reactivity.
Perkins, Robert J. Chem. Educ. 1995, 72, 124.
Molecular Properties / Structure |
Chirality / Optical Activity |
Nomenclature / Units / Symbols |
Enantiomers |
Diastereomers
A Microscale Isolation of Limonene from Orange Peels  Garner, Charles M.; Garibaldi, Chad
A rapid and reliable extractive microscale isolation of limonene.
Garner, Charles M.; Garibaldi, Chad J. Chem. Educ. 1994, 71, A146.
Microscale Lab |
Separation Science |
Natural Products |
Gas Chromatography |
IR Spectroscopy |
Enantiomers
An Experiment in trans-cis Isomerization: Synthesis and Kinetics of trans-Dichlorotetraamminecobalt(III) Chloride  Borer, Londa L.; Erdman, Howard W.
Synthesis and kinetics investigation of trans-dichlorotetraamminecobalt(III) chloride.
Borer, Londa L.; Erdman, Howard W. J. Chem. Educ. 1994, 71, 332.
Diastereomers |
Synthesis |
Kinetics |
Coordination Compounds |
UV-Vis Spectroscopy |
IR Spectroscopy |
Conductivity
Isomers of Benzene  Gutman, I.; Potgieter, J. H.
Summary of isomers and valence isomers of benzene.
Gutman, I.; Potgieter, J. H. J. Chem. Educ. 1994, 71, 222.
Aromatic Compounds |
Diastereomers |
Covalent Bonding
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
Microscale yeast mediated enantiospecific reduction of vanillin, and the absolute configuration of (-)-(R)-[alpha]-deuteriovanillyl alcohol: A bioorganic chemistry experiment   Lee, Moses
An experiment is introduced to a sophomore chemistry course that demonstrates the effeciency and enantiospecificity of microbial/enzyme-mediated reactions and the use of NMR methods in determining the optical activity and absolute configuration of chiral alcohols.
Lee, Moses J. Chem. Educ. 1993, 70, A155.
Enantiomers |
Alcohols |
Bioorganic Chemistry |
Chirality / Optical Activity |
NMR Spectroscopy |
Microscale Lab
Cyclooctane conformational analysis via mechanical and computational models  Fitzgerald, Jeffrey P.
Description of an exercise in which students use both mechanical and computational models to identify and quantify various types of strains in different conformations of a molecule.
Fitzgerald, Jeffrey P. J. Chem. Educ. 1993, 70, 988.
Molecular Modeling |
Alkanes / Cycloalkanes |
Diastereomers
Organometallic benzene complexes  Maslowsky, Edward, Jr.
A look at benzene's flexibility and subsequent interactions with metal atoms.
Maslowsky, Edward, Jr. J. Chem. Educ. 1993, 70, 980.
Organometallics |
Diastereomers |
Aromatic Compounds
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
Alkimers  Hiatt, Richard R.
Tutorial and practice program for isomerism and nomenclature.
Hiatt, Richard R. J. Chem. Educ. 1993, 70, 125.
Diastereomers |
Nomenclature / Units / Symbols
Kaleidoscoptical Activity   Becker, Robert
A procedure of constructing a demonstration of polarized light to illustrate concepts of optical activity.
Becker, Robert J. Chem. Educ. 1993, 70, 74.
Enantiomers
Benzene isomers? (the author replies)  Potgieter, J. H.
Additional isomers of benzene.
Potgieter, J. H. J. Chem. Educ. 1992, 69, 859.
Aromatic Compounds |
Alkenes |
Diastereomers
Benzene isomers?  Reinecke, Manfred G.
Additional isomers of benzene.
Reinecke, Manfred G. J. Chem. Educ. 1992, 69, 859.
Aromatic Compounds |
Diastereomers |
Alkenes
Identification of methylcyclohexanones by NMR  Gurst, Jerome E.
Distinguishing between three isomeric methylcyclohexanones using NMR.
Gurst, Jerome E. J. Chem. Educ. 1992, 69, 774.
Aldehydes / Ketones |
NMR Spectroscopy |
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
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
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
Microscale resolution of racemic 1-phenylethylamine and chiral high performance liquid chromatography (HPLC) in undergraduate chemistry   Krumpolc, Miroslav
A standard experiment has been modified to incorporate microscale techniques and employ chiral high performance liquid chromatography to determine enantiomeric purity.
Krumpolc, Miroslav J. Chem. Educ. 1991, 68, A176.
Enantiomers |
Amides |
Diastereomers |
Physical Properties |
Microscale Lab
Isomerization of dimethyl maleate to dimethyl fumarate: An undergraduate experiment illustrating amine-catalyzed alkene isomerization, stereochemical principles, sublimation, and product identification by spectroscopic methods  Fryhle, Craig B.; Rybak, Carol M.; Pulley, Kenneth E.
An undergraduate experiment illustrating amine-catalyzed alkene isomerization, stereochemical principles, sublimation, and product identification by spectroscopic methods.
Fryhle, Craig B.; Rybak, Carol M.; Pulley, Kenneth E. J. Chem. Educ. 1991, 68, 1050.
Amines / Ammonium Compounds |
Diastereomers |
Gas Chromatography |
NMR Spectroscopy |
Fourier Transform Techniques |
Catalysis
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
A projection for bond location in chair cyclohexane and related structures  Woolf, A. A.
Benefits and drawbacks of 2D representations for chair cyclohexane and related structures.
Woolf, A. A. J. Chem. Educ. 1991, 68, 646.
Alkanes / Cycloalkanes |
Diastereomers |
Enantiomers |
Constitutional Isomers
An NMR study of the stereochemistry of the fumarase-catalyzed hydration of fumaric acid  Olsen, Julie A.; Olsen, Robert J.
An NMR study of the stereochemistry of the fumarase-catalyzed hydration of fumaric acid.
Olsen, Julie A.; Olsen, Robert J. J. Chem. Educ. 1991, 68, 436.
Acids / Bases |
NMR Spectroscopy |
Enzymes |
Molecular Modeling |
Diastereomers
Representing isomeric structures  Thall, Edwin
"Representing isomeric structures" is the name of a technique this author has developed to help students learn to draw molecular structures of isomers in their first organic chemistry class.
Thall, Edwin J. Chem. Educ. 1991, 68, 190.
Constitutional Isomers |
Diastereomers
Friedel-Crafts alkylation products   Kolb, Kenneth E.; Field, Kurt W.
Comments on how two recent papers could compliment one and another.
Kolb, Kenneth E.; Field, Kurt W. J. Chem. Educ. 1991, 68, 86.
Alkylation |
Gas Chromatography |
Diastereomers |
Aromatic Compounds
Microscale synthesis of cis-diamminedihaloplatinum(II) and a corresponding trans isomer: A rapid and convenient method of preparing cisplatin - An anticancer drug. A laboratory experiment for inorganic and bioinorganic chemistry  Singh, Mono M.; Szafran, Zvi; Pike, Ronald M.
Involves drug synthesis, application of the trans effect, and preparation and characterization of isomers under different reaction conditions.
Singh, Mono M.; Szafran, Zvi; Pike, Ronald M. J. Chem. Educ. 1990, 67, A261.
Microscale Lab |
Synthesis |
Drugs / Pharmaceuticals |
Bioinorganic Chemistry |
Diastereomers
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 derivation of the Masamune rule of multiplicativity in double asymmetric induction  Nakayama, Kensaku
The ability to prepare one diastereomeric or enantiomeric isomer in excess in a given chemical transformation where a stereoisomeric distribution of products is possible is currently one of the most highly sought goals in the field of synthetic organic chemistry.
Nakayama, Kensaku J. Chem. Educ. 1990, 67, 20.
Synthesis |
Diastereomers |
Enantiomers
The resolution of a completely inorganic coordination compound: A modified classic experiment for the inorganic laboratory  Yasui, Takaji; Ama, Tomoharu; Kauffman, George B.
Reproducing Alfred Werner's experiment demonstrating the Co(III) possesses an octahedral configuration.
Yasui, Takaji; Ama, Tomoharu; Kauffman, George B. J. Chem. Educ. 1989, 66, 1045.
Coordination Compounds |
Synthesis |
Diastereomers
A demonstration of the optical activity of a pair of enantiomers  Knauer, Bruce
Uses the enantiomers (S)-(+)-carvone and (R)-(-)-carvone and a polarizing sheet to illustrate optical activity.
Knauer, Bruce J. Chem. Educ. 1989, 66, 1033.
Chirality / Optical Activity |
Enantiomers
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
Synthesis of azulene, a blue hydrocarbon  Lemal, David M.; Goldman, Glenn D.
A procedure of the synthesis of this simple, beautiful, and theoretically interesting compound with many unusual properties.
Lemal, David M.; Goldman, Glenn D. J. Chem. Educ. 1988, 65, 923.
MO Theory |
Aromatic Compounds |
Diastereomers |
Synthesis
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
Lecture demonstrations for organic/ biochemistry allied health courses  Deavor, James P.
Simple demonstrations on enantiomeric pairs and protein structure.
Deavor, James P. J. Chem. Educ. 1988, 65, 622.
Enantiomers |
Chirality / Optical Activity |
Proteins / Peptides |
Nonmajor Courses |
Amino Acids
cis and trans-Stilbenes: Chromatographic separation and photochemical isomerization  Levine, Samuel G.; Barhoriak, Kathleen Doubek; Cho, Ho S.
An organic chemistry laboratory that has historic significance.
Levine, Samuel G.; Barhoriak, Kathleen Doubek; Cho, Ho S. J. Chem. Educ. 1988, 65, 79.
Separation Science |
Photochemistry |
Diastereomers |
Chromatography
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
Mnemonic for Z and E nomenclature  Thomas, C. W.
A visual reminder that makes it unnecessary to memorize the German terms.
Thomas, C. W. J. Chem. Educ. 1988, 65, 44.
Diastereomers |
Alkenes |
Nomenclature / Units / Symbols
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
Simple rule for the conversion of Fischer monosaccharide projection formulas into Haworth representations  Argiles, J. M.
Many students struggle with memorizing Haworth structures, the authors provide some insight on this topic to help students.
Argiles, J. M. J. Chem. Educ. 1986, 63, 927.
Molecular Properties / Structure |
Enantiomers |
Chirality / Optical Activity |
Carbohydrates |
Molecular Modeling
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
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
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
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
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
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
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
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
Degas' dancers: an illustration for rotational isomers  Hargittai, Istvan
Two drawings by Degas provide an opportunity to introduce the concepts of staggered and eclipsed conformations of A2B-BC2 molecules in a concrete, interesting, and aesthetic way.
Hargittai, Istvan J. Chem. Educ. 1983, 60, 94.
Molecular Properties / Structure |
Nomenclature / Units / Symbols |
Constitutional Isomers |
Diastereomers
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
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
Determination of chiral molecule configuration in Fischer projections  Epling, Gary A.
A non-mathematical procedure that students can use to master and remember the determination of R or S configuration.
Epling, Gary A. J. Chem. Educ. 1982, 59, 650.
Chirality / Optical Activity |
Molecular Properties / Structure |
Enantiomers
Reactions between chiral molecules: A handy analogy  Richardson, W. S.
Simulating a reaction between R and S structures through the shaking of hands.
Richardson, W. S. J. Chem. Educ. 1982, 59, 649.
Chirality / Optical Activity |
Molecular Properties / Structure |
Enantiomers |
Reactions
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
An undergraduate laboratory program project involving photocyclizations in independent syntheses of novel chrysenes and phenanthrenes  Letcher, R. M.
This experiment attempts to fulfill such objectives as providing meaningful and viable preparative reactions, providing an opportunity for independent laboratory work within a project framework and under conditions of nearly equal opportunity and experience.
Letcher, R. M. J. Chem. Educ. 1981, 58, 1020.
Undergraduate Research |
Synthesis |
Aromatic Compounds |
Photochemistry |
Diastereomers |
NMR Spectroscopy |
Alcohols |
Thin Layer Chromatography
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
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
Rubber gloves, rubber balls, and optical activity  Perkins, Robert
Several demonstrations aimed at helping students to understand optical activity.
Perkins, Robert J. Chem. Educ. 1980, 57, 809.
Chirality / Optical Activity |
Molecular Properties / Structure |
Enantiomers
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
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
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
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
Conformations of substituted ethanes  Kingsbury, Charles A.
Provides a state-of-the-art view of conformational analysis, with an emphasis on sp3 hybridized acyclic molecules.
Kingsbury, Charles A. J. Chem. Educ. 1979, 56, 431.
Molecular Properties / Structure |
Conformational Analysis |
Alkanes / Cycloalkanes |
Diastereomers
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
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
Amine-catalyzed isomerization of diethylmaleate to diethylfumarate  Glover, Irving T.; Cushing, Gary W.; Windsor, Chris M.
The authors have used the reaction in this paper in their introductory organic chemistry course to illustrate principles of GLC , geometric isomerism, homogeneous catalysis, and activation energy determinations.
Glover, Irving T.; Cushing, Gary W.; Windsor, Chris M. J. Chem. Educ. 1978, 55, 812.
Diastereomers |
Enantiomers |
Catalysis |
Gas Chromatography
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
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
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
Chirality, diastereoisomerism, and the Narwhal  Stirling, C. J.
There are many simple examples of enantiomeric objects, both natural and man-made and their static interrelationship is directly and tellingly examined with the aid of a mirror.
Stirling, C. J. J. Chem. Educ. 1978, 55, 32.
Enantiomers |
Chirality / Optical Activity
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
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
Addendum to "Simple demonstration of optical activity"  Dean, Walter K.
Modifications to an earlier demonstration on optical activity.
Dean, Walter K. J. Chem. Educ. 1977, 54, 494.
Chirality / Optical Activity |
Molecular Properties / Structure |
Enantiomers
A Device for easy demonstration of optical activity and optical rotatory dispersion  Kinney, John B.; Skinner, James F.
Describes a portable device that can be used for the simultaneous demonstration of both optical activity and optical rotatory dispersion for individual students and for a class with an overhead projector.
Kinney, John B.; Skinner, James F. J. Chem. Educ. 1977, 54, 494.
Chirality / Optical Activity |
Molecular Properties / Structure |
Enantiomers |
Laboratory Equipment / Apparatus
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
Isomerism about a double bond: Use of cis and trans   Fernelius, W. Conard; Loening, Kurt; Adams, Roy M.
Limitations of the cis and trans nomenclature.
Fernelius, W. Conard; Loening, Kurt; Adams, Roy M. J. Chem. Educ. 1976, 53, 727.
Diastereomers |
Nomenclature / Units / Symbols
A polarimeter experiment for introductory courses  Gibas, Murray A.
This note describes an experiment which can be done with an inexpensive polarimeter, requires only about 20 minutes per student, and yet gives results accurate enough to satisfy the students.
Gibas, Murray A. J. Chem. Educ. 1976, 53, 462.
Enantiomers |
Carbohydrates |
Equilibrium
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
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
Rediscovery in a course for nonscientists. Use of molecular models to solve classical structural problems  Wood, Gordon W.
Describes exercises using simple ball and stick models that students with no chemistry background can solve in the context of the original discovery.
Wood, Gordon W. J. Chem. Educ. 1975, 52, 177.
Molecular Modeling |
Molecular Properties / Structure |
Chirality / Optical Activity |
Enantiomers |
Nonmajor Courses
Determining homotopic, enantiotopic, and diastereotopic faces in organic molecules  Ayral Kaloustian, Semiramis; Kaloustian, Moses K.
Presents a simple set of rules, based on considerations of symmetry, that allows a succinct classification of the five types of molecular faces of interest to the organic chemist and the biochemist.
Ayral Kaloustian, Semiramis; Kaloustian, Moses K. J. Chem. Educ. 1975, 52, 56.
Molecular Properties / Structure |
Diastereomers
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
The photoisomerization of cyclic ketones: An experiment in organic chemistry  Haas, J. W., Jr.
This experiment deals with parameters such as the nature of the excited state, effect of triplet quenchers on product formation, chemical structure and reaction rate and quantum yield when cyclopentanone and cyclohexanone are irradiated at 254nm. These cyclic ketones provide a variety of photolysis information in a short time span, are conveniently analyzed by gas chromatography, and are readily available at the requisite levels of purity.
Haas, J. W., Jr. J. Chem. Educ. 1974, 51, 346.
Aldehydes / Ketones |
Aromatic Compounds |
Photochemistry |
Diastereomers |
Gas Chromatography
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 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
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
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
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
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
An integrated nmr and photochemical organic chemistry experiment  Glaros, George; Cromwell, Norman H.
The authors describe a photochemical experiment involving a compound that was prepared in the authors' previous paper.
Glaros, George; Cromwell, Norman H. J. Chem. Educ. 1971, 48, 204.
Aromatic Compounds |
Diastereomers
A model for demonstrating the rotation of polarized light by an asymmetric molecule  Berry, James P.
A nut and bolt (representing an asymmetric molecule and a beam of plane-polarized light) are used to illustrate that regardless of which face of the nut is up, one must rotate the bolt counterclockwise to cause it to pass downward through the nut.
Berry, James P. J. Chem. Educ. 1970, 47, 659.
Molecular Properties / Structure |
Molecular Mechanics / Dynamics |
Chirality / Optical Activity |
Enantiomers
A weevil's loss is our gain or sex strikes the pages on the Journal.  Brasted, Robert C.
The trans-isomer of the boll weevil sex attractant is a million times more active than the cis-isomer.
Brasted, Robert C. J. Chem. Educ. 1970, 47, 447.
Natural Products |
Diastereomers |
Molecular Properties / Structure |
Agricultural Chemistry |
Applications of Chemistry
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
The resolution of DL-histidine: An organic chemistry experiment using an ion exchange resin  Bosch, Arthur J.
This experiment involves the isolation of the amino acid, D-histidine, from DL-histidine, and gives a product with high optical purity while demonstrating the use of an ion exchange resin and mixed solvent recrystallization.
Bosch, Arthur J. J. Chem. Educ. 1969, 46, 691.
Ion Exchange |
Amino Acids |
Chirality / Optical Activity |
Enantiomers
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
Wooden models of asymmetric structures  Nye, Martin J.
Wooden blocks are cut to represent molecules of a pair of enantiomers, and are constructed so that they may be readily stacked together to show crystal structure.
Nye, Martin J. J. Chem. Educ. 1969, 46, 175.
Molecular Modeling |
Molecular Properties / Structure |
Enantiomers |
Crystals / Crystallography
The photoisomerization of azobenzene: A TLC experiment for the undergraduate organic laboratory  Janssen, Jerry F.
The photoisomerization of azobenzene provides a rare opportunity to explore molecular photochemistry in undergraduate organic chemistry.
Janssen, Jerry F. J. Chem. Educ. 1969, 46, 117.
Chromatography |
Thin Layer Chromatography |
Photochemistry |
Diastereomers
A simplified proof of the constitution and configuration of D-glucose  Frohwein, Y, Z.
Presents a simplified proof of the constitution and configuration of D-glucose for students being introduced to carbohydrate chemistry.
Frohwein, Y, Z. J. Chem. Educ. 1969, 46, 55.
Carbohydrates |
Molecular Properties / Structure |
Enantiomers |
Chirality / Optical Activity
Simple models for polymer stereochemistry  Rodriguez, F.
Models made by drawing on folding transparent plastic sheets are proposed as being an alternative for illustrating polymer structures.
Rodriguez, F. J. Chem. Educ. 1968, 45, 507.
Molecular Modeling |
Molecular Properties / Structure |
Diastereomers
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
Concepts of species and state in chemistry and molecular physics  Goodfriend, P. L.
This article examines the concepts of species and state in chemistry and molecular physics.
Goodfriend, P. L. J. Chem. Educ. 1966, 43, 95.
Quantum Chemistry |
Diastereomers |
Molecular Properties / Structure
An aid to visualizing fused ring systems  Vogel, George
Presents a method for visualizing fused ring systems without the use of models.
Vogel, George J. Chem. Educ. 1965, 42, 278.
Molecular Modeling |
Molecular Properties / Structure |
Diastereomers
Resolution of D,L-alpha-phenylethylamine: An introductory organic chemistry experiment  Ault, Addison
This experiment clarifies several of the concepts of optical isomerism and introduces the techniques of recrystallization, extraction, and distillation.
Ault, Addison J. Chem. Educ. 1965, 42, 269.
Amines / Ammonium Compounds |
Enantiomers |
Chirality / Optical Activity
Optical rotation  Evans, J. O. M.; Tietze, H. R.
The angle of rotation of sucrose can be easily determined using this simple demonstration.
Evans, J. O. M.; Tietze, H. R. J. Chem. Educ. 1964, 41, A973.
Molecular Properties / Structure |
Chirality / Optical Activity |
Enantiomers
Systematic names for the tartaric acids  Baxter, J. N.
Examines the use of the small capital letters D and L in naming tartaric acids.
Baxter, J. N. J. Chem. Educ. 1964, 41, 619.
Nomenclature / Units / Symbols |
Acids / Bases |
Carbohydrates |
Chirality / Optical Activity |
Enantiomers
The rotation of optically pure 2-bromooctane  Traynham, James C.
This paper reviews the various values reported for the optical rotation of pure 2-bromooctane and makes a case for its most probable value.
Traynham, James C. J. Chem. Educ. 1964, 41, 617.
Chirality / Optical Activity |
Enantiomers |
Molecular Properties / Structure
Resolving coordination compounds by a second order asymmetric synthesis  Kauffman, George B.; Sugisaka, Nobuyuki; Reid, Ian K.
This experiment involves the resolution of an optically active complex cation, the trisoxalatochromate(III) ion and provides the student with an excellent introduction to the phenomenon of second order asymmetric synthesis.
Kauffman, George B.; Sugisaka, Nobuyuki; Reid, Ian K. J. Chem. Educ. 1964, 41, 461.
Diastereomers |
Coordination Compounds |
Chirality / Optical Activity
An introduction to the sequence rule: A system for the specification of absolute configuration  Cahn, R. S.
This paper describes the relatively simple methods that suffice for specifying the absolute configuration of the majority of optically active organic compounds - those containing asymmetric carbon atoms.
Cahn, R. S. J. Chem. Educ. 1964, 41, 116.
Molecular Properties / Structure |
Chirality / Optical Activity |
Enantiomers |
Nomenclature / Units / Symbols
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
Letters  Koons, Lawrence F.
Calls attention to a demonstration similar to that described in an earlier article.
Koons, Lawrence F. J. Chem. Educ. 1962, 39, 318.
Chirality / Optical Activity |
Enantiomers |
Molecular Properties / Structure
Resolution by the method of racemic modification: A demonstration of analogy  Williams, Francis T.
Using shaking hands to demonstrate resolution by the method of racemic modification.
Williams, Francis T. J. Chem. Educ. 1962, 39, 211.
Molecular Properties / Structure |
Diastereomers |
Enantiomers
Dipole moments of symmetrical organic molecules  Moulton, W. N.
Examines the use of dipole moments to assign cis or trans configurations to olefins.
Moulton, W. N. J. Chem. Educ. 1961, 38, 522.
Molecular Properties / Structure |
Diastereomers
The criterion for optical isomerism  Thompson, H. Bradford
The absence of planes or centers of symmetry is not a criterion for optical isomerism.
Thompson, H. Bradford J. Chem. Educ. 1960, 37, 530.
Chirality / Optical Activity |
Enantiomers |
Molecular Properties / Structure
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
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
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
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
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
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
Student experiments on derivatives of 1,2-diphenylethane  Fieser, Louis F.
Johannes Thiele's classical demonstration of 1,4-addition by reductive acetylation of benzil is used to present a number of interesting theoretical points and an opportunity to separate cis- and trans- isomers through chromatography.
Fieser, Louis F. J. Chem. Educ. 1954, 31, 291.
Molecular Properties / Structure |
Diastereomers |
Chromatography
Isomers of octahedral complexes with nonbranching ligands  Trimble, Russell F., Jr.
The purpose of this paper is to present a tabulation of the various ways in which ligands can be distributed about an octahedral frame.
Trimble, Russell F., Jr. J. Chem. Educ. 1954, 31, 176.
Coordination Compounds |
Molecular Biology |
Diastereomers
Aspects of isomerism and mesomerism. III. Stereoisomerism  Bent, Richard L.
Examines the tetrahedral nature of carbon, multiple bonds, enantiomorphism, diastereoisomerism, and geometric isomerism.
Bent, Richard L. J. Chem. Educ. 1953, 30, 328.
Molecular Properties / Structure |
Enantiomers |
Diastereomers |
Constitutional Isomers
Aspects of isomerism and mesomerism. II. Structural isomerism  Bent, Richard L.
Examines the relationship between structural, optical, and geometric isomerism.
Bent, Richard L. J. Chem. Educ. 1953, 30, 284.
Molecular Properties / Structure |
Constitutional Isomers |
Enantiomers |
Diastereomers