| Journal Articles: 413 results |
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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 protonproton 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
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Borohydride Reduction of Estrone Animesh Aditya, David E. Nichols, and G. Marc Loudon
This experiment presents a guided-inquiry approach to the demonstration of diastereoselectivity using chiral hindered ketones that undergo facile reduction with sodium borohydride. The resulting diastereomeric estradiols can be analyzed and differentiated by thin-layer chromatography and melting point.
Aditya, Animesh; Nichols, David E.; Loudon, G. Marc. J. Chem. Educ. 2008, 85, 1535.
Aldehydes / Ketones |
Diastereomers |
IR Spectroscopy |
Microscale Lab |
Stereochemistry |
Steroids |
Thin Layer Chromatography
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Percy Julian, Robert Robinson, and the Identity of Eserethole Addison Ault
The Nova production Percy JulianForgotten 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
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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 centurya 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
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Simple Potentiometric Determination of Reducing Sugars Henry Moresco, Pedro Sanson, and Gustavo Seoane
Describes a potentiometric method for reducing sugar quantification. Its advantages include simplicity, low cost, and the ability to be conducted in colored and turbid samples. This analysis is also safer than the standard LaneEynon method for the determination of reducing sugars.
Moresco, Henry; Sanson, Pedro; Seoane, Gustavo. J. Chem. Educ. 2008, 85, 1091.
Carbohydrates |
Potentiometry |
Quantitative Analysis
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Evaluating Mechanisms of Dihydroxylation by Thin-Layer Chromatography Benjamin T. Burlingham and Joseph C. Rettig
Presents a microscale experiment in which cyclohexene is dihydroxylated under three sets of conditions and the products determined through thin-layer chromatography. Teams of students evaluate proposed mechanisms for each dihydroxylation in light of the data collected.
Burlingham, Benjamin T.; Rettig, Joseph C. J. Chem. Educ. 2008, 85, 959.
Addition Reactions |
Alkenes |
Diastereomers |
Mechanisms of Reactions |
Microscale Lab |
Stereochemistry |
Synthesis |
Thin Layer Chromatography
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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
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Mosher Amides: Determining the Absolute Stereochemistry of Optically-Active Amines Damian A. Allen, Anthony E. Tomaso, Jr., Owen P. Priest, David F. Hindson, and Jamie L. Hurlburt
In this experiment, teams of students are given an optically-pure amine of known structure but unknown stereochemistry. Different teams derivatize samples of the amine with (R) and (S) conformations of Mosher's acid chloride. The resulting diastereomers are analyzed by NMR to determine the absolute configuration of the initial, unknown amine.
Allen, Damian A.; Tomaso, Anthony E., Jr.; Priest, Owen P.; Hindson, David F.; Hurlburt, Jamie L. J. Chem. Educ. 2008, 85, 698.
Amides |
Chirality / Optical Activity |
Chromatography |
Diastereomers |
Microscale Lab |
NMR Spectroscopy |
Stereochemistry
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Converting Municipal Waste into Automobile Fuel: Ethanol from Newspaper Mark Mascal and Richard Scown
In this experiment, waste newspaper is pulped with acid and its cellulose hydrolyzed to produce glucose syrup that is fermented and distilled to yield ethanol. In doing so, students are introduced to carbohydrate chemistry and the use of fermentation in organic synthesis.
Mascal, Mark; Scown, Richard. J. Chem. Educ. 2008, 85, 546.
Acids / Bases |
Alcohols |
Applications of Chemistry |
Biotechnology |
Carbohydrates |
Qualitative Analysis |
Synthesis |
Thin Layer Chromatography
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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
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A Simple Method for Drawing Chiral Mononuclear Octahedral Metal Complexes Aminou Mohamadou and Arnaud Haudrechy
This article presents a simple and progressive method to draw all of the octahedral complexes of coordination units with at least two different monodentate ligands and show their chiral properties.
Mohamadou, Aminou; Haudrechy, Arnaud. J. Chem. Educ. 2008, 85, 436.
Asymmetric Synthesis |
Chirality / Optical Activity |
Coordination Compounds |
Diastereomers |
Enantiomers |
Molecular Properties / Structure |
Stereochemistry |
Transition Elements
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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
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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
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Biochemical View: A Web Site Providing Material for Teaching Biochemistry Using Multiple Approaches Fernanda C. Dórea, Higor S. Rodrigues, Oscar M. M. Lapouble, Márcio R. Pereira, Mariana S. Castro, and Wagner Fontes
Biochemical View is a free, full access Web site whose main goals are to complement existing biochemistry instruction and materials, provide material to teachers preparing conventional and online courses, and popularize the use of these resources in undergraduate courses.
Dórea, Fernanda C.; Rodrigues, Higor S.; Lapouble, Oscar M. M.; Pereira, Márcio R.; Castro, Mariana S.; Fontes, Wagner. J. Chem. Educ. 2007, 84, 1866.
Amino Acids |
Bioenergetics |
Carbohydrates |
Enzymes |
Glycolysis |
Lipids |
Metabolism |
Fatty Acids
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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
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Structures for the ABO(H) Blood Group: Which Textbook Is Correct? John M. Risley
Six textbooks and two Internet sites show different structures for the A, B, and O(H) antigens of the ABO(H) blood group, but none of them are correct. This article emphasizes the correct molecular structures because it is important to distinguish between those carbohydrates that make up the antigens and those that are not part of the antigenic structures.
Risley, John M. J. Chem. Educ. 2007, 84, 1546.
Bioorganic Chemistry |
Carbohydrates |
Natural Products |
Molecular Properties / Structure
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The A1c Blood Test: An Illustration of Principles from General and Organic Chemistry Robert C. Kerber
The glycated hemoglobin blood test is a key measure of the effectiveness of glucose control in diabetics. The chemistry of glucose in the bloodstream, which underlies the test and its impact, provides an illustration of the importance of chemical equilibrium and kinetics to a major health problem.
Kerber, Robert C. . J. Chem. Educ. 2007, 84, 1541.
Applications of Chemistry |
Bioinorganic Chemistry |
Carbohydrates |
Mechanisms of Reactions |
Proteins / Peptides |
Bioorganic Chemistry
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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 Hckel-aromatic and chiral Mbius-aromatic transition states.
Rzepa, Henry S. J. Chem. Educ. 2007, 84, 1535.
Alkanes / Cycloalkanes |
Alkenes |
Aromatic Compounds |
Mechanisms of Reactions |
Stereochemistry
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Synthesis of Anomeric Methyl Fructofuranosides and Their Separation on an Ion-exchange Resin Erkki Nurminen, Päivi Poijärvi, Katja Koskua, and Jari Hovinen
Treatment of d-fructose with methanol in the presence of acid as a catalyst gives a mixture of methyl--d-fructopyranoside, methyl-a-D-fructofuranoside, and methyl--d- fructofuranoside, which are separated on an ion exchange column and characterized polarimetrically.
Nurminen, Erkki; Poijärvi, Päivi; Koskua, Katja; Hovinen, Jari. J. Chem. Educ. 2007, 84, 1480.
Carbocations |
Chirality / Optical Activity |
Chromatography |
Ion Exchange |
NMR Spectroscopy |
Synthesis |
Thin Layer Chromatography |
Carbohydrates
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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 GCMS, 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
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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
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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
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Dynamic Stereochemistry: A Simple Approach To Delineating Relative Configuration Dipak K. Mandal
A simple approach is presented for delineating relative stereochemistry of the product in reactions involving stereogenic center(s).
Mandal, Dipak K. J. Chem. Educ. 2007, 84, 274.
Chirality / Optical Activity |
Diastereomers |
Enantiomers |
Molecular Properties / Structure |
Stereochemistry
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Popcorn—What's in the Bag? Marissa B. Sherman and Thomas A. Evans
Three independent activities explore microwave popcorn, the nature of the packaging, and the popcorn produced.
Sherman, Marissa B.; Evans, Thomas A. J. Chem. Educ. 2006, 83, 416A.
Carbohydrates |
Nutrition |
Physical Properties |
Solutions / Solvents |
Water / Water Chemistry
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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
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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
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Precision in Stereochemical Terminology LeRoy G. Wade, Jr.
This article recommends that instructors use the precise terms asymmetric carbon atom and chirality center when they apply, and use the broader term stereocenter only when there is a need to include stereogenic atoms that are not chirality centers.
Wade, LeRoy G., Jr. J. Chem. Educ. 2006, 83, 1793.
Chemical Technicians |
Diastereomers |
Enantiomers |
Stereochemistry |
Nomenclature / Units / Symbols |
Chirality / Optical Activity
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The Step-by-Step Robinson Annulation of Chalcone and Ethyl Acetoacetate. An Advanced Undergraduate Project in Organic Synthesis and Structural Analysis Lionel Delaude, Jean Grandjean, and Alfred F. Noels
The Robinson annulation is a three-step process involving a Michael addition followed by an internal aldol condensation and a dehydration. It is possible to stop the reaction after every step and to isolate the three products, allowing students to confirm the validity of the stepwise mechanism and develop a more thorough understanding of the whole process.
Delaude, Lionel; Grandjean, Jean; Noels, Alfred F. J. Chem. Educ. 2006, 83, 1225.
Catalysis |
Chirality / Optical Activity |
Conformational Analysis |
Diastereomers |
IR Spectroscopy |
Synthesis |
NMR Spectroscopy |
Stereochemistry
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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
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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
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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
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Acetal Protecting Groups in the Organic Laboratory: Synthesis of Methyl 4,6-O-Benzylidene-α-D-Glucopyranoside Alexei V. Demchenko, Papapida Pornsuriyasak, and Cristina De Meo
The synthesis of methyl 4,6-O-benzylidene-a-D-glucopyranoside provides an opportunity to synthesize a cyclic acetal; stereoselectively introduce a chirality center; and learn extraction, evaporation, precipitation, optical rotation, melting point measurement, thin-layer chromatography, IR-spectroscopy, mass spectrometry, and various NMR techniques.
Demchenko, Alexei V.; Pornsuriyasak, Papapida; De Meo, Cristina. J. Chem. Educ. 2006, 83, 782.
Carbohydrates |
IR Spectroscopy |
Medicinal Chemistry |
NMR Spectroscopy |
Thin Layer Chromatography |
Synthesis
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The Chemistry of Popcorn: Polymers of Glucose William F. Coleman
The Featured Molecules this month are all polymers of glucose and include cellobiose, maltose, 10-mer of cellulose, 40-mer of amylose, and an amylopectin fragment.
Coleman, William F. J. Chem. Educ. 2006, 83, 413.
Molecular Modeling |
Molecular Properties / Structure |
Carbohydrates
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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
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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 ahydroxyketones 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
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Glycosyltransferases A and B: Four Critical Amino Acids Determine Blood Type Natisha L. Rose, Monica M. Palcic, and Stephen V. Evans
Human A, B, and O blood type is determined by the presence or absence of distinct carbohydrate structures on red blood cells. In this review the chemistry of the blood group ABO system and the role of glycosyltransferase A, glycosyltransferase B, and the four amino acids critical to determining blood group status are discussed.
Rose, Natisha L.; Palcic, Monica M.; Evans, Stephen V. J. Chem. Educ. 2005, 82, 1846.
Carbohydrates |
Enzymes |
Kinetics |
Bioorganic Chemistry |
Crystals / Crystallography |
Molecular Biology |
X-ray Crystallography |
Amino Acids
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Cotton Effect in Copper–Proline Complexes in the Visible Region Victor Volkov and Rolf Pfister
This article suggests taking advantage of the visible dd 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
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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 DielsAlder 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
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The Addition of Bromine to 1,2-Diphenylethene Judith C. Amburgey-Peters and LeRoy W. Haynes
We investigated the reaction of (Z)-1,2-diphenylethene (cis-stilbene) with various brominating reagents and solvents following directions in standard organic chemistry manuals. We were particularly interested in learning which combination of brominating reagent and solvent gave the best yield of (d,l)-1,2-dibromo-1,2-diphenylethane without the formation of significant amounts of meso-1,2-dibromo-1,2-diphenylethane, which is essentially the sole product from the reaction of bromine with (E)-1,2-diphenylethene (trans-stilbene). Based on the results from the standard preparatory methods, some permutations of solvent and brominating reagent were tried.
Amburgey-Peters, Judith C.; Haynes, LeRoy W. J. Chem. Educ. 2005, 82, 1051.
Addition Reactions |
Alkenes |
Carbocations |
Diastereomers |
Enantiomers |
Mechanisms of Reactions |
Stereochemistry
|
Use of Enzymes in Organic Synthesis: Reduction of Ketones by Baker's Yeast Revisited James Patterson and Snorri Th. Sigurdsson
The undergraduate organic laboratory Bakers 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
|
Demonstrating Encapsulation and Release: A New Take on Alginate Complexation and the Nylon Rope Trick Andrienne C. Friedli and Inge R. Schlager
Three variations on a classroom demonstration of the encapsulation of droplets and evidence for release of the interior solution are described. The first two demonstrations mimic biocompatible applications of encapsulation. A third encapsulation exercise exploits the irreversible interfacial polymerization of diamine and diacid chloride to form membranes and illustrates the detection of diamine release from the capsule using an indicator.
Friedli, Andrienne C.; Schlager, Inge R. J. Chem. Educ. 2005, 82, 1017.
Biotechnology |
Acids / Bases |
Applications of Chemistry |
Carbohydrates |
Consumer Chemistry |
Membranes
|
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 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
|
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
|
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 Dambaski
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; Dambaski, Zdravko. J. Chem. Educ. 2004, 81, 1026.
Heterocycles |
Alkenes |
Stereochemistry |
Synthesis |
NMR Spectroscopy
|
Essentials of Carbohydrate Chemistry and Biochemistry, 2nd Edition (Thisbe K. Lindhorst) David J. A. Schedler
This book is aptly named: it is a well organized, well written presentation of the essentials of carbohydrate chemistry and their relationship to biochemistry.
Schedler, David J. A. J. Chem. Educ. 2004, 81, 808.
Carbohydrates
|
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 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
|
Food: The Chemistry of Its Components, 4th Edition (T. P. Coultrate) Richard Pagni
The book begins with an extensive discussion of the major constituents of food: sugars and their polymers, lipids, and amino acids and their polymers. This is followed by fascinating chapters on colors and flavors, the ingredients that do so much to make food enjoyable.
Pagni, Richard. J. Chem. Educ. 2004, 81, 39.
Consumer Chemistry |
Food Science |
Applications of Chemistry |
Carbohydrates |
Proteins / Peptides |
Lipids
|
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
|
Tensile Strength Measurements on Biopolymer Films Eugene S. Stevens and Mark D. Poliks
Measuring the tensile strength of biopolymer films using a simple student apparatus; results are compared with data obtained from industry-standard equipment.
Stevens, Eugene S.; Poliks, Mark D. J. Chem. Educ. 2003, 80, 810.
Biotechnology |
Carbohydrates |
Industrial Chemistry |
Laboratory Equipment / Apparatus |
Materials Science |
Proteins / Peptides
|
"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 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
|
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
|
Application of Datalogger in Biosensing: A Glucose Biosensor Martin M. F. Choi and Pui Shan Wong
Using an eggshell as a platform for the immobilization of glucose oxidase while determining glucose concentration through the depletion of oxygen as measured by an oxygen sensor and datalogger.
Choi, Martin M. F.; Wong, Pui Shan. J. Chem. Educ. 2002, 79, 982.
Carbohydrates |
Enzymes |
Instrumental Methods |
Laboratory Computing / Interfacing |
Qualitative Analysis |
Quantitative Analysis
|
Carbohydrate Analysis: Can We Control the Ripening of Bananas? S. Todd Deal, Catherine E. Farmer, and Paul F. Cerpovicz
Procedure to determine the carbohydrate composition of bananas at various stages of ripeness and testing various methods of storage for their effectiveness in preserving desirable qualities.
Deal, S. Todd; Farmer, Catherine E.; Cerpovicz, Paul F. J. Chem. Educ. 2002, 79, 479.
Carbohydrates |
Nutrition |
Food Science
|
Integrating HPLC and Electrochemistry: A LabVIEW-Based Pulsed Amperometric Detection System Mark B. Jensen
Using the voltametry of glucose to develop a method for the pulsed amperometric detection of carbohydrates (glucose, fructose, and sucrose) following their separation by liquid chromatography.
Jensen, Mark B. J. Chem. Educ. 2002, 79, 345.
Chromatography |
Electrochemistry |
Instrumental Methods |
HPLC |
Carbohydrates |
Separation Science |
Oxidation / Reduction
|
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
|
Factors Affecting Reaction Kinetics of Glucose Oxidase Kristin A. Johnson
Demonstration based on a biochemical kinetics experiment in which the rate of reaction varies with the enzyme concentration, substrate concentration, substrate used in the reaction, and temperature.
Johnson, Kristin A. J. Chem. Educ. 2002, 79, 74.
Enzymes |
Kinetics |
Proteins / Peptides |
Carbohydrates |
Catalysis |
Rate Law
|
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
|
An Inexpensive Water Jacket for a Polarimeter Tube F. A. Kundell and W. A. Adkins
Design and construction of an inexpensive water jacket for a polarimeter tube.
Kundell, F. A.; Adkins, W. A. J. Chem. Educ. 2001, 78, 1516.
Carbohydrates |
Kinetics |
Laboratory Equipment / Apparatus |
Laboratory Management
|
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
|
Chemical Laboratory Information Profile: Sucrose Jay A. Young
Properties, hazards, and storage requirements for sucrose.
Young, Jay A. J. Chem. Educ. 2001, 78, 1460.
Laboratory Management |
Physical Properties |
Carbohydrates
|
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
|
A Modification of a Lactase Experiment by Use of Commercial Test Strips Tammy J. Melton
Using urinalysis test strips to detect the presence of glucose.
Melton, Tammy J. J. Chem. Educ. 2001, 78, 1243.
Carbohydrates |
Catalysis |
Drugs / Pharmaceuticals |
Enzymes |
Nonmajor Courses |
Qualitative Analysis |
Laboratory Equipment / Apparatus
|
Ethanol Metabolism and the Transition from Organic Chemistry to Biochemistry Richard D. Feinman
Introducing alcohol dehydrogenase and aldehyde dehydrogenase reactions in organic chemistry to ease transition to biochemistry.
Feinman, Richard D. J. Chem. Educ. 2001, 78, 1215.
Metabolism |
Oxidation / Reduction |
Reactions |
Mechanisms of Reactions |
Alcohols |
Carbohydrates
|
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
|
Bioanalytical Experiments for the Undergraduate Laboratory: Monitoring Glucose in Sports Drinks J. Justin Gooding, Wenrong Yang, and Manihar Situmorang
Introducing students to the techniques of bioanalytical chemistry by using a solution-based enzyme assay and an enzyme electrode for the analysis of glucose concentrations in sports drinks.
Gooding, J. Justin; Yang, Wenrong; Situmorang, Manihar. J. Chem. Educ. 2001, 78, 788.
Electrochemistry |
Enzymes |
Food Science |
Quantitative Analysis |
Applications of Chemistry |
Carbohydrates
|
Surfactant-Induced Osazone Formation at Room Temperature K. Nagajyothi, P. S. Raghavan, and R. Gopalan
Using surfactants for speedy and easy identification of reducing sugars without heating.
Nagajyothi, K.; Raghavan, P. S.; Gopalan, R. J. Chem. Educ. 2001, 78, 728.
Catalysis |
Micelles |
Surface Science |
Carbohydrates |
Qualitative Analysis
|
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
|
Glycolysis Wordsearch Terry L. Helser
Puzzle with 30 names, terms, prefixes, and acronyms that describe glycolysis and fermentation.
Helser, Terry L. J. Chem. Educ. 2001, 78, 503.
Metabolism |
Nomenclature / Units / Symbols |
Carbohydrates
|
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
|
Correction to "Drug Metabolism: The Body's Defense against Chemical Attack" (J. Chem. Educ. 2000, 77, 349-353)
Corrections to molecular structures.
J. Chem. Educ. 2001, 78, 312.
Carbohydrates |
Drugs / Pharmaceuticals |
Enzymes |
Medicinal Chemistry |
Metabolism |
Synthesis
|
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
|
Enzymatic Spectrophotometric Reaction Rate Determination of Glucose in Fruit Drinks and Carbonated Beverages. An Analytical Chemistry Laboratory Experiment for Food Science-Oriented Students Argyro-Maria G. Vasilarou and Constantinos A. Georgiou
This laboratory experiment demonstrates the implementation of reaction rate kinetic methods of analysis, the use of enzymes as selective analytical reagents for the determination of substrates, the kinetic masking of ascorbic acid interference, and the analysis of glucose in drinks and beverages.
Vasilarou, Argyro-Maria G.; Georgiou, Constantinos A. J. Chem. Educ. 2000, 77, 1327.
Enzymes |
Food Science |
Kinetics |
Quantitative Analysis |
Carbohydrates
|
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
|
Letters
Points out that solid NaHSO3 does not exist.
Tudela, David. J. Chem. Educ. 2000, 77, 830.
Gases |
Oxidation / Reduction |
Carbohydrates
|
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
|
Sugar Wordsearch Terry L. Helser
Wordsearch puzzle containing 29 names, terms, prefixes and acronyms that describe sugars and their polymers.
Helser, Terry L. J. Chem. Educ. 2000, 77, 480.
Carbohydrates |
Nomenclature / Units / Symbols
|
An Analytical Laboratory Experiment in Error Analysis: Repeated Determination of Glucose Using Commercial Glucometers Paul L. Edmiston and Theodore R. Williams
Glucometers measure reflectance from enzyme test strips to quantitate glucose concentrations in blood. Since the typical measurement takes less than two minutes, large data sets can be obtained for statistical analysis. Students design experiments to answer specific questions concerning the performance of the glucometers.
Edmiston, Paul L.; Williams, Theodore R. J. Chem. Educ. 2000, 77, 377.
Chemometrics |
Carbohydrates |
Enzymes
|
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
|
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
|
An Alternative Procedure for the Glucose Oxidase Assay of Glucose as Applied to the Lactase Activity Assay T. Corbin Mullis, Jeffery T. Winge, and S. Todd Deal
The glucose oxidase assay of glucose has been modified to eliminate the use of micropipets. The modification involves the use of disposable Pasteur pipets and a specified number of drops of each reagent. This simplified technique gives accurate and reproducible results.
Mullis, T. Corbin; Winge, Jeffery T.; Deal, S. Todd. J. Chem. Educ. 1999, 76, 1711.
Enzymes |
Carbohydrates |
Laboratory Equipment / Apparatus |
Laboratory Management
|
Identifying Softwoods and Hardwoods by Infrared Spectroscopy Brady Barker and Noel L. Owen
Infrared spectra of 45 softwoods and hardwoods have been recorded. The wavenumber values of the carbonyl stretching vibration and one of the ring-breathing modes of lignin are used to distinguish softwoods from hardwoods. The differences between the absorption bands for the softwoods and hardwoods in each instance are shown to be statistically significant.
Barker, Brady; Owen, Noel L. J. Chem. Educ. 1999, 76, 1706.
Carbohydrates |
Instrumental Methods |
IR Spectroscopy |
Plant Chemistry |
Molecular Properties / Structure
|
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
|
Demonstration of Optical Rotatory Dispersion of Sucrose S. M. Mahurin, R. N. Compton, and Richard N. Zare
A method for demonstrating and measuring the optical activity of chiral molecules in solution is described in which the rotation of linearly polarized light is directly observed at right angles to the propagation of light in the liquid.
Mahurin, S. M.; Compton, Robert N.; Zare, Richard N. J. Chem. Educ. 1999, 76, 1234.
Instrumental Methods |
Lasers |
Spectroscopy |
Carbohydrates
|
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
|
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
|
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
|
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
|
A Simple Method To Demonstrate the Enzymatic Production of Hydrogen from Sugar Natalie Hershlag, Ian Hurley, and Jonathan Woodward
In the experimental protocol described here, it has been demonstrated that the common sugar glucose can be used to produce hydrogen using two enzymes, glucose dehydrogenase and hydrogenase. No sophisticated or expensive hydrogen detection equipment is required-only a redox dye, benzyl viologen, which turns purple when it is reduced. The color can be detected by a simple colorimeter.
Hershlag, Natalie; Hurley, Ian; Woodward, Jonathan. J. Chem. Educ. 1998, 75, 1270.
Enzymes |
Kinetics |
UV-Vis Spectroscopy |
Carbohydrates |
Applications of Chemistry
|
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
|
Working with Enzymes - Where Is Lactose Digested? An Enzyme Assay for Nutritional Biochemistry Laboratories Sandi R. Pope, Tonya D. Tolleson, R. Jill Williams, Russell D. Underhill, and S. Todd Deal
An enzyme assay utilizing lactase enzyme from crushed LactAid tablets and a 5% lactose solution ("synthetic milk"). In the experiment, the students assay the activity of the enzyme on the "synthetic milk" at pHs of approximately 1, 6, and 8 with the stated goal of determining where lactose functions in the digestive tract. The activity of the lactase may be followed chromatographically or spectrophotometrically.
Pope, Sandi R.; Tolleson, Tonya D.; Williams, R. Jill; Underhill, Russell D.; Deal, S. Todd. J. Chem. Educ. 1998, 75, 761.
Enzymes |
Carbohydrates |
Catalysis |
Chromatography |
Spectroscopy |
Nutrition
|
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
|
A Mini-Qualitative Carbohydrate Analysis Session Johannes S. Malherbe and Cornelius J. Meyer
A qualitative analysis scheme for a limited selection of carbohydrates (i.e. some mono- and disaccharides) using a flowchart approach. Procedures, for the preparation of all reagents, the tests and a brief description of the results are detailed.
Malherbe, Johannes S.; Meyer, Cornelius J. J. Chem. Educ. 1997, 74, 1304.
Carbohydrates |
Qualitative Analysis |
Nonmajor Courses
|
Protecting Groups in Carbohydrate Chemistry Sigthór Pétursson
The most important protecting groups in carbohydrate chemistry are reviewed. The paper is aimed at those beginning to specialize in synthetic carbohydrate chemistry and at teachers with other specialties who wish to go beyond the content of general organic chemistry textbooks.
Petursson, Sigthor. J. Chem. Educ. 1997, 74, 1297.
Carbohydrates |
Molecular Properties / Structure |
Synthesis
|
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
|
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
|
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
|
Laser-Based Liquid Prism Sucrosemeter - A Precision Optical Method to Find Sugar Concentration V. Anantha Narayanan and Radha Narayanan
A hollow prism was used in the minimum deviation position to investigate the refraction in a series of aqueous solutions of varying sucrose content. The 6328 A red line of the He-Ne 1 mW laser was used as the light source. Calibration graph of % weight of sucrose vs minimum linear deviation between incident and refracted rays is given. Sources of errors are discussed. The calibration graph was tested with success on three control sugar solutions.
Narayanan, V. Anantha; Narayanan, Radha. J. Chem. Educ. 1997, 74, 221.
Carbohydrates |
Lasers
|
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
|
Following Microscale Organic Reactions Using FT-IR Janice Ems-Wilson
This article describes an experiment that encourages discussion of carbohydrate chemistry in terms of reaction mechanisms, conformational analysis, and spectroscopy. The specific experiment involves the preparation of the bis(acetonide) of D-(+)-mannose.
Ems-Wilson, Janice. J. Chem. Educ. 1996, 73, A170.
Microscale Lab |
Carbohydrates |
Mechanisms of Reactions |
Conformational Analysis |
Spectroscopy |
Synthesis |
Aldehydes / Ketones |
Alcohols
|
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
|
The Use of a "Qual" Centrifuge for Greatly Simplifying and Speeding the Study of Milk Quentin R. Petersen
Laboratory study of the constituents of milk is almost always slowed by difficult separation of relatively large amounts of curd and whey by filtration. In the two-and-one-half hour experiment described, only 5 mL of skim milk is used and the curd is separated from the whey by using a simple "qual" centrifuge.
J. Chem. Educ. 1996, 73, 848.
Proteins / Peptides |
Carbohydrates |
Qualitative Analysis
|
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
|
A Simple Experiment Demonstrating the Temperature Effect in Supramolecular Chemistry Pawel K. Zarzycki and Henryk Lamparczyk
The aim of the experiment described in this article is to demonstrate the temperature influence on creation of an inclusion complex in which beta-cyclodextrin is the host molecule and phenolophtalein is the guest.
Zarzycki, Pawel K.; Lamparczyk, Henryk. J. Chem. Educ. 1996, 73, 459.
Molecular Properties / Structure |
Carbohydrates |
Separation Science
|
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
|
Procedure Modification for the Use of Corn Starch Packing Puffs for Titration Endpoints Judith M. Bonicamp
This short article describes the use of Eco-Foam cornstarch packing puffs to make starch indicator solution.
Bonicamp, Judith M. J. Chem. Educ. 1996, 73, 258.
Titration / Volumetric Analysis |
Acids / Bases |
Carbohydrates
|
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
|
Methods in Carbohydrate Chemistry. Volume 10, Enzymic Methods (BeMiller, James N.)
New title in a continuing series.
J. Chem. Educ. 1995, 72, A109.
Carbohydrates |
Enzymes
|
Car + Bow + Hide + 8 + Chemist Tree Terry L. Helser
Carbohydrate rebus puzzle.
Helser, Terry L. J. Chem. Educ. 1995, 72, 1124.
Carbohydrates |
Enrichment / Review Materials
|
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
|
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
|
Di-O-Isopropylidene-Mannofuranose: An Introduction to Sugar Protecting Groups Darcy, Raphael
The author describes the preparation of di-O-isopropylidene mannose as an introduction to sugar protecting-group chemistry, and an update for undergraduate sugar chemistry.
Darcy, Raphael J. Chem. Educ. 1994, 71, 1090.
Carbohydrates
|
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
|
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
|
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
|
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
|
A Handy Reagent for Testing the Reducing Power of Sugars Sandell, Arvid
Using the reduction of copper(II) as a semi-quantitative test for reducing sugars.
Sandell, Arvid J. Chem. Educ. 1994, 71, 346.
Carbohydrates |
Oxidation / Reduction |
Coordination Compounds
|
The Blue Bottle Experiment Revisited: How Blue? How Sweet? Cook, A. Gilbert; Tolliver, Randi M.; Williams, Janelle E.
Determining whether other colors and carbohydrates are possible with the "Blue Bottle" reaction.
Cook, A. Gilbert; Tolliver, Randi M.; Williams, Janelle E. J. Chem. Educ. 1994, 71, 160.
Aromatic Compounds |
Reactions |
Rate Law |
Mechanisms of Reactions |
Carbohydrates |
Oxidation / Reduction
|
An Informative Model of Haworth Structures Rowe, H. Alan.
Exercise that gives students experience in manipulating Hawthorn structures.
Rowe, H. Alan. J. Chem. Educ. 1994, 71, 131.
Molecular Properties / Structure |
Carbohydrates
|
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
|
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
|
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
|
An inexpensive gel-filtration chromatography experiment: A simple biochemical laboratory exercise for high school and undergraduate students who make their own column and apply simple detection techniques Rowe, H. Alan
The experiment described in this paper can be conducted with a minimum of supplies and equipment at the high school or undergraduate level thus lowering the usual barriers an exercise of this type presents.
Rowe, H. Alan J. Chem. Educ. 1993, 70, 415.
Chromatography |
Bioorganic Chemistry |
Laboratory Equipment / Apparatus |
Carbohydrates |
Proteins / Peptides
|
Biodegradable films: Based on partially hydrolyzed corn starch or potato starch Sommerfeld, Herbert; Blume, Rudiger
Demonstration of the promising developments in starch chemistry can be done with short and relevant classroom experiments.
Sommerfeld, Herbert; Blume, Rudiger J. Chem. Educ. 1992, 69, A151.
Carbohydrates |
Natural Products
|
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
|
New source for starch solutions: Biodegradable pellets de Moura, John M.
Convenient way to prepare starch indicator for use in iodine titrations or in "clock" reactions.
de Moura, John M. J. Chem. Educ. 1992, 69, 860.
Carbohydrates |
Titration / Volumetric Analysis
|
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
|
Preparation of sucrose octaacetate-A bitter-tasting compound. Mann, Thierry D.; Mosher, James D.; Wood, William F.
Acetylation of the eight hydroxy groups of sucrose changes its sweet taste to intensely bitter.
Mann, Thierry D.; Mosher, James D.; Wood, William F. J. Chem. Educ. 1992, 69, 668.
Synthesis |
Carbohydrates |
Catalysis
|
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
|
The howling gummy bear Sullivan, Dan M.
This demonstration illustrates the fact that we consume high-energy foods in order to obtain the reduced carbon they contain.
Sullivan, Dan M. J. Chem. Educ. 1992, 69, 326.
Carbohydrates |
Food Science |
Calorimetry / Thermochemistry
|
Inclass interactive worksheets for organic chemistry Ostercamp, Daryl L.
The author has designed two in-class worksheets for use near the end of a two semester organic chemistry course, one dealing with mono- and disaccharides and the second dealing with alpha-amino acids and dipeptides.
Ostercamp, Daryl L. J. Chem. Educ. 1992, 69, 318.
Carbohydrates |
Amino Acids |
Proteins / Peptides
|
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
|
NMR and the structure of D-glucose Gurst, Jerome E.
A discussion of typical organic chemistry textbook treatment of NMR evidence of glucose structure.
Gurst, Jerome E. J. Chem. Educ. 1991, 68, 1003.
Carbohydrates |
NMR Spectroscopy
|
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
|
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
|
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
|
The energetics of aerobic versus anaerobic respiration: A biophysical chemistry laboratory experiment using an adiabatic calorimeter Champion, Timothy D.; Schwenz, Richard W.
The authors describe an exercise in which they measure the difference in energy gained from aerobic and anaerobic oxidation of glucose.
Champion, Timothy D.; Schwenz, Richard W. J. Chem. Educ. 1990, 67, 528.
Calorimetry / Thermochemistry |
Biophysical Chemistry |
Carbohydrates
|
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
|
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
|
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
|
Using an oval to represent carbohydrates with hexopyranose rings Fulkrod, John E.
An shorthand alternative to representing hexopyranose rings using chair conformation structures.
Fulkrod, John E. J. Chem. Educ. 1989, 66, 485.
Carbohydrates |
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
|
Qualitative versus quantitative results: An experimental introduction to data interpretation Johnson, Eric R.; Alter, Paula
This paper describes an experiment in which the student can ascertain the meaning of a negative result from a quantitative test on the same sample.
Johnson, Eric R.; Alter, Paula J. Chem. Educ. 1989, 66, 440.
Qualitative Analysis |
Quantitative Analysis |
Carbohydrates
|
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
|
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
|
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
|
The biochemistry of brewing Bering, Charles L.
There are few topics that hold the attention of students as much as the one presented in this paper.
Bering, Charles L. J. Chem. Educ. 1988, 65, 519.
Biological Cells |
Carbohydrates |
Applications of Chemistry |
Alcohols |
Metabolism |
Enzymes |
Biotechnology |
Molecular Biology |
Consumer Chemistry
|
A laboratory exercise in the determination of carbohydrate structures White, Bernard J.; Robyt, John F.
A laboratory exercise in the determination of carbohydrate structures that introduces students to important aspects of science, such as designing experiments, making observations, and testing hypotheses.
White, Bernard J.; Robyt, John F. J. Chem. Educ. 1988, 65, 164.
Carbohydrates
|
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
|
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
|
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
|
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
|
Tollens's test, fulminating silver, and silver fulminate Jenkins, Ian D.
Preparation, application, and misinformation regarding Tollens's test for aldehydes and reducing sugars.
Jenkins, Ian D. J. Chem. Educ. 1987, 64, 164.
Aldehydes / Ketones |
Carbohydrates |
Qualitative Analysis |
Laboratory Management
|
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
|
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
|
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
|
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
|
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
|
Total Synthesis of Natural Products: The 'Chiron' Approach (Hanessian, Stephen) Wade, Leroy G., Jr.
Details the use of carbohydrate derivatives as chiral starting points for the synthesis of chiral products.
Wade, Leroy G., Jr. J. Chem. Educ. 1985, 62, A190.
Natural Products |
Synthesis |
Carbohydrates |
Chirality / Optical Activity
|
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
|
Biochemistry off the shelf Wilson, Jerry L.
Rather than using animal sources for biochemistry experiments, non-animal sources are inexpensive, readily available, and require no special storage.
Wilson, Jerry L. J. Chem. Educ. 1985, 62, 796.
Enzymes |
Carbohydrates |
Lipids |
Metabolism
|
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
|
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
|
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
|
[Brand] rand the name with the linkage of the same Garrett, James M.
Tool for helping to remember the configuration of the glucosidic linkages in maltose and cellobiose.
Garrett, James M. J. Chem. Educ. 1984, 61, 665.
Carbohydrates |
Molecular Properties / Structure
|
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
|
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
|
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
|
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
|
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
|
A correction on the Benedict test Hill, William D., Jr.
Sodium hydroxide is also needed for the formation of copper(I) oxide in the identification of carbohydrates.
Hill, William D., Jr. J. Chem. Educ. 1982, 59, 334.
Qualitative Analysis |
Carbohydrates
|
Invert sugar (and a honey of a problem) Wendland, Ray
Question regarding the optical rotation of sucrose, and a sucrose/dextrose/levulose mixture.
Wendland, Ray J. Chem. Educ. 1982, 59, 217.
Carbohydrates |
Chirality / Optical Activity |
Enzymes
|
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
|
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
|
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
|
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
|
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
|
The metabolism of carbohydrates
Traces the metabolism of carbohydrates and the flow of materials among the various resource pools in living systems.
J. Chem. Educ. 1979, 56, 534.
Carbohydrates |
Metabolism |
Bioenergetics
|
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
|
Salt effects on the hydrolysis of sucrose Dordick, Robert S.; Clarke, George A.
Under the appropriate conditions, the acid-catalyzed hydrolysis of sucrose follows pseudo-first order kinetics.
Dordick, Robert S.; Clarke, George A. J. Chem. Educ. 1979, 56, 352.
Carbohydrates |
Catalysis |
Kinetics
|
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
|
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
|
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
|
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
|
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
|
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
|
Cycloamyloses Bergeron, Raymond J.
Examines an unusual carbohydrate system of current interest in the hope of generating some enthusiasm for the topic.
Bergeron, Raymond J. J. Chem. Educ. 1977, 54, 204.
Carbohydrates |
Molecular Properties / Structure |
Thermodynamics |
Kinetics |
Enzymes |
Spectroscopy
|
Starch solubility Mitchell, W. A.
To state categorically that amylose is insoluble in water will leave many puzzled.
Mitchell, W. A. J. Chem. Educ. 1977, 54, 132.
Precipitation / Solubility |
Carbohydrates
|
Paper chromatography of carbohydrates Croft, L. R.; Haghighi, S.
A simple detection reagent for carbohydrates.
Croft, L. R.; Haghighi, S. J. Chem. Educ. 1977, 54, 112.
Chromatography |
Separation Science |
Carbohydrates
|
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
|
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
|
a[alpha]- and [bet]a-D-glucose pentaacetate. An experiment in structure assignment using NMR Pearson, Wesley A.; Spessard, Gary O.
The synthesis and structural determination of alpha- and beta-D-glucose pentaacetate.
Pearson, Wesley A.; Spessard, Gary O. J. Chem. Educ. 1975, 52, 814.
NMR Spectroscopy |
Carbohydrates |
Synthesis
|
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
|
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
|
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
|
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
|
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
|
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
|
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
|
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
|
Questions [and] Answers Campbell, J. A.
Five questions requiring an application of chemical principles and their solutions.
Campbell, J. A. J. Chem. Educ. 1973, 50, 128.
Enrichment / Review Materials |
Proteins / Peptides |
pH |
Carbohydrates |
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
|
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
|
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
|
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
|
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
|
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
|
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
|
Letter to the editor Bhatnagar, Vijay Mohan
Distinguishes between alpha- and beta-amylose and their mixtures, particular with respect to iodimetric titrations.
Bhatnagar, Vijay Mohan J. Chem. Educ. 1967, 44, 771.
Titration / Volumetric Analysis |
Carbohydrates
|
Reaction rate analysis and instrumentation: An experiment for the analytical laboratory Pardue, Harry L.; Burke, Michael F.; Jones, David O.
This experiment exemplifies the use of operational amplifiers for measurement and analog computation in determining the glucose utilizing glucose enzyme.
Pardue, Harry L.; Burke, Michael F.; Jones, David O. J. Chem. Educ. 1967, 44, 684.
Kinetics |
Rate Law |
Catalysis |
Enzymes |
Carbohydrates
|
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
|
The use of talc as a tlc adsorbent Walsh, Brother Joseph M.
Describes the use of talc as a thin layer chromatography adsorbent, particularly with respect to the separation of flavonoids, sugars, and proteins.
Walsh, Brother Joseph M. J. Chem. Educ. 1967, 44, 294.
Thin Layer Chromatography |
Chromatography |
Separation Science |
Proteins / Peptides |
Carbohydrates
|
Determination of glucose: A kinetics experiment for the analytical course Toren, E. Clifford, Jr.
This determination of glucose demonstrates both kinetic and enzymatic methods of analysis.
Toren, E. Clifford, Jr. J. Chem. Educ. 1967, 44, 172.
Quantitative Analysis |
Carbohydrates |
Kinetics |
Enzymes
|
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
|
Letter to the editor Garrigan, George A.
Comments on the teaching potential of an earlier published experiment involving the acid catalyzed hydrolysis of sucrose.
Garrigan, George A. J. Chem. Educ. 1966, 43, 681.
Carbohydrates |
Mechanisms of Reactions |
Catalysis
|
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
|
Polyethylene and pipecleaner models of biological polymers Pollard, Harvey Bruce
An accurate method for modeling polysaccharides, nucleic acids, and proteins involves the use of pipecleaners, polyethylene tubing, and proteins.
Pollard, Harvey Bruce J. Chem. Educ. 1966, 43, 327.
Proteins / Peptides |
Molecular Modeling |
Molecular Properties / Structure |
Carbohydrates
|
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
|
A panoramic approach to the proof of configuration of aldohexoses Rosenblatt, David H.
Presents a didactic approach to the classical proofs of configuration of aldohexoses.
Rosenblatt, David H. J. Chem. Educ. 1965, 42, 271.
Molecular Properties / Structure |
Carbohydrates
|
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
|
Effect of liquid NH3 on wood: A demonstration of the alcohol structure of cellulose Hirsch, Phillis R.
A lecture demonstration of the plasticization of wood with liquid ammonia can be a very effective tool for teaching the alcohol structure of cellulose to any class studying basic organic chemistry.
Hirsch, Phillis R. J. Chem. Educ. 1964, 41, 605.
Carbohydrates |
Alcohols |
Molecular Properties / Structure
|
Evidence for the configuration on carbon 1 of d-glucose Sickels, Jackson P.; Schultz, Harry P.
The pyranose forms of alpha- and beta-D-glucose, because of the cyclohexane conformations of their six-membered rings, do not explain the results of the conductivity of these sugars in boric acid.
Sickels, Jackson P.; Schultz, Harry P. J. Chem. Educ. 1964, 41, 343.
Molecular Properties / Structure |
Carbohydrates
|
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
|
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
|
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
|
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
|
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
|
The geometry of giant molecules Price, Charles C.
The author examines a variety of specific examples of natural and synthetic polymer molecules and describes how their geometric molecular arrangements influence their properties.
Price, Charles C. J. Chem. Educ. 1959, 36, 160.
Molecular Properties / Structure |
Proteins / Peptides |
Carbohydrates
|
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
|
Ciphered formulas in carbohydrate chemistry Difini, Alvaro; Neto, Jose Difini
Describes the use of schematic formulas as an aid to rapidly representing configurations for monosaccharides.
Difini, Alvaro; Neto, Jose Difini J. Chem. Educ. 1958, 35, 38.
Carbohydrates |
Nomenclature / Units / Symbols |
Molecular Properties / Structure |
Chirality / Optical Activity
|
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
|
Schematic models of biochemical polymers Blackwell, R. Quentin
Demonstrates the use of plastic necklace beads to represent polysaccharides, peptides and proteins, and nucleotides.
Blackwell, R. Quentin J. Chem. Educ. 1957, 34, 500.
Molecular Modeling |
Molecular Properties / Structure |
Proteins / Peptides |
Carbohydrates
|
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 mnemonic for the monosaccharides Leary, R. H.
Presents a mnemonic for the D-series monosaccharides.
Leary, R. H. J. Chem. Educ. 1955, 32, 409.
Carbohydrates
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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
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A mnemonic acid for aldoses Deloach, Will S.; Brandon, Ann
Presents a mnemonic aid for remembering the D-aldoses (through the hexoses).
Deloach, Will S.; Brandon, Ann J. Chem. Educ. 1955, 32, 136.
Nomenclature / Units / Symbols |
Carbohydrates
|
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
|
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