TIGER

Journal Articles: 406 results
Designing and Conducting a Purification Scheme as an Organic Chemistry Laboratory Practical  Kate J. Graham, Brian J. Johnson, T. Nicholas Jones, Edward J. McIntee, and Chris P. Schaller
Describes an open-ended laboratory practical that challenges students to evaluate when different purification techniques are appropriate.
Graham, Kate J.; Johnson, Brian J.; Jones, T. Nicholas; McIntee, Edward J.; Schaller, Chris P. J. Chem. Educ. 2008, 85, 1644.
IR Spectroscopy |
Microscale Lab |
Molecular Properties / Structure |
NMR Spectroscopy |
Physical Properties |
Separation Science
NMR and IR Spectroscopy for the Structural Characterization of Edible Fats and Oils  Molly W. Crowther
This article describes an upper-level instrumental laboratory for undergraduates that explores the complementary nature of IR and NMR spectroscopy in the analysis of five edible and structurally similar fats and oils for average chain length, degree of unsaturation, and trans fat content.
Crowther, Molly W. J. Chem. Educ. 2008, 85, 1550.
Consumer Chemistry |
Food Science |
IR Spectroscopy |
NMR Spectroscopy |
Qualitative Analysis |
Spectroscopy |
Fatty Acids
The Synthesis of a Cockroach Pheromone  Patty L. Feist
This paper describes the synthesis of gentisyl quinone isovalerate or blattellaquinone, a sex pheromone of the German cockroach and a compound with real-world applications. The experiment also affords students practice in extraction as well as IR and NMR spectroscopy.
Feist, Patty L. J. Chem. Educ. 2008, 85, 1548.
Esters |
IR Spectroscopy |
Natural Products |
NMR Spectroscopy |
Oxidation / Reduction |
Synthesis
A More Challenging Interpretative Nitration Experiment Employing Substituted Benzoic Acids and Acetanilides  Edward M. Treadwell and Tung-Yin Lin
An experiment is described involving the nitration of ortho or meta, monosubstituted benzoic acids and monochlorinated acetanilides with nitric acid to evaluate the regioselectivity of addition through computational methods and 1H NMR spectroscopy.
Treadwell, Edward M.; Lin, Tung-Yin. J. Chem. Educ. 2008, 85, 1541.
Aromatic Compounds |
Computational Chemistry |
Electrophilic Substitution |
Molecular Modeling |
NMR Spectroscopy |
Synthesis
The Synthesis of N-Benzyl-2-azanorbornene via Aqueous Hetero Diels–Alder Reaction  Xavier Sauvage and Lionel Delaude
Characterization of the product of this organic synthesis through IR and NMR data analysis provides valuable material to familiarize students with different types of protonproton coupling patterns and their typical ranges, serves to illustrate the concepts of green chemistry and atom efficiency, and can be used to exemplify structural analysis and computational studies.
Sauvage, Xavier; Delaude, Lionel. J. Chem. Educ. 2008, 85, 1538.
Alkenes |
Aqueous Solution Chemistry |
Conformational Analysis |
Green Chemistry |
IR Spectroscopy |
Molecular Modeling |
NMR Spectroscopy |
Stereochemistry |
Synthesis
A One-Pot, Asymmetric Robinson Annulation in the Organic Chemistry Majors Laboratory  Kiel E. Lazarski, Alan A. Rich, and Cheryl M. Mascarenhas
Describes a one-pot, enantioselective, Robinson annulation geared towards the second-year organic chemistry major and demonstrating aspects of green chemistry.
Lazarski, Kiel E.; Rich, Alan A.; Mascarenhas, Cheryl M. J. Chem. Educ. 2008, 85, 1531.
Aldehydes / Ketones |
Asymmetric Synthesis |
Catalysis |
Chirality / Optical Activity |
Gas Chromatography |
HPLC |
NMR Spectroscopy |
Synthesis |
Green Chemistry
Synthesis of the Commercial Antidepressant Moclobemide   Jesse D. More
Describes an experiment for the undergraduate organic chemistry laboratory in which students synthesize the commercial antidepressant drug moclobemide, marketed under the trade name Manerix, in one step using commercially available material. The purity and identity of the product are confirmed by melting point and NMR and IR spectroscopy.
More, Jesse D. J. Chem. Educ. 2008, 85, 1424.
Drugs / Pharmaceuticals |
IR Spectroscopy |
Medicinal Chemistry |
NMR Spectroscopy |
Synthesis
Quantitative Analysis of Nail Polish Remover Using Nuclear Magnetic Resonance Spectroscopy Revisited  Markus M. Hoffmann, Joshua T. Caccamis, Mark P. Heitz, and Kenneth D. Schlecht
Substantial modifications intended for a second- or third-year laboratory course in analytical chemistry are presented for a previously described procedure using NMR spectroscopy to quantitatively determine analytes in commercial nail polish remover. The revised experiment introduces student collaboration to critically interpret a relatively large set of data.
Hoffmann, Markus M.; Caccamis, Joshua T.; Heitz, Mark P.; Schlecht, Kenneth D. J. Chem. Educ. 2008, 85, 1421.
Alcohols |
Aldehydes / Ketones |
Consumer Chemistry |
Instrumental Methods |
Laboratory Equipment / Apparatus |
NMR Spectroscopy |
Quantitative Analysis
The Discovery-Oriented Approach to Organic Chemistry. 7. Rearrangement of trans-Stilbene Oxide with Bismuth Trifluoromethanesulfonate and Other Metal Triflates  James E. Christensen, Matthew G. Huddle, Jamie L. Rogers, Herbie Yung, and Ram S. Mohan
Presents a microscale, green organic chemistry laboratory experiment that illustrates the utility of metal triflates, especially bismuth triflate, as a Lewis acid catalyst. Bismuth compounds are especially attractive for use as catalysts in organic synthesis because of their low toxicity, low cost, and ease of handling.
Christensen, James E.; Huddle, Matthew G.; Rogers, Jamie L.; Yung, Herbie; Mohan, Ram S. J. Chem. Educ. 2008, 85, 1274.
Catalysis |
Epoxides |
Green Chemistry |
Lewis Acids / Bases |
Mechanisms of Reactions |
Microscale Lab |
NMR Spectroscopy
The Comparative Nucleophilicity of Naphthoxide Derivatives in Reactions with a Fast-Red TR Dye  Cheryl M. Mascarenhas
In this experiment, organic chemistry students perform reactions between three naphthyl acetate derivatives and the diazonium salt Fast-Red TR. Students discover under what conditions the hydrolysis and electrophilic aromatic substitution is fastest and slowest, allowing them to conclude that latter, rather than the former, is rate-limiting.
Mascarenhas, Cheryl M. J. Chem. Educ. 2008, 85, 1271.
Alcohols |
Aromatic Compounds |
Dyes / Pigments |
Esters |
IR Spectroscopy |
NMR Spectroscopy |
Synthesis |
Thin Layer Chromatography |
UV-Vis Spectroscopy
"As Simple as Possible, but Not Simpler"—The Case of Dehydroascorbic Acid  Robert C. Kerber
Textbooks routinely assign dehydroascorbic acid a tricarbonyl structure that is highly improbable in aqueous solution and inconsistent with its colorless appearance. Studies of oxidized forms of ascorbic acid are summarized here, and a plea is entered for accurate descriptions of chemical structures in this and other cases, even at the cost of some simplicity.
Kerber, Robert C. J. Chem. Educ. 2008, 85, 1237.
Bioorganic Chemistry |
Free Radicals |
Natural Products |
NMR Spectroscopy |
Vitamins
The Iodochlorination of Styrene: An Experiment That Makes a Difference  R. Gary Amiet and Sylvia Urban
This purpose of this laboratory exercise is to determine the various substitution and elimination products generated in the iodochlorination of styrene and their relative proportions through the application of mechanistic principles and a basic knowledge of GCMS and NMR.
Amiet, R. Gary; Urban, Sylvia. J. Chem. Educ. 2008, 85, 962.
Alkenes |
Constitutional Isomers |
Gas Chromatography |
Instrumental Methods |
Mass Spectrometry |
Mechanisms of Reactions |
NMR Spectroscopy |
Synthesis |
Student-Centered Learning
The Preparation and Enzymatic Hydrolysis of a Library of Esters  Elizabeth M. Sanford and Traci L. Smith
In this investigative case study, students work collaboratively to prepare and characterize a library of esters using Fischer esterification and alcoholysis of acid chlorides and their subsequent enzymatic hydrolysis by pig liver and orange peel esterases.
Sanford, Elizabeth M.; Smith, Traci L. J. Chem. Educ. 2008, 85, 944.
Drugs / Pharmaceuticals |
Enzymes |
Esters |
Industrial Chemistry |
IR Spectroscopy |
NMR Spectroscopy |
Synthesis |
Thin Layer Chromatography
Polymer-Supported Reagents and 1H–19F NMR Couplings: The Synthesis of 2-Fluoroacetophenone  Nicola Pohl and Kimberly Schwarz
Describes an experiment in which 2-bromoacetophenone is converted to 2-fluoroacetophenone using a solid-phase nucleophilic fluorine source. The experiment introduces students to the utility of solid-phase reagents in organic synthesis, to NMR-active nuclei other than 1H without the requirement of a special NMR probe, and to the unique uses of fluorine in molecular design.
Pohl, Nicola; Schwarz, Kimberly. J. Chem. Educ. 2008, 85, 834.
Aldehydes / Ketones |
NMR Spectroscopy |
Nucleophilic Substitution |
Synthesis
Identification of an Unknown Compound by Combined Use of IR, 1H NMR, 13C NMR, and Mass Spectrometry: A Real-Life Experience in Structure Determination  Louis J. Liotta and Magdalena James-Pederson
In this introductory organic chemistry experiment, students are expected to operate NMR, IR, and GCMS instrumentation to obtain spectra which are interpreted to elucidate the chemical structure of the assigned compounds without the benefit of a list of possible unknowns.
Liotta, Louis J.; James-Pederson, Magdalena. J. Chem. Educ. 2008, 85, 832.
Gas Chromatography |
Instrumental Methods |
IR Spectroscopy |
Mass Spectrometry |
Molecular Properties / Structure |
NMR Spectroscopy |
Qualitative Analysis |
Spectroscopy
Acid-Catalyzed Enolization of β-Tetralone  Brahmadeo Dewprashad, Anthony Nesturi, and Joel Urena
This experiment allows students to use 1H NMR to compare the rates of substitution of benzylic and non-benzylic a hydrogens of -tetralone and correlate their findings with predictions made by resonance theory.
Dewprashad, Brahmadeo; Nesturi, Anthony; Urena, Joel. J. Chem. Educ. 2008, 85, 829.
Aldehydes / Ketones |
Isotopes |
Mechanisms of Reactions |
NMR Spectroscopy |
Reactive Intermediates |
Resonance Theory |
Synthesis
The Baeyer–Villiger Oxidation with Trifluoroacetic Acid and Household Sodium Percarbonate  Richard A. Kjonaas and Anthony E. Clemons
Reports a method for carrying out the BaeyerVilliger oxidation of cyclopentanone to d-valerolactone in a large-section introductory organic chemistry laboratory course.
Kjonaas, Richard A.; Clemons, Anthony E. J. Chem. Educ. 2008, 85, 827.
Aldehydes / Ketones |
Esters |
NMR Spectroscopy |
Oxidation / Reduction |
Synthesis
Mosher Amides: Determining the Absolute Stereochemistry of Optically-Active Amines  Damian A. Allen, Anthony E. Tomaso, Jr., Owen P. Priest, David F. Hindson, and Jamie L. Hurlburt
In this experiment, teams of students are given an optically-pure amine of known structure but unknown stereochemistry. Different teams derivatize samples of the amine with (R) and (S) conformations of Mosher's acid chloride. The resulting diastereomers are analyzed by NMR to determine the absolute configuration of the initial, unknown amine.
Allen, Damian A.; Tomaso, Anthony E., Jr.; Priest, Owen P.; Hindson, David F.; Hurlburt, Jamie L. J. Chem. Educ. 2008, 85, 698.
Amides |
Chirality / Optical Activity |
Chromatography |
Diastereomers |
Microscale Lab |
NMR Spectroscopy |
Stereochemistry
A Nitration Reaction Puzzle for the Organic Chemistry Laboratory  Milton J. Wieder and Russell Barrows
Treatment of phenylacetic acid with different concentrations of nitric acid yields two different products. Using 1H NMR and IR spectral data, students are asked to deduce the structures of the two products, thus illustrating fundamental concepts in electrophilic aromatic substitution while posing an interesting structure elucidation puzzle.
Wieder, Milton J.; Barrows, Russell. J. Chem. Educ. 2008, 85, 549.
Constitutional Isomers |
Mass Spectrometry |
NMR Spectroscopy |
Synthesis |
Titration / Volumetric Analysis
Alternative pH-Shift Ion-Exchange Chromatography: Quantitative Spectroscopic Monitoring of the Progress of a Reaction   Concepción López, Manuel Martínez, Mercè Rocamora, and Laura Rodríguez
In this experiment, the solvolysis of [CoCl(NH3)5]2+ in nonaqueous (H3PO4) is followed by an alternative way of using ion-exchange chromatography that relies on changing the charge of the product through a shift in pH. Subsequent hydrolysis of the resulting complex is monitored and compared using UVvis and 31P NMR spectroscopy.
López, Concepción; Martínez, Manuel; Rocamora, Mercè; Rodríguez, Laura. J. Chem. Educ. 2008, 85, 426.
Chromatography |
Coordination Compounds |
Ion Exchange |
NMR Spectroscopy |
UV-Vis Spectroscopy
A Three-Step Laboratory Sequence To Prepare a Carbene Complex of Silver(I) Chloride  John P. Canal, Taramatee Ramnial, Lisa D. Langlois, Colin D. Abernethy, and Jason A. C. Clyburne
Presents a multistep inorganic synthesisof N-heterocyclic carbenes that introduces students to modern organometallic chemistry, multinuclear NMR (1H and 13C) spectroscopy, and novel coordination geometries and valence states of carbon.
Canal, John P.; Ramnial, Taramatee; Langlois, Lisa D.; Abernethy, Colin D.; Clyburne, Jason A. C. J. Chem. Educ. 2008, 85, 416.
Coordination Compounds |
NMR Spectroscopy |
Organometallics |
Synthesis
Synthesis and Characterization of 9-Hydroxyphenalenone Using 2D NMR Techniques  Benjamin Caes and Dell Jensen Jr.
The synthesis of 9-Hydroxyphenalenone produces a planar multicyclic beta-ketoenol, the tautomerization of which results in C2v symmetry on the NMR time scale, thus simplifying the spectra and providing a unique structure for teaching 2D NMR spectroscopy.
Caes, Benjamin; Jensen, Dell, Jr. J. Chem. Educ. 2008, 85, 413.
Alcohols |
Aldehydes / Ketones |
Aromatic Compounds |
IR Spectroscopy |
NMR Spectroscopy |
Synthesis
Why Are 1H NMR Integrations Not Perfect? An Inquiry-Based Exercise for Exploring the Relationship Between Spin Dynamics and NMR Integration in the Organic Lab  Haim Weizman
When FT-NMR is used to collect data without a sufficient delay time between subsequent pulses, the integrated area under certain peaks may result in a lower value than should be observed under appropriate conditions. This exercise is designed to raise awareness of this issue in students and to serve as an inquiry-based stepping-stone into basic FT-NMR.
Weizman, Haim. J. Chem. Educ. 2008, 85, 294.
Aldehydes / Ketones |
Microscale Lab |
NMR Spectroscopy
Peer Mentoring in the General Chemistry and Organic Chemistry Laboratories  Caleb A. Arrington, Jameica B. Hill, Ramin Radfar, David M. Whisnant, and Charles G. Bass
This article describes a discovery experiment in which organic chemistry students act as mentors to general chemistry students. Members from both groups work together to isolate an unknown compound using distillation. The structure of the product is then determined collaboratively using IR and NMR spectroscopy.
Arrington, Caleb A.; Hill, Jameica B.; Radfar, Ramin; Whisnant, David M.; Bass, Charles G. J. Chem. Educ. 2008, 85, 288.
IR Spectroscopy |
NMR Spectroscopy
Regioselectivity in Organic Synthesis: Preparation of the Bromohydrin of α-Methylstyrene  Brad Andersh, Kathryn N. Kilby, Meghan E. Turnis, and Drew L. Murphy
In the described experiment, the regiochemical outcome of the addition of "HOBr" to a-methylstyrene is investigated. Although both "classic" qualitative analysis and instrumental techniques are described, the emphasis of this experiment is on the utilization 13C and DEPT-135 NMR spectroscopy to determine the regiochemical outcome of the addition.
Andersh, Brad; Kilby, Kathryn N.; Turnis, Meghan E.; Murphy, Drew L. J. Chem. Educ. 2008, 85, 102.
Addition Reactions |
Alcohols |
Alkenes |
Constitutional Isomers |
IR Spectroscopy |
Microscale Lab |
NMR Spectroscopy |
Synthesis
A Discovery-Based Experiment Involving Rearrangement in the Conversion of Alcohols to Alkyl Halides  Richard A. Kjonaas and Ryand J. F. Tucker
This article reports a discovery-based experiment in which students convert three alcohols to alkyl halides under acidic conditions and record the 13C NMR spectrum in each case. By comparing the number of resonances observed with the number of resonances predicted for each possible product, students draw several conclusions about the resulting rearrangement.
Kjonaas, Richard A.; Tucker, Ryand J. F. J. Chem. Educ. 2008, 85, 100.
Alcohols |
Carbocations |
Gas Chromatography |
NMR Spectroscopy |
Nucleophilic Substitution
Microwave-Assisted Organic Synthesis in the Organic Teaching Lab: A Simple, Greener Wittig Reaction  Eric Martin and Cynthia Kellen-Yuen
A microwave-assisted Wittig reaction has been developed for the organic teaching laboratory. Utilizing this technique, a variety of styrene derivatives have been synthesized from aromatic aldehydes in good yields. The mixture of cis and trans alkenes produced also provides instructors with opportunities to emphasize the spectroscopic analysis of product mixtures.
Martin, Eric; Kellen-Yuen, Cynthia. J. Chem. Educ. 2007, 84, 2004.
Aldehydes / Ketones |
Alkenes |
Chromatography |
Green Chemistry |
Mass Spectrometry |
NMR Spectroscopy |
Spectroscopy |
Synthesis
Synthesis of Quaternary Ammonium Salts of Tricyclic Cationic Drugs: A One-Pot Synthesis for the Bioorganic Chemistry Laboratory  Linda S. Brunauer, Abid C. Mogannam, Won B. Hwee, and James Y. Chen
Describes a one-pot conversion of tricyclic cationic drugs to their quaternary ammonium forms for a widely used bioactive drug, chlorpromazine, a phenothiazine-based antipsychotic. The conversion of parent drug to the methylated form was evaluated by qualitatively measuring its ability to induce alterations in the shape of mammalian erythrocytes.
Brunauer, Linda S.; Mogannam, Abid C.; Hwee, Won B.; Chen, James Y. J. Chem. Educ. 2007, 84, 1992.
Amines / Ammonium Compounds |
Bioorganic Chemistry |
Drugs / Pharmaceuticals |
IR Spectroscopy |
Microscale Lab |
NMR Spectroscopy |
Synthesis |
Thin Layer Chromatography
Isolation of Betulin and Rearrangement to Allobetulin  Brian Green, Michael D. Bentley, Bong Y. Chung, Nicholas G. Lynch, and Bruce L. Jensen
Betulin is obtained by extraction from birch bark and converted to allobetulin. Both compounds display 1H NMR spectra that include axialequatorial coupling characteristic of a C3-alcohol, conformational analysis by the use of dihedral angles and the Karplus equation, coupling patterns caused by diastereotopic protons and long-range interactions, and chemical shift values that are influenced by electronegativity and stereochemistry.
Green, Brian; Bentley, Michael D.; Chung, Bong Y.; Lynch, Nicholas G.; Jensen, Bruce L. J. Chem. Educ. 2007, 84, 1985.
Biosynthesis |
IR Spectroscopy |
Microscale Lab |
NMR Spectroscopy |
Synthesis |
Natural Products
Using Ozone in Organic Chemistry Lab: The Ozonolysis of Eugenol  Bruce M. Branan, Joshua T. Butcher, and Lawrence R. Olsen
This organic laboratory involves the ozonolysis of eugenol (clove oil) followed by a reductive workup that generates an aldehyde easily identified by its NMR and IR spectra.
Branan, Bruce M.; Butcher, Joshua T.; Olsen, Lawrence R. J. Chem. Educ. 2007, 84, 1979.
Aldehydes / Ketones |
Gases |
IR Spectroscopy |
Laboratory Equipment / Apparatus |
Natural Products |
NMR Spectroscopy |
Synthesis |
Oxidation / Reduction
Making Student-Acquired Spectra Available via a Web Browser  Jennifer L. Muzyka, Ian M. Kaster, and Lucas W. Hatcher
This paper reports on an approach to make student-acquired spectral data available via a Web browser that allows instrument time to be dedicated to acquisition of spectra rather than time-consuming integration and printing.
Muzyka, Jennifer L.; Kaster, Ian M.; Hatcher, Lucas W. J. Chem. Educ. 2007, 84, 1871.
IR Spectroscopy |
Laboratory Computing / Interfacing |
NMR Spectroscopy |
Spectroscopy
Determination of Solvent Effects on Keto—Enol Equilibria of 1,3-Dicarbonyl Compounds Using NMR  A. Gilbert Cook and Paul M. Feltman
Expands the classic physical chemistry experiment using of proton NMR to determine the equilibrium position of tautomeric 1,3-dicarbonyl compounds in various solvents.
Cook, A. Gilbert; Feltman, Paul M. J. Chem. Educ. 2007, 84, 1827.
Aldehydes / Ketones |
Equilibrium |
Hydrogen Bonding |
Molecular Modeling |
Molecular Properties / Structure |
NMR Spectroscopy |
Solutions / Solvents |
Thermodynamics
Synthesis and Characterization of Aldol Condensation Products from Unknown Aldehydes and Ketones  Nicholas G. Angelo, Laura K. Henchey, Adam J. Waxman, James W. Canary, Paramjit S. Arora, and Donald Wink
Describes an experiment in which students perform the aldol condensation on an unknown aldehyde and ketone and make use of TLC, column chromatography, recrystallization, and characterization by 1H NMR, GCMS, and FTIR.
Angelo, Nicholas G.; Henchey, Laura K.; Waxman, Adam J.; Canary, James W.; Arora, Paramjit S.; Wink, Donald. J. Chem. Educ. 2007, 84, 1816.
Aldehydes / Ketones |
Chromatography |
Gas Chromatography |
IR Spectroscopy |
Mass Spectrometry |
NMR Spectroscopy |
Spectroscopy |
Thin Layer Chromatography
Determination of the Rotational Barrier for Kinetically Stable Conformational Isomers via NMR and 2D TLC  Gregory T. Rushton, William G. Burns, Judi M. Lavin, Yong S. Chong, Perry Pellechia, and Ken D. Shimizu
After the synthesis of a N,N'-diaryl naphthalene diimide, students estimate the rotational barrier about a CarylNimidesingle bond by studying the reequilibration of the two resulting isomers using two-dimensional thin-layer chromatography, followed by a more accurate determination through a 1H NMR time study.
Rushton, Gregory T.; Burns, William G.; Lavin, Judi M.; Chong, Yong S.; Pellechia, Perry; Shimizu, Ken D. J. Chem. Educ. 2007, 84, 1499.
Alcohols |
Chromatography |
Conformational Analysis |
Equilibrium |
Kinetics |
NMR Spectroscopy |
Physical Properties |
Rate Law |
Thin Layer Chromatography
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
A Knoevenagel Initiated Annulation Reaction Using Room Temperature or Microwave Conditions  A. Gilbert Cook
The product of a Knoevenagel initiated annulation reaction is identified through a guided prelab exercise of the synthesis of the Hagemann ester, and then through the analysis of GCMS, NMR, and IR spectra. The stereochemistry of the product is determined through the NMR spectrum and Karplus curve, and the student is required to write a mechanism for the reaction.
Cook, A. Gilbert. J. Chem. Educ. 2007, 84, 1477.
Aldehydes / Ketones |
Conformational Analysis |
Gas Chromatography |
IR Spectroscopy |
Mass Spectrometry |
Mechanisms of Reactions |
NMR Spectroscopy |
Stereochemistry |
Synthesis
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
A New Tool To Aid Students in NMR Interpretation  John V. McClusky
Presents a tool that allows students to logically analyze NMR spectra and to visualize how peak multiplicity reveals molecular connectivity.
McClusky, John V. J. Chem. Educ. 2007, 84, 983.
NMR Spectroscopy |
Spectroscopy
Oxidation of Aromatic Aldehydes Using Oxone  Rajani Gandhari, Padma P. Maddukuri, and Thottumkara K. Vinod
Describes an eco-friendly procedure for the oxidation of aldehydes to carboxylic acids in water or a water-ethanol mixture using Oxone as the oxidant. The use of eco-friendly solvents, a non-toxic reagent, and the elimination of extraction solvents in the procedure demonstrate important green chemistry themes to students.
Gandhari, Rajani; Maddukuri, Padma P.; Vinod, Thottumkara K. J. Chem. Educ. 2007, 84, 852.
Aldehydes / Ketones |
Aromatic Compounds |
Aqueous Solution Chemistry |
Carboxylic Acids |
Green Chemistry |
Mechanisms of Reactions |
NMR Spectroscopy |
Oxidation / Reduction
A Short History of Three Chemical Shifts  Shin-ichi Nagaoka
Regrettably, the term "chemical shift" to designate the position of a spectral signal has a poor reputation as a technical term. Nevertheless, the "chemical" environment around an atom of interest influences the electronic environment and hence, leads to spectral shifts, making the prefix "chemical" appropriate.
Nagaoka, Shin-ichi. J. Chem. Educ. 2007, 84, 801.
NMR Spectroscopy |
Spectroscopy |
Nomenclature / Units / Symbols
A Green Alternative to Aluminum Chloride Alkylation of Xylene  Grigoriy A. Sereda and Vikul B. Rajpara
Presents a simple laboratory experiment that introduces organic chemistry students to the basic principles of green technologies, such as lack of toxic or bulk byproducts, nontoxicity, and reusability of the catalyst.
Sereda, Grigoriy A.; Rajpara, Vikul B. J. Chem. Educ. 2007, 84, 692.
Alkylation |
Green Chemistry |
Catalysis |
NMR Spectroscopy |
Reactions |
Synthesis
Using a Premade Grignard Reagent To Synthesize Tertiary Alcohols in a Convenient Investigative Organic Laboratory Experiment  Michael A. G. Berg and Roy D. Pointer
Describes the use of a commercially available Grignard reagent in a Grignard synthesis that avoided the failures typically associated with the Grignard reaction.
Berg, Michael A. G.; Pointer, Roy D. J. Chem. Educ. 2007, 84, 483.
Aldehydes / Ketones |
Grignard Reagents |
IR Spectroscopy |
NMR Spectroscopy |
Organometallics |
Synthesis
The Aldol Addition and Condensation: The Effect of Conditions on Reaction Pathway  R. David Crouch, Amie Richardson, Jessica L. Howard, Rebecca L. Harker, and Kathryn H. Barker
Describes an experiment offering the opportunity for students to observe the critical role that reaction temperature and base strength have in determining the product of the base-mediated addition of a ketone to an aldehyde.
Crouch, R. David; Richardson, Amie; Howard, Jessica L.; Harker, Rebecca L.; Barker, Kathryn H. J. Chem. Educ. 2007, 84, 475.
Addition Reactions |
Aldehydes / Ketones |
Green Chemistry |
NMR Spectroscopy |
Reactions |
Synthesis
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
Photochemical Dimerization of Dibenzylideneacetone. A Convenient Exercise in [2+2] Cycloaddition Using Chemical Ionization Mass Spectrometry  G. Nageswara Rao, Chelli Janardhana, V. Ramanathan, T. Rajesh, and P. Harish Kumar
Presents a laboratory procedure for the photochemical dimerization of dibenzylideneacetone, a dienone. The dimerization is confirmed by chemical ionization mass spectrometry, and other spectroscopic techniques are used to establish the structure of the product.
Rao, G. Nageswara; Janardhana, Chelli; Ramanathan, V.; Rajesh, T.; Kumar, P. Harish. J. Chem. Educ. 2006, 83, 1667.
Aldehydes / Ketones |
Alkenes |
Chromatography |
IR Spectroscopy |
Mass Spectrometry |
NMR Spectroscopy |
Photochemistry |
Thin Layer Chromatography
Microwave-Mediated Synthesis of Lophine: Developing a Mechanism To Explain a Product   R. David Crouch, Jessica L. Howard, Jennifer L. Zile, and Kathryn H. Barker
Describes the microwave-mediated preparation of lophine (2,4,5-triphenylimidazole). The experiment also provides an opportunity for students to employ the principles of carbonyl chemistry in devising a mechanism to explain the formation of the product.
Crouch, R. David; Howard, Jessica L.; Zile, Jennifer L.; Barker, Kathryn H. J. Chem. Educ. 2006, 83, 1658.
Aldehydes / Ketones |
Amines / Ammonium Compounds |
Aromatic Compounds |
Microscale Lab |
Molecular Modeling |
Synthesis |
NMR Spectroscopy
Developing Critical Thinking Skills: The "Sabotaged" Synthesis of Methyl p-Bromobenzoate  Eric J. Mahan and Mary Alice Nading
Before beginning an experiment, students are told that someone might have sabotaged their experiment to produce other-than-expected results. The objective is to perform the experiment, determine if any sabotage has occurred, and, if so, identify the changes that were made to the reagents as well as the person responsible.
Mahan, Eric J.; Nading, Mary Alice. J. Chem. Educ. 2006, 83, 1652.
Alcohols |
Carboxylic Acids |
Esters |
IR Spectroscopy |
NMR Spectroscopy |
Mass Spectrometry |
Synthesis
3,5-Diarylisoxazoles: Individualized Three-Step Synthesis and Isomer Determination Using 13C NMR or Mass Spectroscopy  Chad E. Stephens and Reem K. Arafa
Describes the three-step synthesis and definitive characterization of a 3,5-diarylisoxazole via the chalcone and chalcone dibromide. The project is individualized with regard to compound purification, characterization, and literature searches as each student prepares a differently substituted chalcone.
Stephens, Chad E.; Arafa, Reem K. J. Chem. Educ. 2006, 83, 1336.
Alkenes |
Heterocycles |
IR Spectroscopy |
Mass Spectrometry |
NMR Spectroscopy |
Synthesis |
Spectroscopy
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
Synthesis and Analysis of a Versatile Imine for the Undergraduate Organic Chemistry Laboratory  Jacqueline Bennett, Kristen Meldi, and Christopher Kimmell II
In this experiment students prepare and analyze N-p-methoxyphenyl (N-PMP) alpha-imino ethyl glyoxalate, an imine that has been used in the synthesis of biologically active molecules. The stability and versatility of this imine allow it to be used in subsequent reactions, offering a variety of possible multistep synthetic strategies.
Bennett, Jacqueline; Meldi, Kristen; Kimmell, Christopher, II. J. Chem. Educ. 2006, 83, 1221.
Aldehydes / Ketones |
Gas Chromatography |
Green Chemistry |
Mass Spectrometry |
NMR Spectroscopy |
Synthesis
Purification and Modification of Fullerene C60 in the Undergraduate Laboratory  Tracey Spencer, Barney Yoo, and Kent Kirshenbaum
Describes an experiment for the extraction and column purification of buckminsterfullerene from fullerene-rich soot followed by a one-pot 1,3-dipolar cycloaddition of an azomethine ylide. Characterization of the starting material and product can be performed by UVVis, MS, 1H NMR, and 13C NMR.
Spencer, Tracey; Yoo, Barney; Kirshenbaum, Kent. J. Chem. Educ. 2006, 83, 1218.
Aromatic Compounds |
Chromatography |
NMR Spectroscopy |
UV-Vis Spectroscopy |
Synthesis |
Nanotechnology |
Reactions
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
Regiospecific Epoxidation of Carvone: A Discovery-Oriented Experiment for Understanding the Selectivity and Mechanism of Epoxidation Reactions  Kendrew K. W. Mak, Y. M. Lai, and Yuk-Hong Siu
Peroxy acids and alkaline H2O2 are two commonly used reagents for alkene epoxidation. The former react preferentially with electron-rich alkenes while the latter works better with a,-unsaturated carbonyl compounds. The selectivity of these two reagents on carvone, a naturally occurring compound that contains both types of C=C bonds, is investigated.
Mak, Kendrew K. W.; Lai, Y. M.; Siu, Yuk-Hong. J. Chem. Educ. 2006, 83, 1058.
Alkenes |
Chromatography |
Epoxides |
IR Spectroscopy |
NMR Spectroscopy |
Synthesis |
Mechanisms of Reactions
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
Usnic Acid and the Intramolecular Hydrogen Bond. A Computational Experiment for the Organic Laboratory  Thomas K. Green and Charles A. Lane
A computational experiment is described for the organic chemistry laboratory that allows students to estimate the relative strengths of the intramolecular hydrogen bonds of usnic and isousnic acids, two related lichen secondary metabolites.
Green, Thomas K.; Lane, Charles A. J. Chem. Educ. 2006, 83, 1046.
Computational Chemistry |
Hydrogen Bonding |
IR Spectroscopy |
NMR Spectroscopy |
Laboratory Computing / Interfacing
Evaluating the Internal Charge-Transfer in Benzylidene Derivatives of N,N′-Dimethylbarbituric Acid  Marcos Caroli Rezende, Francisco Jara, and Moisés Domínguez
Four benzylidene derivatives of N,N'-dimethylbarbituric acid are prepared and their UVvisible and 1H NMR spectra used to characterize the molecular internal charge-transfer in the molecules.
Rezende, Marcos Caroli; Jara, Francisco; Domínguez, Moisés. J. Chem. Educ. 2006, 83, 937.
Aqueous Solution Chemistry |
Aromatic Compounds |
Dyes / Pigments |
Molecular Properties / Structure |
NMR Spectroscopy |
Synthesis |
UV-Vis Spectroscopy
A Sequence of Linked Experiments, Suitable for Practical Courses of Inorganic, Organic, Computational Chemistry, and NMR Spectroscopy  Grigoriy A. Sereda
A sequence of investigations associated with the iodochlorination of styrene and 1-hexene is described. The sequence is flexible enough to be used in inorganic, organic, computational, and instrumental courses.
Sereda, Grigoriy A. J. Chem. Educ. 2006, 83, 931.
Alkenes |
Computational Chemistry |
Constitutional Isomers |
MO Theory |
NMR Spectroscopy |
Synthesis
Reductive Amination: A Remarkable Experiment for the Organic Laboratory  Kim M. Touchette
The synthesis of N-(2-hydroxy-3-methoxybenzyl)-N-p-tolylacetamide is a fast, simple three-step sequence that serves as a useful example of the reductive amination reaction for the organic chemistry laboratory.
Touchette, Kim M. J. Chem. Educ. 2006, 83, 929.
Aldehydes / Ketones |
Amines / Ammonium Compounds |
Green Chemistry |
Instrumental Methods |
IR Spectroscopy |
NMR Spectroscopy |
Oxidation / Reduction |
Solids
Enhancements on the Photochromism of 2-(2,4-Dinitrobenzyl)pyridine: Molecular Modeling, NMR Spectrometry, Photo- and Solvent-Bleaching  Ernest C. McGoran, Kevin Hintz, Kristin Hoffman, and Ramon Iovin
Describes molecular-modeling studies on the photochromism of 2-(2,4-dinitrobenzyl)pyridine (a-DNBP) that focus on the hydrogen atom migratory distances and the energies for the two very different tautomers arising from the photo-induced proton transfers.
McGoran, Ernest C.; Hintz, Kevin; Hoffman, Kristin; Iovin, Ramon. J. Chem. Educ. 2006, 83, 923.
Constitutional Isomers |
Molecular Modeling |
NMR Spectroscopy |
Photochemistry
Iodolactonization of 4-Pentenoic Acid   R. David Crouch, Alexander Tucker-Schwartz, and Kathryn Barker
Describes an experiment in which 4-pentenoic acid is converted into a lactone via iodolactonization.
Crouch, R. David; Tucker-Schwartz, Alexander; Barker, Kathryn. J. Chem. Educ. 2006, 83, 921.
Alkenes |
Carboxylic Acids |
IR Spectroscopy |
Mechanisms of Reactions |
NMR Spectroscopy |
Reactions |
Synthesis
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
A Quick and Easy Simplification of Benzocaine's NMR Spectrum  Suzanne R. Carpenter and Richard H. Wallace
An inexpensive, quick, and effective method for simplifying the NMR spectrum of benzocaine is reported. The method results in a spectrum that is cleanly integrated and more easily interpreted.
Carpenter, Suzanne R.; Wallace, Richard H. J. Chem. Educ. 2006, 83, 637.
Drugs / Pharmaceuticals |
NMR Spectroscopy |
Solutions / Solvents
A Greener Approach to Aspirin Synthesis Using Microwave Irradiation  Ingrid Montes, David Sanabria, Marilyn García,, Joaudimir Castro, and Johanna Fajardo
Presents an inquiry-based laboratory experience based on the use of a microwave oven as a means for a comparative study of the effect of different catalysts in the synthesis of aspirin.
Montes, Ingrid; Sanabria, David; García,, Marilyn; Castro, Joaudimir; Fajardo, Johanna. J. Chem. Educ. 2006, 83, 628.
Drugs / Pharmaceuticals |
Esters |
Green Chemistry |
NMR Spectroscopy |
Reactions |
Synthesis |
Thin Layer Chromatography
A Laboratory Assignment in 1H NMR Spectroscopy: A Comparative Analysis of Calculated and Experimental 1H NMR Chemical Shifts  Susan D. Van Arnum
A computer program is used to determine the proton NMR chemical shifts of endo- and exo-norbornenyl ketones and these values are compared to empirical results.
Van Arnum, Susan D. J. Chem. Educ. 2006, 83, 429.
Constitutional Isomers |
NMR Spectroscopy |
Photochemistry
Synthesis of Unsymmetrical Alkynes via the Alkylation of Sodium Acetylides. An Introduction to Synthetic Design for Organic Chemistry Students  Jennifer N. Shepherd and Jason R. Stenzel
Teams of students design a microscale synthesis of an unsymmetrical alkyne using commercially available terminal alkynes and alkyl halides and characterize the resulting products using TLC, IR, and 1H NMR spectroscopy. Depending on the chosen reactants, students observe both substitution and elimination products, or in some cases, no reaction at all.
Shepherd, Jennifer N.; Stenzel, Jason R. J. Chem. Educ. 2006, 83, 425.
Alkylation |
Alkynes |
Elimination Reactions |
IR Spectroscopy |
Microscale Lab |
NMR Spectroscopy |
Nucleophilic Substitution |
Synthesis
Mechanisms That Interchange Axial and Equatorial Atoms in Fluxional Processes: Illustration of the Berry Pseudorotation, the Turnstile, and the Lever Mechanisms via Animation of Transition State Normal Vibrational Modes  Marion E. Cass, King Kuok Hii, and Henry S. Rzepa
Teaching the Berry pseudorotation mechanism presents particular pedagogic problems due to both its dynamic and three dimensional character. The approach described here illustrates these processes using interactive animations embedded in a Web page.
Cass, Marion E.; Hii, King Kuok; Rzepa, Henry S. J. Chem. Educ. 2006, 83, 336.
Computational Chemistry |
Enantiomers |
Molecular Mechanics / Dynamics |
Molecular Properties / Structure |
Mechanisms of Reactions |
NMR Spectroscopy |
Nonmetals
4-Dimethylaminopyridine or Acid-Catalyzed Syntheses of Esters: A Comparison  Annemieke W. C. van den Berg and Ulf Hanefeld
Students compare acid-catalyzed ester synthesis and the 4-dimethylaminopyridine-catalyzed reaction. Based on the outcome of the experiments, students discuss the different reaction mechanisms and reason why different products are formed.
van den Berg, Annemieke W. C.; Hanefeld, Ulf. J. Chem. Educ. 2006, 83, 292.
Acids / Bases |
Catalysis |
Chromatography |
Esters |
IR Spectroscopy |
NMR Spectroscopy |
Mass Spectrometry |
Synthesis |
Mechanisms of Reactions
Convenient Microscale Synthesis of a Coumarin Laser Dye Analog  Evangelos Aktoudianakis and Andrew P. Dicks
Describes the Knoevenagel synthesis of 3-acetyl-7-(diethylamino)-2H-1-benzopyran-2-one, a fluorescent coumarin laser dye analog.
Aktoudianakis, Evangelos; Dicks, Andrew P. J. Chem. Educ. 2006, 83, 287.
Aromatic Compounds |
Fluorescence Spectroscopy |
IR Spectroscopy |
Microscale Lab |
Synthesis |
NMR Spectroscopy |
UV-Vis Spectroscopy
Synthesis of Methyl Diantilis, a Commercially Important Fragrance  William H. Miles and Katelyn B. Connell
Describes the synthesis of a family of fragrances, including the commercially important Methyl Diantilis, and provides an excellent introduction to intellectual property laws.
Miles, William H.; Connell, Katelyn B. J. Chem. Educ. 2006, 83, 285.
Alcohols |
Food Science |
Catalysis |
Ethers |
Industrial Chemistry |
IR Spectroscopy |
Lewis Acids / Bases |
NMR Spectroscopy |
Oxidation / Reduction |
Synthesis
Grubbs's Cross Metathesis of Eugenol with cis-2-Butene-1,4-diol To Make a Natural Product. An Organometallic Experiment for the Undergraduate Lab   Douglass F. Taber and Kevin J. Frankowski
Describes the ruthenium catalyzed cross metathesis of eugenol with cis-1,4-butenediol. The experiment is an excellent example of the powerful selectivity possible with the Grubbs' catalyst, demonstrating the preference for trans over cis alkene formation and for cross metathesis over homodimerization.
Taber, Douglass F.; Frankowski, Kevin J. J. Chem. Educ. 2006, 83, 283.
Alkenes |
Catalysis |
IR Spectroscopy |
Mass Spectrometry |
Mechanisms of Reactions |
Microscale Lab |
Natural Products |
NMR Spectroscopy |
Organometallics |
Stereochemistry |
Synthesis |
Thin Layer Chromatography |
Transition Elements
Microwave-Assisted Synthesis of a Natural Insecticide on Basic Montmorillonite K10 Clay. Green Chemistry in the Undergraduate Organic Laboratory  Matthew R. Dintzner, Paul R. Wucka, and Thomas W. Lyons
Describes a microwave-assisted, solvent-free, one-pot synthesis of a naturally occurring insecticide catalyzed by naturally benign, base-washed Montmorillonite K10 clay. The reaction features several interesting mechanistic considerations, including an electrophilic aromatic addition, dehydration, and intramolecular hetero-DielsAlder cyclization.
Dintzner, Matthew R.; Wucka, Paul R.; Lyons, Thomas W. J. Chem. Educ. 2006, 83, 270.
Chromatography |
Green Chemistry |
Mass Spectrometry |
NMR Spectroscopy |
Synthesis |
IR Spectroscopy |
Spectroscopy
Diastereoselectivity in the Reduction of α-Hydroxyketones. An Experiment for the Chemistry Major Organic Laboratory  David B. Ball
Describes a research type, inquiry-based project where students synthesize racemic ahydroxyketones using umpolung, a polarity-reversal approach; investigate chelating versus non-chelating reducing agents; and determine the diastereoselectivity of these reducing processes by NMR spectroscopy.
Ball, David B. J. Chem. Educ. 2006, 83, 101.
Addition Reactions |
Aldehydes / Ketones |
Chirality / Optical Activity |
Chromatography |
Conferences |
Constitutional Isomers |
Enantiomers |
NMR Spectroscopy |
Stereochemistry |
Synthesis |
Conformational Analysis
Derivatization of Fullerenes: An Organic Chemistry Laboratory  Charles T. Cox Jr. and Melanie M. Cooper
Presents two undergraduate organic chemistry laboratories detailing the synthesis of fullerene derivatives, using the Bingel (carbene insertion) and Prato (1,3-dipolar addition) protocols.
Cox, Charles T., Jr.; Cooper, Melanie M. J. Chem. Educ. 2006, 83, 99.
Acids / Bases |
Addition Reactions |
Chromatography |
Heterocycles |
IR Spectroscopy |
Microscale Lab |
NMR Spectroscopy |
Synthesis |
UV-Vis Spectroscopy
Just Click It: Undergraduate Procedures for the Copper(I)-Catalyzed Formation of 1,2,3-Triazoles from Azides and Terminal Acetylenes  William D. Sharpless, Peng Wu, Trond Vidar Hansen, and James G. Lindberg
In keeping with the defining aspects of click chemistry, this reaction is high-yielding, requires no chromatography, is easily monitored by TLC, and displays distinct peaks in both IR and 1H-NMR. Virtually all products precipitate, and with just a few different starting blocks, every student, or pair of lab partners, can produce a unique "clicked" compound.
Sharpless, William D.; Wu, Peng; Hansen, Trond Vidar; Lindberg, James G. J. Chem. Educ. 2005, 82, 1833.
Catalysis |
Heterocycles |
Alkynes |
IR Spectroscopy |
NMR Spectroscopy |
Reactions |
Thin Layer Chromatography |
Synthesis
Acid-Catalyzed Isomerization of Carvone to Carvacrol  Richard A. Kjonaas and Shawn P. Mattingly
Describes the acid-catalyzed isomerization of carvone (oil of spearmint) to carvacrol (oil of origanum). The experiment demonstrates several important concepts including formation of a carbocation by protonation of an alkene, rearrangement of a carbocation, deprotonation of a carbocation, acid-catalyzed enolization, and aromaticity.
Kjonaas, Richard A.; Mattingly, Shawn P. J. Chem. Educ. 2005, 82, 1813.
Aromatic Compounds |
Medicinal Chemistry |
Natural Products |
NMR Spectroscopy
The Virtual ChemLab Project: A Realistic and Sophisticated Simulation of Organic Synthesis and Organic Qualitative Analysis  Brian F. Woodfield, Merritt B. Andrus, Gregory L. Waddoups, Melissa S. Moore, Richard Swan, Rob Allen, Greg Bodily, Tricia Andersen, Jordan Miller, Bryon Simmons, and Richard Stanger
Describes a set of sophisticated and realistic laboratory simulations for use in freshman- and sophomore-level chemistry classes and laboratories called Virtual ChemLab. The purpose of these simulations is to reinforce concepts taught in the classroom, provide an environment for creative learning, and emphasize the thinking behind instructional laboratory experiments.
Woodfield, Brian F.; Andrus, Merritt B.; Waddoups, Gregory L.; Moore, Melissa S.; Swan, Richard; Allen, Rob; Bodily, Greg; Andersen, Tricia; Miller, Jordan; Simmons, Bryon; Stanger, Richard. J. Chem. Educ. 2005, 82, 1728.
IR Spectroscopy |
NMR Spectroscopy |
Qualitative Analysis |
Synthesis |
Reactions |
Thin Layer Chromatography
A Template-Controlled Solid-State Reaction for the Organic Chemistry Laboratory  Tomislav Friscic, Tamara D. Hamilton, Giannis S. Papaefstathiou, and Leonard R. MacGillivray
Describes a laboratory experiment that employs linear hydrogen-bond templates to direct [2 + 2] photodimerization in the solid state. The experiment introduces undergraduates to supramolecular and solid-state chemistry, as well as aspects of green chemistry.
Friscic, Tomislav; Hamilton, Tamara D.; Papaefstathiou, Giannis S.; MacGillivray, Leonard R. J. Chem. Educ. 2005, 82, 1679.
Green Chemistry |
Solid State Chemistry |
Crystals / Crystallography |
Alkenes |
Alkanes / Cycloalkanes |
Hydrogen Bonding |
Materials Science |
NMR Spectroscopy
The Discovery-Oriented Approach to Organic Chemistry. 6. Selective Reduction in Organic Chemistry: Reduction of Aldehydes in the Presence of Esters Using Sodium Borohydride  Ashvin R. Baru and Ram S. Mohan
Describes two discovery oriented lab experiments involving the chemoselective reduction of vanillin acetate and methyl 4-formylbenzoate in the presence of esters using sodium borohydride, followed by product identification using 1H and 13C NMR spectroscopy.
Baru, Ashvin R.; Mohan, Ram S. J. Chem. Educ. 2005, 82, 1674.
NMR Spectroscopy |
Alcohols |
Aldehydes / Ketones |
Esters |
Oxidation / Reduction |
Thin Layer Chromatography |
Synthesis
Diels–Alder Synthesis of endo-cis-N-Phenylbicyclo[2.2.2]oct-5-en-2,3-dicarboximide  Marsha R. Baar and Kristin Wustholz
endo-cis-N-Phenylbicyclo[2.2.2]oct-5-en-2,3-dicarboximide was synthesized by a DielsAlder cycloaddition of 1,3-cyclohexadiene and N-phenylmaleimide in ethyl acetate. 1,3-Cyclohexadiene and N-phenylmaleimide were selected to illustrate the Alder rule, which reflects a preference for endo products and to overcome the difficulties associated with the traditional combination of 1,3-cyclopentadiene and maleic anhydride.
Baar, Marsha R.; Wustholz, Kristin. J. Chem. Educ. 2005, 82, 1393.
Asymmetric Synthesis |
Microscale Lab |
Stereochemistry |
Addition Reactions |
Alkenes |
IR Spectroscopy |
NMR Spectroscopy
Measurement of the Isotopic Ratio of 10B/11B in NaBH4 by 1H NMR  Murray Zanger and Guillermo Moyna
A simple and remarkably accurate method for estimating the isotopic ratio between 10B and 11B through the use of 1H nuclear magnetic resonance (NMR) spectroscopy is presented. The experiment relies on the splitting caused by 10B (I = 3) and 11B (I = 3/2) on the 1H signal of a proton directly bound to boron, a phenomenon readily observed on an aqueous sample of NaBH4. In combination with a brief lecture or prelaboratory presentation, this laboratory can serve to introduce students to magnetic properties as well as theoretical and experimental aspects of NMR spectroscopy as early as the freshman-level chemistry.
Zanger, Murray; Moyna, Guillermo. J. Chem. Educ. 2005, 82, 1390.
Instrumental Methods |
Magnetic Properties |
NMR Spectroscopy |
Atomic Properties / Structure |
Isotopes
Monoterpene Unknowns Identified Using IR, 1H-NMR, 13C-NMR, DEPT, COSY, and HETCOR  Lisa T. Alty
This set of NMR experiments can be a capstone experience for a spectroscopy or advanced laboratory course following organic chemistry. Students are given a monoterpene to identify using IR, 1H-NMR, 13C-NMR, and DEPT data. Once the unknown is identified, they can fully interpret and assign each carbon and each proton signal to the structure using COSY and HETCOR along with the one-dimensional NMR data. The rigidity of the ring systems and the chiral centers in all of the compounds present diastereotopic hydrogens and, in some cases, diastereotopic methyl groups.
Alty, Lisa T. J. Chem. Educ. 2005, 82, 1387.
Natural Products |
NMR Spectroscopy |
Diastereomers |
Chirality / Optical Activity |
IR Spectroscopy |
Undergraduate Research
NMR Analysis of Unknowns: An Introduction to 2D NMR Spectroscopy  David E. Alonso and Steven E. Warren
Second-year organic chemistry students analyze and compare the spectral data of three unknown ketones (2-heptanone, 3-heptanone, and 4-heptanone). Students acquire one-dimensional proton and carbon NMR data for each unknown and make signal assignments based on chemical shifts, integration values, and splitting patterns of signals. Difficulties are encountered during interpretation of NMR data for 2- and 3-heptanone. Acquiring and analyzing the two-dimensional NMR spectra of the heptanones resolve these problems.
Alonso, David E.; Warren, Steven E. J. Chem. Educ. 2005, 82, 1385.
Instrumental Methods |
NMR Spectroscopy |
Qualitative Analysis
Organic Spectroscopy Laboratory: Utilizing IR and NMR in the Identification of an Unknown Substance  Neil M. Glagovich and Timothy D. Shine
An undergraduate organic laboratory designed to teach the use of IR and NMR spectra interpretation in the identification of an unknown substance has been developed. This laboratory requires the student to obtain the IR spectrum of an unknown substance and, from the interpretation of that spectrum, determine which of several possible functional groups is present in the molecule. Using this information and either the melting point or boiling point of the unknown, the student is able to determine a list of likely candidates (usually between eight and twelve suspects collated from a supplied table of possible compounds). The student will then draw the structures for all candidate compounds and, from those structures, predict the 1H- and 13C-NMR spectra for each.
Glagovich, Neil M.; Shine, Timothy D. J. Chem. Educ. 2005, 82, 1382.
IR Spectroscopy |
NMR Spectroscopy |
Qualitative Analysis |
Solids |
Liquids
Thermal Degradation and Identification of Heat-Sensitive Polymers. Applications of Pyrolysis and Distillation and Instrumental Methods of Analysis  Stuart C. Clough and Emma W. Goldman
An experiment for undergraduate teaching laboratories is described that involves the identification of samples of polystyrene and poly(methyl methacrylate). This involves the thermal degradation of the polymers (a destructive distillation) into their respective monomers. The monomers are then identified using infrared spectroscopy, proton nuclear magnetic resonance spectroscopy, and gas chromatographymass spectrometry.
Clough, Stuart C.; Goldman, Emma W. J. Chem. Educ. 2005, 82, 1378.
Nonmajor Courses |
IR Spectroscopy |
Mass Spectrometry |
NMR Spectroscopy |
Polymerization
A Networked NMR Spectrometer: Configuring a Shared Instrument  David Alonso, G. William Mutch, Peter Wong, Steven Warren, Bal Barot, Jan Kosinski, and Mark Sinton
Andrews University, Lake Michigan College, and Southwestern Michigan College established an educational consortium in southwest lower Michigan. An FT-NMR spectrometer was installed at AU and networked with the community colleges. Students and faculty from LMC and SMC visit Andrews on a regular basis to receive training and operate the NMR. The instrument is accessible via the Internet for data acquisition, processing, and transfer. The spectrometer has helped the consortium schools improve the quality of chemistry education, exposed students in chemistry courses to the concepts and techniques of modern NMR spectroscopy, and strengthened the collaboration between the chemistry faculty of the three schools. This article describes the NMR network configuration and the methodology for NMR data acquisition and distribution.
Alonso, David; Mutch, G. William; Wong, Peter; Warren, Steven; Barot, Bal; Kosinski, Jan; Sinton, Mark. J. Chem. Educ. 2005, 82, 1342.
Instrumental Methods |
NMR Spectroscopy
Application of ChemDraw NMR Tool: Correlation of Program-Generated 13C Chemical Shifts and pKa Values of para-Substituted Benzoic Acids  Hongyi Wang
An application of ChemDraw NMR Tool was demonstrated by correlation of program-generated 13C NMR chemical shifts and pKa values of para-substituted benzoic acids. Experimental 13C NMR chemical shifts were analyzed in the same way for comparison. The project can be used as an assignment at the end of the first-year organic chemistry course to review topics or explore new techniques: Hammett equation, acidbase equilibrium theory, electronic nature of functional groups, inductive and resonance effects, structurereactivity relationship, NMR spectroscopy, literature search, database search, and ChemDraw software.
Wang, Hongyi. J. Chem. Educ. 2005, 82, 1340.
Acids / Bases |
Equilibrium |
NMR Spectroscopy |
Aqueous Solution Chemistry |
Carboxylic Acids
Conversion of an Aziridine to an Oxazolidinone Using a Salt and Carbon Dioxide in Water  Justin R. Wallace, Deborah L. Lieberman, Matthew T. Hancock, and Allan R. Pinhas
An undergraduate laboratory experiment that allows for optimization of experimental reaction conditions for the conversion of a readily-available aziridine to the corresponding oxazolidinone using only carbon dioxide and a salt in water is discussed. A variety of salts were used to determine their effect on the reaction. In all cases, either no reaction occurred or a high yield of product was obtained. Ring opening of the less substituted carbonnitrogen bond predominates. This experiment allows students to optimize reaction conditions to obtain predominantly one of two regioisomers.
Wallace, Justin R.; Lieberman, Deborah L.; Hancock, Matthew T.; Pinhas, Allan R. J. Chem. Educ. 2005, 82, 1229.
Heterocycles |
Synthesis |
Aqueous Solution Chemistry |
Constitutional Isomers |
Mechanisms of Reactions |
NMR Spectroscopy |
Quantitative Analysis
Generation, Isolation, and Characterization of a Stable Enol from Grignard Addition to a Bis-Ester. A Microscale Experiment for the Undergraduate Organic Chemistry Laboratory  Olivier J.-C. Nicaise, Kyle F. Ostrom, and Brent J. Dalke
A microscale experiment for the undergraduate organic chemistry laboratory that consists of preparing and characterizing an alpha-ketoester and its corresponding, remarkably stable enol form, has been developed. The reaction is that of a Grignard reagent with a bis-ester. A difference in reaction temperature is responsible for the selective generation of the alpha-ketoester and the enol ester. Analysis of spectral data (1H NMR and IR) and a knowledge of organic reactions allows the students to determine the detailed structure of the two reaction products and also to suggest a mechanism for their formation. This experiment introduces students to the concept of stability of the tetrahedral intermediate in acyl-transfer reactions. It also gives them a taste of the unexpected.
Nicaise, Olivier J.-C.; Ostrom, Kyle F.; Dalke, Brent J. J. Chem. Educ. 2005, 82, 1059.
IR Spectroscopy |
Mechanisms of Reactions |
Microscale Lab |
NMR Spectroscopy |
Organometallics |
Reactive Intermediates |
Synthesis
The Ethylene Ketal Protecting Group Revisited: The Synthesis of 4-Hydroxy-4,4-diphenyl-2-butanone  Marsha R. Baar, Charles E. Russell, and Kristin L. Wustholz
The multistep synthesis of 4-hydroxy-4,4-diphenyl-2-butanone from ethyl acetoacetate illustrates the use of a ketal protecting group. Reaction of ethyl acetoacetate with ethylene glycol with p-TsOH in toluene produced the ketal ester. Reaction of the crude ketal ester with two equivalents of phenyl magnesium bromide followed by an aqueous acid workup generated the tertiary alcohol and simultaneously removed the ketal protecting group to produce the hydroxyketone. Our procedure is a modification of a previously published synthesis whose end product was 4,4-diphenyl-3-buten-2-one, the dehydrated analog.
Baar, Marsha R.; Russell, Charles E.; Wustholz, Kristin L. J. Chem. Educ. 2005, 82, 1057.
Synthesis |
Grignard Reagents |
IR Spectroscopy |
Mechanisms of Reactions |
NMR Spectroscopy
Use of Enzymes in Organic Synthesis: Reduction of Ketones by Baker's Yeast Revisited  James Patterson and Snorri Th. Sigurdsson
The undergraduate organic laboratory Bakers Yeast Reduction of Ethyl Acetoacetate has been improved in two different ways. First, the addition of small quantities of hexane to the aqueous yeast system along with an improved workup protocol has dramatically increased the yield and reproducibility of the ketone conversion to the corresponding alcohol with a high enantiomeric excess. Second, the enantiomeric excess of the alcohol product was ascertained by coupling the alcohol mixture with a chiral acid and analyzing the resulting mixture of diastereomeric esters by proton NMR.
Patterson, James; Sigurdsson, Snorri Th. J. Chem. Educ. 2005, 82, 1049.
Enzymes |
NMR Spectroscopy |
Stereochemistry |
Gas Chromatography |
Synthesis
Formation of α-Tetralone by Intramolecular Friedel–Crafts Acylation  Michael S. Holden, R. David Crouch, and Kathryn A. Barker
A microscale procedure is described for the formation of the industrially-important compound alpha-tetralone. This is an example of an intramolecular FriedelCrafts acylation, utilizing 4-phenylbutanoic acid and a proton source. The title reaction demonstrates the concept of ring-forming reactions and highlights the use of carboxylic acids as an electrophile precursor in electrophilic aromatic substitution reactions.
Holden, Michael S.; Crouch, R. David; Barker, Kathryn A. J. Chem. Educ. 2005, 82, 934.
Aromatic Compounds |
Microscale Lab |
Synthesis |
Carboxylic Acids |
IR Spectroscopy |
NMR Spectroscopy
Isolation of Shikimic Acid from Star Aniseed  Richard Payne and Michael Edmonds
The isolation of shikimic acid from star aniseed is described. This experiment uses Soxhlet extraction followed by ion exchange chromatography to isolate crude shikimic acid from the star aniseed. Subsequent charcoal decolorization and recrystallization from toluene and methanol afford the pure shikimic acid in 27% w/w yield.
Payne, Richard; Edmonds, Michael. J. Chem. Educ. 2005, 82, 599.
Bioorganic Chemistry |
Natural Products |
NMR Spectroscopy |
Plant Chemistry
Introducing JCE ChemInfo: Organic  Hans J. Reich
JCE ChemInfo: Organic is a collection of Web pages containing information useful to teachers, researchers, and students in organic chemistry, biochemistry, and medicinal chemistry. The pages have been selected for ease of use, broad applicability, and quality of coverage. Topics will include structural information, organic reactions, nomenclature, physical properties, and spectroscopic data. These Web pages will be updated when possible and additional Web pages will be added as they become available.
Reich, Hans J. J. Chem. Educ. 2005, 82, 495.
Medicinal Chemistry |
Nomenclature / Units / Symbols |
NMR Spectroscopy
The Sharpless Asymmetric Dihydroxylation in the Organic Chemistry Majors Laboratory  Christopher J. Nichols and Melissa R. Taylor
A six-period laboratory exercise has been developed that uses the convenient Sharpless asymmetric dihydroxylation (AD) to illustrate the principles of a chiral synthesis. Using one particular alkene, students perform a racemic dihydroxylation, an AD using a commercially available AD-mix, and then an AD using an ester derivative of dihydroquinidine that they synthesized themselves. The structures of the products are confirmed with 1H NMR spectroscopy and the enantiomeric excesses of the diols are determined using a chiral GC column.
Nichols, Christopher J.; Taylor, Melissa R. J. Chem. Educ. 2005, 82, 105.
Chirality / Optical Activity |
Chromatography |
IR Spectroscopy |
NMR Spectroscopy |
Synthesis |
Alkenes |
Addition Reactions
A Discovery-Based Friedel–Crafts Acylation Experiment: Student-Designed Experimental Procedure  Anne McElwee Reeve
A discovery-based FriedelCrafts acylation experiment that includes a student-designed procedure, spectroscopic analysis of an unknown aromatic product, and molecular modeling is described. Students design the synthetic procedure and workup for the acylation of an unknown aromatic starting material in an instructor-guided classroom discussion that integrates concepts from the first semester of organic lab into a new context.
Reeve, Anne McElwee. J. Chem. Educ. 2004, 81, 1497.
Aromatic Compounds |
Chromatography |
IR Spectroscopy |
Molecular Modeling |
NMR Spectroscopy |
Synthesis
Solvent-Free Wittig Reaction: A Green Organic Chemistry Laboratory Experiment  Sam H. Leung and Stephen A. Angel
In this experiment (E)- and (Z)-1-(4-bromophenyl)-2-phenylethene are synthesized by a solvent-free Wittig reaction. The reaction is effected by grinding the reactants in a mortar with a pestle. Both the E and Z isomers of the product are produced as evidenced by thin-layer chromatography and 1H NMR analysis. The E isomer is isolated by crystallization with ethanol in this experiment. In addition to learning about the Wittig reaction, students are also introduced to the ideas of mechanochemistry and green chemistry.
Leung, Sam H.; Angel, Stephen A. J. Chem. Educ. 2004, 81, 1492.
Chromatography |
Green Chemistry |
Microscale Lab |
NMR Spectroscopy |
Synthesis |
Reactions |
Aldehydes / Ketones |
Alkenes
Two-Step Semi-Microscale Preparation of a Cinnamate Ester Sunscreen Analog  Ryan G. Stabile and Andrew P. Dicks
The two-step synthesis and characterization of a sunscreen analog (ethyl trans-4-methoxycinnamate) is presented. This experiment is tailored towards students with a sound theoretical understanding of organic chemistry and related laboratory techniques. Appropriate synthetic discussion topics include carbonyl condensation reactions, carboxylic acid esterifications, and the so-called "cesium effect" in organic synthesis.
Stabile, Ryan G.; Dicks, Andrew P. J. Chem. Educ. 2004, 81, 1488.
Conductivity |
IR Spectroscopy |
Mechanisms of Reactions |
Microscale Lab |
NMR Spectroscopy |
Synthesis |
UV-Vis Spectroscopy |
Consumer Chemistry
Solvent-Free Synthesis of Chalcones  Daniel R. Palleros
The solvent-free synthesis of 20 chalcones was carried out by grinding the benzaldehyde (unsubstituted, 4-methyl, 4-methoxy, 3-chloro, or 4-chloro) and the acetophenone (unsubstituted, 4-methyl, 4-bromo, or 4-methoxy) in the presence of solid sodium hydroxide with a mortar and pestle. In general, the chalcones were obtained in high yields and high purity. Minor quantities of ketol and Michael addition product were detected by NMR spectroscopy. These side-products were easily removed by recrystallization.
Palleros, Daniel R. J. Chem. Educ. 2004, 81, 1345.
Green Chemistry |
NMR Spectroscopy |
Synthesis |
Solids |
Laboratory Management
Superoxygenated Water as an Experimental Sample for NMR Relaxometry  Nikolaus Nestle, Marwan Dakkouri, and Hubert Rauscher
Measuring the oxygen content in superoxygenated table waters, and following the oxygen loss upon storage of such waters in open containers, is presented as an experiment for NMR relaxometry in the student lab.
Nestle, Nikolaus; Dakkouri, Marwan; Rauscher, Hubert. J. Chem. Educ. 2004, 81, 1040.
Water / Water Chemistry |
NMR Spectroscopy |
Nutrition |
Food Science |
Instrumental Methods
Determination of Spin—Lattice Relaxation Time Using 13C NMR. An Undergraduate Physical Chemistry Laboratory Experiment  Zbigniew L. Gasyna and Antoni Jurkiewicz
A 13C NMR experiment is proposed in which spinlattice relaxation time T1 is determined for carbon atoms in a sample of liquid n-hexanol.
Gasyna, Zbigniew L.; Jurkiewicz, Antoni. J. Chem. Educ. 2004, 81, 1038.
NMR Spectroscopy |
Kinetics
A Solid–State NMR Experiment: Analysis of Local Structural Environments in Phosphate Glasses  Stanley E. Anderson, David Saiki, Hellmut Eckert, and Karin Meise-Gresch
The solid state 31P NMR wideline spectra of a series of student-prepared sodium phosphate glasses can easily be measured using a standard multinuclear FTNMR spectrometer.
Anderson, Stanley E.; Saiki, David; Eckert, Hellmut; Meise-Gresch, Karin. J. Chem. Educ. 2004, 81, 1034.
Solid State Chemistry |
NMR Spectroscopy |
Molecular Properties / Structure
An NMR Study of Isotope Effect on Keto–Enol Tautomerization. A Physical Organic Chemistry Experiment  D. Atkinson and V. Chechik
A series of physical organic chemistry experiments suitable for second- or third-year undergraduate students is presented.
Atkinson, D.; Chechik, V. J. Chem. Educ. 2004, 81, 1030.
NMR Spectroscopy |
Isotopes |
Kinetics |
Mechanisms of Reactions
Regioselective Synthesis of a Stereodefined Heterocyclic Push–Pull Alkene. 1H NMR Studies and Two-Dimensional TLC Illustrating Z/E Isomerization  Rade Markovi, Marija Baranac, Vesna Jovanovi, and Zdravko Dambaski
Facile and direct regioselective synthesis of the 4-oxothiazolidine derivative from inexpensive chemicals as an example of kinetic versus thermodynamic control is described.
Markovi, Rade; Baranac, Marija; Jovanovi, Vesna; Dambaski, Zdravko. J. Chem. Educ. 2004, 81, 1026.
Heterocycles |
Alkenes |
Stereochemistry |
Synthesis |
NMR Spectroscopy
Spectroscopic Properties of Some Simple Esters. A Practical Application of Synthesis and Spectroscopy in the Undergraduate Organic Laboratory  David P. Brown, Haris Durutlic, and Didier Juste
This exercise, the synthesis and spectroscopic analysis of the allyl esters of some aromatic carboxylic acids, consists of a series of open-ended experiments.
Brown, David P.; Durutlic, Haris; Juste, Didier. J. Chem. Educ. 2004, 81, 1016.
Esters |
Synthesis |
NMR Spectroscopy |
IR Spectroscopy |
Chromatography
Introducing the gNMR Program in an Introductory NMR Spectrometry Course To Parallel Its Use by Spectroscopists  Jackie M. Rummey and Mary C. Boyce
The approach described in this article includes NMR spectral simulation and so parallels developments in the way spectroscopists now solve problems.
Rummey, Jackie M.; Boyce, Mary C. J. Chem. Educ. 2004, 81, 762.
NMR Spectroscopy |
Learning Theories
Syntheses and Characterization of Ruthenium(II) Tetrakis(Pyridine) Complexes. An Advanced Coordination Chemistry Experiment or Mini-Project  Benjamin J. Coe
This experiment involves the syntheses of several coordination complexes of ruthenium(II) and their characterization by using various spectroscopic and spectrometric techniques.
Coe, Benjamin J. J. Chem. Educ. 2004, 81, 718.
Coordination Compounds |
IR Spectroscopy |
Synthesis |
Mass Spectrometry |
NMR Spectroscopy |
UV-Vis Spectroscopy
The Complexation of the Na+ by 18–Crown–6 Studied via Nuclear Magnetic Resonance  Steven J. Peters and Cheryl D. Stevenson
A novel NMR experiment used in the undergraduate physical chemistry laboratory is described.
Peters, Steven J.; Stevenson, Cheryl D. J. Chem. Educ. 2004, 81, 715.
NMR Spectroscopy |
Equilibrium
The Synthesis and Isolation of N-tert-Butyl-2-phenylsuccinamic Acid and N-tert-Butyl-3-phenylsuccinamic Acid. An Undergraduate Organic Chemistry Laboratory Experiment  Victor Cesare, Ishwar Sadarangani, Janet Rollins, and Dennis Costello
This experiment, which demonstrates that two isomeric products are obtained when an unsymmetrical anhydride is reacted with a nucleophile and that these isomers are easily separated based on their difference in acidity, is useful in introducing the topic of carboxylic acid derivatives into the organic chemistry laboratory.
Cesare, Victor; Sadarangani, Ishwar; Rollins, Janet; Costello, Dennis. J. Chem. Educ. 2004, 81, 713.
Synthesis |
Chirality / Optical Activity |
NMR Spectroscopy
The Darzens Condensation: Structure Determination through Spectral Analysis and Understanding Substrate Reactivity  R. David Crouch, Michael S. Holden, and Candice A. Romany
The Darzens condensation involves two steps that are typically included in the sophomore organic curriculum: an aldol reaction followed by an intramolecular nucleophilic substitution.
Crouch, R. David; Holden, Michael S.; Romany, Candice A. J. Chem. Educ. 2004, 81, 711.
NMR Spectroscopy |
Synthesis |
Stereochemistry |
Mechanisms of Reactions |
Aldehydes / Ketones
Use of Optical Rotation and NMR Signal Counting To Identify Common Aldoses  John Almy
An inexpensive, small scale experiment for second semester organic students describes the unambiguous identification of a common aldose "unknown" from five possible candidates: glucose, mannose, galactose, arabinose, or xylose
Almy, John. J. Chem. Educ. 2004, 81, 708.
NMR Spectroscopy |
Carbohydrates |
Microscale Lab |
Molecular Properties / Structure |
Stereochemistry
Modern Projects in Organic Chemistry: Miniscale and Standard Taper Microscale, 2nd Edition (Jerry R. Mohrig, Christina Noring Hammond, Paul F. Schatz, and Terence C. Morrill)  Richard Pagni
Modern Projects and Experiments in Organic Chemistry comes in two closely related versions, one for miniscale and standard taper microscale and the other for miniscale and Williamson microscale, in conjunction with the authors techniques in organic chemistry book.
Pagni, Richard. J. Chem. Educ. 2004, 81, 649.
Chromatography |
Gases |
IR Spectroscopy |
Laboratory Equipment / Apparatus |
NMR Spectroscopy |
Physical Properties |
Synthesis
Developing Investigation Skills in an Introductory Multistep Synthesis Using Fluorene Oxidation and Reduction  Mark G. Stocksdale, Steven E. S. Fletcher, Ian Henry, Paul J. Ogren, Michael A. G. Berg, Roy D. Pointer, and Barrett W. Benson
A two-step reaction sequence in the beginning organic laboratory provides a useful introduction to the importance of multistep synthesis. In addition to introducing several common synthetic methods and techniques, a two-step preparation can quickly establish the importance of testing alternative reactions in order to optimize intermediate yields.
Stocksdale, Mark G.; Fletcher, Steven E. S.; Henry, Ian; Ogren, Paul J.; Berg, Michael A. G.; Pointer, Roy D.; Benson, Barrett W. J. Chem. Educ. 2004, 81, 388.
Chromatography |
IR Spectroscopy |
NMR Spectroscopy |
Synthesis |
Aromatic Compounds |
Oxidation / Reduction
The Separation and Identification of Two Unknown Solid Organic Compounds: An Experiment for the Sophomore Organic Chemistry Laboratory  Patty L. Feist
Students are given a mixture of a solid ketone and a solid alcohol and asked to separate and identify the two components. First the students use TLC to determine the optimum solvent system to separate the two compounds, then they separate the unknowns on a microscale flash chromatography column. The students acquire the melting point, and if possible, the IR and 1H NMR spectra for each separated compound and identify them by matching the observed data with that of known compounds.
Feist, Patty L. J. Chem. Educ. 2004, 81, 109.
Chromatography |
IR Spectroscopy |
Microscale Lab |
NMR Spectroscopy |
Separation Science |
Qualitative Analysis
Remote NMR Data Acquisition and Processing in the Organic Chemistry Curriculum  Caleb Benefiel, Ron Newton, Gregory J. Crouch, and Karen Grant
A procedure for enabling remote and hands-on access to a Varian Mercury 300 MHz Nuclear Magnetic Resonance (NMR) spectrometer in a large organic chemistry laboratory is described. Additionally, procedures for remotely connecting two high schools and a community college to the NMR are also described.
Benefiel, Caleb; Newton, Ron; Crouch, Gregory J.; Grant, Karen. J. Chem. Educ. 2003, 80, 1494.
Laboratory Computing / Interfacing |
NMR Spectroscopy |
Instrumental Methods
Microscale Synthesis and Spectroscopic Analysis of Flutamide, an Antiandrogen Prostate Cancer Drug  Ryan G. Stabile and Andrew P. Dicks
The synthesis involves N-acylation of a trisubstituted aromatic compound, 3-trifluoromethyl-4-nitroaniline. The procedure is easily adapted to generate structural analogues of flutamide. A significant feature is the curricular flexibility afforded by this experiment.
Stabile, Ryan G.; Dicks, Andrew P. J. Chem. Educ. 2003, 80, 1439.
Drugs / Pharmaceuticals |
IR Spectroscopy |
Mechanisms of Reactions |
Microscale Lab |
NMR Spectroscopy |
Synthesis |
Aromatic Compounds
A Series of Small-Scale, Discovery-Based Organic Laboratory Experiments Illustrating the Concepts of Addition, Substitution, and Rearrangement  Judith S. Moroz, Janice L. Pellino, and Kurt W. Field
Multistep, microscale organic laboratory experiments are presented that illustrate addition, substitution, and rearrangement reactions.
Moroz, Judith S.; Pellino, Janice L.; Field, Kurt W. J. Chem. Educ. 2003, 80, 1319.
IR Spectroscopy |
Mass Spectrometry |
Microscale Lab |
NMR Spectroscopy |
Synthesis |
Addition Reactions |
Mechanisms of Reactions
The Base-Induced Reaction of Salicylaldehyde with 1-Bromobutane in Acetone: Two Related Examples of Chemical Problem Solving  Holly D. Bendorf and Chriss E. McDonald
Each student performs his or her own experimental work, running one of the two reactions, and acquiring the proton and carbon NMR, IR, and mass spectra. The students work in groups to propose structures for the products and mechanisms for their formation. The students are also asked to address why the reactions take different courses.
Bendorf, Holly D.; McDonald, Chriss E. J. Chem. Educ. 2003, 80, 1185.
Chromatography |
Mass Spectrometry |
NMR Spectroscopy |
Aromatic Compounds |
Aldehydes / Ketones |
Ethers |
Phenols |
IR Spectroscopy
C–H and C–D Bonds: An Experimental Approach to the Identity of C–H Bonds by Their Conversion to C–D Bonds  Alex T. Rowland
Three experiments that allow students to determine the relative reactivity of C-H bonds that are aliphatic, alpha, benzylic, or aromatic by the ease of substitution of deuterium for oxygen.
Rowland, Alex T. J. Chem. Educ. 2003, 80, 311.
Acids / Bases |
IR Spectroscopy |
Isotopes |
NMR Spectroscopy |
Undergraduate Research |
Alkanes / Cycloalkanes |
Aromatic Compounds |
Carboxylic Acids
Organic Spectroscopy–A Capstone Experience  Jan M. Fleischer
Experiment requiring students to make decisions regarding the likely structure of their sample based upon an IR spectrum before a final analysis with NMR spectroscopy.
Fleischer, Jan M. J. Chem. Educ. 2002, 79, 1247.
IR Spectroscopy |
Mass Spectrometry |
Fourier Transform Techniques |
NMR Spectroscopy |
Molecular Properties / Structure
Spectroscopy for Schools and Colleges [CD-ROM] (by the Royal Society of Chemistry and GlaxoWellcome)  Thomas H. Eberlein
Interactive CR-ROM to assist in learning the fundamentals of interpreting spectroscopy in organic chemistry.
Eberlein, Thomas H. J. Chem. Educ. 2002, 79, 1204.
Spectroscopy |
NMR Spectroscopy |
IR Spectroscopy |
Mass Spectrometry |
Physical Properties |
Molecular Properties / Structure |
Enrichment / Review Materials
Preparing Students for Research: Synthesis of Substituted Chalcones as a Comprehensive Guided-Inquiry Experience  James R. Vyvyan, Donald L. Pavia, Gary M. Lampman, and George S. Kriz Jr.
An aldol condensation of substituted benzaldehydes with substituted acetophones to produce substituted benzalacetophenones (chalcones) in a guided-inquiry approach.
Vyvyan, James R.; Pavia, Donald L.; Lampman, Gary M.; Kriz, George S., Jr. J. Chem. Educ. 2002, 79, 1119.
Medicinal Chemistry |
Microscale Lab |
Natural Products |
NMR Spectroscopy |
Synthesis |
Aromatic Compounds |
Aldehydes / Ketones
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
Fractional Distillation and GC Analysis of Hydrocarbon Mixtures  Craig J. Donahue
Separating and identifying the components of a three-hydrocarbon mixture through fractional distillation and gas chromatography.
Donahue, Craig J. J. Chem. Educ. 2002, 79, 721.
Chromatography |
Gas Chromatography |
Separation Science |
Alkanes / Cycloalkanes |
Alkenes |
Aromatic Compounds |
IR Spectroscopy |
NMR Spectroscopy |
Qualitative Analysis
NMR and Chemistry: An Introduction to Modern NMR Spectrocopy, 4th Edition (by J. W. Akitt and B. E. Mann)  Manish Mehta
Text intended to impart a working knowledge of NMR spectroscopy to a student of chemistry.
Mehta, Manish. J. Chem. Educ. 2002, 79, 677.
NMR Spectroscopy
Impact of Incorporation of High Field FT-NMR Spectroscopy into the Undergraduate Chemistry Curriculum  David B. Ball and Randy Miller
Purchase of a high field FT-NMR spectrometer to incorporate 13C NMR spectroscopy into a year-long organic chemistry course.
Ball, David B.; Miller, Randy. J. Chem. Educ. 2002, 79, 665.
NMR Spectroscopy |
Molecular Properties / Structure
The Mechanism of the Ritter Reaction in Combination with Wagner-Meerwein Rearrangements. A Cooperative Learning Experience  María I. Colombo, María L. Bohn, and Edmundo A. Rúveda
Procedure in which students develop analytical and problem-solving skills by investigating an organic reaction mechanism, predicting the most likely products, and suggesting experiments to test the postulated mechanistic pathways and possible intermediates.
Colombo, María I.; Bohn, María L.; Rúveda, Edmundo A. J. Chem. Educ. 2002, 79, 484.
Mechanisms of Reactions |
Reactive Intermediates |
Amides |
Thin Layer Chromatography |
NMR Spectroscopy
An Organic Puzzle Using Meldrum's Acid  R. David Crouch and Michael S. Holden
Organic synthesis in which the product is not easily predicted, requiring identification through an analysis of the data and consideration of possible reactions of the reagents and solvent.
Crouch, R. David; Holden, Michael S. J. Chem. Educ. 2002, 79, 477.
NMR Spectroscopy |
Synthesis |
Microscale Lab |
Esters |
Synthesis
The Influence of Modern NMR Spectroscopy on Undergraduate Organic, Inorganic, and Physical Chemistry at Florida State University  Joseph B. Vaughn, Jr.
Survey of student attitudes toward having state-of-the-art NMR spectra available.
Vaughn, Joseph B., Jr. J. Chem. Educ. 2002, 79, 306.
Laboratory Equipment / Apparatus |
NMR Spectroscopy
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
Effect of Anisotropy on the Chemical Shift of Vinyl Protons in trans- and cis-1,2-Dibenzoylethylenes. A Small-Group or Recitation Activity  Roosevelt Shaw, David Roane, and Sean Nedd
Procedure to help students explain chemical shift differences for vinyl protons in alkene diastereomers.
Shaw, Roosevelt; Roane, David; Nedd, Sean. J. Chem. Educ. 2002, 79, 67.
Magnetic Properties |
NMR Spectroscopy |
Undergraduate Research |
Diastereomers |
Aromatic Compounds |
Alkenes |
Photochemistry |
Molecular Properties / Structure
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
An Improved Preparation of a-D-(+)-Glucopyranose Pentaacetate  Paul F. Schatz
Using iodine rather than zinc chloride as a Lewis-acid catalyst in the preparation of alpha-(+)-glucopyranose pentaacetate.
Schatz, Paul F. J. Chem. Educ. 2001, 78, 1378.
NMR Spectroscopy |
Synthesis |
Laboratory Management |
Catalysis
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
Investigation of Secondary Metabolites in Plants. A General Protocol for Undergraduate Research in Natural Products  Jonathan Cannon, Du Li, Steven G. Wood, Noel L. Owen, Alexandra Gromova, and Vladislav Lutsky
Typical experimental procedures to extract and isolate individual chemical constituents from a plant, suggestions for some simple procedures to test for selected bioactivity, and explain how the molecular structures of natural products may be determined using spectroscopic techniques.
Cannon, Jonathan; Li, Du; Wood, Steven G.; Owen, Noel L.; Gromova, Alexandra; Lutsky, Vladislav. J. Chem. Educ. 2001, 78, 1234.
Chromatography |
Natural Products |
NMR Spectroscopy |
Separation Science |
Plant Chemistry |
Molecular Properties / Structure |
Drugs / Pharmaceuticals |
Separation Science
Personalized Combined Organic Spectroscopy Problems--Online and in the Lab  Marjorie Kandel and Peter J. Tonge
Assigning individualized spectroscopy problems from SDBS, the Japanese National Institute of Materials and Chemical Research Spectroscopic Database, combined with a laboratory unknown.
Kandel, Marjorie; Tonge, Peter J. J. Chem. Educ. 2001, 78, 1208.
Spectroscopy |
IR Spectroscopy |
NMR Spectroscopy |
Mass Spectrometry
Teaching the Fundamentals of Pulsed NMR Spectroscopy in an Undergraduate Physical Chemistry Laboratory  Gary A. Lorigan, Robert E. Minto, and Wei Zhang
An undergraduate physical chemistry laboratory experiment that utilizes a commercially available bench-top pulsed NMR spectrometer; students assemble the components of an NMR spectrometer, program a variety of pulse sequences, and collect T1 and T2 relaxation data.
Lorigan, Gary A.; Minto, Robert E.; Zhang, Wei. J. Chem. Educ. 2001, 78, 956.
Kinetics |
NMR Spectroscopy |
Laboratory Equipment / Apparatus
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
Isolation and Spectral Analysis of Naturally Occurring Thiarubrine A  Juan Reyes, Melita Morton, Kelsey Downum, and Kevin E. O'Shea
An experiment in which students isolate (from ragweed) and characterize thiarubrine A; thiarubrines are an important class of compounds which have recently received attention because of their unusual reactivity, unique biological activity, and potential medicinal applications.
Reyes, Juan; Morton, Melita; Downum, Kelsey; O'Shea, Kevin E. J. Chem. Educ. 2001, 78, 781.
Aromatic Compounds |
IR Spectroscopy |
Natural Products |
NMR Spectroscopy |
UV-Vis Spectroscopy |
Medicinal Chemistry
A More Realistic Teaching Style in Spectroscopic Instruction  Mar Gómez Gallego, Santiago Romano, Miguel A. Sierra, and Enrique Nieto
A practical application of spectroscopic analysis in intermediate and advanced organic chemistry to determine reaction mechanisms and identify products; provides three specific problems.
Gallego, Mar Gómez; Romano, Santiago; Sierra, Miguel A.; Nieto, Enrique. J. Chem. Educ. 2001, 78, 765.
Mechanisms of Reactions |
NMR Spectroscopy |
Learning Theories |
Spectroscopy |
Molecular Properties / Structure |
Qualitative Analysis
Synthesis of Substituted Butenolides. An Undergraduate Organic Laboratory Experiment Utilizing Two 3-Step Preparatory Sequences  Géraldine Maheut, Liang Liao, Jean-Marie Catel, Paul-Alain Jaffrès, and Didier Villemin
The synthesis of substituted butenolide in two, 3-step sequences that illustrate five basic organic reactions (alkyne hydration, Knoevenagel condensation, lactonization, aldolization-type reaction, and hydration of nitrile); the products have pedagogical interest for IR and NMR spectroscopy (diastereotopic effect).
Maheut, Géraldine; Liao, Liang; Catel, Jean-Marie; Jaffrès, Paul-Alain; Villemin, Didier. J. Chem. Educ. 2001, 78, 654.
IR Spectroscopy |
Molecular Modeling |
NMR Spectroscopy |
Synthesis |
Undergraduate Research |
Reactions
Molecular Mechanics and Variable-Temperature 1H NMR Studies on N,N-Diethyl-m-toluamide. An Undergraduate NMR and Molecular Modeling Experiment  Bruce L. Jensen and Raymond C. Fort Jr.
A combination of molecular modeling and variable-temperature NMR experiments is used to analyze the barrier to rotation about the amide bond of N,N-diethyl-m-toluamide (DEET). This approach utilizes the ability of computers to calculate the potential energy of a set of conformations obtained from a dihedral drive around the N-CO bond.
Jensen, Bruce L.; Fort, Raymond C. Jr. J. Chem. Educ. 2001, 78, 538.
Molecular Modeling |
Molecular Properties / Structure |
NMR Spectroscopy |
Amides
The Dibenzalacetone Reaction Revisited  Leslie A. Hull
Groups of students are assigned target molecules of the dibenzalketone type and are given a sample procedure for the parent dibenzalacetone reaction. They are asked to design a synthesis of their target based on the model reaction and to modify the model reaction so it will work for their synthesis. They show they have synthesized the target with 1H NMR.
Hull, Leslie A. J. Chem. Educ. 2001, 78, 226.
Microscale Lab |
Molecular Modeling |
NMR Spectroscopy |
Synthesis
A Short History of the Chemical Shift  Samuel G. Levine
The term chemical shift is shown to have originated in the mistaken assumption that nuclei of a given element will all undergo resonance at the same frequency regardless of their environment.
Levine, Samuel G. J. Chem. Educ. 2001, 78, 133.
Instrumental Methods |
Magnetic Properties |
NMR Spectroscopy
Teaching 1H NMR Spectrometry Using Computer Modeling  Yoichi Habata and Sadatoshi Akabori
Use of computer modeling for teaching 1H NMR spectroscopy is described. The direction of the induced magnetic field is clarified by displaying the electrostatic potential on the molecule, when the magnetic anisotropy effect is taught.
Habata, Yoichi; Akabori, Sadatoshi. J. Chem. Educ. 2001, 78, 121.
Molecular Properties / Structure |
NMR Spectroscopy |
Molecular Modeling
WebSpectra: Online NMR and IR Spectra for Students  Craig A. Merlic, Barry C. Fam, and Michael M. Miller
WebSpectra is a World Wide Web site at UCLA through which organic chemistry students have convenient access to a library of problems in NMR and IR spectroscopy, ranging in difficulty from introductory to advanced. Students are presented with high-resolution spectra of unknown compounds in addition to the molecular formula.
Merlic, Craig A.; Fam, Barry C.; Miller, Michael M. J. Chem. Educ. 2001, 78, 118.
IR Spectroscopy |
NMR Spectroscopy |
Molecular Properties / Structure
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 Discovery-Oriented Approach to Organic Chemistry. 4. Epoxidation of p-Methoxy-trans-b-methylstyrene: An Exercise in NMR and IR Spectroscopy for Sophomore Organic Laboratories  Rebecca S. Centko and Ram S. Mohan
Illustrates epoxidation of alkenes as well as the reactivity of epoxides toward acids. The experiment involves reaction of p-methoxy-trans-beta-methylstyrene (trans-anethole) with m-chloroperoxybenzoic acid (MCPBA), in both the absence and presence of a buffer, followed by product identification using 1H NMR, 13C NMR, and IR spectroscopy
Centko, Rebecca S.; Mohan, Ram S. J. Chem. Educ. 2001, 78, 77.
IR Spectroscopy |
NMR Spectroscopy |
Epoxides |
Alkenes
Organic-Solvent-Free Phase-Transfer Oxidation of Alcohols Using Hydrogen Peroxide  Martin Hulce and David W. Marks
Six representative alcohols are oxidized to the corresponding aldehyde or ketone, integrating the various techniques of extraction, drying, filtration, column chromatography, gas chromatography, NMR and IR spectroscopy, and reaction kinetics.
Hulce, Martin; Marks, David W. J. Chem. Educ. 2001, 78, 66.
Catalysis |
Oxidation / Reduction |
Reactions |
Kinetics |
Chromatography |
Gas Chromatography |
Separation Science |
NMR Spectroscopy |
IR Spectroscopy |
Alcohols |
Phenols
Hybridization and Structural Properties
(re
J. Chem. Educ. 1998, 75, 888-890)  Victor M. S. Gil
Clarifying cause-effect relationships between orbital hybridization and structural properties.
Gil, Victor M. S. J. Chem. Educ. 2001, 78, 31.
MO Theory |
Instrumental Methods |
NMR Spectroscopy |
Molecular Properties / Structure
Hybridization and Structural Properties
(re
J. Chem. Educ. 1998, 75, 888-890)  Victor M. S. Gil
Clarifying cause-effect relationships between orbital hybridization and structural properties.
Gil, Victor M. S. J. Chem. Educ. 2001, 78, 31.
MO Theory |
Instrumental Methods |
NMR Spectroscopy |
Molecular Properties / Structure
Elucidation of Molecular Structure Using NMR Long-Range Coupling: Determination of the Single Isomer Formed in a Regiospecific Reaction  Samuel Delagrange and Françoise Nepveu
The experiment presented in this article introduces students to the main concepts of two essential NMR techniques for investigating molecular structure. Heteronuclear multiple bond connectivity (HMBC) and proton-coupled 13C NMR are used to determine which isomer, from a possible two, is formed by a regiospecific reaction. The demonstration, based on long-range coupling between quaternary carbons and protons on neighboring carbons, is presented step by step.
Delagrange, Samuel; Nepveu, Françoise. J. Chem. Educ. 2000, 77, 895.
Molecular Properties / Structure |
NMR Spectroscopy |
Synthesis |
Carboxylic Acids |
Reactions |
Diastereomers
The Discovery Approach to NMR: Development of Chemical-Shift Additivity Tables and Application to Product Identification  Eric Bosch
A discovery-based approach to the preparation and application of chemical-shift additivity tables is presented to give students insight into the development of NMR spectral prediction software.
Bosch, Eric. J. Chem. Educ. 2000, 77, 890.
Laboratory Computing / Interfacing |
NMR Spectroscopy |
Aromatic Compounds |
Molecular Properties / Structure
Simple and Inexpensive Classroom Demonstrations of Nuclear Magnetic Resonance and Magnetic Resonance Imaging  Joel A. Olson, Karen J. Nordell, Marla A. Chesnik, Clark R. Landis, and Arthur B. Ellis, M. S. Rzchowski, S. Michael Condren, and George C. Lisensky
Several demonstrations of resonance phenomena associated with nuclear magnetic resonance (NMR) and magnetic resonance imaging (MRI) are described. Complete instructions for the construction of the demonstrations, which can be used on an overhead projector, are included.
Olson, Joel A.; Nordell, Karen J.; Chesnik, Marla A.; Rzchowski, M. S.; Condren, S. Michael; Landis, Clark R.; Lisensky, George C.; Ellis, Arthur B. J. Chem. Educ. 2000, 77, 882.
Instrumental Methods |
Magnetic Properties |
NMR Spectroscopy
150 and More Basic NMR Experiments: A Practical Course, 2nd Edition (by S. Braun, H.-O. Kalinowski, and S. Berger)  reviewed by Nancy Mills
Encyclopedia of the techniques a modern NMR spectroscopist might need.
Mills, Nancy. J. Chem. Educ. 2000, 77, 831.
NMR Spectroscopy
Application of the Correlation Method to Vibrational Spectra of C60 and Other Fullerenes: Predicting the Number of IR- and Raman-Active Bands  Kazuo Nakamoto and Michael A. McKinney
The C60 molecule (Buckyball/soccer ball) exhibits only 4 IR and 10 Raman bands although it possesses 174 (3 x 60 - 6) normal vibrations. This striking reduction in the number of observed bands is evidently due to the molecule's extremely high symmetry (Ih point group).
Nakamoto, Kazuo; McKinney, Michael A. J. Chem. Educ. 2000, 77, 775.
Chirality / Optical Activity |
Group Theory / Symmetry |
IR Spectroscopy |
NMR Spectroscopy |
Raman Spectroscopy |
Molecular Properties / Structure |
Molecular Modeling
The Heck Reaction: A Microscale Synthesis Using a Palladium Catalyst  William B. Martin and Laura J. Kateley
The microscale synthesis described uses a reaction between a bromoiodobenzene and acrylic acid to produce a bromocinnamic acid. Structure verification for the product uses IR and 1H NMR spectroscopy.
Martin, William B.; Kateley, Laura J. J. Chem. Educ. 2000, 77, 757.
Catalysis |
Microscale Lab |
Synthesis |
IR Spectroscopy |
NMR Spectroscopy |
Aromatic Compounds |
Mechanisms of Reactions
Reaction of Dibenzoylethylene with Hydriodic Acid  Fred H. Greenberg
Dibenzoylethylene is treated with hydriodic acid in acetone at room temperature to obtain dibenzoylethane rather than the expected dibenzoyliodoethane. Students identify the product by the use of NMR and IR spectra and are given a nonpictorial representation of a mechanism and asked to supply the structures of the relevant intermediates.
Greenberg, Fred H. J. Chem. Educ. 2000, 77, 505.
Microscale Lab |
Synthesis |
NMR Spectroscopy |
IR Spectroscopy |
Mechanisms of Reactions |
Reactive Intermediates
Multicomponent Reactions: A Convenient Undergraduate Organic Chemistry Experiment  Ricardo Bossio, Stefano Marcaccini, Carlos F. Marcos, and Roberto Pepino
Two experiments for the synthesis of a -lactam and a succinimide, based on a 4-component Ugi condensation. The experimental procedures for both syntheses are identical except for the choice of the starting amine, whose electron richness is controlled by the presence or absence of an electron-withdrawing group.
Bossio, Ricardo; Marcaccini, Stefano; Marcos, Carlos F.; Pepino, Roberto. J. Chem. Educ. 2000, 77, 382.
Synthesis |
Drugs / Pharmaceuticals |
IR Spectroscopy |
NMR Spectroscopy |
Mechanisms of Reactions |
Molecular Properties / Structure
Isolating trans-Anethole from Anise Seeds and Elucidating Its Structure: A Project Utilizing One- and Two-Dimensional NMR Spectrometry  Joseph W. LeFevre
This three-week project involves isolating and purifying a natural product and determining its structure. trans-Anethole is isolated from anise seeds by steam distillation and liquid-liquid extraction. The crude product is analyzed by thin-layer chromatography and purified by flash chromatography.
LeFevre, Joseph W. . J. Chem. Educ. 2000, 77, 361.
Chromatography |
IR Spectroscopy |
Natural Products |
NMR Spectroscopy |
Separation Science |
Molecular Properties / Structure |
Thin Layer Chromatography
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
Understanding NMR Multiplet Structure with WinDNMR  N. Bampos and A. Vidal-Ferran
Employing interactive, user-friendly software packages (such as WinDNMR) on a conventional personal computer to investigate the effect of changing the constituent coupling constants on the appearance of a multiplet. As an example, a multiplet representing a proton coupled to three neighboring environments (four-spin system) is treated in detail.
Bampos, N.; Vidal-Ferran, A. J. Chem. Educ. 2000, 77, 130.
NMR Spectroscopy |
Instrumental Methods
Student-Determined Values for the Calculation of Chemical Shifts of Methylene Protons in Different Chemical Environments  Gary W. Breton
A laboratory experiment in which students themselves determine values for the calculation of chemical shifts of methylene protons in a variety of chemical environments. Although these values come from single determinations of representative compounds from several different classes, the alpha-parameter values obtained are in close agreement with literature data.
Breton, Gary W. J. Chem. Educ. 2000, 77, 81.
Laboratory Equipment / Apparatus |
NMR Spectroscopy
The Discovery-Oriented Approach to Organic Chemistry. 3. Rearrangement of cis- and trans-Stilbene Oxides with Boron Trifluoride Etherate. An Exercise in 1H NMR Spectroscopy for Sophomore Organic Laboratories  Erik A. Sgariglia, Regina Schopp, Kostas Gavardinas, and Ram S. Mohan
A discovery-oriented laboratory experiment that involves the rearrangement of both cis- and trans-stilbene oxides with boron trifluoride etherate.
Sgariglia, Erik A.; Schopp, Regina; Gavardinas, Kostas; Mohan, Ram S. J. Chem. Educ. 2000, 77, 79.
Mechanisms of Reactions |
NMR Spectroscopy |
Constitutional Isomers
Keep Going with Cyclooctatetraene!  Addison Ault
This paper shows how some simple properties of cyclooctatetraene can indicate important ideas about the structure of cyclooctatetraene.
Ault, Addison. J. Chem. Educ. 2000, 77, 55.
Aromatic Compounds |
NMR Spectroscopy |
Mechanisms of Reactions |
Molecular Properties / Structure
The Hofmann Rearrangement Using Household Bleach: Synthesis of 3-Nitroaniline  Keith A. Monk and Ram S. Mohan
A simple experiment that involves the Hofmann rearrangement of 3-nitrobenzamide to give 3-nitroaniline using household bleach. The synthesis of 3-nitrobenzamide by nitration of benzamide and the subsequent Hofmann rearrangement can be carried out in two-and-a-half hours, making this a new and simple two-step reaction sequence for the organic laboratory.
Monk, Keith A.; Mohan, Ram S. J. Chem. Educ. 1999, 76, 1717.
NMR Spectroscopy |
Synthesis
Incorporation of FT-NMR throughout the Chemistry Curriculum  D. Scott Davis and Dale E. Moore
Through funding from the former Instrumentation and Laboratory Improvement (ILI) program of the National Science Foundation, Mercer University has purchased a 300 MHz Nuclear Magnetic Resonance spectrometer. The redesign of a standard undergraduate chemistry curriculum to an inquiry-based curriculum with NMR as a central learning theme is described.
Davis, D. Scott; Moore, Dale E. J. Chem. Educ. 1999, 76, 1617.
NMR Spectroscopy |
Laboratory Equipment / Apparatus |
Fourier Transform Techniques
The Preparation of a UV-Light-Absorbing Polymer: A Project-Oriented Laboratory Experiment for the Introductory Organic Chemistry Curriculum  Thomas Poon, Jean P. McIntyre, Andrea Dorigo, Drew J. Davis, Matthew A. Davis, Crystal F. Eller, Leah R. Eller, Heather K. Izumi, Kenya M. Jones, Kurt H. Kelley, William Massello, Megan L. Melamed, Cynthia M. Norris, Jeffrey A. Oelrich, Thomas A. Pluim, Sarah E. Poplawski, Jason M. St. Clair, Matthew P. Stokes, Wells C. Wheeler, and Erin E. Wilkes
A laboratory experiment is described that combines organic synthesis, spectroscopy, and polymer chemistry and is suitable for the sophomore organic chemistry curriculum. In this three-week sequence, students synthesize and characterize the UV-absorber 2-(2',4'-dimethylbenzoyl)benzoic acid and incorporate it into films of polymethylmethacrylate.
Poon, Thomas; McIntyre, Jean P.; Dorigo, Andrea; Davis, Drew J.; Davis, Matthew A.; Eller, Crystal F.; Eller, Leah R.; Izumi, Heather K.; Jones, Kenya M.; Kelley, Kurt H.; Massello, William; Melamed, Megan L.; Norris, Cynthia M.; Oelrich, Jeffrey A.; Pluim, Thomas A.; Poplawski, Sarah E.; St. Clair, Jason M.; Stokes, Matthew P.; Wheeler, Wells C.; Wilkes, Erin E. J. Chem. Educ. 1999, 76, 1523.
Synthesis |
UV-Vis Spectroscopy |
NMR Spectroscopy |
IR Spectroscopy |
Free Radicals
Analysis of Soft Drinks Using Nuclear Magnetic Resonance Spectroscopy: A Mentorship  Arkim Wilson, Craig Myers, George Crull, Michael Curtis, and Pamela Pasciak Patterson
This mentorship was designed to expose a student to the laboratory routine for a chemist at Bristol Myers Squibb Company (BMS). The student visited BMS, collaborated with BMS scientists, and actually completed a project on site. He was asked to determine the identity of an unknown sample of soft drink retrieved from a fictitious crime scene using NMR spectroscopy.
Wilson, Arkim; Myers, Craig; Crull, George; Curtis, Michael; Pasciak, Pamela M. J. Chem. Educ. 1999, 76, 1414.
Instrumental Methods |
Atomic Properties / Structure |
NMR Spectroscopy |
Qualitative Analysis |
Separation Science |
Student / Career Counseling
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
Gradualism: A Method for Primary Instruction on Spectroscopic Analysis in Introductory Organic Chemistry  Christopher W. Alexander, Gary L. Asleson, Charles F. Beam, Marion T. Doig, Frederick J. Heldrich*, and Shannon Studer-Martinez
The pedagogical style of gradualism is described for the instruction of spectroscopic analysis in the introductory organic chemistry laboratory. Gradualism is defined as a series of steps or lessons that build one upon the other until the student is able to solve complex problems.
Alexander, Christopher W.; Asleson, Gary L.; Beam, Charles F.; Doig, Marion T.; Heldrich, Frederick J.; Studer-Martinez, Shannon. J. Chem. Educ. 1999, 76, 1297.
IR Spectroscopy |
Mass Spectrometry |
NMR Spectroscopy |
UV-Vis Spectroscopy |
Learning Theories
Spectroscopic Instruction in Introductory Organic Chemistry: Results of a National Survey  Christopher W. Alexander, Gary L. Asleson, Marion T. Doig, and Frederick J. Heldrich*
The survey results indicated that the spectroscopic techniques of IR, MS, proton NMR, and carbon NMR are core techniques in most courses. A considerable amount of the instruction in spectroscopy is occurring in both the laboratory and the lecture portions of the course.
Alexander, Christopher W.; Asleson, Gary L.; Doig, Marion T.; Heldrich, Frederick J. J. Chem. Educ. 1999, 76, 1294.
IR Spectroscopy |
Mass Spectrometry |
NMR Spectroscopy |
UV-Vis Spectroscopy |
Spectroscopy
The Discovery-Oriented Approach to Organic Chemistry 2. Selectivity in Alcohol Oxidation: An Exercise in 1H NMR Spectroscopy for Sophomore Organic Laboratories  Steven R. Shadwick and Ram S. Mohan
A simple oxidation experiment that presents the student with a puzzle and is a good exercise in 1H NMR spectroscopy. The experiment, which illustrates the important concept of selectivity in organic synthesis, involves selective oxidation of a mixture of 1-heptanol and 2-heptanol using commercial swimming pool chlorine.
Shadwick, Steven R.; Mohan, Ram S. J. Chem. Educ. 1999, 76, 1121.
NMR Spectroscopy |
Alcohols |
Oxidation / Reduction |
Synthesis
A Simple and Convenient Method for Generation and NMR Observation of Stable Carbanions  Hamid S. Kasmai
A simple and convenient method for the generation and NMR study of stable carbanions is described. The data and sample spectra illustrate that reliable and good quality NMR spectra of stable carbanions may be obtained. The experiments described provide a good opportunity for students to apply the basic principles of 1H and 13C NMR spectrometry and the interesting topic of the exchange phenomenon in NMR.
Kasmai, Hamid S. J. Chem. Educ. 1999, 76, 830.
Acids / Bases |
Reactive Intermediates |
NMR Spectroscopy |
Aromatic Compounds
Synthesis of a 7-Oxanorbornene Monomer: A Two-Step Sequence Preparation for the Organic Laboratory  Marcia B. France, Lisa T. Alty, and T. Markley Earl
The Diels-Alder reaction and solvolysis of an anhydride accompanied by Fischer esterification. Both of these steps produce crystals in a dramatic manner that catches the students' attention. This sequence can stand on its own as part of an organic laboratory, or the product can be utilized as a monomer for ring-opening metathesis polymerization (ROMP) studies.
France, Marcia B.; Alty, Lisa T.; Earl, T. Markley. J. Chem. Educ. 1999, 76, 659.
Synthesis |
NMR Spectroscopy
Employing NMR Spectroscopy To Evaluate Transmission of Electronic Effects in 4-Substituted Chalcones  Nanette Wachter-Jurcsak and Hossein Zamani
Described is an organic synthesis experiment that demonstrates the electronic transmission by substituents. The effect of substitution at the para-position of the styryl ring of 1,3-diphenyl-2-propenones (chalcones) by typical electron-donating or -accepting groups can be observed by proton and carbon-13 NMR spectroscopy.
Wachter-Jurcsak, Nanette; Zamani, Hossein. J. Chem. Educ. 1999, 76, 653.
NMR Spectroscopy |
Synthesis
The Discovery-Oriented Approach to Organic Chemistry. 1. Nitration of Unknown Organic Compounds. An Exercise in 1H NMR and 13C NMR Spectrosopy for Sophomore Organic Laboratories  Sonia R. McElveen, Kostas Gavardinas, Jean A. Stamberger, and Ram S. Mohan
Two simple nitration experiments that present the student with a puzzle and are a good exercise in 1H NMR and 13C NMR spectroscopy. The experiment involves nitration of unknown organic compounds and product analysis by 1H NMR and 13C NMR spectroscopy, which enables the student to determine the identity of the unknown.
McElveen, Sonia R.; Gavardinas, Kostas; Stamberger, Jean A.; Mohan, Ram S. J. Chem. Educ. 1999, 76, 535.
NMR Spectroscopy |
Synthesis |
Reactions
A Safe Simple Halogenation Experiment  Hilton M. Weiss and Lara Ganz
This experiment is designed to be a safe and experimentally simple procedure appropriate to the early weeks of a course when halogenation is the only reaction which has been discussed in the lecture. It can also provide some early experience with simple interpretation of NMR spectra.
Weiss, Hilton M.; Ganz, Lara. J. Chem. Educ. 1999, 76, 534.
Synthesis |
Free Radicals |
Reactions |
NMR Spectroscopy
A Complete Introduction to Modern NMR Spectroscopy (by Rodger S. Macomber)  Raymond L. Ward
Text for a beginning student or research person starting or thinking about using NMR as a method to obtain structural information about organic molecules.
Ward, Raymond L. J. Chem. Educ. 1999, 76, 473.
Spectroscopy |
NMR Spectroscopy
Microscale Synthesis and 1H NMR Analysis of Tetraphenylporphyrins  RaeAnne E. Falvo, Larry M. Mink, and Diane F. Marsh
The synthesis of tetraphenylporphyrin, H2[TPP], and para-substituted tetraphenylporphyrins, H2[(p-X)4TPP], where X = CN, CH3, and OCH3, is easily accomplished using microscale glassware. The compounds are synthesized from inexpensive starting reagents.
Falvo, RaeAnne E.; Mink, Larry M.; Marsh, Diane F. J. Chem. Educ. 1999, 76, 237.
Instrumental Methods |
Microscale Lab |
NMR Spectroscopy |
Synthesis
Spectroscopy of Simple Molecules  C. Baer and K. Cornely
A spectroscopy experiment in which students utilize IR and NMR spectroscopy to identify the structures of three unknowns from a list of 15 carefully chosen simple organic molecules. In taking IR and NMR spectra, students learn to use state-of-the-art instrumentation that is used by practicing chemists.
Baer, Carl; Cornely, Kathleen. J. Chem. Educ. 1999, 76, 89.
Instrumental Methods |
IR Spectroscopy |
NMR Spectroscopy |
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
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 19F NMR Study of Enzyme Activity  Keith E. Peterman, Kevin Lentz, and Jeffery Duncan
This basic enzyme activity laboratory experiment demonstrates how 19F NMR can be used in biochemical studies and presents the advantages of 19F NMR over 1H NMR for studies of this nature. This is a viable laboratory experiment for junior/senior-level courses in instrumental analytical chemistry, biochemistry, molecular biology, or spectroscopy.
Peterman, Keith E.; Lentz, Kevin; Duncan, Jeffery. J. Chem. Educ. 1998, 75, 1283.
Instrumental Methods |
Enzymes |
NMR Spectroscopy |
Spectroscopy
Chromatographic Separation Techniques for Undergraduates  Darwin B. Dahl, John T. Riley, and Thomas K. Green
Over the past several years the Chemistry Department at Western Kentucky University (WKU) has sought to strengthen its undergraduate program departmental through acquisition of FT-NMR, fluorescence, electrochemical, thermal analysis, laser Raman, microscale organic, and polymer laboratory instrumentation; this has enabled the department to build a successful undergraduate program.
Dahl, Darwin B.; Riley, John T.; Green, Thomas K. J. Chem. Educ. 1998, 75, 1209.
Separation Science |
Chromatography |
Fourier Transform Techniques |
NMR Spectroscopy |
Raman Spectroscopy |
Electrochemistry |
Photochemistry |
Thermal Analysis |
Microscale Lab
Fourier Transform Nuclear Magnetic Resonance Spectroscopy Experiment for Undergraduate and Graduate Students  Matthew A. Doscotch, John F. Evans, and Eric J. Munson
We have designed a FT-NMR spectrometer composed of self-contained components (i.e. mixers, switches, amplifiers) that has been successfully incorporated into laboratory experiments for both undergraduate and graduate students. The undergraduate instrumental analysis experiment allows students to examine the spectrometer on a component by component basis.
Doscotch, Matthew A.; Evans, John F.; Munson, Eric J. J. Chem. Educ. 1998, 75, 1008.
Laboratory Equipment / Apparatus |
NMR Spectroscopy |
Fourier Transform Techniques
A Strategy for Incorporating 13C NMR into the Organic Chemistry Lecture and Laboratory Courses  Perry C. Reeves and Chris P. Chaney
The use of spectroscopy in establishing the structures of molecules is an important component of the first course in Organic Chemistry. However, the point in the course at which these techniques are best introduced remains uncertain. We suggest that carbon nuclear magnetic resonance spectroscopy should be introduced at an early stage of the lecture course, specifically while studying the alkanes, and used extensively for structure determination throughout the course.
Reeves, Perry C.; Chaney, Chris P. J. Chem. Educ. 1998, 75, 1006.
Instrumental Methods |
NMR Spectroscopy |
Fourier Transform Techniques |
Alkanes / Cycloalkanes |
Molecular Properties / Structure
Synthesis and Structure-Property Relationships in (h6-Arene)Cr(CO)3 Chemistry: From Guided Experiments to Discovery Research  Allen D. Hunter, Larry J. Bianconi, Steven J. DiMuzio, and Dianne L. Braho
Since instructors can have each student prepare a different complex, they are ideal targets for student directed "discovery research" lab projects. Teams of students can compare how their syntheses and the physical, spectroscopic, and electrochemical properties of their products vary as a function of the arenes' structures.
Hunter, Allen D.; Bianconi, Larry J.; DiMuzio, Steven J.; Braho, Dianne L. J. Chem. Educ. 1998, 75, 891.
Microscale Lab |
Organometallics |
IR Spectroscopy |
NMR Spectroscopy |
Electrochemistry |
Synthesis |
Coordination Compounds
NMR Spectroscopy: Processing Strategies (by Peter Bigler)   Nancy S. Mills
Part of a four-volume series planned to deal with all aspects of a standard NMR experiment, this text, and the accompanying exercises based on data contained on a CD-ROM, goes a long way to fill in the gaps and clarify misunderstandings about NMR processing.
Mills, Nancy S. J. Chem. Educ. 1998, 75, 696.
NMR Spectroscopy |
Molecular Properties / Structure
Spectra Interpretation of Organic Compounds (by Erno Pretsch and Jean Thomas Clerc)  Phyllis A. Leber
An interactive spectroscopy course via the iterative solution of 15 spectral problems. An ancillary CD-ROM containing the SpecTeach version of the SpecTool software is provided with the text.
Leber, Phyllis A. J. Chem. Educ. 1998, 75, 695.
Spectroscopy |
IR Spectroscopy |
UV-Vis Spectroscopy |
NMR Spectroscopy |
Molecular Properties / Structure
Incorporating Organic Name Reactions and Minimizing Qualitative Analysis in an Unknown Identification Experiment  Claire Castro and William Karney
The authors have developed a new type of unknown identification experiment for the introductory organic chemistry laboratory. The unknown sample the student is provided with is the product of an organic name reaction. The student is only informed of the starting material and conditions used in the compound's synthesis, and must then: (1) deduce the compound's structure, (2) determine the name reaction and corresponding mechanism that yields the compound, and (3) present his/her results to the class.
Claire Castro and William Karney. J. Chem. Educ. 1998, 75, 472.
IR Spectroscopy |
NMR Spectroscopy |
Qualitative Analysis |
Nomenclature / Units / Symbols |
Reactions |
Mechanisms of Reactions |
Molecular Properties / Structure
Educational NMR Software  Peter Lundberg
A description of a compilation of computer programs (EduNMRSoft) suitable for teaching NMR at an introductory to advanced level is presented. Each program is categorized and described by function, hardware requirements, availability, author, and references in the list.
Lundberg, Peter. J. Chem. Educ. 1997, 74, 1489.
Instrumental Methods |
NMR Spectroscopy |
Spectroscopy
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
The Diels-Alder Reaction of 2,4-Hexadien-1-ol with Maleic Anhydride: A Novel Preparation for the Undergraduate Organic Chemistry Laboratory Course  Keith F. McDaniel and R. Matthew Weekly
The reaction of 2,4-hexadien-1-ol with maleic anhydride provides an excellent exercise for undergraduate laboratory courses. In addition to the expected Diels-Alder reaction, which takes place readily in refluxing toluene, subsequent intramolecular cleavage of the resulting bicyclic anhydride by the pendant hydroxy group generates a lactone. Thus, two important organic reactions can be carried out in a single laboratory session.
McDaniel, Keith F.; Weekley, R. Matthew. J. Chem. Educ. 1997, 74, 1465.
Synthesis |
NMR Spectroscopy |
Molecular Properties / Structure |
Alcohols
Acetone and Ethyl Acetate in Commercial Nail Polish Removers: A Quantitative NMR Experiment Using an Internal Standard  David W. Clarke
The qualitative and quantitative analysis of commercial nail polish removers is performed on a 60 MHz NMR spectrometer. After taking NMR spectra of the polish removers, students can make peak assignments for the known components of acetone and ethyl acetate. Using these spectra, students are also able to identify the unknown alcohol present in the remover as ethanol.
Clarke, David W. J. Chem. Educ. 1997, 74, 1464.
Laboratory Equipment / Apparatus |
NMR Spectroscopy |
Aldehydes / Ketones
Regioselective Hydrochlorination: An Experiment for the Undergraduate Laboratory  Philip Boudjouk, Beon-Kyu Kim, and Byung-Hee Han
A simple and convenient procedure for the addition of hydrogen chloride to a variety of olefins is described. Conventional glassware is used and product isolation is straightforward using distillation techniques.
Boudjouk, Philip; Kim, Beon-Kyu; Han, Byung-Hee. J. Chem. Educ. 1997, 74, 1223.
Learning Theories |
NMR Spectroscopy |
Synthesis |
Electrophilic Substitution
ACD/ChemSketch 1.0 (freeware); ACD/ChemSketch 2.0 and its Tautomers, Dictionary, and 3D Plug-ins; ACD/HNMR 2.0; ACD/CNMR 2.0  reviewed by Allen D. Hunter
Chemistry drawing and NMR prediction packages.
Hunter, Allen D. . J. Chem. Educ. 1997, 74, 905.
NMR Spectroscopy |
Molecular Modeling |
Molecular Properties / Structure
Synthesis of Tetrahydro-2-(2-propynyloxy)-2H-pyran: Illustrating Markownikov Addition, Protecting Groups, and Advance 1H-NMR Phenomena  Ronald G. Brisbois, William G. Batterman, and Scott R. Kragerud
Synthesis of the target compound illustrates Markownikov Addition and formation of a THP-ether protecting group, produces an acetal functional group, and models a recently developed resin used in combinatorial chemistry. Purification of the target compound via flash column chromatography exposes students to a central technique of modern synthetic methodology.
Brisbois, Ronald G. ; Batterman, William G. ; Kragerud, Scott R. . J. Chem. Educ. 1997, 74, 834.
Catalysis |
NMR Spectroscopy |
Microscale Lab |
Combinatorial Chemistry
The Synthesis, Characterization, and Lewis Acidity of SnI2 and SnI4  Richard W. Schaeffer, Benny Chan, Michael Molinaro, Susan Morissey, Claude H. Yoder, Carolyn S. Yoder, and Stephanie Shenk
In this project the student has the opportunity to learn about: a) the direct synthesis of compounds from the elements, b) stoichiometry and limiting reagent, c) isolation by recrystallization, d) use of inert atmosphere, e) identification by melting point, gravimetric analysis, powder x-ray diffraction, and NMR spectroscopy, and f) at least one method for determination of relative Lewis acidity.
Schaeffer, Richard W. ; Chan, Benny ; Molinaro, Michael; Morissey, Susan ; Yoder, Claude H.; Yoder, Carolyn S.; Shenk, Stephanie. J. Chem. Educ. 1997, 74, 575.
Acids / Bases |
Synthesis |
Stoichiometry |
Lewis Acids / Bases |
NMR Spectroscopy
The FT-NMR Free Induction Decay Archive  Craig B. Fryhle, Dean A. Waldow, and J. Chris Bock
The on-line FTNMR Free Induction Decay (FID) Archive offers a free and readily accessible means by which students and faculty can obtain high field FTNMR data for processing on personal computers.
Fryhle, Craig B.; Waldow, Dean A.; Bock, J. Chris. J. Chem. Educ. 1997, 74, 442.
Fourier Transform Techniques |
NMR Spectroscopy
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
An Analogy To Assist Understanding of Splitting Patterns in NMR Spectra  Dianne A. Thoben and Thomas H. Lowry
An analogy to the "point of view shot" as used in the movies is used to help students understand and interpret splitting patterns in proton NMR spectra.
Thoben, Dianne A.; Lowry, Thomas H. J. Chem. Educ. 1997, 74, 68.
NMR Spectroscopy |
Molecular Properties / Structure
Grignard Reaction of an Epoxide: A Mechanistic Study  James A. Ciaccio, Sabrina Volpi, Ransford Clarke
Unlike most undergraduate Grignard experiments which are performed merely for the sake of illustrating a textbook reaction, this Grignard synthesis is performed to probe the reactivity of styrene oxide. Students are required to analyze their products by TLC and NMR spectroscopy (instead of just submitting them for a grade) in order to obtain the data necessary for making mechanistic conclusions.
Ciaccio, James A.; Volpi, Sabrina; Clarke, Ransford. J. Chem. Educ. 1996, 73, 1196.
Grignard Reagents |
Epoxides |
Thin Layer Chromatography |
NMR Spectroscopy |
Synthesis
Four Programs for Windows: Abstract of Volume 4D, Number 2: SPECPNMR: A Proton NMR Slide Show  Adrian J. Blackman
SPECPNMR is one of a set of programs developed as an aid for teaching introductory spectroscopy to organic chemistry students. It includes a brief introduction to nuclear magnetic resonance spectroscopy followed by a detailed look at proton magnetic resonance spectroscopy. The program generates electronic slides for display in a lecture theatre on a large screen using a video projector or LCD panel and overhead projector. The slides are designed to help a lecturer teach spectroscopy.
Blackman, Adrian J. J. Chem. Educ. 1996, 73, 1078.
NMR Spectroscopy |
Spectroscopy
Four Programs for Windows: Abstract of Volume 4D, Number 2: HIPPO-CNMRS: Highly Improved Prediction Program of Carbon Nuclear Magnetic Resonance Shifts  Helmut Honig
HIPPO-CNMRS is a "highly improved" version of a 13C-NMR program previously available from the author. It can predict the 13C NMR spectrum for most substituted alicyclic saturated and aromatic ring systems (cyclopropane to cyclooctane; benzene, naphthalene, anthracene; cis- and trans-decaline; some heterocyclic systems like furan, tetrahydofuran, pyridine, piperidine and quinoline; most substituted acyclic compounds with up to six carbons in the parent structure; and simple olefins and alkynes.
Honig, Helmut. J. Chem. Educ. 1996, 73, 1078.
NMR Spectroscopy
The Quantitative Analysis of an Analgesic Tablet: An NMR Experiment for the Instrumental Analysis Course   Thomas A. Schmedake, Lawrence E. Welch
Initial work utilizes a known compound (acenapthene) to assess the type of NMR experiment necessary to achieve a proportional response from all of the carbons in the compound. Once the experiments with the known compound have illuminated the merits of the differing strategies for obtaining a proportional carbon response, a quantitative assessment of an unknown analgesic tablet is undertaken. The amounts of the two major components of the tablet, acetaminophen and aspirin, are determined following addition of an internal standard to the mixture.
Schmedake, Thomas A.; Welch, Lawrence E. J. Chem. Educ. 1996, 73, 1045.
Quantitative Analysis |
Drugs / Pharmaceuticals |
NMR Spectroscopy |
Instrumental Methods
A New Photochemistry Experiment, A Simple 2+2 Photocycloaddition that Poses an Interesting NMR Problem   John T. Magner, Matthias Selke, Arlene A. Russell, Orville L. Chapman
The cycloaddition of -nitrostyrene to 2,3-dimethyl-1,3-butadiene provides an extremely clean example of 2 + 2 cycloaddition. This laboratory exercise combines theory, technique, spectroscopy, and data interpretation.
J. Chem. Educ. 1996, 73, 854.
Photochemistry |
NMR Spectroscopy |
Qualitative Analysis |
Instrumental Methods |
Addition Reactions |
Mechanisms of Reactions
The Sharp Electronic Organizer--A Warning  Thomas A. Eaton
Tutorial that prepares students to obtain and study crystallographic and NMR models of proteins, nucleic acids, and other biomolecules; includes web-address to obtain copies of the program.
Eaton, Thomas A. J. Chem. Educ. 1995, 72, A178.
NMR Spectroscopy |
X-ray Crystallography
Organic Qualitative Analysis at the Microscale Level  Craig, Rhoda E. R.; Kaufman, Kurt K.
Project requiring students to identify pure unknowns and the components of mixtures using a variety of chromatography and spectrometry techniques.
Craig, Rhoda E. R.; Kaufman, Kurt K. J. Chem. Educ. 1995, 72, A102.
NMR Spectroscopy |
IR Spectroscopy |
Chromatography |
Separation Science |
Qualitative Analysis |
Acids / Bases
The Baylis-Hillman Reaction: Synthesizing a Compound and Explaining Its Formation  Crouch, R. David; Nelson, Todd D.
Experimental procedure for the synthesis of an unpredictable and unknown mechanism to be identified and described by students through analytical techniques (spectroscopy).
Crouch, R. David; Nelson, Todd D. J. Chem. Educ. 1995, 72, A6.
Synthesis |
Mechanisms of Reactions |
NMR Spectroscopy |
IR Spectroscopy |
UV-Vis Spectroscopy |
Microscale Lab
WinDNMR: Dynamic NMR Spectra for Windows  Hans J. Reich
Program to demonstrate important concepts in NMR spectroscopy.
Reich, H. J. . J. Chem. Educ. 1995, 72, 1086.
NMR Spectroscopy
1H NMR, 13C NMR, and Mass Spectrometry of 1-Phenyl-1,2-Dihaloethanes  Joseph R. Gandler, Kevin W. Kittredge, and Oliver L. Saunders
Procedure to introduce organic chemistry students to spectroscopic methods for characterizing structure and calculating 13C NMR chemical shifts.
Gandler, Joseph R.; Kittredge, Kevin W.; Saunders, Oliver L. . J. Chem. Educ. 1995, 72, 855.
NMR Spectroscopy |
Mass Spectrometry
Proton NMR Basics  Carolyn S. Judd, Joel D. Morrisett, Mohan V. Chari, and Jeffrey L. Browning
Multimedia tutorial to introduce and develop understanding of NMR spectroscopy concepts and techniques.
Judd, C. Sweeney; Morrisett, J. D.; Chari, M. V. ; Browning, J. L. J. Chem. Educ. 1995, 72, 706.
NMR Spectroscopy
Charge Distribution in 1,1-Dicyano-2-Arylethenes: An Undergraduate Organic Experiment Utilizing the Knoevenagel Condensation and NMR Spectroscopy  Rowland, Alex T.
Organic synthesis illustrating the effect of ring substituents on an aromatic ring.
Rowland, Alex T. J. Chem. Educ. 1995, 72, 548.
Mechanisms of Reactions |
Synthesis |
NMR Spectroscopy |
Aromatic Compounds
3,9-Diaryl-2,4,8,10-Tetraoxaspiro[5.5]Undecanes by Rapid Microscale Preparation: Products with Instructive NMR Spectra  Clark, Thomas J.
Organic synthesis designed to produce product with an interesting structure to illustrate the effects of conformation and symmetry on NMR spectra; includes sample data and analysis.
Clark, Thomas J. J. Chem. Educ. 1995, 72, 375.
Synthesis |
NMR Spectroscopy |
Molecular Properties / Structure |
Synthesis |
Microscale Lab
Hammett Correlations of Amide Proton Chemical Shifts: An Organic or Spectroscopy Experiment  Setliff, F. L.; Soman, N. G.; Toland, A. D.
Experiment designed to illustrate the quantitative relationship between an easily measurable property (amide proton NMR chemical shift) and the electronic effect of several different substituents on substituted benzanilides; includes sample data and analysis.
Setliff, F. L.; Soman, N. G.; Toland, A. D. J. Chem. Educ. 1995, 72, 362.
Synthesis |
NMR Spectroscopy |
Molecular Properties / Structure |
Amides
Characterization of Low-Valent Nickel Complexes Stabilized by Bis(diphenylphosphino)methane Using Multinuclear NMR and IR Spectroscopy.  Trumpy, Valory A.; Oriskovich, Tracy A.; Gallaher, Thomas N.; Schreiner, Serge
Experimental method for the synthesis of zero-valent nickel complexes containing bis(diphenylphosphino)methane and identification through NMR and IR spectroscopy; sample data and analysis included.
Trumpy, Valory A.; Oriskovich, Tracy A.; Gallaher, Thomas N.; Schreiner, Serge J. Chem. Educ. 1995, 72, 357.
Metals |
NMR Spectroscopy |
IR Spectroscopy |
Atomic Properties / Structure |
Coordination Compounds |
Synthesis
Using Fourier Transforms to Understand Spectral Line Shapes  Grunwald, Ernest; Herzog, Jonathan; Steel, Colin
Using a computerized Fast Fourier Transforms (FFT) algorithm to analyze the rates of physical and chemical processes through dynamic spectroscopy.
Grunwald, Ernest; Herzog, Jonathan; Steel, Colin J. Chem. Educ. 1995, 72, 210.
Fourier Transform Techniques |
NMR Spectroscopy |
Chemometrics
Hydrogen-Bonding Equilibrium in Phenol Analyzed by NMR Spectroscopy  Lessinger, Leslie
Experimental procedure for determining the equilibrium constant for the hydrogen-bonding equilibrium of phenol in carbon tetrachloride solution; data and analysis included.
Lessinger, Leslie J. Chem. Educ. 1995, 72, 85.
Equilibrium |
Noncovalent Interactions |
NMR Spectroscopy |
Hydrogen Bonding |
Aromatic Compounds |
Alcohols
Hands-on Use of High-Field NMR without the NMR  Swartz, James E.; Vojta, Gail M.; Erickson, Luther E.
The authors describe how and why they provide students with free induction decay data for an unknown and the students work on the unknown on a personal computer using spectral analysis software.
Swartz, James E.; Vojta, Gail M.; Erickson, Luther E. J. Chem. Educ. 1994, 71, 1069.
NMR Spectroscopy
A Qualitative Experiment for Organic Chemistry Lab  Hermann, Christine K. F.
This experiment was introduced near the end of second semester. The students were told that the unknowns were either an alcohol, a carboxylic acid, an amine, an aldehyde, or a ketone. The identifications were based on melting points or boiling points, the IR and NMR spectra, and a set of four classification tests.
Hermann, Christine K. F. J. Chem. Educ. 1994, 71, 991.
Qualitative Analysis |
IR Spectroscopy |
NMR Spectroscopy
Platinum(II) Chemistry Monitored by NMR Spectroscopy  Berry, David E.
Preparation and characterization of three platinum coordination compounds.
Berry, David E. J. Chem. Educ. 1994, 71, 899.
NMR Spectroscopy |
Synthesis |
Molecular Properties / Structure |
Coordination Compounds
PCNMR4Windows  Bemis, John M.
Program designed for the routine workup of spectral data without tying up an NMR spectrometer console.
Bemis, John M. J. Chem. Educ. 1994, 71, 558.
NMR Spectroscopy
Computer-Generated Edited DEPT NMR Spectra  Gurst, Jerome E.
159. Bits and pieces, 51. Modification to simplify an earlier approach to sophomore organic chemistry.
Gurst, Jerome E. J. Chem. Educ. 1994, 71, 234.
NMR Spectroscopy
FT NMR in the Instrumental Analysis Course: A Curriculum and a Laboratory  Fuson, Michael M.
Discussion of NMR in the context of instrumental analysis should focus on the nature of the FT NMR experiment; a procedure to support this discussion is provided.
Fuson, Michael M. J. Chem. Educ. 1994, 71, 126.
Fourier Transform Techniques |
NMR Spectroscopy |
Instrumental Methods
Microscale qualitative organic analysis   Goller, Edwin J.; Miller, John H.
Students gain critical thinking skills in an organic chemistry course by selecting their own chemical tests.
Goller, Edwin J.; Miller, John H. J. Chem. Educ. 1993, 70, A159.
Qualitative Analysis |
Spectroscopy |
Fourier Transform Techniques |
NMR Spectroscopy |
Gas Chromatography |
Mass Spectrometry |
Microscale Lab
Microscale yeast mediated enantiospecific reduction of vanillin, and the absolute configuration of (-)-(R)-[alpha]-deuteriovanillyl alcohol: A bioorganic chemistry experiment   Lee, Moses
An experiment is introduced to a sophomore chemistry course that demonstrates the effeciency and enantiospecificity of microbial/enzyme-mediated reactions and the use of NMR methods in determining the optical activity and absolute configuration of chiral alcohols.
Lee, Moses J. Chem. Educ. 1993, 70, A155.
Enantiomers |
Alcohols |
Bioorganic Chemistry |
Chirality / Optical Activity |
NMR Spectroscopy |
Microscale Lab
A kinetic study of the isomerization of eugenol: The quantitative use of NMR, GC, and HPLC in a single organic laboratory experiment that demonstrates alternative approaches to solving a problem   Peterson, Thomas H.; Bryan, James H.; Keevil, Thomas A.
Description of an experiment that allows students to be aware that there is often more than one approach to designing an experiment,and that the quality of the experimental results often depend on the proper choice of instrument(s).
Peterson, Thomas H.; Bryan, James H.; Keevil, Thomas A. J. Chem. Educ. 1993, 70, A96.
Aromatic Compounds |
NMR Spectroscopy |
Alcohols |
Kinetics
Nitration of phenols: A two-phase system  Zeegers, Petrus J.
Nitration of phenols is often overlooked in undergraduate organic chemistry courses.
Zeegers, Petrus J. J. Chem. Educ. 1993, 70, 1036.
Phenols |
Aromatic Compounds |
Reactions |
Quantitative Analysis |
Mechanisms of Reactions |
Chromatography |
NMR Spectroscopy
A convenient method of esterification of fatty acids: An undergraduate organic laboratory experiment  Di Raddo, Pasquale
A convenient method of esterification of fatty acids for undergraduate organic chemistry lab.
Di Raddo, Pasquale J. Chem. Educ. 1993, 70, 1034.
Carboxylic Acids |
Esters |
Gas Chromatography |
NMR Spectroscopy |
Fatty Acids
Oxidation of (R)-(+)-pulegone to (R)-(+)-3-methyladipic acid  Scott, William J.; Hammond, Gerald B.; Becicka, Brian T.; Wiemer, David F.
This paper addresses the demand for microscale laboratories and minimizes waste disposal while linking students to current organic chemistry research.
Scott, William J.; Hammond, Gerald B.; Becicka, Brian T.; Wiemer, David F. J. Chem. Educ. 1993, 70, 951.
Microscale Lab |
Undergraduate Research |
NMR Spectroscopy |
IR Spectroscopy
Hydrochlorination of 1-propynylbenzene on alumina: A demonstration of kinetic and thermodynamic control using HCl produced in situ and molecular modeling  Pienta, Norbert J.; Crawford, Scott D.; Kropp, Paul J.
A hydrochlorination experiment that provides sufficient latitude in choice of conditions.
Pienta, Norbert J.; Crawford, Scott D.; Kropp, Paul J. J. Chem. Educ. 1993, 70, 682.
Molecular Modeling |
Alkynes |
Alkenes |
Gas Chromatography |
NMR Spectroscopy |
Microscale Lab
NMR spectroscopy: An introduction to the operation of modern instrumentation: Using commercial acquisition and analysis software giving students experience with a graphical workstation and notefile  Prais, Michael G.
149. To give students insight into the operation of modern instrumentation, an experiment was developed to exhibit the steps necessary to acquire, analyze, and present data from an NMR spectrometer by a personal computer.
Prais, Michael G. J. Chem. Educ. 1993, 70, 381.
Laboratory Computing / Interfacing |
NMR Spectroscopy
Whether organic qual will wither?   Zieger, Herman E.
Author argues the important pedagogic purposes of organic qualitative analysis.
Zieger, Herman E. J. Chem. Educ. 1993, 70, 230.
Spectroscopy |
Qualitative Analysis |
IR Spectroscopy |
NMR Spectroscopy
The Aqueous Ring-Opening Metathesis Polymerization of Furan-Maleic Anhydride Adduct: Increased Catalytic Activity Using a Recyclable Transition Metal Catalyst  Viswanathan, Tito; Jethmalani, Jagdish
ROMP offers an opportunity for an experiment that should fit well within the context of a laboratory in organic or polymer chemistry because the experimental yield can be characterized at the molecular level.
Viswanathan, Tito; Jethmalani, Jagdish J. Chem. Educ. 1993, 70, 165.
Polymerization |
NMR Spectroscopy
A Simplified Version of a Classic Proton Exchange NMR Experiment  Pagnotta, Marco; Carter, James; Armsby, Carrie
A simple upgrade of a classic alcohol exchange experiment that demonstrates changes in chemical shift, spin-spin coupling, and integration for use as an introduction to using NMR.
Pagnotta, Marco; Carter, James; Armsby, Carrie J. Chem. Educ. 1993, 70, 162.
NMR Spectroscopy |
Quantum Chemistry
The microscale synthesis and the structure determination of endo-9-methoxycarbonyl-3-oxatricyclo[4,2,1,0 4,5]-2-nonanone.  Lee, Moses.
The microscale synthesis and the structure determination of endo-9-methoxycarbonyl-3-oxatricyclo[4,2,1,0 4,5]-2-nonanone.
Lee, Moses. J. Chem. Educ. 1992, 69, A172.
Microscale Lab |
Synthesis |
Aldehydes / Ketones |
Fourier Transform Techniques |
NMR Spectroscopy |
IR Spectroscopy |
Gas Chromatography |
Thin Layer Chromatography |
Instrumental Methods
Microscale reactions of vanillin   Fowler, Rosemary G.
In this paper five microscale experiments which allow first-year organic student sot study the properties and reactions of vanillin are presented.
Fowler, Rosemary G. J. Chem. Educ. 1992, 69, A43.
Aldehydes / Ketones |
Aromatic Compounds |
Phenols |
Microscale Lab |
IR Spectroscopy |
NMR Spectroscopy
NMR tube cleaner  Denton, T. T.; Eisenbraun, E.
An inexpensive, rugged, and easily constructed alternative to all-glass, NMR-tube cleaners.
Denton, T. T.; Eisenbraun, E. J. Chem. Educ. 1992, 69, 1036.
NMR Spectroscopy |
Laboratory Equipment / Apparatus |
Laboratory Management
1H NMR analysis of mixtures using internal standards: A quantitative experiment for the instrumental analysis laboratory  Peterson, Jim
Procedure to illustrate the general principles of quantitative NMR methodology.
Peterson, Jim J. Chem. Educ. 1992, 69, 843.
NMR Spectroscopy |
Quantitative Analysis |
Instrumental Methods
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
Identification of methylcyclohexanones by NMR  Gurst, Jerome E.
Distinguishing between three isomeric methylcyclohexanones using NMR.
Gurst, Jerome E. J. Chem. Educ. 1992, 69, 774.
Aldehydes / Ketones |
NMR Spectroscopy |
Diastereomers
Using spin-spin decoupling NMR for structure elucidation in the extraction of cinnamaldehyde.  Ganjian, I.; Baumgarten, R. L.; Valenzuela, R. J.
Interesting extraction in which students learn to interpret spectra and see the power of second-order spectral analysis in NMR work.
Ganjian, I.; Baumgarten, R. L.; Valenzuela, R. J. J. Chem. Educ. 1992, 69, 511.
NMR Spectroscopy |
Separation Science |
Molecular Properties / Structure
An introduction to NMR titration for studying rapid reversible complexation  Macomber, Roger S.
Nuclear magnetic resonance spectrospcopy is one of the most useful techniques available to chemists for the investigation of dynamic molecular processes.
Macomber, Roger S. J. Chem. Educ. 1992, 69, 375.
NMR Spectroscopy |
Titration / Volumetric Analysis |
Solutions / Solvents |
Qualitative Analysis
A new twist to an old favorite: The hydrolysis of tert-butyl chloride.  Turner, J.
The author describes a common kinetics experiment in which NMR spectroscopy is used to study the reaction kinetics rather than a titration.
Turner, J. J. Chem. Educ. 1992, 69, 242.
Kinetics |
NMR Spectroscopy |
Reactions
Utilizing the Evans method with a superconducting NMR spectrometer in the undergraduate laboratory  Schubert, Ernest M.
Using the Evans method has become a standard experiment in many physical chemistry laboratory texts. However, these texts make no mention of the inherent difference between conventional and high field NMR instruments.
Schubert, Ernest M. J. Chem. Educ. 1992, 69, 62.
NMR Spectroscopy
Proton and carbon-13 NMR simulation of mixtures  Bell, Harold M.
133. Bits and pieces, 47. The program for simulation of spectra of mixtures can accommodate five components, each containing as many as six coupled nuclei.
Bell, Harold M. J. Chem. Educ. 1992, 69, 44.
NMR Spectroscopy
Isomerization of dimethyl maleate to dimethyl fumarate: An undergraduate experiment illustrating amine-catalyzed alkene isomerization, stereochemical principles, sublimation, and product identification by spectroscopic methods  Fryhle, Craig B.; Rybak, Carol M.; Pulley, Kenneth E.
An undergraduate experiment illustrating amine-catalyzed alkene isomerization, stereochemical principles, sublimation, and product identification by spectroscopic methods.
Fryhle, Craig B.; Rybak, Carol M.; Pulley, Kenneth E. J. Chem. Educ. 1991, 68, 1050.
Amines / Ammonium Compounds |
Diastereomers |
Gas Chromatography |
NMR Spectroscopy |
Fourier Transform Techniques |
Catalysis
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
Hydroboration-oxidation of (1R)-(+)-alpha-pinene to isopinocampheol: A microscale experiment that displays regio- and stereochemistry using NMR spectroscopy and molecular mechanics calculations  Blankespoor, Ronald L.; Piers, Kenneth
The hydroboration-oxidation of alkenes is an important route to alcohols and therefore receives considerable treatment in standard organic textbooks. These authors present their findings of an example (an alkene that undergoes the hydroboration oxidation process) that displays both regiochemistry and stereochemistry.
Blankespoor, Ronald L.; Piers, Kenneth J. Chem. Educ. 1991, 68, 693.
Alkenes |
Oxidation / Reduction |
NMR Spectroscopy |
Alcohols
Undergraduate organic and polymer lab experiments that exemplify structure determination by NMR  Viswanathan, T.; Watson, F.; Yang, D. T. C.
Where in the curriculum is the best place to teach experimental NMR methods that are so essential to chemists and chemistry? These authors are of the opinion that NMR must be given more than a cursory introduction involving a single experiment, and present a series of experiments.
Viswanathan, T.; Watson, F.; Yang, D. T. C. J. Chem. Educ. 1991, 68, 685.
Instrumental Methods |
NMR Spectroscopy
A laboratory study of 1,3-dipole-dipolarophile addition: An extension of the Diels Alder reaction  Gingrich, Henry L.; Pickering, Miles
Some easy organic reactions that can also be used as the basis for puzzles, or as facile heterocyclic syntheses: an area neglected in the student experiment literature.
Gingrich, Henry L.; Pickering, Miles J. Chem. Educ. 1991, 68, 614.
Mechanisms of Reactions |
Addition Reactions |
Synthesis |
Heterocycles |
Physical Properties |
NMR Spectroscopy
A problem-solving approach to teaching organic laboratory  Cooley, James H.
This paper describes the author's continuing efforts to provide greater intellectual challenge to students in the organic chemistry laboratory.
Cooley, James H. J. Chem. Educ. 1991, 68, 503.
NMR Spectroscopy
An NMR study of the stereochemistry of the fumarase-catalyzed hydration of fumaric acid  Olsen, Julie A.; Olsen, Robert J.
An NMR study of the stereochemistry of the fumarase-catalyzed hydration of fumaric acid.
Olsen, Julie A.; Olsen, Robert J. J. Chem. Educ. 1991, 68, 436.
Acids / Bases |
NMR Spectroscopy |
Enzymes |
Molecular Modeling |
Diastereomers
Synthesis of a bicyclo[2.2.1]heptene Diels-Alder adduct: An organic chemistry experiment utilizing NMR spectroscopy to assign endo stereochemistry  Harrison, Ernest A., Jr.
An organic chemistry experiment utilizing NMR spectroscopy to assign endo stereochemistry via synthesis of a bicyclo[2.2.1]heptene Diels-Alder adduct.
Harrison, Ernest A., Jr. J. Chem. Educ. 1991, 68, 426.
Alkanes / Cycloalkanes |
Synthesis |
Alkenes |
Aromatic Compounds |
NMR Spectroscopy |
Thin Layer Chromatography
Proton-carbon chemical shift correlations  Macomber, Roger S.
The purpose of this paper is to examine the correlation between H-1 chemical shifts and C-13 chemical shifts in some detail.
Macomber, Roger S. J. Chem. Educ. 1991, 68, 284.
NMR Spectroscopy |
Instrumental Methods
A convenient synthesis of 3,4-pentadien-1-ol from 3-butyn-1-ol: Spectral analysis and unusual durability of the allene moiety  Price, William A.; Patten, Timothy E.
Description of a convenient synthesis of 3,4-pentadien-1-ol from 3-butyn-1-ol: Spectral analysis and unusual durability of the allene moiety.
Price, William A.; Patten, Timothy E. J. Chem. Educ. 1991, 68, 256.
Synthesis |
Alcohols |
Alkenes |
NMR Spectroscopy
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
Fabric softeners as phase transfer catalyst in organic synthesis  Lee, Albert W. M.; Yip, W. C.
Phase transfer catalysts such as quaternary ammonium compounds are often found in commercial fabric softeners due to their antistatic properties.
Lee, Albert W. M.; Yip, W. C. J. Chem. Educ. 1991, 68, 69.
Gas Chromatography |
NMR Spectroscopy |
Catalysis |
Synthesis
Introduction to Spectroscopy, IR, NMR, & CMR (Clough, Fred W.)  Byrd, James E.
Set of programs designed to help students analyze and interpret infrared, 1H-NMR and 13C-NMR spectra.
Byrd, James E. J. Chem. Educ. 1990, 67, A194.
Spectroscopy |
IR Spectroscopy |
NMR Spectroscopy |
Instrumental Methods
The Fourier transform in chemistry--NMR: Part 4. Two-dimensional methods   Williams, Kathryn R.; King, Roy W.
This article will conclude the series with an examination of some of the most important types of two-dimensional spectra.
Williams, Kathryn R.; King, Roy W. J. Chem. Educ. 1990, 67, A125.
Fourier Transform Techniques |
NMR Spectroscopy
The Fourier transform in chemistry--NMR: A glossary of NMR terms   King, Roy W.; Williams, Kathryn R.
This glossary is a resource for anyone new to the literature of the Fourier transform.
King, Roy W.; Williams, Kathryn R. J. Chem. Educ. 1990, 67, A100.
Fourier Transform Techniques |
NMR Spectroscopy
The Fourier transform in chemistry--NMR: Part 3. Multiple-pulse experiments   Williams, Kathryn R.; King, Roy W.
This paper will provide the average chemist with an introduction to the information that can be gained from Fourier transform in chemistry.
Williams, Kathryn R.; King, Roy W. J. Chem. Educ. 1990, 67, A93.
Fourier Transform Techniques |
NMR Spectroscopy
Synthesis of 5-nitrofurfural diacetate and 5-nitrofurfural semicarbazone: An undergraduate laboratory experiment  Li, Xiaorong; Liu, Qianguang; Chang, James C.
Demonstrates how to nitrate an aromatic compound having an aldehyde group that can be oxidized by nitrating agents.
Li, Xiaorong; Liu, Qianguang; Chang, James C. J. Chem. Educ. 1990, 67, 986.
Synthesis |
Aldehydes / Ketones |
Esters |
Ethers |
Electrophilic Substitution |
Aromatic Compounds |
NMR Spectroscopy
NMR analysis of product mixtures in electrophilic aromatic substitution  Clark, Mary Ann; Duns, Glenn; Golberg, Danny; Karwowska, Anna; Turgeon, Andree; Turley, Jolanda
Use of mole fraction analysis permits precise quantitative product mixture analysis, a large improvement over qualitative and semiquantitative techniques.
Clark, Mary Ann; Duns, Glenn; Golberg, Danny; Karwowska, Anna; Turgeon, Andree; Turley, Jolanda J. Chem. Educ. 1990, 67, 802.
NMR Spectroscopy |
Electrophilic Substitution |
Aromatic Compounds |
Quantitative Analysis
A demonstration of imaging on an NMR spectrometer  Hull, L. A.
A simple demonstration illustrating a relationship between magnetic resonance imaging and NMR spectroscopy.
Hull, L. A. J. Chem. Educ. 1990, 67, 782.
NMR Spectroscopy |
Medicinal Chemistry
Proton NMR simulator  Black, Kersey A.
Software designed to help students learn how to correlate proton NMR spectral data with molecular structure.
Black, Kersey A. J. Chem. Educ. 1990, 67, 589.
NMR Spectroscopy |
Molecular Properties / Structure
The addition of hydrogen bromide to unsymmetrical alkenes: Introductory experiments in NMR spectroscopy and mechanistic chemistry  Brown, Trevor M.; Dronsfield, Alan T.; Ellis, Robert
As an introduction to NMR the authors center their work around the addition of hydrogen bromide to unsymmetrical alkenes and use the coupling patterns in the proton NMR spectra to establish whether the addition product is consistent with the Markovnikov rule.
Brown, Trevor M.; Dronsfield, Alan T.; Ellis, Robert J. Chem. Educ. 1990, 67, 518.
NMR Spectroscopy |
Alkenes |
Mechanisms of Reactions
A simple method for drying an NMR spinner air supply  Holden, Michael S.; Ogren, Paul J.; Lainhart, Steven D.
A simple alternative to a commercial dryer is a modified cold trap.
Holden, Michael S.; Ogren, Paul J.; Lainhart, Steven D. J. Chem. Educ. 1990, 67, 445.
NMR Spectroscopy |
Laboratory Equipment / Apparatus
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
Grignard reagent additions to alpha, beta-ethylenic nitriles: 1,4- vs. 1,2- additions  Kulp, Stuart S.; DiConcetto, Joseph A.
The easily synthesized alpha-phenylcinnamonitrile serves as an excellent starting material to illustrate conjugate (1,4) vs. simple (1,2) addition of various reactants.
Kulp, Stuart S.; DiConcetto, Joseph A. J. Chem. Educ. 1990, 67, 271.
Grignard Reagents |
Aromatic Compounds |
IR Spectroscopy |
NMR Spectroscopy
LAOCOON PC: NMR simulation on a personal computer  Clark, Matthew; Thrasher, Joseph S.
112. Bits and pieces, 43. The authors have developed a modern version of an NMR simulation program.
Clark, Matthew; Thrasher, Joseph S. J. Chem. Educ. 1990, 67, 235.
Laboratory Computing / Interfacing |
NMR Spectroscopy
The Fourier transform in chemistry. Part 1. Nuclear magnetic resonance: Introduction  King, Roy W.; Williams, Kathryn R.
Provides a fundamental understanding and appreciation of FT-NMR.
King, Roy W.; Williams, Kathryn R. J. Chem. Educ. 1989, 66, A213.
Fourier Transform Techniques |
NMR Spectroscopy |
Instrumental Methods
Organic spectroscopy  Hiatt, Richard
Six programs that generate and display infrared, proton NMR, carbon-13 NMR, and mass spectra.
Hiatt, Richard J. Chem. Educ. 1989, 66, 927.
Spectroscopy |
IR Spectroscopy |
NMR Spectroscopy |
Mass Spectrometry
A comparison of FT NMR and FT IR techniques  Ahn, Myong-Ku
A comparison of FT NMR and FT IR based on the examination of electromagnetic waves.
Ahn, Myong-Ku J. Chem. Educ. 1989, 66, 802.
Fourier Transform Techniques |
NMR Spectroscopy |
IR Spectroscopy
Synthesis and reactivity of ?5-cyclopentadienylruthenium compounds: An organometallic chemistry experiment  Ballester, L.; Gutierrez, A.; Perpinan, M. F.
Procedure permits the application of concepts regarding the reactivity of organometallic compounds and the use of IR and NMR spectral data in the characterization of the synthesized complexes.
Ballester, L.; Gutierrez, A.; Perpinan, M. F. J. Chem. Educ. 1989, 66, 777.
Organometallics |
IR Spectroscopy |
NMR Spectroscopy |
Coordination Compounds
Student comparisons of analytical chemical methods in undergraduate chemistry courses  Harrison, Aline M.; Peterman, Keith E.
Four experiments in which different analytical methods are used to make the same measurement for purposes of comparison.
Harrison, Aline M.; Peterman, Keith E. J. Chem. Educ. 1989, 66, 772.
Gravimetric Analysis |
Atomic Properties / Structure |
Titration / Volumetric Analysis |
NMR Spectroscopy |
UV-Vis Spectroscopy |
Enzymes |
Quantitative Analysis
Teaching magnetic resonance imaging using computer animation  Browne, David S.; Ellsworth, Presley E., IV; Hornak, Joseph P.
105. Bits and pieces, 41. A computer-based teaching package for the principles of NMR imaging written in Turbo Pascal.
Browne, David S.; Ellsworth, Presley E., IV; Hornak, Joseph P. J. Chem. Educ. 1989, 66, 647.
NMR Spectroscopy
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
The isolation of sesquiterpenes from Artemisia annua  Roth, Ronald J.; Acton, Nancy.
Artemisia annua is a Eurasian import in North America and has been found growing in diverse parts of the United States. Procedures have been reported for the isolation of arteannuin B and of arteannuic acid.
Roth, Ronald J.; Acton, Nancy. J. Chem. Educ. 1989, 66, 349.
Plant Chemistry |
Natural Products |
IR Spectroscopy |
NMR Spectroscopy
Fourier analysis and structure determination. Part II. Pulse NMR and NMR imaging  Chesick, John P.
In this paper the authors seek to extend and amplify two previous articles dealing with pulse NMR with extension in more detail to the application of NMR imaging.
Chesick, John P. J. Chem. Educ. 1989, 66, 283.
Fourier Transform Techniques |
NMR Spectroscopy
Fourier analysis and structure determination. Part I. Fourier transforms  Chesick, John P.
In this part, Part I, the authors provide a brief introduction to Fourier analysis and some definitions and properties of Fourier transforms that are needed in Parts II and III for the discussions of NMR imaging and X-ray crystal structure analysis.
Chesick, John P. J. Chem. Educ. 1989, 66, 128.
Fourier Transform Techniques |
NMR Spectroscopy
Nuclear magnetic resonance spectroscopy in biochemistry   Cheatham, Steve
This review will discuss the nature of the NMR experiment, the techniques used, the types of structural and dynamic information one obtains, and how one can view and refine structures using computer graphics techniques in combination with NMR data.
Cheatham, Steve J. Chem. Educ. 1989, 66, 111.
NMR Spectroscopy
Trifluoroacetylation of unknown alcohols: An integrated microscale organic experiment using spectroscopic methods  Piers, Kenneth; Hsung, Richard
The authors have found that trifluoroacetylation of unknown alcohols is a fast, clean, easily performed microscale experiment that integrates a number of aspects of laboratory work, viz. synthesis, isolation, characterization, spectroscopic measurement, and interpretation, and unknown identification.
Piers, Kenneth; Hsung, Richard J. Chem. Educ. 1989, 66, 90.
Alcohols |
Microscale Lab |
Qualitative Analysis |
NMR Spectroscopy |
IR Spectroscopy
Constants of 1:1 complexes from NMR or spectrophotometric measurements  Nurchi, Valeria; Crisponi, Guido
99. Bits and pieces, 39. The authors have written a BASIC program for obtaining reliable estimates of K and spectral parameters for the 1:1 complex formation.
Nurchi, Valeria; Crisponi, Guido J. Chem. Educ. 1989, 66, 54.
NMR Spectroscopy |
Spectroscopy
A simple computer program for the calculation of 13C-NMR chemical shifts  Olivieri, Alejandro C.; Kaufman, Teodoro S.
99. Bits and pieces, 39. The authors have written a computer program in which the characteristics of any given carbon atom are introduced as a succession of letter and numbers in a predetermined order.
Olivieri, Alejandro C.; Kaufman, Teodoro S. J. Chem. Educ. 1989, 66, 53.
NMR Spectroscopy
NMR simulation and interactive drill/interpretation  Badger, Robert; Lesniak, Joseph; Rutta, Stephen
99. Bits and pieces, 39. The purpose of this project was to develop an interactive computer program that would provide many examples and help students develop a systematic approach to master these skills.
Badger, Robert; Lesniak, Joseph; Rutta, Stephen J. Chem. Educ. 1989, 66, 52.
NMR Spectroscopy |
Enrichment / Review Materials
NMR simulator (Schatz, Paul)  Newland, Robert J.; Ticknor, Donna L.
Two reviews of a software program that is an impressive NMR simulator.
Newland, Robert J.; Ticknor, Donna L. J. Chem. Educ. 1988, 65, A296.
NMR Spectroscopy |
Laboratory Computing / Interfacing
A step-by-step picture of pulsed (time domain) NMR  Schwartz, Leslie J.
The goal of this paper is to describe a pulsed NMR experiment that is as simple and pictorial as possible, but that stops short of dangerous generalizations and oversimplifications that can lead to contradictions.
Schwartz, Leslie J. J. Chem. Educ. 1988, 65, 752.
NMR Spectroscopy |
Magnetic Properties |
Instrumental Methods
The correlation of multinuclear spectral data for selectively fluorinated organic compounds  Everett, T. Stephen
This article presents a general discussion of fluorine-19 NMR spectroscopy, spectral data for two series of selectively fluorinated compounds, and the detailed correlation of multinuclear data for one specific compound.
Everett, T. Stephen J. Chem. Educ. 1988, 65, 422.
Aromatic Compounds |
NMR Spectroscopy |
Isotopes
Fourier transforms for chemists. Part 2. Fourier transforms in chemistry and spectroscopy  Glasser, L.
Considers the number of data channels in a spectrometer, the dispersive element as a delay device, the Fourier transform technique and its advantages, the fast Fourier transform technique and its advantages, and applications of these techniques to chemistry.
Glasser, L. J. Chem. Educ. 1987, 64, A260.
Fourier Transform Techniques |
Spectroscopy |
Instrumental Methods |
IR Spectroscopy |
NMR Spectroscopy
An application of the NMR method for determination of magnetic moments to study anomalous paramagnetism in some iron(III) chelates  Hughes, Jeffrey G.; Lawson, Peter J.
An application of the NMR method for determination of magnetic moments to study anomalous paramagnetism in iron(III) N,N-dialkyldithiocarbamates.
Hughes, Jeffrey G.; Lawson, Peter J. J. Chem. Educ. 1987, 64, 973.
Magnetic Properties |
NMR Spectroscopy |
Coordination Compounds |
Crystal Field / Ligand Field Theory
A very brief, rapid, simple, and unified method for estimating carbon-13 NMR chemical shifts: The BS method  Shoulders, Hen; Welch, Steven C.
The "BS" method is so brief and simple that students can memorize and use it to interpret 13C NMR spectra with ease.
Shoulders, Hen; Welch, Steven C. J. Chem. Educ. 1987, 64, 915.
NMR Spectroscopy |
Alkanes / Cycloalkanes |
Alkenes |
Alkynes |
Instrumental Methods
A new microcell technique for NMR analysis  Yu, Sophia J.
Eliminating expensive microcells and replacing them with disposable units.
Yu, Sophia J. J. Chem. Educ. 1987, 64, 812.
NMR Spectroscopy |
Laboratory Equipment / Apparatus |
Instrumental Methods
A straightforward way to determine relative intensities of spin-spin splitting lines of equivalent nuclei in NMR spectra  Orcutt, Ronald H.
Because of the increasingly widespread availability of FT-NMR spectrometers with multinuclear capability, it is desirable to have a simple rule for predicting relative intensities to be expected in spin systems other than {-1/2, +1/2}.
Orcutt, Ronald H. J. Chem. Educ. 1987, 64, 763.
NMR Spectroscopy |
Fourier Transform Techniques
Characterizing a tetrahedral intermediate in an acyl transfer reaction: An undergraduate 1H NMR demonstration  Rzepa, Henry S.; Lobo, Ana M.; Marques, M. Matilde; Prabhakar, Sundaresan
A simple experiment involving the detection by 1H NMR spectroscopy of a stable intermediate formed by nucleophilic attack and its characterization as a chiral species.
Rzepa, Henry S.; Lobo, Ana M.; Marques, M. Matilde; Prabhakar, Sundaresan J. Chem. Educ. 1987, 64, 725.
NMR Spectroscopy |
Nucleophilic Substitution |
Chirality / Optical Activity
"Solvent" effects in 1H NMR spectroscopy: A simple undergraduate experiment  Cavaleiro, Jose A. S.
A series of simple NMR experiments to familiarize students with "solvent effects" on 1H NMR chemical shifts.
Cavaleiro, Jose A. S. J. Chem. Educ. 1987, 64, 549.
NMR Spectroscopy |
Solutions / Solvents
The structure of bis(trimethylsilyl) amides: A multinuclear NMR project  Samples, Majorie S.; Yoder, Claude H.; Schaeffor, Charles D., Jr.
A project designed to illustrate the great value of observing nuclei other than 1H and 13C (29Si, 14N, 17O).
Samples, Majorie S.; Yoder, Claude H.; Schaeffor, Charles D., Jr. J. Chem. Educ. 1987, 64, 177.
Molecular Properties / Structure |
Amides |
NMR Spectroscopy
Synthesis and proton NMR spectrum of p-xylylenebis(2-(2-ethyl-1,3-propanediol))  Lisensky, George C.; Friedman, Robert M.
An experiment that is suitable for a second semester organic class where both the isolation of the product and the NMR spectral interpretation are straightforward.
Lisensky, George C.; Friedman, Robert M. J. Chem. Educ. 1986, 63, 644.
NMR Spectroscopy |
Synthesis
NMR simulation program for the ZX81 computer  Starkey, Ronald
73. Bits and pieces, 29. A report of an NMR simulation program the author created.
Starkey, Ronald J. Chem. Educ. 1986, 63, 625.
NMR Spectroscopy |
Laboratory Computing / Interfacing
Empirical NMR chemical shift correlation's for methine protons  Friedrich, Edwin C.; Runkle, Katherine Gates
Empirical NMR chemical shift correlation's for methine protons.
Friedrich, Edwin C.; Runkle, Katherine Gates J. Chem. Educ. 1986, 63, 127.
NMR Spectroscopy
The Nebraska instrument sharing consortium  Smith, David H.
A small group of colleges have banded together to solve one of the pressing problems in chemical education today- how to provide modern instrumentation to students at an affordable price.
Smith, David H. J. Chem. Educ. 1986, 63, 68.
Laboratory Equipment / Apparatus |
Laboratory Management |
NMR Spectroscopy |
UV-Vis Spectroscopy
NMR Chemistry: An Introduction to the Fourier Transform-Multinuclear Era (Akitt, J. W.)  Acrivos, Juana V.
A thorough review of the theory of spin-spin coupling necessary to interpret 1H and 13C NMR spectra.
Acrivos, Juana V. J. Chem. Educ. 1985, 62, A134.
NMR Spectroscopy |
Fourier Transform Techniques
The esterification of trifluoroacetic acid: An NMR kinetics experiment  Minter, David E.; Villarreal, Mark C.
Procedure to determine pseudo-first-order rate constants for the esterification of trifluoroacetic acid.
Minter, David E.; Villarreal, Mark C. J. Chem. Educ. 1985, 62, 911.
NMR Spectroscopy |
Kinetics |
Instrumental Methods
Acetylation of an unknown alcohol: An introductory 1H-NMR experiment  Branz, Stephen E.
Students use NMR analysis to identify the acetylation product of an unknown alcohol.
Branz, Stephen E. J. Chem. Educ. 1985, 62, 899.
Alcohols |
NMR Spectroscopy
Proton NMR spectra: Deceptively simple and deceptively complex examples  Gurst, J. E.; Dellinger, C. M.; Jacobus, John
NMR experiments that result in deceptively simple and deceptively complex spectra.
Gurst, J. E.; Dellinger, C. M.; Jacobus, John J. Chem. Educ. 1985, 62, 871.
NMR Spectroscopy
Van der Waals compression of hydrogen atoms by geminal alkyl groups  Qureshi, Mohammad Ismail
The intramolecular van der Waals compression has a wider role in determining the chemical shifts of protons than hitherto believed.
Qureshi, Mohammad Ismail J. Chem. Educ. 1985, 62, 861.
NMR Spectroscopy |
Molecular Properties / Structure
An analogy of the NMR effect  Lee, Albert W. M.
Analogy using the difference between standing upright and on one's head in the earth's gravitational field.
Lee, Albert W. M. J. Chem. Educ. 1985, 62, 319.
NMR Spectroscopy
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
A primer on Fourier transform NMR  Macomber, Roger S.
Written to give the beginning student some insight about how data are collected in the time domain, as well as how these data are transformed into the frequency domain.
Macomber, Roger S. J. Chem. Educ. 1985, 62, 213.
NMR Spectroscopy |
Fourier Transform Techniques
A short set of 13C-NMR correlation tables  Brown, D. W.
The object of these tables is to enable a student to calculate rapidly approximate d values for 13C nuclei in as wide a variety of compounds as possible.
Brown, D. W. J. Chem. Educ. 1985, 62, 209.
NMR Spectroscopy |
Molecular Properties / Structure |
Alkanes / Cycloalkanes |
Alkenes |
Alkynes |
Aromatic Compounds |
Amides |
Carboxylic Acids |
Esters
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
Quantitative analysis of a mixture by NMR spectroscopy  Wallace, Tim
Adding a measured quantity of an inert, easily removed reference compound with a simple NMR signal that does not overlap with the mixture's signal can provide the basis for an instructive experiment.
Wallace, Tim J. Chem. Educ. 1984, 61, 1074.
Qualitative Analysis |
NMR Spectroscopy |
Instrumental Methods
Using the QCPE holdings in chemical education: Molecular models in the organic chemistry laboratory  Lipkowitz, Kenny
A laboratory experiment that compares the strengths and weaknesses of mechanical and computer models.
Lipkowitz, Kenny J. Chem. Educ. 1984, 61, 1051.
Molecular Modeling |
Molecular Properties / Structure |
Conformational Analysis |
NMR Spectroscopy
Empirical NMR chemical shift correlations for methyl and methylene protons  Friedrich, Edwin C.; Runkle, Katherine Gates
Provides Shoolery-type chemical shift substituent constants and observed and calculated chemical shifts of XCH2Y protons for selected methylene derivatives.
Friedrich, Edwin C.; Runkle, Katherine Gates J. Chem. Educ. 1984, 61, 830.
NMR Spectroscopy |
Molecular Properties / Structure
Nuclear magnetic resonance interpretation with graphics  Draper, R. D.; Penfold, B. R.
54. Bits and pieces, 21. A suite of programs to help students interpret NMR spectra.
Draper, R. D.; Penfold, B. R. J. Chem. Educ. 1984, 61, 789.
NMR Spectroscopy |
Enrichment / Review Materials
Introductory use of infrared spectra: A formalized approach  McMinn, Dennis
A strategy for introducing the interpretation of IR spectra by looking for the presence (or absence) of peaks in six key regions
McMinn, Dennis J. Chem. Educ. 1984, 61, 708.
Spectroscopy |
IR Spectroscopy |
NMR Spectroscopy |
Molecular Properties / Structure
Interpreting infrared and nuclear magnetic resonance spectra of simple organic compounds for the beginner  Ingham, A. M.; Henson, R. C.
Flowcharts to help the beginner become proficient in interpreting infrared and nuclear magnetic resonance spectra of simple organic compounds.
Ingham, A. M.; Henson, R. C. J. Chem. Educ. 1984, 61, 704.
Spectroscopy |
IR Spectroscopy |
NMR Spectroscopy |
Molecular Properties / Structure
An alternative method of learning characteristic spectroscopic signals  Butler, J. Keith
Producing a colored chart correlating functional groups with shifts of frequency.
Butler, J. Keith J. Chem. Educ. 1984, 61, 703.
Spectroscopy |
IR Spectroscopy |
NMR Spectroscopy |
Molecular Properties / Structure
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
An analysis of a commercial furniture refinisher: a comprehensive introductory NMR experiment  Markow, Peter G.; Cramer, John A.
The author presents a laboratory experiment which introduces undergraduate students to the techniques of NMR through the analysis of a commercial furniture refinisher.
Markow, Peter G.; Cramer, John A. J. Chem. Educ. 1983, 60, 1078.
NMR Spectroscopy |
Consumer Chemistry
NMR spectra of cobaloximes: unexpected nonequivalence of methyl groups  Clifford, Ben; Cullen, William R.
Students are often puzzled by the doublet for the four ligand methyl groups. This author helps explain this phenomenon.
Clifford, Ben; Cullen, William R. J. Chem. Educ. 1983, 60, 554.
NMR Spectroscopy |
Coordination Compounds
Prediction of the appearance of non-first-order proton NMR spectra   Macomber, Roger S.
Undergraduates generally become equipped only to handle only first-order coupling patterns. This means that they have a hard time understanding a real spectra. By scaffolding students through the synthesis level of Bloom's taxonomy, students can work toward a more expert level of understanding.
Macomber, Roger S. J. Chem. Educ. 1983, 60, 525.
NMR Spectroscopy |
Aldehydes / Ketones |
Learning Theories
Computer simulation of NMR spectra   Ellison, A.
40. A new PASCAL program has been written to provide for the interactive analysis and display of the high resolution NMR spectra.
Ellison, A. J. Chem. Educ. 1983, 60, 425.
NMR Spectroscopy
Principles of Fourier-transform nuclear magnetic resonance   Blunt, J. W.
37. Bits and pieces, 14. Microcomputer-generated animated graphics can aid in the teaching of Fourier-transform NMR theory and practice.
Blunt, J. W. J. Chem. Educ. 1983, 60, 97.
NMR Spectroscopy |
Fourier Transform Techniques
Structure elucidation of a natural product  Letcher, Roy M.
This experiment is an attempt to simulate a real-life structure elucidation problem through the isolation, characterization, and chemical transformation of an unknown naturally occurring monoterpene, with extensive use being made of spectroscopy and aided by biogenetic considerations.
Letcher, Roy M. J. Chem. Educ. 1983, 60, 79.
Natural Products |
Separation Science |
NMR Spectroscopy |
UV-Vis Spectroscopy |
Reactions
A reinvestigation of the synthesis of 4-methyl-3-heptanol  Hoffman, Robert V.; Alexander, M. D.; Buntain, Gregory; Hardenstein, Richard; Mattox, Cynthia; McLaughlin, Susan; McMinn, Denise; Spray, Scott; White, Steven
A previously reported laboratory may have reported gas chromatographic separation of the 4-methyl-3-heptanol diastereomiers in error. The side reactions in the Grignard reaction account for the observed results.
Hoffman, Robert V.; Alexander, M. D.; Buntain, Gregory; Hardenstein, Richard; Mattox, Cynthia; McLaughlin, Susan; McMinn, Denise; Spray, Scott; White, Steven J. Chem. Educ. 1983, 60, 78.
Hormones |
Alcohols |
Grignard Reagents |
IR Spectroscopy |
NMR Spectroscopy |
Aldehydes / Ketones |
Gas Chromatography |
Synthesis |
Natural Products
Carbon-13, Nuclear Magnetic Resonance Spectroscopy, 2nd Edition (Levy, George C.; Lichter, Robert L.; Nelson, Gordon L.)  Gust, Devens
Theory and application of carbon-13 NMR.
Gust, Devens J. Chem. Educ. 1982, 59, A29.
Isotopes |
NMR Spectroscopy
Isobutylene revisited: An experiment introducing both qualitative and quantitative application of NMR spectroscopy  Tremelling, Michael J.; Hammond, Christina N.
The product distribution is a contradiction to the general rule that the more highly substituted alkene is more stable.
Tremelling, Michael J.; Hammond, Christina N. J. Chem. Educ. 1982, 59, 697.
Alkenes |
NMR Spectroscopy |
Addition Reactions |
Molecular Properties / Structure
Hydrogen bonding and proton transfer  Joesten, Melvin D.
A review of the types of hydrogen bonds and discussion of the application of spectroscopic and diffraction methods to studies of moderate and strong hydrogen bonds.
Joesten, Melvin D. J. Chem. Educ. 1982, 59, 362.
Hydrogen Bonding |
Acids / Bases |
IR Spectroscopy |
NMR Spectroscopy |
Spectroscopy
Sulcatol: Synthesis of an aggregation pheromone  Black, Shirley-Ann; Slessor, Keith N.
Synthesis of the aggregation pheromone of the ambrosia beetle, an insect pest of harvested timber in the Pacific North Coast.
Black, Shirley-Ann; Slessor, Keith N. J. Chem. Educ. 1982, 59, 255.
Synthesis |
Natural Products |
Molecular Properties / Structure |
Chirality / Optical Activity |
NMR Spectroscopy |
IR Spectroscopy |
Applications of Chemistry
A demonstration of the basic principle of NMR  Meloan, Clifton, E.
Uses a toy gyroscope, wire, and two waste baskets.
Meloan, Clifton, E. J. Chem. Educ. 1982, 59, 154.
NMR Spectroscopy |
Magnetic Properties
Nuclear magnetic resonance coupling constants and electronic structure in molecules  Venanzi, Thomas J.
Describes the theory of NMR spin-spin coupling constants, the nature of the three types of coupling mechanisms contributing to the overall spin-spin coupling constant, and the results for two different types of coupling constants in molecules (carbon-carbon and carbon-nitrogen coupling).
Venanzi, Thomas J. J. Chem. Educ. 1982, 59, 144.
NMR Spectroscopy |
Molecular Properties / Structure
Penholder adapters for the Perkin-Elmer 710B, 137 IR and Varian T-60 NMR instruments  Bailey, R. A.; Zubrick, J. W.
Adapters that permit the use of ordinary felt-tipped pens.
Bailey, R. A.; Zubrick, J. W. J. Chem. Educ. 1982, 59, 21.
Laboratory Equipment / Apparatus |
NMR Spectroscopy |
Laboratory Management
High resolution NMR theory and chemical applications, 2nd edition (Becker, Edwin D.)  Hayes, Robert G.

Hayes, Robert G. J. Chem. Educ. 1981, 58, A226.
NMR Spectroscopy
An undergraduate laboratory program project involving photocyclizations in independent syntheses of novel chrysenes and phenanthrenes  Letcher, R. M.
This experiment attempts to fulfill such objectives as providing meaningful and viable preparative reactions, providing an opportunity for independent laboratory work within a project framework and under conditions of nearly equal opportunity and experience.
Letcher, R. M. J. Chem. Educ. 1981, 58, 1020.
Undergraduate Research |
Synthesis |
Aromatic Compounds |
Photochemistry |
Diastereomers |
NMR Spectroscopy |
Alcohols |
Thin Layer Chromatography
Spectroscopy in organic chemistry at the introductory level  Gurst, Jerome E.
This author has found that the use of a limited series of compounds allow students to focus attention on the spectra rather than the structural formulas of many compounds. This allows students to grasp the significance of the spectral measurements in a minimal time period.
Gurst, Jerome E. J. Chem. Educ. 1981, 58, 511.
Spectroscopy |
UV-Vis Spectroscopy |
Mass Spectrometry |
IR Spectroscopy |
NMR Spectroscopy
An efficient and inexpensive device for washing NMR tubes  Angrick, Michael; Bauer, Hans
Improvements on two earlier devices.
Angrick, Michael; Bauer, Hans J. Chem. Educ. 1980, 57, 680.
NMR Spectroscopy |
Laboratory Equipment / Apparatus |
Laboratory Management
Allyl alcohol plant stream analysis: Relating industrial chemistry to the undergraduate laboratory  Bard, James R.; Sandoval, Antonio A.
Exercise that seeks to familiarize students with an industrial chemical process using a reaction not normally found in undergraduate textbooks and to broaden appreciation of NMR spectroscopy to include its analytical capabilities and limitations by showing how NMR could be used for analysis of a typical plant stream.
Bard, James R.; Sandoval, Antonio A. J. Chem. Educ. 1980, 57, 218.
Alcohols |
Industrial Chemistry |
Applications of Chemistry |
NMR Spectroscopy
Cleaning NMR Tubes  Luberoff, B. J.
Uses a vacuum chamber.
Luberoff, B. J. J. Chem. Educ. 1979, 56, 768.
Spectroscopy |
NMR Spectroscopy |
Laboratory Management
Use of general purpose microcomputers to synthesize hypothetical spectra for the nmr recorder  Wright, John R.; Robinson, Jack L.

Wright, John R.; Robinson, Jack L. J. Chem. Educ. 1979, 56, 643.
Spectroscopy |
NMR Spectroscopy
Purification of chloroform for NMR spectroscopy  Burfield, David R.
Chloroform can be readily purified by simply standing the solvent over activated molecular sieves.
Burfield, David R. J. Chem. Educ. 1979, 56, 486.
Spectroscopy |
NMR Spectroscopy |
Laboratory Management |
Separation Science
Friedel-Crafts acylation: An experiment incorporating spectroscopic structure determination  Schatz, Paul F.
Students use IR and NMR methods to determine the product of an aromatic substitution.
Schatz, Paul F. J. Chem. Educ. 1979, 56, 480.
Spectroscopy |
IR Spectroscopy |
NMR Spectroscopy |
Molecular Properties / Structure |
Aromatic Compounds
A student synthesis of the housefly sex attractant  Cormier, Russell A.; Duc Phan, M.; Graddis, Thomas; Singer, Richard
This multi-step synthetic sequence illustrates several important laboratory techniques, including ir and nmr spectroscopy, thin-layer and column chromatography, rotary evaporation, recrystallization, and vacuum distillation.
Cormier, Russell A.; Duc Phan, M.; Graddis, Thomas; Singer, Richard J. Chem. Educ. 1979, 56, 345.
Synthesis |
Natural Products |
IR Spectroscopy |
NMR Spectroscopy |
Chromatography |
Thin Layer Chromatography
A simple and inexpensive modification for coaxial nmr cells  Nelson, Harold C.
Employing sections of various gauge, Teflon tubing that encircle the reference tube.
Nelson, Harold C. J. Chem. Educ. 1979, 56, 306.
Laboratory Equipment / Apparatus |
Spectroscopy |
NMR Spectroscopy
A simple device for washing nmr tubes  De Lucchi, Ottorino; Miozzo, Gian Franco
A device that can be constructed by a skilled glassblower.
De Lucchi, Ottorino; Miozzo, Gian Franco J. Chem. Educ. 1979, 56, 124.
Laboratory Equipment / Apparatus |
Laboratory Management |
Spectroscopy |
NMR Spectroscopy
Phosphorus coupling in 13C and 1H NMR  Krudy, George A.; Macomber, Roger S.
Provides a variety of spectra of organophosphorus compounds that exhibit informative 1H and 13C spectra.
Krudy, George A.; Macomber, Roger S. J. Chem. Educ. 1979, 56, 109.
Spectroscopy |
NMR Spectroscopy
Group electronegativity by NMR  Greever, Joe C.
The purpose of this experiment is to allow the student to observe the correlation between chemical shift and electronegativity.
Greever, Joe C. J. Chem. Educ. 1978, 55, 538.
NMR Spectroscopy |
Periodicity / Periodic Table
Computer assisted analysis of nuclear magnetic resonance spectra  Calkins, Keith G.; Daley, Richard F.
The authors have implemented an interactive computer program designed to assist the beginning student in interpreting NMR data.
Calkins, Keith G.; Daley, Richard F. J. Chem. Educ. 1978, 55, 322.
NMR Spectroscopy
Boron-11 nmr  Smith, Wayne L.
Principles of 11B NMR and the interpretation of representative spectra.
Smith, Wayne L. J. Chem. Educ. 1977, 54, 469.
Spectroscopy |
NMR Spectroscopy
A "simple" approach to teaching hydrogen chemical shifts  Smith, S. L.
An approach that aids students in organizing information on inductive substituent effects on chemical shifts and has the pedagogical advantage of building on previously learned basic material from the periodic table.
Smith, S. L. J. Chem. Educ. 1977, 54, 255.
Spectroscopy |
NMR Spectroscopy
NMR resolution analogy  Bank, Shelton
A visual analogy for the resolving power of the NMR spectrometer.
Bank, Shelton J. Chem. Educ. 1977, 54, 237.
Spectroscopy |
NMR Spectroscopy
Analysis of complex NMR spectra. A dry-lab spectral analysis experiment  Bell, Harold M.
Affords students the opportunity to obtain practical experience in the techniques of spectral analysis of some more complex systems.
Bell, Harold M. J. Chem. Educ. 1977, 54, 180.
Spectroscopy |
NMR Spectroscopy
NMR chemical shift correlations. A student oriented project  Sikorski, John; Schaffhausen, John G.
The authors propose a project that utilizes NMR technology to serve as a learning aid for the student and as a tool for the researcher.
Sikorski, John; Schaffhausen, John G. J. Chem. Educ. 1976, 53, 761.
NMR Spectroscopy
NMR spectral analysis. An experiment involving complete lineshape analysis of a two-site exchange problem  Bell, Harold M.
The experiment described in this article is designed to avoid problems such as insufficient access to computers for analysis and lack of access to an NMR machine that can alter temperatures.
Bell, Harold M. J. Chem. Educ. 1976, 53, 665.
NMR Spectroscopy
Interpretation of a 13C magnetic resonance spectrum  Dorn, Harry C.; Kingston, David G. I.; Simpers, Bruce R.
The analysis and interpretation of the cmr spectrum of bis-(2-ethylhexyl) phthalate (I) provides an instructive and simple example of the utility of this technique. [Original feature title: Interpretative Experiments.]
Dorn, Harry C.; Kingston, David G. I.; Simpers, Bruce R. J. Chem. Educ. 1976, 53, 584.
Nuclear / Radiochemistry |
Isotopes |
NMR Spectroscopy
The design of integrated inorganic experiments. An example from organo-transition-element chemistry  Hunt, G. R. A.
This lab was designed in response to a need for an integrated exercise in undergraduate practical chemistry.
Hunt, G. R. A. J. Chem. Educ. 1976, 53, 53.
Descriptive Chemistry |
NMR Spectroscopy |
Organometallics |
Transition Elements
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
A novel communications-skills-based approach to the instrumental laboratory  Varnes, Arthur W.; Wetmore, David E.
Describes the approach used in a course designed to stress the importance of good writing style in laboratory reports.
Varnes, Arthur W.; Wetmore, David E. J. Chem. Educ. 1975, 52, 801.
Instrumental Methods |
Spectroscopy |
UV-Vis Spectroscopy |
IR Spectroscopy |
Gas Chromatography |
NMR Spectroscopy
Isomer analysis by spectral methods  Poulton, Gerald A.
The use of NMR, UV and mass spectroscopy and gas chromatography to introduce students to the use of spectra to determine the products of a reaction and their relative amounts.
Poulton, Gerald A. J. Chem. Educ. 1975, 52, 397.
Spectroscopy |
UV-Vis Spectroscopy |
NMR Spectroscopy |
Mass Spectrometry |
Gas Chromatography
The preparation and spectral analysis of toluene-a[alpha]-d  Ellis, Jerry W.; Buchanan, David H.
Provides dramatic visual evidence of the changes in IR, NMR, and mass spectra upon substitution of deuterium for hydrogen in a simple molecule.
Ellis, Jerry W.; Buchanan, David H. J. Chem. Educ. 1975, 52, 265.
IR Spectroscopy |
NMR Spectroscopy |
Mass Spectrometry |
Spectroscopy
An integrated synthesis laboratory for the sophomore year  Pearson, Wesley A.; Finholt, Albert E.
Outlines the compounds synthesized and the techniques used in a two-semester integrated laboratory sequence for sophomores.
Pearson, Wesley A.; Finholt, Albert E. J. Chem. Educ. 1975, 52, 236.
Synthesis |
Coordination Compounds |
IR Spectroscopy |
NMR Spectroscopy |
UV-Vis Spectroscopy |
Chromatography
Academic vitamins: The development and utility of course supplements  Lindberg, James G.
A course on NMR spectroscopy taught concurrently with organic chemistry, and ideas for other such supplementary courses.
Lindberg, James G. J. Chem. Educ. 1975, 52, 86.
NMR Spectroscopy |
Spectroscopy
The effects of aryl substituents on ir, nmr, and mass spectra of N-t-butylbenzamides  Rubottom, George M.
The authors have developed this experiment in order to give students the opportunity to carry out a high yield synthetic reaction coupled with an analysis of the effects of substituents on the IR, NMR, and mass spectral properties of the compounds prepared.
Rubottom, George M. J. Chem. Educ. 1974, 51, 616.
IR Spectroscopy |
NMR Spectroscopy |
Mass Spectrometry
Conversion of a primary alcohol to an alkyl halide via a tosylate intermediate  Wiseman, Park A.; Betras, Steve; Lindley, Barry
The experiment in this article was designed primarily for and has been performed successfully by sophomore chemistry majors.
Wiseman, Park A.; Betras, Steve; Lindley, Barry J. Chem. Educ. 1974, 51, 348.
Alcohols |
Alkylation |
Reactions |
Aromatic Compounds |
NMR Spectroscopy
Relative carbonium ion stabilization energies: an nmr experiment for the undergraduate organic laboratory  Kenny, David H.; Sandel, Vernon R.; Osterby, Bruce R.
An nmr experiment for the undergraduate organic laboratory studying relative arbonium ion stabilization energies.
Kenny, David H.; Sandel, Vernon R.; Osterby, Bruce R. J. Chem. Educ. 1974, 51, 253.
NMR Spectroscopy
A series of related organic experiments with optional structure determinations  Fairless, Billy J.; Ragsdale, Gary; Kerby, Claudia
The authors wish to report three related experiments that have been received with enthusiasm by organic students.
Fairless, Billy J.; Ragsdale, Gary; Kerby, Claudia J. Chem. Educ. 1974, 51, 61.
Phenols |
Alkenes |
NMR Spectroscopy
Troublesome concepts in NMR spectrometry  Silverstein, Robert M.; Silberman, Robert G.
Offers definitions, explanations, and suggests references for NMR topics, including spin system, set of nuclei, chemical shift equivalence, magnetic equivalence, and virtual coupling.
Silverstein, Robert M.; Silberman, Robert G. J. Chem. Educ. 1973, 50, 484.
Spectroscopy |
NMR Spectroscopy
NMR Hammett correlation. A laboratory experiment  Salmon, Manuel; Jimenez, Adolfo; Salazar, Ignacio; Zawadzki, Rainer
A simple NMR experiment to familiarize students with the concept and uses provided by the Hammett equation, as well as introduce them to the use of NMR apparatus, chemical shift tabulation, and the application of linear regression analysis.
Salmon, Manuel; Jimenez, Adolfo; Salazar, Ignacio; Zawadzki, Rainer J. Chem. Educ. 1973, 50, 370.
NMR Spectroscopy
The analysis of high resolution nmr spectra (Abraham, R. J.)  Reinheimer, John D.

Reinheimer, John D. J. Chem. Educ. 1972, 49, A603.
NMR Spectroscopy
Paramagnetic moment measurements by nmr. A micro technique  Loliger, J.; Scheffold, R.
Design of a coaxial cell consisting of a simple melting point tube that is used to to determine the paramagnetic moment of a given substance.
Loliger, J.; Scheffold, R. J. Chem. Educ. 1972, 49, 646.
NMR Spectroscopy |
Microscale Lab |
Magnetic Properties |
Instrumental Methods
A computer program for plotting nmr spectra  Clark, P. E.; Berlin, K. D.
Describes a Fortran IV program for plotting nmr spectra.
Clark, P. E.; Berlin, K. D. J. Chem. Educ. 1972, 49, 362.
NMR Spectroscopy
An interactive NMR chemical shift search program  Heller, Stephen R.; Feldmann, Richard J.
A computer program has been developed to rapidly search for spectra containing specified chemical shifts from proton nmr spectral data.
Heller, Stephen R.; Feldmann, Richard J. J. Chem. Educ. 1972, 49, 291.
NMR Spectroscopy |
Spectroscopy |
Molecular Properties / Structure
Inexpensive, efficient NMR tube cleaner  Ladner, Kenneth H.; Hinton, James F.
A simple device that cleans NMR tubes quickly and efficiently is presented.
Ladner, Kenneth H.; Hinton, James F. J. Chem. Educ. 1970, 47, 704.
NMR Spectroscopy |
Laboratory Equipment / Apparatus |
Laboratory Management
The hexaphenylethane landmark falls  Smith, William B.
A reexamination of Gomberg's discovery that the treatment of triphenylmethyl chloride with silver results in hexaphenylethane has demonstrated that the dimer formed is not hexaphenylethane; a new product has been proposed.
Smith, William B. J. Chem. Educ. 1970, 47, 535.
Reactions |
Molecular Properties / Structure |
NMR Spectroscopy
An apparatus for washing NMR tubes  Jacobsen, N. W.
A small glass unit is convenient for cleaning, rinsing, and drying eight standard size NMR tubes simultaneously.
Jacobsen, N. W. J. Chem. Educ. 1970, 47, 507.
Laboratory Equipment / Apparatus |
NMR Spectroscopy |
Laboratory Management
On-line computer printing of NMR spectra  Rondeau, Roger E.; Rish, Hughey A. III
The program described reduces the probability of assignment error while also eliminating the most tedious task in the analysis of complex NMR spectra.
Rondeau, Roger E.; Rish, Hughey A. III J. Chem. Educ. 1970, 47, 139.
Spectroscopy |
NMR Spectroscopy |
Qualitative Analysis
An integrated NMR and synthetic organic chemistry experiment  Glaros, George; Cromwell, Norman H.
Presents a synthetic sequence that involves procedures of general utility and results in products illustrative of the basic principles of NMR spectroscopy.
Glaros, George; Cromwell, Norman H. J. Chem. Educ. 1969, 46, 854.
Spectroscopy |
NMR Spectroscopy |
Synthesis |
Mechanisms of Reactions |
Aromatic Compounds
Nmr analysis of water-acetic acid solutions  Brabson, G. Dana
Presents an experiment intended to teach the operation of NMR instrumentation and the interpretation of the data it collects, as well as demonstrate a significant principle of chemistry.
Brabson, G. Dana J. Chem. Educ. 1969, 46, 754.
NMR Spectroscopy |
Aqueous Solution Chemistry |
Instrumental Methods
LTE. A TMS sampling technique  Montecalvo, Donald F.; Lawlor, Joseph F.
Calls attention to an alternative simple technique for the transfer of tetramethylsilane into NMR sample tubes.
Montecalvo, Donald F.; Lawlor, Joseph F. J. Chem. Educ. 1969, 46, 701.
NMR Spectroscopy |
Laboratory Management |
Liquids
The two forms of aluminum isopropoxide: An NMR experiment  Worrall, I. J.
This experiment prepares tetrameric and trimeric forms of aluminum isopropoxide and analyzes the structure of each through PMR spectroscopy.
Worrall, I. J. J. Chem. Educ. 1969, 46, 510.
NMR Spectroscopy |
Molecular Properties / Structure
Problems in spectroscopy - Organic structure determination by NMR, IR, UV, and mass spectra (Trost, Barry M.)  Danforth, Joseph D.

Danforth, Joseph D. J. Chem. Educ. 1968, 45, A242.
Molecular Properties / Structure |
NMR Spectroscopy |
UV-Vis Spectroscopy |
Mass Spectrometry
Spectrometric identification of insect sex attractants  Silverstein, Robert M.
Uses spectrometric methods to identify the sex attractants of three types of beetle pests.
Silverstein, Robert M. J. Chem. Educ. 1968, 45, 794.
Spectroscopy |
IR Spectroscopy |
UV-Vis Spectroscopy |
Qualitative Analysis |
Mass Spectrometry |
NMR Spectroscopy
A simple convenient method to obtain NMR spectra on milligram samples  Provost, L. R.; Jardine, R. V.
A simple convenient method to obtain NMR spectra of milligram quantities is through the use of a melting point tube with a well-rounded end.
Provost, L. R.; Jardine, R. V. J. Chem. Educ. 1968, 45, 675.
NMR Spectroscopy
Analysis of complex NMR spectra for the organic chemist. I. Second-order approach with specific application to the two spin system  Garbisch, Edgar W., Jr.
Complex spectra of systems containing up to four spins can often be analyzed satisfactorily by hand and offer advantages at the instructive level.
Garbisch, Edgar W., Jr. J. Chem. Educ. 1968, 45, 311.
Spectroscopy |
NMR Spectroscopy
A proton magnetic resonance coordination number study. AlCl3 in aqueous solvent mixtures  Fratiello, Anthony; Schuster, Ronald E.
Coordination numbers can be evaluated directly and unambiguously by integrating separate nmr peaks.
Fratiello, Anthony; Schuster, Ronald E. J. Chem. Educ. 1968, 45, 91.
NMR Spectroscopy |
Molecular Properties / Structure |
Coordination Compounds |
Spectroscopy
Nuclear magnetic resonance for organic chemists (Mathieson, D. W., ed.)  Lambert, Joseph B.

Lambert, Joseph B. J. Chem. Educ. 1967, 44, A758.
NMR Spectroscopy
Introduction to magnetic resonance: with applications to chemistry and chemical physics (Carrington, Alan; McLachlan, Andre D.)  Fessenden, Richard W.

Fessenden, Richard W. J. Chem. Educ. 1967, 44, 772.
NMR Spectroscopy
The acetone-chloroform system: An nmr study  Bell, Jerry A.; Snider, William H.
The procedure involves an introduction to NMR analysis and includes sample spectra and other data so that even those without an NMR spectrometer may conduct the activity.
Bell, Jerry A.; Snider, William H. J. Chem. Educ. 1967, 44, 200.
NMR Spectroscopy
An inexpensive coaxial NMR cell  Hinton, J. F.; Amis, E. S.
This paper describes an inexpensive coaxial NMR cell with a number of advantages.
Hinton, J. F.; Amis, E. S. J. Chem. Educ. 1966, 43, 443.
NMR Spectroscopy
Instructional NMR instrument  Proffitt, Michael H.; Gardiner, W. C., Jr.
Presents circuit diagrams for the components of an instructional NMR instrument.
Proffitt, Michael H.; Gardiner, W. C., Jr. J. Chem. Educ. 1966, 43, 152.
NMR Spectroscopy |
Instrumental Methods |
Laboratory Equipment / Apparatus
Simulation of NMR spectra: Computers as teaching devices  Wilkins, Charles L.; Klopfenstein, Charles E.
Presents nuclear magnetic resonance theory and describes an NMR simulation program.
Wilkins, Charles L.; Klopfenstein, Charles E. J. Chem. Educ. 1966, 43, 10.
Spectroscopy |
NMR Spectroscopy
Applications absorption spectroscopy of organic compounds (Dyer, John R.)  Williams, Theodore R.

Williams, Theodore R. J. Chem. Educ. 1965, 42, 690.
Spectroscopy |
UV-Vis Spectroscopy |
IR Spectroscopy |
NMR Spectroscopy
NMR spectra: Appearance of patterns from small spin systems  Becker, Edwin D.
This article seeks to clarify some confusing points in the interpretation of NMR spectra.
Becker, Edwin D. J. Chem. Educ. 1965, 42, 591.
Spectroscopy |
NMR Spectroscopy |
Molecular Properties / Structure
Instrumentation teaching equipment. Part three: Miscellaneous  Eisner, Leonard
Considers magnetic resonance spectroscopy, magnetic susceptibility, atomic beam spectroscopy, mass spectrometers, chromatography, electrochemistry, electron diffraction, field emission microscopes, glass blowing and vacuum systems, high and low temperatures, and ultrasonics.
Eisner, Leonard J. Chem. Educ. 1964, 41, A607.
NMR Spectroscopy |
Spectroscopy |
Instrumental Methods |
Mass Spectrometry |
Magnetic Properties |
Chromatography |
Electrochemistry |
Laboratory Equipment / Apparatus
An NMR demonstration of isotopic exchange  Lapidot, Aviva; Reuben, Jack; Samuel, David
Hydracrylonitrile (beta-hydroxypropionitrile) is used in a simple NMR experiment to demonstrate the isotopic exchange of deuterium.
Lapidot, Aviva; Reuben, Jack; Samuel, David J. Chem. Educ. 1964, 41, 570.
NMR Spectroscopy |
Isotopes |
Kinetics |
Rate Law
Quantitative analysis using NMR  Smith, William B.
Describes the quantitative analysis of mixtures of organic compounds using NMR spectroscopy.
Smith, William B. J. Chem. Educ. 1964, 41, 97.
Quantitative Analysis |
NMR Spectroscopy
Characteristic NMR spectral positions for hydrogen in organic structures  Mohacsi, Erno
This is a table indicating the characteristic NMR spectral positions for hydrogen in organic structures.
Mohacsi, Erno J. Chem. Educ. 1964, 41, 38.
NMR Spectroscopy |
Molecular Properties / Structure
A qualitative approach to the study of complex NMR spectra  McGreer, Donald E.; Mocek, M. M.
Presents an extension of an earlier description of NMR that involves transforming a simple spectrum into a more complex spectrum.
McGreer, Donald E.; Mocek, M. M. J. Chem. Educ. 1963, 40, 358.
NMR Spectroscopy
NMR and EPR spectroscopy (The NMR-EPR Staff of Varian Associates)  Hollahan, John R.

Hollahan, John R. J. Chem. Educ. 1962, 39, A136.
NMR Spectroscopy |
EPR / ESR Spectroscopy |
Spectroscopy
Spectrometric identification of organic compounds  Silverstein, Robert M.; Bassler, G. Clayton
Presents a sequence of procedures for identifying an unknown organic liquid using mass, NMR, IR, and UV spectroscopy, along with specific examples of unknowns and their spectra,
Silverstein, Robert M.; Bassler, G. Clayton J. Chem. Educ. 1962, 39, 546.
Spectroscopy |
Qualitative Analysis |
Mass Spectrometry |
IR Spectroscopy |
NMR Spectroscopy |
UV-Vis Spectroscopy
Nuclear magnetic resonance spectroscopy  Roberts, J. D.
Presents nuclear magnetic spectroscopy in a manner that makes it suitable for presentation to undergraduates.
Roberts, J. D. J. Chem. Educ. 1961, 38, 581.
NMR Spectroscopy |
Spectroscopy
NMR spectroscopy as an analytical tool in organic chemistry  Martin, J. C.
This article introduces the theory of NMR spectroscopy and its use as an analytical tool in organic chemistry.
Martin, J. C. J. Chem. Educ. 1961, 38, 286.
NMR Spectroscopy
Nuclear magnetic resonance  Richter, Henry L.
This review summarizes the many applications of nuclear magnetic resonance to various fields of chemistry and physics.
Richter, Henry L. J. Chem. Educ. 1957, 34, 618.
NMR Spectroscopy