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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
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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
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"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
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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
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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
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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
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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
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A Knoevenagel Initiated Annulation Reaction Using Room Temperature or Microwave Conditions A. Gilbert Cook The product of a Knoevenagel initiated annulation reaction is identified through a guided prelab exercise of the synthesis of the Hagemann ester, and then through the analysis of GCMS, NMR, and IR spectra. The stereochemistry of the product is determined through the NMR spectrum and Karplus curve, and the student is required to write a mechanism for the reaction. Cook, A. Gilbert. J. Chem. Educ. 2007, 84, 1477.
Aldehydes / Ketones |
Conformational Analysis |
Gas Chromatography |
IR Spectroscopy |
Mass Spectrometry |
Mechanisms of Reactions |
NMR Spectroscopy |
Stereochemistry |
Synthesis
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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
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Keeping Your Students Awake: Facile Microscale Synthesis of Modafinil, a Modern Anti-Narcoleptic Drug Evangelos Aktoudianakis, Rui Jun Lin, and Andrew P. Dicks Describes the microscale preparation of modafinil, a pharmaceutical recently approved for the treatment of narcolepsy, by a sulfide oxidation reaction. An unusual feature of modafinil is the presence of a chiral sulfoxide functionality where a sulfur atom acts as a stereocenter, demonstrating that atoms other than carbon can act as centers of chirality. Aktoudianakis, Evangelos; Lin, Rui Jun; Dicks, Andrew P. J. Chem. Educ. 2006, 83, 1832.
Chirality / Optical Activity |
Drugs / Pharmaceuticals |
Synthesis |
Mechanisms of Reactions |
IR Spectroscopy |
NMR Spectroscopy |
Microscale Lab |
Stereochemistry
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
|
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
|
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
|
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
|
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
|
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
|
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
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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
|
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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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