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Journal Articles: 17 results
"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
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 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
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
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
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 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
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
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
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
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
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
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
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
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
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
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