| Journal Articles: 15 results |
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Experimental Design and Optimization: Application to a Grignard Reaction Naoual Bouzidi and Christel Gozzi
This 5-week project, which systematically investigates optimizing the synthesis of benzyl-1-cyclopentan-1-ol, constitutes an initiation into research methodology and experimental design to prepare the student-engineer for an industry internship. Other pedagogical goals include experience in synthetic techniques, obtaining reproducible yields, and using quantitative analysis methods.
Bouzidi, Naoual; Gozzi, Christel. J. Chem. Educ. 2008, 85, 1544.
Addition Reactions |
Alcohols |
Aldehydes / Ketones |
Chemometrics |
Gas Chromatography |
Organometallics |
Synthesis
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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
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Grubbs's Cross Metathesis of Eugenol with cis-2-Butene-1,4-diol To Make a Natural Product. An Organometallic Experiment for the Undergraduate Lab Douglass F. Taber and Kevin J. Frankowski
Describes the ruthenium catalyzed cross metathesis of eugenol with cis-1,4-butenediol. The experiment is an excellent example of the powerful selectivity possible with the Grubbs' catalyst, demonstrating the preference for trans over cis alkene formation and for cross metathesis over homodimerization.
Taber, Douglass F.; Frankowski, Kevin J. J. Chem. Educ. 2006, 83, 283.
Alkenes |
Catalysis |
IR Spectroscopy |
Mass Spectrometry |
Mechanisms of Reactions |
Microscale Lab |
Natural Products |
NMR Spectroscopy |
Organometallics |
Stereochemistry |
Synthesis |
Thin Layer Chromatography |
Transition Elements
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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
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A Convenient Method for Dispensing Organometallic Reagents Thomas A. Newton
The construction of a simple apparatus for dispensing air-sensitive organometallic reagents is described.
Newton, Thomas A. J. Chem. Educ. 2005, 82, 936.
Organometallics |
Instrumental Methods |
Synthesis
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Suzuki Cross-Coupling Reactions: Synthesis of Unsymmetrical Biaryls in the Organic Laboratory Christopher S. Callam and Todd L. Lowary
Laboratory that exposes students to organometallic chemistry and application of the Suzuki reaction.
Callam, Christopher S.; Lowary, Todd L. J. Chem. Educ. 2001, 78, 947.
Aromatic Compounds |
Metals |
Synthesis |
Organometallics |
Transition Elements |
Mechanisms of Reactions
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Diastereoselective Synthesis of (+/-)-1,2-Diphenyl-1,2-propanediol. A Discovery-Based Grignard Reaction Suitable for a Large Organic Lab Course James A. Ciaccio, Roxana P. Bravo, Antoinette L. Drahus, John B. Biggins, Rosalyn V. Concepcion, and David Cabrera
An experiment that probes the diastereoselectivity of the reaction between a Grignard reagent and a common, inexpensive alpha-chiral ketone; introduces students to pi-facial discrimination by having them establish the stereochemical course of kinetically controlled nucleophilic addition to a carbonyl.
Ciaccio, James A.; Bravo, Roxana P.; Drahus, Antoinette L.; Biggins, John B.; Concepcion, Rosalyn V.; Cabrera, David. J. Chem. Educ. 2001, 78, 531.
Mechanisms of Reactions |
Synthesis |
Organometallics |
Stereochemistry |
Grignard Reagents |
Aldehydes / Ketones
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Organometallic chemistry: A course designed for sophomore chemistry students Miessler, Gary L.; Spessard, Gary O.
Descriptin of a new course offered during the one-month January interim session for students who have completed one semester of organic chemistry. This paper describes the course so that it may be adapted at other institutions. Students have responded favorably to this course.
Miessler, Gary L.; Spessard, Gary O. J. Chem. Educ. 1991, 68, 16.
Organometallics
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The early history of organotin chemistry Nicholson, John W.
Survey of the first 35 years of organotin chemistry.
Nicholson, John W. J. Chem. Educ. 1989, 66, 621.
Organometallics
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Starting recalcitrant Grignard reactions Clough, S.; Goldman, E.; Williams, S.; George, B.
This note offers a tip on starting a Gringard reaction.
Clough, S.; Goldman, E.; Williams, S.; George, B. J. Chem. Educ. 1986, 63, 176.
Laboratory Management |
Grignard Reagents |
Organometallics
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Organometallic chemistry (Rochow, Eugene G.) Eblin, Lawrence P.
Eblin, Lawrence P. J. Chem. Educ. 1965, 42, A66.
Organometallics
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One hundred years of organosilicon chemistry Muller, Richard
Summarizes the history organosilicon chemistry to commemorate the early contributions of Charles Friedel and James Mason Crafts.
Muller, Richard J. Chem. Educ. 1965, 42, 41.
Organometallics
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Multicenter and assisted mechanistic pathways in the reactions of organometallic compounds Dessy, Raymond E.; Paulik, Frank
Examines a variety of nucleophilic and electrophilic, multicenter and assisted mechanistic pathways in the reactions of organometallic compounds.
Dessy, Raymond E.; Paulik, Frank J. Chem. Educ. 1963, 40, 185.
Organometallics |
Mechanisms of Reactions |
Nucleophilic Substitution |
Electrophilic Substitution
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Organometallic derivatives of the transition elements Kaesz, Herbert D.
Summarizes recent research regarding organometallic derivatives of the transition elements.
Kaesz, Herbert D. J. Chem. Educ. 1963, 40, 159.
Organometallics |
Transition Elements |
Coordination Compounds |
Metals
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Functionally-substituted aromatic silanes Neville, Roy G.
The purpose of this article is to present a brief account of the functionally-substituted aromatic silanes.
Neville, Roy G. J. Chem. Educ. 1962, 39, 276.
Aromatic Compounds |
Organometallics
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