| Journal Articles: 98 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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Evaluating Mechanisms of Dihydroxylation by Thin-Layer Chromatography Benjamin T. Burlingham and Joseph C. Rettig
Presents a microscale experiment in which cyclohexene is dihydroxylated under three sets of conditions and the products determined through thin-layer chromatography. Teams of students evaluate proposed mechanisms for each dihydroxylation in light of the data collected.
Burlingham, Benjamin T.; Rettig, Joseph C. J. Chem. Educ. 2008, 85, 959.
Addition Reactions |
Alkenes |
Diastereomers |
Mechanisms of Reactions |
Microscale Lab |
Stereochemistry |
Synthesis |
Thin Layer Chromatography
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Pyrolysis of Aryl Sulfonate Esters in the Absence of Solvent: E1 or E2? A Puzzle for the Organic Laboratory John J. Nash, Marnie A. Leininger, and Kurt Keyes
An aryl sulfonate ester is synthesized and then pyrolyzed at reduced pressure. The volatile products are analyzed using gas chromatography to determine whether the thermal decomposition occurs via an E1 or E2 mechanism.
Nash, John J.; Leininger, Marnie A.; Keyes, Kurt . J. Chem. Educ. 2008, 85, 552.
Alkenes |
Carbocations |
Elimination Reactions |
Gas Chromatography |
Mechanisms of Reactions |
Synthesis
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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
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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
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Hydration of Acetylene: A 125th Anniversary Dmitry A. Ponomarev and Sergey M. Shevchenko
The discovery the hydration of alkynes catalyzed by mercury ions by Mikhail Kucherov made possible industrial production of acetaldehyde from acetylene and had a profound effect on the development of industrial chemistry in the 1920th centuries.
Ponomarev, Dmitry A.; Shevchenko, Sergey M. J. Chem. Educ. 2007, 84, 1725.
Addition Reactions |
Aldehydes / Ketones |
Alkynes |
Catalysis |
Industrial Chemistry |
Reactions
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An Improved Method for Studying the Enzyme-Catalyzed Oxidation of Glucose Using Luminescent Probes William D. Bare, Chi V. Pham, Matthew Cuber, and J. N. Demas
A new method is presented for measuring the rate of glucose oxidation in the presence of glucose oxidase that employs a low-cost fluorescence instrument to directly determine the concentration of oxygen in real time, thus obviating complicated reaction schemes. The method can also be used to investigate specificity and inhibition.
Bare, William D.; Pham, Chi V.; Cuber, Matthew; Demas, J. N. J. Chem. Educ. 2007, 84, 1511.
Carbocations |
Coordination Compounds |
Enzymes |
Fluorescence Spectroscopy |
Spectroscopy |
Instrumental Methods |
Carbohydrates |
Kinetics
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Synthesis of Anomeric Methyl Fructofuranosides and Their Separation on an Ion-exchange Resin Erkki Nurminen, Päivi Poijärvi, Katja Koskua, and Jari Hovinen
Treatment of d-fructose with methanol in the presence of acid as a catalyst gives a mixture of methyl--d-fructopyranoside, methyl-a-D-fructofuranoside, and methyl--d- fructofuranoside, which are separated on an ion exchange column and characterized polarimetrically.
Nurminen, Erkki; Poijärvi, Päivi; Koskua, Katja; Hovinen, Jari. J. Chem. Educ. 2007, 84, 1480.
Carbocations |
Chirality / Optical Activity |
Chromatography |
Ion Exchange |
NMR Spectroscopy |
Synthesis |
Thin Layer Chromatography |
Carbohydrates
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A Guided-Inquiry Approach to the Sodium Borohydride Reduction and Grignard Reaction of Carbonyl Compounds Robert E. Rosenberg
Students teams identify unknowns and their reaction products and use their data to deduce that esters are less electrophilic than the other carbonyl compounds present, that Grignard reagents are more nucleophilic than sodium borohydride, and that carboxylic acid derivatives do not undergo the nucleophilic addition reactions that are characteristic of aldehydes and ketones.
Rosenberg, Robert E. J. Chem. Educ. 2007, 84, 1474.
Addition Reactions |
Aldehydes / Ketones |
Esters |
Grignard Reagents |
IR Spectroscopy |
Oxidation / Reduction |
Reactions |
Student-Centered Learning
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Reaction-Map of Organic Chemistry Steven Murov
The Reaction-Map of Organic Chemistry has been designed to provide an overview of most of the reactions needed for the organic chemistry course and should help students develop synthetic routes from one functional group to another.
Murov, Steven. J. Chem. Educ. 2007, 84, 1224.
Addition Reactions |
Electrophilic Substitution |
Elimination Reactions |
Nucleophilic Substitution |
Oxidation / Reduction |
Periodicity / Periodic Table |
Reactions |
Synthesis |
Enrichment / Review Materials
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Markovnikov's Rule Predrag-Peter Ilich
More insight into the mechanisms of addition reactions to alkenes is needed before completely abandoning Markovnikov and anti-Markovnikov terminology
Ilich, Predrag-Peter. J. Chem. Educ. 2007, 84, 1109.
Addition Reactions |
Reactions |
Mechanisms of Reactions
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Markovnikov's Rule Robert C. Kerber
The use of Markovniknov and anti-Markovnikov to describe addition reactions and their products has long outlived its utility.
Kerber, Robert C. . J. Chem. Educ. 2007, 84, 1109.
Addition Reactions |
Reactions |
Mechanisms of Reactions
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Markovnikov's Rule Robert C. Kerber
The use of Markovniknov and anti-Markovnikov to describe addition reactions and their products has long outlived its utility.
Kerber, Robert C. . J. Chem. Educ. 2007, 84, 1109.
Addition Reactions |
Reactions |
Mechanisms of Reactions
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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
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A Green Enantioselective Aldol Condensation for the Undergraduate Organic Laboratory George D. Bennett
The proline-catalyzed aldol condensation between acetone and isobutyraldehyde proceeds in good yield and with high enantioselectivity at room temperature. This multi-week experiment also illustrates a number of principles and trade-offs of green chemistry.
Bennett, George D. J. Chem. Educ. 2006, 83, 1871.
Addition Reactions |
Aldehydes / Ketones |
Asymmetric Synthesis |
Catalysis |
Chirality / Optical Activity |
Green Chemistry |
Mechanisms of Reactions |
Stereochemistry
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Polar Addition to C=C Group: Why Is Anti-Markovnikov Hydroboration–Oxidation of Alkenes Not "Anti-"? Predrag-Peter Ilich, Lucas S. Rickertsen, and Erienne Becker
The authors redefine Markovnikov or anti-Markovnikov regioselectivity and propose that the teaching of organic chemistry should be based on robust and portable concepts such as energy difference and atomic charge rather than historical labels.
Ilich, Predrag-Peter; Rickertsen, Lucas S.; Becker, Erienne. J. Chem. Educ. 2006, 83, 1681.
Addition Reactions |
Alkenes |
Computational Chemistry |
Mechanisms of Reactions |
Molecular Modeling
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The Hammett Equation: Probing the Mechanism of Aromatic Semicarbazone Formation Glenn K. Ikeda, Karen Jang, Scott O. C. Mundle, and Andrew P. Dicks
An organic class project is described where upper-level undergraduates measure kinetic rate constants for semicarbazone formation by reacting semicarbazide with a meta- or para-substituted benzaldehyde.
Ikeda, Glenn K.; Jang, Karen; Mundle, Scott O. C.; Dicks, Andrew P. J. Chem. Educ. 2006, 83, 1341.
Addition Reactions |
Aldehydes / Ketones |
Kinetics |
Mechanisms of Reactions |
UV-Vis Spectroscopy
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Was Markovnikov's Rule an Inspired Guess? Peter Hughes
A study of 19th century literature shows that neither Markovnikov nor any of his contemporaries carried out the reactions often attributed to himthe addition of hydrogen bromide or hydrogen chloride to propene. Since there is little evidence for Markovnikov's rule in his 1870 article, it is likely that it was more of an inspired guess than a rational conclusion.
Hughes, Peter. J. Chem. Educ. 2006, 83, 1152.
Addition Reactions |
Alkenes |
Mechanisms of Reactions
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Rapid and Stereoselective Conversion of a trans-Cinnamic Acid to a β-Bromostyrene Thomas A. Evans
The stereoselective synthesis of an aryl vinyl bromide is accomplished in a rapid microscale reaction of trans-4-methoxycinnamic acid with N-bromosuccinimide in dichloromethane. This guided-inquiry experiment links reactivity, stereochemistry, and mechanism in electrophilic addition reactions of alkenes and in E1 and E2 elimination reactions that form alkenes.
Evans, Thomas A. J. Chem. Educ. 2006, 83, 1062.
Alkenes |
Carbocations |
Gas Chromatography |
Mechanisms of Reactions |
Microscale Lab |
NMR Spectroscopy |
Stereochemistry
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Reactivity of the Monoterpenoid Nerol with p-Toluenesulfonic and Chlorosulfonic Acids: Selective Syntheses of α-Terpineol and α-Cyclogeraniol. An Activity for the Undergraduate Organic Lab Pablo J. Linares-Palomino, Sofía Salido, Joaquín Altarejos, Manuel Nogueras, and Adolfo Sánchez
Describes the selective syntheses of the cyclic monoterpenoids a-terpineol or a-cyclogeraniol from the acyclic monoterpenoid nerol using p-toluenesulfonic acid or chlorosulfonic acid as cyclizing agents.
Linares-Palomino, Pablo J.; Salido, Sofía; Altarejos, Joaquín; Nogueras, Manuel; Sánchez, Adolfo. J. Chem. Educ. 2006, 83, 1052.
Alcohols |
Carbocations |
Gas Chromatography |
Mechanisms of Reactions |
Microscale Lab |
Synthesis |
Natural Products |
Alkenes
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An Exploration of a Photochemical Pericyclic Reaction Using NMR Data Sara M. Hein
This inexpensive, small-scale experiment for advanced organic students describes the unambiguous identification of a photochemical dimerization product from eleven possible candidates.
Hein, Sara M. J. Chem. Educ. 2006, 83, 940.
Addition Reactions |
Alkanes / Cycloalkanes |
Alkenes |
Carboxylic Acids |
Conformational Analysis |
NMR Spectroscopy |
Photochemistry |
Synthesis
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Electrophilic Additions to Alkenes Thomas M. Bertolini and Phuc D. Tran
A worksheet of 18 reactions is presented as a learning aid to comprehend the regiochemistry and stereochemistry of alkene electrophilic addition.
Bertolini, Thomas M.; Tran, Phuc D. J. Chem. Educ. 2006, 83, 590.
Addition Reactions |
Alkenes |
Reactions
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Microwave-Induced Chain Transfer Polymerization of a Stimuli-Responsive Polymer and Determination of Its Critical Solution Temperature F. Fischer and R. Freitag
This experiment provides an introduction for undergraduate students to the concepts of living radical polymerization (oligomerization) and to stimuli-responsive materials, namely, those showing a critical solution temperature in aqueous solution.
Fischer, F.; Freitag, R. J. Chem. Educ. 2006, 83, 447.
Addition Reactions |
Free Radicals |
Mass Spectrometry |
Materials Science |
NMR Spectroscopy |
Polymerization |
UV-Vis Spectroscopy
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Polymerization and Characterization of PMMA. Polymer Chemistry Laboratory Experiments for Undergraduate Students Caroline Duval-Terrié and Laurent Lebrun
This experiment gives students the opportunity to prepare polymethylmethacrylate (PMMA), one of the most important industrial polymers. Two syntheses are described, involving either free radical or anionic polymerization.
Duval-Terrié, Caroline; Lebrun, Laurent. J. Chem. Educ. 2006, 83, 443.
Addition Reactions |
Free Radicals |
Industrial Chemistry |
NMR Spectroscopy |
Polymerization |
Thermal Analysis
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Diastereoselectivity in the Reduction of α-Hydroxyketones. An Experiment for the Chemistry Major Organic Laboratory David B. Ball
Describes a research type, inquiry-based project where students synthesize racemic ahydroxyketones using umpolung, a polarity-reversal approach; investigate chelating versus non-chelating reducing agents; and determine the diastereoselectivity of these reducing processes by NMR spectroscopy.
Ball, David B. J. Chem. Educ. 2006, 83, 101.
Addition Reactions |
Aldehydes / Ketones |
Chirality / Optical Activity |
Chromatography |
Conferences |
Constitutional Isomers |
Enantiomers |
NMR Spectroscopy |
Stereochemistry |
Synthesis |
Conformational Analysis
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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
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Diels–Alder Synthesis of endo-cis-N-Phenylbicyclo[2.2.2]oct-5-en-2,3-dicarboximide Marsha R. Baar and Kristin Wustholz
endo-cis-N-Phenylbicyclo[2.2.2]oct-5-en-2,3-dicarboximide was synthesized by a DielsAlder cycloaddition of 1,3-cyclohexadiene and N-phenylmaleimide in ethyl acetate. 1,3-Cyclohexadiene and N-phenylmaleimide were selected to illustrate the Alder rule, which reflects a preference for endo products and to overcome the difficulties associated with the traditional combination of 1,3-cyclopentadiene and maleic anhydride.
Baar, Marsha R.; Wustholz, Kristin. J. Chem. Educ. 2005, 82, 1393.
Asymmetric Synthesis |
Microscale Lab |
Stereochemistry |
Addition Reactions |
Alkenes |
IR Spectroscopy |
NMR Spectroscopy
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The Addition of Bromine to 1,2-Diphenylethene Judith C. Amburgey-Peters and LeRoy W. Haynes
We investigated the reaction of (Z)-1,2-diphenylethene (cis-stilbene) with various brominating reagents and solvents following directions in standard organic chemistry manuals. We were particularly interested in learning which combination of brominating reagent and solvent gave the best yield of (d,l)-1,2-dibromo-1,2-diphenylethane without the formation of significant amounts of meso-1,2-dibromo-1,2-diphenylethane, which is essentially the sole product from the reaction of bromine with (E)-1,2-diphenylethene (trans-stilbene). Based on the results from the standard preparatory methods, some permutations of solvent and brominating reagent were tried.
Amburgey-Peters, Judith C.; Haynes, LeRoy W. J. Chem. Educ. 2005, 82, 1051.
Addition Reactions |
Alkenes |
Carbocations |
Diastereomers |
Enantiomers |
Mechanisms of Reactions |
Stereochemistry
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DielsAlder Cycloadditions: A MORE Experiment in the Organic Laboratory Including A Diene Identification Exercise Involving NMR Spectroscopy and Molecular Modeling Roosevelt Shaw, Ashika Severin, Miguel Balfour, and Columbus Nettles
The MORE (microwave-induced organic reaction enhancement) technique has been used successfully to prepare two DielsAlder [p2 + p4] cycloaddition adducts, racemic exo, endo-2,3-dibenzoylbicyclo[2.2.1]hept-5-ene and racemic exo, endo-2,3-dibenzoylbicyclo[2.2.2]octa-5-ene, in high purity and good yields. Microwave synthesis of these two dienes serves as an excellent organic laboratory experiment to demonstrate the rate enhancement advantage of using microwave heating over conventional heating in preparing selected DielsAlder cycloaddition products.
Shaw, Roosevelt; Severin, Ashika; Balfour, Miguel; Nettles, Columbus. J. Chem. Educ. 2005, 82, 625.
Addition Reactions |
Molecular Modeling |
NMR Spectroscopy |
Alkenes
|
"You're Repulsive!"Teaching VSEPR in a Not-So-Elegant Way Robert S. H. Liu
Valence shell electron pair repulsive (VSEPR) interaction is an important concept particularly in discussing structural properties of molecules. In this article we showed five organic examples not commonly associated with VSEPR but yet all involving repulsive interactions of valence electrons, which provides ready explanations for altered chemical reactivity and spectroscopic properties of organic compounds. The ready catchy phrase Youre Repulsive! is the common thread used throughout these five examples.
Liu, Robert S. H. J. Chem. Educ. 2005, 82, 558.
Mechanisms of Reactions |
UV-Vis Spectroscopy |
Reactions |
Addition Reactions |
Electrophilic Substitution
|
Green Chemistry Laboratory: Benign Synthesis of 4,6-Diphenyl[2,2']bipyridine via Sequential Solventless Aldol and Michael Addition Reactions Gareth W. V. Cave and Colin L. Raston
Solventless reaction methodology avoids the use of hazardous and toxic solvents and minimizes generation of waste, thereby addressing some of the principles of green chemistry. 2,4,6-Trisubstituted pyridines are readily prepared in high yield using this methodology in three steps: (i) solventless aldol condensation of benzaldehyde and acetophenone, (ii) solventless Michael addition of 2-acetylpyridine to the previously formed 1,3-diphenylpropenone, and (iii) the ring closure of the resulting 1,5-diketone in acetic acid with ammonium acetate.
Cave, Gareth W. V.; Raston, Colin L. J. Chem. Educ. 2005, 82, 468.
Green Chemistry |
IR Spectroscopy |
NMR Spectroscopy |
Synthesis |
Addition Reactions
|
The Evolution of a Green Chemistry Laboratory Experiment: Greener Brominations of Stilbene Lallie C. McKenzie, Lauren M. Huffman, and James E. Hutchison
We describe two new greener alkene bromination reactions that offer enhanced laboratory safety and convey important green chemistry concepts, in addition to illustrating the chemistry of alkenes. The two alternative reactions, one involving pyridinium tribromide and a second using hydrogen peroxide and hydrobromic acid, are compared to the traditional bromination of stilbene through the application of green metrics, including atom economy, percent experimental atom economy, E factor, and effective mass yield.
McKenzie, Lallie C.; Huffman, Lauren M.; Hutchison, James E. J. Chem. Educ. 2005, 82, 306.
Synthesis |
Green Chemistry |
Aromatic Compounds |
Addition Reactions |
Alkenes
|
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 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
|
Spiral Puzzle for Organic Chemistry Students Ender Erdik
Puzzle to review organic reactions and their reagents.
Erdik, Ender. J. Chem. Educ. 2003, 80, 428.
Synthesis |
Learning Theories |
Enrichment / Review Materials |
Addition Reactions |
Alkylation |
Electrophilic Substitution |
Elimination Reactions |
Reactions |
Nucleophilic Substitution |
Mechanisms of Reactions |
Grignard Reagents
|
Dendrimers: Branching Out of Polymer Chemistry Eric E. Simanek and Sergio O. Gonzalez
Addresses synthetic concepts surrounding dendrimers including the use of protecting groups, functional group interconversions, and convergent and divergent synthetic strategies.
Simanek, Eric E.; Gonzalez, Sergio O. J. Chem. Educ. 2002, 79, 1222.
Materials Science |
Synthesis |
Molecular Properties / Structure |
Addition Reactions |
Aromatic Compounds |
Alkylation |
Nucleophilic Substitution
|
Moving Past Markovnikov's Rule E. Eugene Gooch
Extension of the Markovnikov Rule for addition reactions across a carbon-carbon double bond.
Gooch, E. Eugene. J. Chem. Educ. 2001, 78, 1358.
Synthesis |
Reactions |
Alkenes |
Addition Reactions |
Mechanisms of Reactions
|
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
|
Mechanism Templates: Lecture Aids for Effective Presentation of Mechanism in Introductory Organic Chemistry Brian J. McNelis
To promote active student learning of mechanism in introductory organic chemistry, hand-outs have been developed with incomplete structures for reaction processes depicted, which are called mechanism templates. The key to these lecture aids is to provide only enough detail in the diagram to facilitate notetaking, ensuring that these templates are dynamic learning tools that must be utilized by an engaged and alert student.
Brian J. McNelis. J. Chem. Educ. 1998, 75, 479.
Learning Theories |
Mechanisms of Reactions |
Reactions |
Addition Reactions |
Acids / Bases |
Electrophilic Substitution |
Nucleophilic Substitution
|
A -78°C Sequential Michael Addition for the Organic Lab Michael W. Tanis
This paper introduces a cold-temperature enolate alkylation reaction that can be performed safely and inexpensively by undergraduate students in approximately two 3-hour lab sessions.
Tanis, Michael W. J. Chem. Educ. 1997, 74, 112.
Addition Reactions |
Alkenes |
Aldehydes / Ketones |
Synthesis
|
Carbonyl and Conjugate Additions to Cyclohexenone: Experiments Illustrating Reagent Selectivity Michael G. Organ and Paul Anderson
Undergraduate students leaving an organic chemistry program should have exposure to these concepts and hands-on experience in dealing practically with the issue of selectivity. In this paper, selective addition of a nucleophile to either end of the enone moiety in cyclohexenone is examined.
Organ, Michael G.; Anderson, Paul. J. Chem. Educ. 1996, 73, 1193.
Addition Reactions |
Aldehydes / Ketones |
Mechanisms of Reactions
|
Further Comments upon the Electrophilic Addition to Alkynes: A Response to Criticism from Professor Thomas T.Tidwell Hilton M. Weiss
This paper responds to the preceding article by Professor T. Tidwell in which he provides arguments for vinyl cations being an intermediate in most electrophilic additions to alkynes.
Weiss, Hilton M. J. Chem. Educ. 1996, 73, 1082.
Addition Reactions |
Alkynes |
Mechanisms of Reactions
|
The Electrophilic Addition to Alkynes Revisited Thomas T. Tidwell
A recent claim that vinyl cations are not the predominant intermediates in the electrophilic addition to alkynes is disputed.
Tidwell, Thomas T. J. Chem. Educ. 1996, 73, 1081.
Addition Reactions |
Alkynes |
Mechanisms of Reactions
|
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
|
Regioselective Methoxybromination of Styrene Using TBABr3 in Methanol: An Organic Laboratory Experiment Jacques Berthelot, Yamina Benammar, and Catherine Lange
Methoxybromination of styrene using TBABr3 in methanol.
Bertholet, Jacques; Benammar, Yamina; Lange, Catherine. J. Chem. Educ. 1995, 72, 850.
Synthesis |
Mechanisms of Reactions |
Alkenes |
Addition Reactions
|
The Addition of Hydrogen Bromide to Simple Alkenes Hilton M. Weiss
Synthesis of 1-bromohexane.
Weiss, Hilton M. . J. Chem. Educ. 1995, 72, 848.
Synthesis |
Mechanisms of Reactions |
Addition Reactions |
Alkenes
|
Use of Multimedia in an Introductory Chemistry Course for Student Analysis of Real-Life Situations Joesten, Melvin D.
Award in the Course and Curriculum Development (CCD) program for FY1994.
Joesten, Melvin D. J. Chem. Educ. 1994, 71, 508.
Addition Reactions
|
A New Approach To Teaching Organic Chemical Mechanisms Wentland, Stephen H.
Describing the mechanisms of organic reactions using five simple steps or operations.
Wentland, Stephen H. J. Chem. Educ. 1994, 71, 3.
Mechanisms of Reactions |
Addition Reactions |
Nucleophilic Substitution |
Electrophilic Substitution |
Elimination Reactions |
Resonance Theory |
Molecular Properties / Structure
|
The electrophilic addition to alkynes Weiss, Hilton M.
Electrophilic additions to alkynes traditionally do not receive as much attention in organic textbooks as electrophilic addition to alkenes.
Weiss, Hilton M. J. Chem. Educ. 1993, 70, 873.
Addition Reactions |
Alkynes
|
Products of aldol addition and related reactions: Notation for their prediction Nwaukwai, Stephen O.
A simple method that can be used to predict products of aldols and aldol-tye addition reactions.
Nwaukwai, Stephen O. J. Chem. Educ. 1993, 70, 626.
Addition Reactions |
Aldehydes / Ketones |
Nomenclature / Units / Symbols
|
Synthesis of trans-2-tert-butylcyclohexanol via hydroboration: A microscale organic experiment demonstrating syn addition Wigal, Carl T.; Hopkins, William T.; Ronald, Bruce P.
This microscale experiment demonstrates the relative stereochemistry of the titled addition.
Wigal, Carl T.; Hopkins, William T.; Ronald, Bruce P. J. Chem. Educ. 1991, 68, A299.
Synthesis |
Microscale Lab |
Addition Reactions |
Aromatic Compounds |
Stereochemistry
|
Chelate-assisted carbon-halogen bond cleavage by oxidative addition at a W(O) carbonyl-metal complex: Inorganic-organometallic laboratory experiment for advanced undergraduates Lucht, Brett; Poss, Mitchell J.; Richmond, Thomas G.
These ligands are readily prepared, air-stable, and easily characterized making them the basis of a laboratory experiment suitable for senior undergraduate synthesis.
Lucht, Brett; Poss, Mitchell J.; Richmond, Thomas G. J. Chem. Educ. 1991, 68, 786.
Coordination Compounds |
IR Spectroscopy |
NMR Spectroscopy |
Crystal Field / Ligand Field Theory |
Addition Reactions |
Crystals / Crystallography |
Oxidation / Reduction
|
A quick and effective demonstration of anti-Markovnikov addition to alkenes Brown, Trevor M.; Dronsfield, Alan T.; Hitchcock, Ian
This reaction can be performed in less then 10 minutes and the product is easily identifiable.
Brown, Trevor M.; Dronsfield, Alan T.; Hitchcock, Ian J. Chem. Educ. 1991, 68, 785.
Alkenes |
Addition Reactions
|
A puzzle-solving experiment utilizing a Grignard reagent Silversmith, Ernest F.
Puzzle-solving experiments get away from typical organic laboratories that involve more of a cookbook methodology.
Silversmith, Ernest F. J. Chem. Educ. 1991, 68, 688.
Grignard Reagents |
Addition Reactions
|
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
|
Preparation of 1-phenyl-3-phenylaminopyrrolidine-2,5-dione: An organic laboratory experiment on the Michael addition Ram, Ram N.; Varsha, Kiran
Acylation of aniline with maleic anhydride to give maleanilic acid followed by Michael addition of aniline and cyclization to yield 1-phenyl-3-phenylaminopyrrolidine-2,5-dione.
Ram, Ram N.; Varsha, Kiran J. Chem. Educ. 1990, 67, 985.
Addition Reactions |
Aldehydes / Ketones |
Synthesis
|
Reaction of bromine with hydrocarbons on the overhead, real or simulated Solomon, Sally; Gregory, Michael; Padmanabhan, Sandeep; Smith, Kurt
A simulation that looks like the addition of bromine to hydrocarbons but is not (the bromine is simulated using a mixture of food colorings).
Solomon, Sally; Gregory, Michael; Padmanabhan, Sandeep; Smith, Kurt J. Chem. Educ. 1990, 67, 961.
Alkanes / Cycloalkanes |
Aromatic Compounds |
Addition Reactions
|
The stereochemistry of additions to trans-anethole McGahey, Lawrence
Trans-anethole is brominated with pyridinium bromide perbromide in dichloromethane.
McGahey, Lawrence J. Chem. Educ. 1990, 67, 554.
Addition Reactions |
Stereochemistry |
Mechanisms of Reactions |
Alkenes |
Diastereomers |
Enantiomers
|
Alkyl cations: The first 30 years Traynham, James G.
Historical development of concepts related to carbocations.
Traynham, James G. J. Chem. Educ. 1989, 66, 451.
Carbocations
|
Availability of video tape to clarify the method of standard abbreviations Williams, Kathryn R.
The method of standard addition is recognized as an important calibration technique in instrumental analysis.
Williams, Kathryn R. J. Chem. Educ. 1989, 66, 247.
Calibration |
Addition Reactions |
Instrumental Methods
|
The reactivity selectivity principle: Should it ever be used? Buncel, Erwin; Wilson, Harold
Applications and failures of the reactivity selectivity principle; quantitative aspects of the reactivity selectivity principle; and rationalization of reactivity selectivity principle failures.
Buncel, Erwin; Wilson, Harold J. Chem. Educ. 1987, 64, 475.
Mechanisms of Reactions |
Free Radicals |
Carbocations |
Nucleophilic Substitution
|
Specific-documented assertion of the term "carbonium" as correct and the term "carbocation" as incorrect Schwartz, M. Gerald
Asserts that the term "carbocation" has been incorrectly and inconsistently replacing the term "carbonium ion" in some quarters.
Schwartz, M. Gerald J. Chem. Educ. 1987, 64, 92.
Nomenclature / Units / Symbols |
Carbocations
|
Michael addition and aldol condensation: A simple teaching model for organic laboratory Garcia-Raso, A.; Garcia-Raso, J.; Sinisterra, J. V.; Mestres, R.
Three experiments are presented in this paper: Michael addition; Michael addition followed by aldol addition; and Michael addition followed by aldol condensation.
Garcia-Raso, A.; Garcia-Raso, J.; Sinisterra, J. V.; Mestres, R. J. Chem. Educ. 1986, 63, 443.
Addition Reactions |
Aldehydes / Ketones |
Alcohols
|
Hydroformylation: An old yet new industrial route to alcohols Pruett, Roy L.
This author from Exxon brings us up to date on modern hydroformylation chemistry.
Pruett, Roy L. J. Chem. Educ. 1986, 63, 196.
Organometallics |
Addition Reactions |
Alcohols |
Aldehydes / Ketones |
Coordination Compounds |
Catalysis |
Industrial Chemistry
|
Concertedness of 1,3-dipolar cycloadditions Haque, M. Serajul
The 1,3-dipolar cycloaddition is the union of a 1,3-dipole with a multiple bond system (a dipolarophile) to form a five-membered ring; the process is regarded as one of the most general methods for the synthesis of five-membered heterocycles.
Haque, M. Serajul J. Chem. Educ. 1984, 61, 490.
Addition Reactions |
Alkanes / Cycloalkanes |
Mechanisms of Reactions |
Heterocycles |
Synthesis |
MO Theory
|
Who is anti-Markovnikov? Tedder, J. M.
What are the factors that control the rate and orientation of free radical addition to alkenes?
Tedder, J. M. J. Chem. Educ. 1984, 61, 237.
Mechanisms of Reactions |
Addition Reactions |
Free Radicals |
Alkenes
|
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
|
Student preparation of alkanols from alkenes McKee, J. R.; Kauffman, J. M.
The hydration of 1-hexene to form 2-hexanol demonstrates Markovnikov addition, produces a higher yield of alcohol, and starts with a less expensive alkene than cyclohexene hydrations.
McKee, J. R.; Kauffman, J. M. J. Chem. Educ. 1982, 59, 695.
Alcohols |
Alkenes |
Mechanisms of Reactions |
Addition Reactions
|
Pi bonding without tears Akeroyd, F. Michael
A non-mathematical treatment of sigma-pi bonding applied to conjugation, hyperconjugation, Markovnikoff addition, aromaticity, and aromatic substitution.
Akeroyd, F. Michael J. Chem. Educ. 1982, 59, 371.
Alkenes |
Mechanisms of Reactions |
Addition Reactions |
Aromatic Compounds
|
The problem of syn- versus anti-addition: An organic chemistry laboratory experiment Silversmith, Ernest F.
An experiment that allows a student to determine whether an addition to a carbon-carbon double bond proceeds in syn- or anti-fashion.
Silversmith, Ernest F. J. Chem. Educ. 1982, 59, 346.
Addition Reactions |
Mechanisms of Reactions |
Molecular Properties / Structure |
Stereochemistry |
Synthesis |
Alkenes
|
Are all those sugars really important? Akers, Hugh
A listing of prices of various sugars, including both D- and L-forms.
Akers, Hugh J. Chem. Educ. 1982, 59, 59.
Carbocations |
Consumer Chemistry
|
Block and graft copolymers McGrath, J. E.
Block copolymers; transitional behavior; block copolymer architecture; synthesis; living polymerization sequential addition processes; interaction of functionality terminated oligomers; polymer growth from oligomer end groups; graft copolymers.
McGrath, J. E. J. Chem. Educ. 1981, 58, 914.
Synthesis |
Addition Reactions |
Polymerization
|
The driving force of addition and elimination reactions clarified through the Hellmann-Feynman theorem Blaise, Paul; Pujol, Phillippe; Henri-Rousseau, Olivier
The energy involved in the transition state is explored in this article.
Blaise, Paul; Pujol, Phillippe; Henri-Rousseau, Olivier J. Chem. Educ. 1981, 58, 615.
Thermodynamics |
Addition Reactions |
Elimination Reactions |
Reactions
|
Synthesis of poly([beta]-alanine) and [beta]-alanine Carraher, Charles E., Jr.
A procedure for the synthesis of poly([beta]-alanine) and [beta]-alanine .
Carraher, Charles E., Jr. J. Chem. Educ. 1978, 55, 668.
Amino Acids |
Addition Reactions |
Bioorganic Chemistry
|
Project for problem-oriented undergraduate organic or integrated undergraduate laboratory Silveira, Augustine, Jr.
This paper reports on an open-ended project which allows a great degree of flexibility in the laboratory. The project provided about a 6-week study for groups of 24 students each.
Silveira, Augustine, Jr. J. Chem. Educ. 1978, 55, 57.
Synthesis |
Undergraduate Research |
Spectroscopy |
Diastereomers |
Addition Reactions |
MO Theory |
Elimination Reactions |
Thermodynamics |
Kinetics
|
The methylene group, Karl Marx, and "Das Kapital": An interaction of Nineteenth Century science and philosophy Minnier, Carl E.
A brief outline of the development of the concept of the homologous series and how this concept became intertwined with the development of Marxist philosophy.
Minnier, Carl E. J. Chem. Educ. 1976, 53, 713.
Enrichment / Review Materials |
Addition Reactions
|
Molecular design of compounds via intermolecular Diels-Alder reactions Mehta, Goverdhan
The Diels-Alder reaction involving a cycloaddition between a diene and dienophile is one of the most versatile and useful reactions in the armory of the synthetic organic chemists.
Mehta, Goverdhan J. Chem. Educ. 1976, 53, 551.
Synthesis |
Addition Reactions |
Aromatic Compounds
|
Preparation of the sweetening agent P4000. A student project de Koning, A. J.
The author presents the procedure for preparation of the sweetening agent P4000 that can be performed by students.
de Koning, A. J. J. Chem. Educ. 1976, 53, 521.
Synthesis |
Food Science |
Carbocations |
Aromatic Compounds
|
Free-radical addition of tetrahalomethanes to [beta]-pinene. Experiments in organic chemistry Kaye, Irving Allan; Odum, Robert A.
This laboratory provides a much needed learning opportunity about free-radicals.
Kaye, Irving Allan; Odum, Robert A. J. Chem. Educ. 1976, 53, 60.
Free Radicals |
Addition Reactions
|
The hydroboration-oxidation of alkenes. A convenient anti-Markownikoff hydration experiment Kabalka, George W.; Hedgecock, Herbert C., Jr.
A hydroboration-oxidation sequence that relies on the borane dimethylsulfide complex as the hydroborating agent and trimethylamine-N-oxide dihydrate as the oxidizing agent.
Kabalka, George W.; Hedgecock, Herbert C., Jr. J. Chem. Educ. 1975, 52, 745.
Alkenes |
Oxidation / Reduction |
Addition Reactions
|
Classification of the electrophilic addition reactions of olefins and acetylenes Wilson, Michael A.
Summarizes a wide variety of electrophiles and substrates and the mechanisms by which they react.
Wilson, Michael A. J. Chem. Educ. 1975, 52, 495.
Addition Reactions |
Reactions |
Mechanisms of Reactions
|
Stereospecific thermal cycloadditions and catalyzed isomerizations: An organic laboratory project Pasto, D. J.; Duncan, J. A.; Silversmith, E. F.
The authors have prepared a sequence of experiments for their undergraduate organic chemistry laboratory concerned with the preparation of cis and trans 1,4-diphenyl-2-butene-1,4diones, their cycloadditions reactions with cyclopentandiene, and with related isomerization reactions of both the sequence, which has met with much success experimentally, clearly and collectively demonstrates certain aspects of the concepts of thermodynamics, kinetics, and stereochemistry and photochemistry.
Pasto, D. J.; Duncan, J. A.; Silversmith, E. F. J. Chem. Educ. 1974, 51, 277.
Photochemistry |
Constitutional Isomers |
Addition Reactions
|
Stereochemistry of carbonyl addition reactions Goller, Edwin J.
This article is a brief summary of some of the more important unifying concepts that have been proposed in the study of the stereo chemistry of carbonyl addition reactions.
Goller, Edwin J. J. Chem. Educ. 1974, 51, 182.
Addition Reactions |
Stereochemistry |
Aldehydes / Ketones |
Aromatic Compounds
|
Dihalocarbene addition reaction Goh, S. H.
This experiment illustrates the synthetic utility of carbenes and that of phase transfer catalysis.
Goh, S. H. J. Chem. Educ. 1973, 50, 678.
Alkenes |
Addition Reactions |
Reactions |
Mechanisms of Reactions |
Catalysis |
Synthesis
|
Structures containing cationic carbon Dermer, O. C.; Traynham, James C.
Reviews nomenclature conventions for structures containing cationic carbon.
Dermer, O. C.; Traynham, James C. J. Chem. Educ. 1973, 50, 545.
Nomenclature / Units / Symbols |
Carbocations
|
An application of GC and IR to follow the progress of chemical reactions Lires, O. A.; Molinari, M. A.
Two examples of preparing chloro derivatives of hydrocarbons for analysis by gas chromatography and infrared spectroscopy.
Lires, O. A.; Molinari, M. A. J. Chem. Educ. 1973, 50, 492.
Gas Chromatography |
IR Spectroscopy |
Reactions |
Addition Reactions |
Alkenes |
Alkylation
|
Carbenes in insertion and addition reactions Buehler, Calvin A.
Summarizes the reactions typical of insertion and addition.
Buehler, Calvin A. J. Chem. Educ. 1972, 49, 239.
Addition Reactions |
Reactive Intermediates |
Mechanisms of Reactions |
Synthesis
|
Donor-acceptor interactions in organic chemistry Sunderwirth, S. G.
The purpose of this article is to aid teachers in making even more effective use of theoretical considerations in teaching organic chemistry; the primary objective is to emphasize the underlying principles that are common to the following four basic types of reactions: substitution, addition, elimination, and rearrangement.
Sunderwirth, S. G. J. Chem. Educ. 1970, 47, 728.
Reactions |
Mechanisms of Reactions |
Addition Reactions |
Elimination Reactions |
Nucleophilic Substitution
|
Woodward-Hoffmann rules: Cycloaddition reactions Vollmer, John J.; Servis, Kenneth L.
Applies Woodward-Hoffmann rules to a wide variety of cycloaddition reactions.
Vollmer, John J.; Servis, Kenneth L. J. Chem. Educ. 1970, 47, 491.
Mechanisms of Reactions |
Addition Reactions |
Alkenes
|
A modern look at Markovnikov's rule and the peroxide effect Isenberg, Norbert; Grdinic, Marcel
Presents a "carbonium ion" definition of Markovnikov's Rule and examines the peroxide effect.
Isenberg, Norbert; Grdinic, Marcel J. Chem. Educ. 1969, 46, 601.
Mechanisms of Reactions |
Stereochemistry |
Diastereomers |
Free Radicals |
Alkenes |
Addition Reactions
|
Organic chemistry Dolbier, William R., Jr.
Presents an explanation that encompasses all electrophilic additions to alkenes within a single, unifying picture.
Dolbier, William R., Jr. J. Chem. Educ. 1969, 46, 342.
Addition Reactions |
Alkenes |
Mechanisms of Reactions |
Stereochemistry
|
Preparation of p-anisole: An organic chemistry experiment Smith, Richard F.; Bates, Alvin C.
In this experiment, p-anisaldehyde is converted to p-anisonitrile by a modification of the three-step aldehyde-nitrile synthesis of Smith and Walker.
Smith, Richard F.; Bates, Alvin C. J. Chem. Educ. 1969, 46, 174.
Synthesis |
Mechanisms of Reactions |
Addition Reactions |
Nucleophilic Substitution |
Elimination Reactions |
Catalysis
|
Reaction mechanisms in organic chemistry. I. The experimental approach Caserio, Marjorie C.
Reviews a variety of method that may be employed to determine the mechanism of organic reactions.
Caserio, Marjorie C. J. Chem. Educ. 1965, 42, 570.
Reactions |
Mechanisms of Reactions |
Reactive Intermediates |
Kinetics |
Nucleophilic Substitution |
Addition Reactions |
Elimination Reactions
|
Nucleophilic reactions at trigonally bonded carbon Cash, R. Vincent
Examines the mechanisms of nucleophilic displacement reactions, nucleophilic addition reactions, and nucleophilic addition with elimination, all at trigonally bonded carbon.
Cash, R. Vincent J. Chem. Educ. 1964, 41, 108.
Nucleophilic Substitution |
Reactions |
Mechanisms of Reactions |
Addition Reactions |
Elimination Reactions
|
Stable gaseous species at high temperatures Siegel, Bernard
Presents a systematic correlation of the bonding in the gaseous elements with the strengths of their respective bonds.
Siegel, Bernard J. Chem. Educ. 1963, 40, 304.
Gases |
Carbocations |
Covalent Bonding
|
Contributions of vinyl polymerization to organic chemistry Mayo, Frank R.
The author illustrates three types of free radical reactions through polymerization data.
Mayo, Frank R. J. Chem. Educ. 1959, 36, 157.
Polymerization |
Free Radicals |
Addition Reactions
|
Textbook errors: Guest column- XIX. The relative reactivity of acetylenes and olefins toward bromine Mysels, Karol J.; Daniels, Ralph; Bauer, Ludwig
Many contemporary textbooks and laboratory manuals in organic chemistry either state explicitly or imply that bromine ass much faster to acetylenes than to olefins.
Mysels, Karol J.; Daniels, Ralph; Bauer, Ludwig J. Chem. Educ. 1958, 35, 444.
Reactions |
Addition Reactions |
Alkylation |
Alkynes
|
New techniques of photochemical synthesis McNesby, J. R.
New techniques of photochemical synthesis reviewed include the addition of free radicals to double bonds and the preparation of specifically deuterated compounds.
McNesby, J. R. J. Chem. Educ. 1957, 34, 130.
Photochemistry |
Synthesis |
Addition Reactions
|
|
