| Journal Articles: 28 results |
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Synthesis Explorer: A Chemical Reaction Tutorial System for Organic Synthesis Design and Mechanism Prediction Jonathan H. Chen and Pierre Baldi
Synthesis Explorer is an interactive tutorial system for organic chemistry that enables students to learn chemical reactions in ways previously unrealized. Pedagogical experiments in undergraduate classes at UC Irvine indicate that the system can improve average student examination performance by ~10%.
Chen, Jonathan H.; Baldi, Pierre. J. Chem. Educ. 2008, 85, 1699.
Mechanisms of Reactions |
Reactions |
Synthesis
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Probing the Rate-Determining Step of the Claisen–Schmidt Condensation by Competition Reactions Kendrew K. W. Mak, Wing-Fat Chan, Ka-Ying Lung, Wai-Yee Lam, Weng-Cheong Ng, and Siu-Fung Lee
This article describes a physical organic experiment to identify the rate-determining step of the ClaisenSchmidt condensation of benzaldehyde and acetophenone by studying the linear free energy relationship.
Mak, Kendrew K. W.; Chan, Wing-Fat; Lung, Ka-Ying; Lam, Wai-Yee; Ng, Weng-Cheong; Lee, Siu-Fung. J. Chem. Educ. 2007, 84, 1819.
Aldehydes / Ketones |
Aromatic Compounds |
Gas Chromatography |
Kinetics |
Mechanisms of 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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Regiospecific Epoxidation of Carvone: A Discovery-Oriented Experiment for Understanding the Selectivity and Mechanism of Epoxidation Reactions Kendrew K. W. Mak, Y. M. Lai, and Yuk-Hong Siu
Peroxy acids and alkaline H2O2 are two commonly used reagents for alkene epoxidation. The former react preferentially with electron-rich alkenes while the latter works better with a,-unsaturated carbonyl compounds. The selectivity of these two reagents on carvone, a naturally occurring compound that contains both types of C=C bonds, is investigated.
Mak, Kendrew K. W.; Lai, Y. M.; Siu, Yuk-Hong. J. Chem. Educ. 2006, 83, 1058.
Alkenes |
Chromatography |
Epoxides |
IR Spectroscopy |
NMR Spectroscopy |
Synthesis |
Mechanisms of Reactions
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The Virtual ChemLab Project: A Realistic and Sophisticated Simulation of Organic Synthesis and Organic Qualitative Analysis Brian F. Woodfield, Merritt B. Andrus, Gregory L. Waddoups, Melissa S. Moore, Richard Swan, Rob Allen, Greg Bodily, Tricia Andersen, Jordan Miller, Bryon Simmons, and Richard Stanger
Describes a set of sophisticated and realistic laboratory simulations for use in freshman- and sophomore-level chemistry classes and laboratories called Virtual ChemLab. The purpose of these simulations is to reinforce concepts taught in the classroom, provide an environment for creative learning, and emphasize the thinking behind instructional laboratory experiments.
Woodfield, Brian F.; Andrus, Merritt B.; Waddoups, Gregory L.; Moore, Melissa S.; Swan, Richard; Allen, Rob; Bodily, Greg; Andersen, Tricia; Miller, Jordan; Simmons, Bryon; Stanger, Richard. J. Chem. Educ. 2005, 82, 1728.
IR Spectroscopy |
NMR Spectroscopy |
Qualitative Analysis |
Synthesis |
Reactions |
Thin Layer Chromatography
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Using Building-Block Puzzles To Practice Drawing Organic Mechanisms Ender Erdik
This pencil-and-paper activity is designed to test the ability of students in writing intermediates and products in the reactions of ketones. An undergraduate student who is successful in organic chemistry at the sophomore level is expected to fill in empty boxes with the appropriate "building blocks", which are atoms and atom groups (neutral or ionic). Solving the puzzle will give the formulas of reactants, reactive intermediates, and products. Students test their understanding of reaction mechanisms while having fun.
Erdik, Ender. J. Chem. Educ. 2005, 82, 1325.
Reactive Intermediates |
Synthesis |
Aldehydes / Ketones |
Mechanisms of Reactions
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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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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 Substitution–Elimination Mechanistic Disc Method Paul T. Buonora and Yu Jin Lim
In this manuscript a mnemonic device designed to facilitate presentation of the competing SN1, SN2, E1, and E2 mechanisms is presented.
Buonora, Paul T.; Lim, Yu Jin. J. Chem. Educ. 2004, 81, 368.
Mechanisms of Reactions |
Elimination Reactions |
Nucleophilic Substitution
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The Michael Reaction Thomas Poon, Bradford P. Mundy, and Thomas W. Shattuck
Biography, overview, computational analysis, and examples of the Michael reaction in organic syntheses and natural systems.
Poon, Thomas; Mundy, Bradford P.; Shattuck, Thomas W. J. Chem. Educ. 2002, 79, 264.
Computational Chemistry |
Synthesis |
Mechanisms of Reactions
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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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A More Realistic Teaching Style in Spectroscopic Instruction Mar Gómez Gallego, Santiago Romano, Miguel A. Sierra, and Enrique Nieto
A practical application of spectroscopic analysis in intermediate and advanced organic chemistry to determine reaction mechanisms and identify products; provides three specific problems.
Gallego, Mar Gómez; Romano, Santiago; Sierra, Miguel A.; Nieto, Enrique. J. Chem. Educ. 2001, 78, 765.
Mechanisms of Reactions |
NMR Spectroscopy |
Learning Theories |
Spectroscopy |
Molecular Properties / Structure |
Qualitative Analysis
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Organizing Organic Reactions: The Importance of Antibonding Orbitals David E. Lewis
It is proposed that unoccupied molecular orbitals arbitrate much organic reactivity, and that they provide the basis for a reactivity-based system for organizing organic reactions. Such a system is proposed for organizing organic reactions according to principles of reactivity, and the system is discussed with examples of the frontier orbitals involved.
Lewis, David E. J. Chem. Educ. 1999, 76, 1718.
Covalent Bonding |
Mechanisms of Reactions |
MO Theory
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Organic Chemistry (by Joseph M. Hornback) R. Daniel Libby
This text uses reaction mechanisms as the organizing principle, introduces structure where it is necessary to support the reactions to be studied, and considers synthesis after the mechanisms of appropriate reactions have been discussed.
Libby, R. Daniel. J. Chem. Educ. 1999, 76, 611.
Mechanisms of Reactions |
Synthesis |
Molecular Properties / Structure
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Incorporating Organic Name Reactions and Minimizing Qualitative Analysis in an Unknown Identification Experiment Claire Castro and William Karney
The authors have developed a new type of unknown identification experiment for the introductory organic chemistry laboratory. The unknown sample the student is provided with is the product of an organic name reaction. The student is only informed of the starting material and conditions used in the compound's synthesis, and must then: (1) deduce the compound's structure, (2) determine the name reaction and corresponding mechanism that yields the compound, and (3) present his/her results to the class.
Claire Castro and William Karney. J. Chem. Educ. 1998, 75, 472.
IR Spectroscopy |
NMR Spectroscopy |
Qualitative Analysis |
Nomenclature / Units / Symbols |
Reactions |
Mechanisms of Reactions |
Molecular Properties / Structure
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Database vs. Expert System Teaching Paradigms: Using Organic Reaction Mechanisms To Teach Chemical Intuition Paul H. Scudder
This paper presents an expert-system-designed course that has worked well to teach students how to formulate reasonable hypotheses in organic chemistry. The course organizes reactants into generic electron sources and sinks, and treats reaction mechanisms as assemblies of a limited number of recognizable mechanistic steps.
Scudder, Paul H. J. Chem. Educ. 1997, 74, 777.
Learning Theories |
Mechanisms of Reactions
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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
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The Baylis-Hillman Reaction: Synthesizing a Compound and Explaining Its Formation Crouch, R. David; Nelson, Todd D.
Experimental procedure for the synthesis of an unpredictable and unknown mechanism to be identified and described by students through analytical techniques (spectroscopy).
Crouch, R. David; Nelson, Todd D. J. Chem. Educ. 1995, 72, A6.
Synthesis |
Mechanisms of Reactions |
NMR Spectroscopy |
IR Spectroscopy |
UV-Vis Spectroscopy |
Microscale Lab
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The AC Rule: An Algorithm for Organic Reactions Edgar F. Kiefer
Algorithm for predicting organic reaction mechanisms.
Kiefer, Edgar F. J. Chem. Educ. 1995, 72, 906.
Mechanisms of Reactions |
Synthesis |
Reactions
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Learning Name Reactions and Name Apparatuses Through Crossword Puzzles Lee, Albert W. M.; Tse, C. L.
These computer generated crossword puzzles consist of 38 organic name reactions and 13 name apparatuses frequently encountered at the undergraduate level.
Lee, Albert W. M.; Tse, C. L. J. Chem. Educ. 1994, 71, 1071.
Laboratory Equipment / Apparatus |
Reactions
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Disconnect by the numbers: A beginner's guide to synthesis Smith, Michael B.
A protocol for planning organic syntheses using the disconnection method.
Smith, Michael B. J. Chem. Educ. 1990, 67, 848.
Synthesis |
Mechanisms of Reactions
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Decarboxylation of a keto acids Hanson, R. W.
Rectifies the lack of information concerning the nonenzymatic decarboxylation of alpha-keto acids found in many textbooks and to correct errors found in others.
Hanson, R. W. J. Chem. Educ. 1987, 64, 591.
Mechanisms of Reactions |
Catalysis
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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
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Favorskii rearrangement in bridged polycyclic compounds Chenier, Philip J.
Favorskii rearrangement in bridged polycyclic compounds: This can be classified as an intramolecular rearrangement from carbon to carbon, involving a migrating group Z moving without its electrons from migrating origin A to an electron-rich terminus B.
Chenier, Philip J. J. Chem. Educ. 1978, 55, 286.
Mechanisms of Reactions |
Carboxylic Acids |
Aldehydes / Ketones |
Aromatic Compounds
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The remarkable reactivity of aryl halides with nucleophiles Bunnett, Joseph F.
Nucleophilic attack on carbon; nucleophilic attack on hydrogen; aryl formation by halide ion loss from o-halophenyl anions; nucleophilic attack on halogen; acceptance of an electron, and its consequences.
Bunnett, Joseph F. J. Chem. Educ. 1974, 51, 312.
Nucleophilic Substitution |
Reactions
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Alkylations in organic chemistry Mundy, Bradford P.
Examines some of the subtle factors involved in alkylations, including alkylations via enolates, alkylations via enamines, and alkylation of enolates derived from reduction of enone systems.
Mundy, Bradford P. J. Chem. Educ. 1972, 49, 91.
Synthesis |
Alkylation |
Aldehydes / Ketones |
Mechanisms of Reactions
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From stoichiometry and rate law to mechanism Edwards, John O.; Greene, Edward F.; Ross, John
Examines the rules used by chemists as guidelines in developing mechanisms from stoichiometric and rate law observations.
Edwards, John O.; Greene, Edward F.; Ross, John J. Chem. Educ. 1968, 45, 381.
Stoichiometry |
Rate Law |
Kinetics |
Mechanisms of Reactions |
Equilibrium |
Reactive Intermediates
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Three-dimensional effects in biochemistry Ingraham, Lloyd L.
Explores stereospecificity and stereoselectivity; rigidity requirements; steric effects; and stereospecificity when not required mechanistically.
Ingraham, Lloyd L. J. Chem. Educ. 1964, 41, 66.
Molecular Properties / Structure |
Catalysis |
Enzymes |
Molecular Recognition |
Mechanisms of Reactions |
Stereochemistry |
Chirality / Optical Activity |
Enantiomers
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