| Journal Articles: 33 results |
|
|
The Synthesis of N-Benzyl-2-azanorbornene via Aqueous Hetero Diels–Alder Reaction Xavier Sauvage and Lionel Delaude
Characterization of the product of this organic synthesis through IR and NMR data analysis provides valuable material to familiarize students with different types of protonproton coupling patterns and their typical ranges, serves to illustrate the concepts of green chemistry and atom efficiency, and can be used to exemplify structural analysis and computational studies.
Sauvage, Xavier; Delaude, Lionel. J. Chem. Educ. 2008, 85, 1538.
Alkenes |
Aqueous Solution Chemistry |
Conformational Analysis |
Green Chemistry |
IR Spectroscopy |
Molecular Modeling |
NMR Spectroscopy |
Stereochemistry |
Synthesis
|
The Same and Not the Same: Chirality, Topicity, and Memory of Chirality Wolfgang H. Kramer and Axel G. Griesbeck
Describes a simple molecular approach that aids students in learning stereochemical terms, definitions, and concepts, particularly when chemical structures are drawn in two dimensions.
Kramer, Wolfgang H.; Griesbeck, Axel G. J. Chem. Educ. 2008, 85, 701.
Chirality / Optical Activity |
Stereochemistry
|
4-Dimethylaminopyridine or Acid-Catalyzed Syntheses of Esters: A Comparison Annemieke W. C. van den Berg and Ulf Hanefeld
Students compare acid-catalyzed ester synthesis and the 4-dimethylaminopyridine-catalyzed reaction. Based on the outcome of the experiments, students discuss the different reaction mechanisms and reason why different products are formed.
van den Berg, Annemieke W. C.; Hanefeld, Ulf. J. Chem. Educ. 2006, 83, 292.
Acids / Bases |
Catalysis |
Chromatography |
Esters |
IR Spectroscopy |
NMR Spectroscopy |
Mass Spectrometry |
Synthesis |
Mechanisms of Reactions
|
"It Gets Me to the Product": How Students Propose Organic Mechanisms Gautam Bhattacharyya and George M. Bodner
Because practicing organic chemists use the arrow-pushing formalism in situations that are far removed from the simple contexts in which they are first presented, this study probed how students enrolled in a first-semester, graduate-level organic chemistry course approached the task of writing the mechanisms for two- to four-step reactions that lacked the typical cues that bring common mechanisms to mind. This article focuses on the students' solutions and discusses possible limitations of their strategies.
Bhattacharyya, Gautam; Bodner, George M. J. Chem. Educ. 2005, 82, 1402.
Mechanisms of Reactions |
Learning Theories |
Constructivism
|
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
|
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
|
Looking beyond the endo Rule in a Diels-Alder Discovery Lab Ronald M. Jarret, Jamie New, Rebecca Hurley, and Laura Gillooly
Procedure to introduce preference for generation of the endo product and the stereochemistry of alkene addition of the Diels-Alder reaction.
Jarret, Ronald M.; New, Jamie; Hurley, Rebecca; Gillooly, Laura. J. Chem. Educ. 2001, 78, 1262.
NMR Spectroscopy |
Synthesis |
Stereochemistry |
Alkenes
|
Molecular Orbital Animations for Organic Chemistry Steven A. Fleming, Greg R. Hart, and Paul B. Savage
Introduces the application of highest occupied and lowest unoccupied molecular orbitals (HOMOs and LUMOs) in animated form.
Fleming, Steven A.; Hart, Greg R.; Savage, Paul B. J. Chem. Educ. 2000, 77, 790.
MO Theory |
Molecular Modeling |
Mathematics / Symbolic Mathematics |
Mechanisms of Reactions |
Electrophilic Substitution |
Nucleophilic Substitution
|
Organic Reactions in Aqueous Media (by Chao-Jun Li and Tak-Hang Chan) reviewed Alan M. Rosan
Selective review of the burgeoning literature on organic reactions conducted in water or in aqueous media as a reaction cosolvent.
Rosan, Alan M. J. Chem. Educ. 2000, 77, 707.
Aqueous Solution Chemistry |
Reactions |
Synthesis |
Mechanisms of Reactions
|
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
|
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
|
Pericyclic Reactions: FMO Approach-Abstract of Issue 9904M Albert W. M. Lee, C. T. So, C. L. Chan, and Y. K. Wu
Pericyclic Reactions: FMO Approach is a program for Macintosh computers in which the frontier molecular orbital approaches to electrocyclic and cycloaddition reactions are animated. The bonding or antibonding interactions of the frontier molecular orbital(s) determine whether the reactions are thermally or photochemically allowed or forbidden.
Lee, Albert W. M.; So, C. T.; Chan, C. L.; Wu, Y. K. J. Chem. Educ. 1999, 76, 720.
MO Theory |
Mechanisms of Reactions
|
Sharpless Asymmetric Dihydroxylation: Effect of Alkene Structure on Rates and Selectivity Alan C. Spivey, R. Hanson, N. Scorah, and S. J. Thorpe
Each student is assigned an alkene and performs three dihydroxylation reactions: one racemic and two enantioselective variants. The products are characterized by 1H NMR, IR, MS, [a]D20, and chiral chromatography (HPLC or GC). Comparison by the students of their results with those reported in the literature, particularly the extensive work of Sharpless, allows an exploration of the validity of Sharpless's mnemonic for predicting the stereochemical outcome of these reactions.
Spivey, Alan C.; Hanson, R.; Scorah, N.; Thorpe, S. J. J. Chem. Educ. 1999, 76, 655.
Synthesis |
Catalysis |
Stereochemistry |
Organometallics |
Molecular Properties / Structure
|
Mechanisms in Motion-Organic Chemistry Animations v 1.5 (by Bruce H. Lipshutz) Alan M. Rosan
This single CD-ROM presents 17 short (2-3-minute) Quicktime, full-color movie animations of selected organic reaction mechanisms, most of which are discussed at the sophomore level.
Rosan, Alan M. J. Chem. Educ. 1998, 75, 980.
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
|
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
|
Organic Chemistry, Third Edition reviewed by Timothy D. Lash
The author continues to stress the use of reaction mechanisms, and this remains a strong point in the new edition. The heart and soul of modern organic chemistry revolves around these concepts, and this framework is essential for a textbook of this type.
Lash, Timothy D. J. Chem. Educ. 1996, 73, A312.
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
|
Optical activity can be created from "nothing" Caswell, Lesley; Garcia-Garibay, Miguel A.; Scheffer, John R.; Trotter, James
Optically active products can be generated from achiral reactants.
Caswell, Lesley; Garcia-Garibay, Miguel A.; Scheffer, John R.; Trotter, James J. Chem. Educ. 1993, 70, 785.
Enantiomers |
Stereochemistry
|
Higher order cycloaddition reactions of adamantyl isobenzofulvene and isobenzofuran: A microscale synthesis illustrating the involvement of highly reactive intermediates and a simple FMO treatment of their cycloaddition periselectivities Russell, Richard A.; Longmore, Robert W.; Warrener, Ronald N.
The authors have developed an undergraduate laboratory experiment to illustrate a cycloaddition reaction using a simple mathematical approach.
Russell, Richard A.; Longmore, Robert W.; Warrener, Ronald N. J. Chem. Educ. 1992, 69, 164.
Microscale Lab |
Alkenes |
Synthesis |
MO Theory
|
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
|
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
|
Three easy puzzles based on the Diels-Alder reaction Pickering, Miles.
This paper recasts some classic systems so that they can be done at room temperature on a small scale in a large lab course without sophisticated instrumentation. Furthermore, they start the student using experimental results to solve mechanistic problems.
Pickering, Miles. J. Chem. Educ. 1990, 67, 524.
Mechanisms of Reactions |
Stereochemistry
|
A Diels-Alder reaction for the overhead projector Kolb, Kenneth E.
Reacting the strong dienophile tetracyanothylene with anthracene as the diene.
Kolb, Kenneth E. J. Chem. Educ. 1989, 66, 955.
Alkenes |
Mechanisms of Reactions
|
A valence isomer trapping procedure for introductory organic laboratory: Synthesis of a homobarrelene derivative Kurtz, David W.; Johnson, Richard P.
Norcaradiene is trapped out of its cycloheptatriene valence isomer in a Diels-Alder reaction with maleic anhydride.
Kurtz, David W.; Johnson, Richard P. J. Chem. Educ. 1989, 66, 873.
Alkenes |
Mechanisms of Reactions
|
Synthesis of azulene, a blue hydrocarbon Lemal, David M.; Goldman, Glenn D.
A procedure of the synthesis of this simple, beautiful, and theoretically interesting compound with many unusual properties.
Lemal, David M.; Goldman, Glenn D. J. Chem. Educ. 1988, 65, 923.
MO Theory |
Aromatic Compounds |
Diastereomers |
Synthesis
|
Organic lecture demonstrations Silversmith, Ernest F.
Organic chemistry may not be known for its spectacular, attention getting chemical reactions. Nevertheless, this author describes a few organic chemistry reactions that put points across and generate interest. This article provides a convenient sources of demonstrations and urges others to add to the collection. Demonstrations concerning: carbohydrates, spectroscopy, proteins, amines, carbohydrates, carboxylic acids, and much more.
Silversmith, Ernest F. J. Chem. Educ. 1988, 65, 70.
Molecular Properties / Structure |
Nucleophilic Substitution |
Acids / Bases |
Physical Properties |
Alkenes |
Stereochemistry |
Enantiomers |
Chirality / Optical Activity |
Aldehydes / Ketones |
Alcohols
|
Toward an organic chemist's periodic table Hall, H. K., Jr.
An analogy between electron transfer reactions of the elements and those of organic molecules.
Hall, H. K., Jr. J. Chem. Educ. 1980, 57, 49.
MO Theory |
Reactions |
Mechanisms of Reactions
|
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
|
Reaction mechanisms in organic chemistry. Concerted reactions Caserio, Marjorie C.
Examines displacement and elimination, cyclization, and rearrangement reactions, as well as theoretical considerations and generalized selection rules.
Caserio, Marjorie C. J. Chem. Educ. 1971, 48, 782.
Mechanisms of Reactions |
Reactions |
Nucleophilic Substitution |
Elimination Reactions
|
Models to illustrate orbital symmetry effects in organic reactions Brown, Peter
From a pedagogic point of view, conservation of orbital symmetry is easily assimilated by students with a rudimentary knowledge of simple MO theory and of symmetry. The author has found in teaching over the past three years at both graduate and undergraduate levels that use of a simple set of orbital models as described in this article has enormous advantages as a visual aid in the construction and assignment of symmetry elements to the appropriate semi-localized Huckel-type MOs and in following their stereo chemical fate in concerned reactions.
Brown, Peter J. Chem. Educ. 1971, 48, 535.
Molecular Modeling |
MO Theory |
Group Theory / Symmetry
|
Fluorine compounds as teaching aids in organic theory Young, John A.
Fluorine compounds do obey the fundamental tenets of organic theory, but their frequent reversal of polarity, relative to hydrocarbon analogs, and the change in emphasis from a positive hydrogen ion to a negative fluoride ion allow the instructor to frame questions that demand reasoning rather than reiteration on the part of the student.
Young, John A. J. Chem. Educ. 1970, 47, 733.
Aromatic Compounds |
Mechanisms of Reactions
|
The chemistry of benzyne Bunnett, Joseph F.
Examines the chemistry of benzyne and alkynes.
Bunnett, Joseph F. J. Chem. Educ. 1961, 38, 278.
Aromatic Compounds |
Reactions |
Mechanisms of Reactions |
Alkynes
|
|
