TIGER

Journal Articles: 18 results
A Three-Step Laboratory Sequence To Prepare a Carbene Complex of Silver(I) Chloride  John P. Canal, Taramatee Ramnial, Lisa D. Langlois, Colin D. Abernethy, and Jason A. C. Clyburne
Presents a multistep inorganic synthesisof N-heterocyclic carbenes that introduces students to modern organometallic chemistry, multinuclear NMR (1H and 13C) spectroscopy, and novel coordination geometries and valence states of carbon.
Canal, John P.; Ramnial, Taramatee; Langlois, Lisa D.; Abernethy, Colin D.; Clyburne, Jason A. C. J. Chem. Educ. 2008, 85, 416.
Coordination Compounds |
NMR Spectroscopy |
Organometallics |
Synthesis
On the Use of "Green" Metrics in the Undergraduate Organic Chemistry Lecture and Lab To Assess the Mass Efficiency of Organic Reactions  John Andraos and Murtuzaali Sayed
This article describes a novel approach to evaluate the complete reaction mass efficiency and raw material cost of any chemical transformation using an Excel spreadsheet.
Andraos, John; Sayed, Murtuzaali. J. Chem. Educ. 2007, 84, 1004.
Green Chemistry |
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
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 DielsAlder 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
Formation of α-Tetralone by Intramolecular Friedel–Crafts Acylation  Michael S. Holden, R. David Crouch, and Kathryn A. Barker
A microscale procedure is described for the formation of the industrially-important compound alpha-tetralone. This is an example of an intramolecular FriedelCrafts acylation, utilizing 4-phenylbutanoic acid and a proton source. The title reaction demonstrates the concept of ring-forming reactions and highlights the use of carboxylic acids as an electrophile precursor in electrophilic aromatic substitution reactions.
Holden, Michael S.; Crouch, R. David; Barker, Kathryn A. J. Chem. Educ. 2005, 82, 934.
Aromatic Compounds |
Microscale Lab |
Synthesis |
Carboxylic Acids |
IR Spectroscopy |
NMR Spectroscopy
A Discovery-Based Friedel–Crafts Acylation Experiment: Student-Designed Experimental Procedure  Anne McElwee Reeve
A discovery-based FriedelCrafts acylation experiment that includes a student-designed procedure, spectroscopic analysis of an unknown aromatic product, and molecular modeling is described. Students design the synthetic procedure and workup for the acylation of an unknown aromatic starting material in an instructor-guided classroom discussion that integrates concepts from the first semester of organic lab into a new context.
Reeve, Anne McElwee. J. Chem. Educ. 2004, 81, 1497.
Aromatic Compounds |
Chromatography |
IR Spectroscopy |
Molecular Modeling |
NMR Spectroscopy |
Synthesis
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
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
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
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
Synthesis of Complex Natural Products as a Vehicle for Student-Centered, Problem-Based Learning  Kevin J. Cannon and Grant R. Krow
Using natural product synthesis as a vehicle, students choose a synthetic problem from the literature, identify the knowledge needed to solve the problem, explore resources for attaining that knowledge, identify the goals and criteria for a successful synthetic plan, and create and do assessments of their work.
Cannon, Kevin J.; Krow, Grant R. J. Chem. Educ. 1998, 75, 1259.
Synthesis |
Natural Products |
Undergraduate Research |
Student-Centered Learning
The Art and Science of Organic and Natural Products Synthesis  K. C. Nicolaou, E. J. Sorensen, and N. Winssinger
In this article, the history of the art and science of organic and natural products synthesis is briefly reviewed and the state of the art is discussed. The impact of this discipline on biology and medicine is amply demonstrated with examples, and projections for future developments in the field are made.
Nicolaou, K. C.; Sorensen, E. J.; Winssinger, N. J. Chem. Educ. 1998, 75, 1225.
Natural Products |
Synthesis |
Medicinal Chemistry |
Applications of Chemistry |
Drugs / Pharmaceuticals
A Grignard-like Organic Reaction in Water  Gary W. Breton and Christine A. Hughey
A known Grignard-like reaction between allyl bromide and benzaldehyde mediated by zinc metal in aqueous media. The procedure retains the desirable features of the traditional Grignard reaction, while eliminating some of the commonly encountered difficulties.
Breton, Gary W.; Hughey, Christine A. J. Chem. Educ. 1998, 75, 85.
Microscale Lab |
Aromatic Compounds |
Aldehydes / Ketones |
Alcohols |
Synthesis |
Mechanisms of Reactions
Wöhler's Synthesis of Urea: How Do the Textbooks Report It?  Paul S. Cohen and Stephen M. Cohen
Most general chemistry and organic chemistry textbooks describe Friedrich Whler's synthesis of urea as the moment when modern organic chemistry was born. We surveyed 35 modern and classic texts to learn what each noted of Whler's work
J. Chem. Educ. 1996, 73, 883.
Synthesis
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
Carbon-11: Where familiar chemistry still holds new challenges  Feliu, Anthony L.
Organic synthesis for biomedical applications with carbon-11 is made feasible by the high activities which can be cyclotron produced compared to the quantity required for a patient study.
Feliu, Anthony L. J. Chem. Educ. 1990, 67, 364.
Isotopes |
Synthesis
A photochemical preparation of indoles: An organic chemistry experiment  Kane, Victoria; Schultz, Arthur G.
Modification of a research-oriented photochemical experiment the provides an early exposure to the synthetic advantages of organic photochemistry and illustrates the formation of a mechanistically interesting carbon-carbon bond.
Kane, Victoria; Schultz, Arthur G. J. Chem. Educ. 1979, 56, 555.
Synthesis |
Photochemistry
a[alpha]- and [bet]a-D-glucose pentaacetate. An experiment in structure assignment using NMR  Pearson, Wesley A.; Spessard, Gary O.
The synthesis and structural determination of alpha- and beta-D-glucose pentaacetate.
Pearson, Wesley A.; Spessard, Gary O. J. Chem. Educ. 1975, 52, 814.
NMR Spectroscopy |
Carbohydrates |
Synthesis