TIGER

Journal Articles: 105 results
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
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
Organic Synthesis: Strategy and Control (Paul Wyatt and Stuart Warren)  Richard Pagni
Organic Synthesis is an excellent resource on organic synthesis. Because of the enormous breadth and complexity of the subject, being able to organize the material into coherent units as well as interconnecting them into a coherent whole is key to writing a successful book on organic synthesis. Wyatt and Warren show this skill in abundance.
Pagni, Richard. J. Chem. Educ. 2008, 85, 785.
Synthesis |
Mechanisms of Reactions
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
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
A Simple Assignment That Enhances Students' Ability To Solve Organic Chemistry Synthesis Problems and Understand Mechanisms  Jennifer Teixeira and R. W. Holman
Describes an original, easily implemented approach in which students construct a "functional group transformation" notebook which helps them to think about organic reactions in both the forward and the reverse (retrosynthetic) sense.
Teixeira, Jennifer; Holman, Robert W. J. Chem. Educ. 2008, 85, 88.
Mechanisms of Reactions |
Synthesis |
Student-Centered Learning
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 ClaisenSchmidt 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
A Knoevenagel Initiated Annulation Reaction Using Room Temperature or Microwave Conditions  A. Gilbert Cook
The product of a Knoevenagel initiated annulation reaction is identified through a guided prelab exercise of the synthesis of the Hagemann ester, and then through the analysis of GCMS, NMR, and IR spectra. The stereochemistry of the product is determined through the NMR spectrum and Karplus curve, and the student is required to write a mechanism for the reaction.
Cook, A. Gilbert. J. Chem. Educ. 2007, 84, 1477.
Aldehydes / Ketones |
Conformational Analysis |
Gas Chromatography |
IR Spectroscopy |
Mass Spectrometry |
Mechanisms of Reactions |
NMR Spectroscopy |
Stereochemistry |
Synthesis
A Green Alternative to Aluminum Chloride Alkylation of Xylene  Grigoriy A. Sereda and Vikul B. Rajpara
Presents a simple laboratory experiment that introduces organic chemistry students to the basic principles of green technologies, such as lack of toxic or bulk byproducts, nontoxicity, and reusability of the catalyst.
Sereda, Grigoriy A.; Rajpara, Vikul B. J. Chem. Educ. 2007, 84, 692.
Alkylation |
Green Chemistry |
Catalysis |
NMR Spectroscopy |
Reactions |
Synthesis
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
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
Keeping Your Students Awake: Facile Microscale Synthesis of Modafinil, a Modern Anti-Narcoleptic Drug  Evangelos Aktoudianakis, Rui Jun Lin, and Andrew P. Dicks
Describes the microscale preparation of modafinil, a pharmaceutical recently approved for the treatment of narcolepsy, by a sulfide oxidation reaction. An unusual feature of modafinil is the presence of a chiral sulfoxide functionality where a sulfur atom acts as a stereocenter, demonstrating that atoms other than carbon can act as centers of chirality.
Aktoudianakis, Evangelos; Lin, Rui Jun; Dicks, Andrew P. J. Chem. Educ. 2006, 83, 1832.
Chirality / Optical Activity |
Drugs / Pharmaceuticals |
Synthesis |
Mechanisms of Reactions |
IR Spectroscopy |
NMR Spectroscopy |
Microscale Lab |
Stereochemistry
Projects That Assist with Content in a Traditional Organic Chemistry Course  John J. Esteb, John R. Magers, LuAnne McNulty, and Anne M. Wilson
Describes two projects in organic chemistry, the reaction notebook and the end-of-semester synthesis activity, that are designed to stimulate student ownership of and engagement with course content.
Esteb, John J.; Magers, John R.; McNulty, LuAnne; Wilson, Anne M. J. Chem. Educ. 2006, 83, 1807.
Enrichment / Review Materials |
Mechanisms of Reactions |
Reactions |
Synthesis |
Student-Centered Learning
Purification and Modification of Fullerene C60 in the Undergraduate Laboratory  Tracey Spencer, Barney Yoo, and Kent Kirshenbaum
Describes an experiment for the extraction and column purification of buckminsterfullerene from fullerene-rich soot followed by a one-pot 1,3-dipolar cycloaddition of an azomethine ylide. Characterization of the starting material and product can be performed by UVVis, MS, 1H NMR, and 13C NMR.
Spencer, Tracey; Yoo, Barney; Kirshenbaum, Kent. J. Chem. Educ. 2006, 83, 1218.
Aromatic Compounds |
Chromatography |
NMR Spectroscopy |
UV-Vis Spectroscopy |
Synthesis |
Nanotechnology |
Reactions
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
Incorporation of Microwave Synthesis into the Undergraduate Organic Laboratory  Alan R. Katritzky, Chunming Cai, Meghan D. Collins, Eric F. V. Scriven, Sandeep K. Singh, and E. Keller Barnhardt
Describes a simple way to effectively implement microwave synthesis into the undergraduate organic laboratory curriculum.
Katritzky, Alan R.; Cai, Chunming; Collins, Meghan D.; Scriven, Eric F. V.;Singh, Sandeep K.; Barnhardt, E. Keller. J. Chem. Educ. 2006, 83, 634.
Aromatic Compounds |
Laboratory Equipment / Apparatus |
Reactions |
Synthesis
Microwave-Assisted Heterocyclic Chemistry for Undergraduate Organic Laboratory  Robert Musiol, Bozena Tyman-Szram, and Jaroslaw Polanski
Microwave-assisted techniques are used to design new environmentally benign syntheses of heterocycles for the undergraduate organic laboratory.
Musiol, Robert; Tyman-Szram, Bozena; Polanski, Jaroslaw. J. Chem. Educ. 2006, 83, 632.
Green Chemistry |
Heterocycles |
Reactions |
Synthesis
A Greener Approach to Aspirin Synthesis Using Microwave Irradiation  Ingrid Montes, David Sanabria, Marilyn García,, Joaudimir Castro, and Johanna Fajardo
Presents an inquiry-based laboratory experience based on the use of a microwave oven as a means for a comparative study of the effect of different catalysts in the synthesis of aspirin.
Montes, Ingrid; Sanabria, David; García,, Marilyn; Castro, Joaudimir; Fajardo, Johanna. J. Chem. Educ. 2006, 83, 628.
Drugs / Pharmaceuticals |
Esters |
Green Chemistry |
NMR Spectroscopy |
Reactions |
Synthesis |
Thin Layer Chromatography
Synthesis of Unsymmetrical Alkynes via the Alkylation of Sodium Acetylides. An Introduction to Synthetic Design for Organic Chemistry Students  Jennifer N. Shepherd and Jason R. Stenzel
Teams of students design a microscale synthesis of an unsymmetrical alkyne using commercially available terminal alkynes and alkyl halides and characterize the resulting products using TLC, IR, and 1H NMR spectroscopy. Depending on the chosen reactants, students observe both substitution and elimination products, or in some cases, no reaction at all.
Shepherd, Jennifer N.; Stenzel, Jason R. J. Chem. Educ. 2006, 83, 425.
Alkylation |
Alkynes |
Elimination Reactions |
IR Spectroscopy |
Microscale Lab |
NMR Spectroscopy |
Nucleophilic Substitution |
Synthesis
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
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
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 ahydroxyketones 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
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
Just Click It: Undergraduate Procedures for the Copper(I)-Catalyzed Formation of 1,2,3-Triazoles from Azides and Terminal Acetylenes  William D. Sharpless, Peng Wu, Trond Vidar Hansen, and James G. Lindberg
In keeping with the defining aspects of click chemistry, this reaction is high-yielding, requires no chromatography, is easily monitored by TLC, and displays distinct peaks in both IR and 1H-NMR. Virtually all products precipitate, and with just a few different starting blocks, every student, or pair of lab partners, can produce a unique "clicked" compound.
Sharpless, William D.; Wu, Peng; Hansen, Trond Vidar; Lindberg, James G. J. Chem. Educ. 2005, 82, 1833.
Catalysis |
Heterocycles |
Alkynes |
IR Spectroscopy |
NMR Spectroscopy |
Reactions |
Thin Layer Chromatography |
Synthesis
Strategic Applications of Named Reactions in Organic Synthesis: Background and Detailed Mechanisms (László Kürti and Barbara Czakó)  R. W. Holman
Krti and Czak use a two-page format that uses four-color graphics to address 250 reactions selected for inclusion based upon their applicability to modern natural products synthesis. Each named reaction is concisely introduced, mechanistically explained, and then set in context with example applications involving the production of natural products.
Holman, R. W. J. Chem. Educ. 2005, 82, 1780.
Synthesis |
Mechanisms of Reactions
Name Reactions and Reagents in Organic Synthesis, 2nd Edition (Bradford P. Mundy, Michael G. Ellerd, and Frank G. Favaloro)  R. W. Holman
Name Reactions and Reagents in Organic Synthesis is an exhaustive collection, addressing more than 500 reactions (and rearrangements). The breadth of coverage extends well beyond the confines of a typical undergraduatebeginning graduate organic chemistry course, although the detail presented for each reaction is minimal.
Holman, R. W. J. Chem. Educ. 2005, 82, 1780.
Synthesis |
Mechanisms of Reactions
Named Organic Reactions, 2nd Edition (Thomas Laue and Andreas Plagens)  R. W. Holman
Named Organic Reactions is a collection of 134 of the most common named organic reactions, with common being defined as those reactions most likely addressed in the combination of a typical sophomore organic chemistry sequence plus an advanced undergraduatebeginning graduate organic reactions and synthesis course.
Holman, R. W. J. Chem. Educ. 2005, 82, 1780.
Synthesis |
Mechanisms of Reactions
Named Organic Reactions, 2nd Edition (Thomas Laue and Andreas Plagens)  R. W. Holman
Named Organic Reactions is a collection of 134 of the most common named organic reactions, with common being defined as those reactions most likely addressed in the combination of a typical sophomore organic chemistry sequence plus an advanced undergraduatebeginning graduate organic reactions and synthesis course.
Holman, R. W. J. Chem. Educ. 2005, 82, 1780.
Synthesis |
Mechanisms of Reactions
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
A GC–MS Analysis of an SN2 Reaction for the Organic Laboratory  Malgorzata M. Clennan and Edward L. Clennan
This experiment utilizes an SN2 reaction between an alkyl bromide and potassium acetate to introduce the use of mass spectrometry for structural identification. It also provides students with experience in organic synthesis, the use of IR to identify functional groups, and the use of gas chromatography and response factors to determine product ratios.
Clennan, Malgorzata M.; Clennan, Edward L. J. Chem. Educ. 2005, 82, 1676.
IR Spectroscopy |
Mass Spectrometry |
Synthesis |
Chromatography |
Esters |
Mechanisms of Reactions |
Microscale Lab |
Gas Chromatography
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
Conversion of an Aziridine to an Oxazolidinone Using a Salt and Carbon Dioxide in Water  Justin R. Wallace, Deborah L. Lieberman, Matthew T. Hancock, and Allan R. Pinhas
An undergraduate laboratory experiment that allows for optimization of experimental reaction conditions for the conversion of a readily-available aziridine to the corresponding oxazolidinone using only carbon dioxide and a salt in water is discussed. A variety of salts were used to determine their effect on the reaction. In all cases, either no reaction occurred or a high yield of product was obtained. Ring opening of the less substituted carbonnitrogen bond predominates. This experiment allows students to optimize reaction conditions to obtain predominantly one of two regioisomers.
Wallace, Justin R.; Lieberman, Deborah L.; Hancock, Matthew T.; Pinhas, Allan R. J. Chem. Educ. 2005, 82, 1229.
Heterocycles |
Synthesis |
Aqueous Solution Chemistry |
Constitutional Isomers |
Mechanisms of Reactions |
NMR Spectroscopy |
Quantitative Analysis
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
The Ethylene Ketal Protecting Group Revisited: The Synthesis of 4-Hydroxy-4,4-diphenyl-2-butanone  Marsha R. Baar, Charles E. Russell, and Kristin L. Wustholz
The multistep synthesis of 4-hydroxy-4,4-diphenyl-2-butanone from ethyl acetoacetate illustrates the use of a ketal protecting group. Reaction of ethyl acetoacetate with ethylene glycol with p-TsOH in toluene produced the ketal ester. Reaction of the crude ketal ester with two equivalents of phenyl magnesium bromide followed by an aqueous acid workup generated the tertiary alcohol and simultaneously removed the ketal protecting group to produce the hydroxyketone. Our procedure is a modification of a previously published synthesis whose end product was 4,4-diphenyl-3-buten-2-one, the dehydrated analog.
Baar, Marsha R.; Russell, Charles E.; Wustholz, Kristin L. J. Chem. Educ. 2005, 82, 1057.
Synthesis |
Grignard Reagents |
IR Spectroscopy |
Mechanisms of Reactions |
NMR Spectroscopy
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
Combinatorial Partial Hydrogenation Reactions of 4-Nitroacetophenone. An Undergraduate Organic Laboratory  Kevin W. Kittredge, Susan S. Marine, and Richard T. Taylor
A combinatorial organic chemistry experiment that utilizes an inexpensive commercially available parallel reactor, Argonaut's FirstMate, is described. Students perform a metal catalyzed partial hydrogenation reaction on a multi-functionalized substrate and analyze product ratios by GCMS. Students evaluate a simple organic reaction that yields four different products. The reactions are performed in the presence and absence of a reaction modifier, methanesulfonic acid. Differing product ratios are obtained with the different types of metal catalysts and with the presence or the absence of the reaction modifier.
Kittredge, Kevin W.; Marine, Susan S.; Taylor, Richard T. J. Chem. Educ. 2004, 81, 1494.
Catalysis |
Combinatorial Chemistry |
Synthesis |
Reactions
Solvent-Free Wittig Reaction: A Green Organic Chemistry Laboratory Experiment  Sam H. Leung and Stephen A. Angel
In this experiment (E)- and (Z)-1-(4-bromophenyl)-2-phenylethene are synthesized by a solvent-free Wittig reaction. The reaction is effected by grinding the reactants in a mortar with a pestle. Both the E and Z isomers of the product are produced as evidenced by thin-layer chromatography and 1H NMR analysis. The E isomer is isolated by crystallization with ethanol in this experiment. In addition to learning about the Wittig reaction, students are also introduced to the ideas of mechanochemistry and green chemistry.
Leung, Sam H.; Angel, Stephen A. J. Chem. Educ. 2004, 81, 1492.
Chromatography |
Green Chemistry |
Microscale Lab |
NMR Spectroscopy |
Synthesis |
Reactions |
Aldehydes / Ketones |
Alkenes
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
The Darzens Condensation: Structure Determination through Spectral Analysis and Understanding Substrate Reactivity  R. David Crouch, Michael S. Holden, and Candice A. Romany
The Darzens condensation involves two steps that are typically included in the sophomore organic curriculum: an aldol reaction followed by an intramolecular nucleophilic substitution.
Crouch, R. David; Holden, Michael S.; Romany, Candice A. J. Chem. Educ. 2004, 81, 711.
NMR Spectroscopy |
Synthesis |
Stereochemistry |
Mechanisms of Reactions |
Aldehydes / Ketones
Microscale Synthesis and Spectroscopic Analysis of Flutamide, an Antiandrogen Prostate Cancer Drug  Ryan G. Stabile and Andrew P. Dicks
The synthesis involves N-acylation of a trisubstituted aromatic compound, 3-trifluoromethyl-4-nitroaniline. The procedure is easily adapted to generate structural analogues of flutamide. A significant feature is the curricular flexibility afforded by this experiment.
Stabile, Ryan G.; Dicks, Andrew P. J. Chem. Educ. 2003, 80, 1439.
Drugs / Pharmaceuticals |
IR Spectroscopy |
Mechanisms of Reactions |
Microscale Lab |
NMR Spectroscopy |
Synthesis |
Aromatic Compounds
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
The Study of Elimination Reactions Using Gas Chromatography: An Experiment for the Undergraduate Organic Laboratory  Devin Latimer
This article describes an investigation of elimination reactions of alkyl halides. 1-Bromopentane or 2-bromopentane are reacted with either sodium ethoxide or potassium tert-butoxide. Gas chromatography is used to monitor the relative amounts of 1-pentene, (E)-2-pentene, and (Z)-2-pentene produced.
Latimer, Devin. J. Chem. Educ. 2003, 80, 1183.
Chromatography |
Instrumental Methods |
Synthesis |
Gas Chromatography |
Elimination Reactions |
Mechanisms of Reactions |
Alkenes |
Stereochemistry
"Chiral Acetate": The Preparation, Analysis, and Applications of Chiral Acetic Acid  Addison Ault
Production of chiral acetic acid using deuterium and tritium and its application to understanding stereochemistry and the specificity of enzymatic reactions.
Ault, Addison. J. Chem. Educ. 2003, 80, 333.
Chirality / Optical Activity |
Enzymes |
Isotopes |
Synthesis |
Stereochemistry |
Enrichment / Review Materials |
Carboxylic Acids |
Enantiomers |
Reactions |
Mechanisms of Reactions
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
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
Preparation of a D-Glucose-Derived Alkene. An E2 Reaction for the Undergraduate Organic Chemistry Laboratory  Peter Norris and Andrew Fluxe
Synthesis of four carbohydrate derivatives that highlight techniques such as inert atmosphere work, rotary evaporators, and flash column chromatography.
Norris, Peter; Fluxe, Andrew. J. Chem. Educ. 2001, 78, 1676.
Carbohydrates |
NMR Spectroscopy |
Synthesis |
Alkenes |
Elimination Reactions |
Chromatography
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
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
Synthesis of Substituted Butenolides. An Undergraduate Organic Laboratory Experiment Utilizing Two 3-Step Preparatory Sequences  Géraldine Maheut, Liang Liao, Jean-Marie Catel, Paul-Alain Jaffrès, and Didier Villemin
The synthesis of substituted butenolide in two, 3-step sequences that illustrate five basic organic reactions (alkyne hydration, Knoevenagel condensation, lactonization, aldolization-type reaction, and hydration of nitrile); the products have pedagogical interest for IR and NMR spectroscopy (diastereotopic effect).
Maheut, Géraldine; Liao, Liang; Catel, Jean-Marie; Jaffrès, Paul-Alain; Villemin, Didier. J. Chem. Educ. 2001, 78, 654.
IR Spectroscopy |
Molecular Modeling |
NMR Spectroscopy |
Synthesis |
Undergraduate Research |
Reactions
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
Elucidation of Molecular Structure Using NMR Long-Range Coupling: Determination of the Single Isomer Formed in a Regiospecific Reaction  Samuel Delagrange and Françoise Nepveu
The experiment presented in this article introduces students to the main concepts of two essential NMR techniques for investigating molecular structure. Heteronuclear multiple bond connectivity (HMBC) and proton-coupled 13C NMR are used to determine which isomer, from a possible two, is formed by a regiospecific reaction. The demonstration, based on long-range coupling between quaternary carbons and protons on neighboring carbons, is presented step by step.
Delagrange, Samuel; Nepveu, Françoise. J. Chem. Educ. 2000, 77, 895.
Molecular Properties / Structure |
NMR Spectroscopy |
Synthesis |
Carboxylic Acids |
Reactions |
Diastereomers
The Heck Reaction: A Microscale Synthesis Using a Palladium Catalyst  William B. Martin and Laura J. Kateley
The microscale synthesis described uses a reaction between a bromoiodobenzene and acrylic acid to produce a bromocinnamic acid. Structure verification for the product uses IR and 1H NMR spectroscopy.
Martin, William B.; Kateley, Laura J. J. Chem. Educ. 2000, 77, 757.
Catalysis |
Microscale Lab |
Synthesis |
IR Spectroscopy |
NMR Spectroscopy |
Aromatic Compounds |
Mechanisms of Reactions
Reaction of Dibenzoylethylene with Hydriodic Acid  Fred H. Greenberg
Dibenzoylethylene is treated with hydriodic acid in acetone at room temperature to obtain dibenzoylethane rather than the expected dibenzoyliodoethane. Students identify the product by the use of NMR and IR spectra and are given a nonpictorial representation of a mechanism and asked to supply the structures of the relevant intermediates.
Greenberg, Fred H. J. Chem. Educ. 2000, 77, 505.
Microscale Lab |
Synthesis |
NMR Spectroscopy |
IR Spectroscopy |
Mechanisms of Reactions |
Reactive Intermediates
Multicomponent Reactions: A Convenient Undergraduate Organic Chemistry Experiment  Ricardo Bossio, Stefano Marcaccini, Carlos F. Marcos, and Roberto Pepino
Two experiments for the synthesis of a -lactam and a succinimide, based on a 4-component Ugi condensation. The experimental procedures for both syntheses are identical except for the choice of the starting amine, whose electron richness is controlled by the presence or absence of an electron-withdrawing group.
Bossio, Ricardo; Marcaccini, Stefano; Marcos, Carlos F.; Pepino, Roberto. J. Chem. Educ. 2000, 77, 382.
Synthesis |
Drugs / Pharmaceuticals |
IR Spectroscopy |
NMR Spectroscopy |
Mechanisms of Reactions |
Molecular Properties / Structure
Introducing Chiroscience into the Organic Laboratory Curriculum  Kenny B. Lipkowitz, Tim Naylor, and Keith S. Anliker
"Chiroscience" is a young but robust industry linking science and technology with chemistry and biology; includes description of an asymmetric reduction of a ketone followed by an assessment of the enantiomeric excess by GC using a chiral stationary phase.
Lipkowitz, Kenny B.; Naylor, Tim; Anliker, Keith S. J. Chem. Educ. 2000, 77, 305.
Chirality / Optical Activity |
Chromatography |
Mechanisms of Reactions |
Synthesis |
Separation Science |
Stereochemistry |
Gas Chromatography |
Aldehydes / Ketones
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
Side Reactions in a Grignard Synthesis  Hilton M. Weiss
This experiment describes a standard Grignard synthesis of a secondary alcohol, 3-heptanol. It brings attention to a significant side product, 3-heptanone, and suggests ways of understanding and utilizing the formation of this product. The experiment is intended to stimulate creative thought in the undergraduate organic chemistry course.
Weiss, Hilton M. J. Chem. Educ. 1999, 76, 76.
Mechanisms of Reactions |
Synthesis |
Grignard Reagents
Grignard Synthesis of Various Tertiary Alcohols  T. Stephen Everett
A general Grignard procedure is presented for the synthesis of aliphatic, tertiary alcohols containing six to nine carbons. Without revealing the specific starting materials, students are challenged to identify their unknown products from physical (boiling points, refractive indices) and spectral (infrared O-H, C-H and fingerprint regions) data.
Everett, T. Stephen. J. Chem. Educ. 1998, 75, 86.
IR Spectroscopy |
Alcohols |
Mechanisms of Reactions |
Synthesis
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
Organic Reactions, Volume 45 (Paquette, Leo A.)  
Continuing series.
J. Chem. Educ. 1995, 72, A94.
Synthesis |
Reactions
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
Baeyer-Villiger Oxidation of Indane-1-ones: Monitoring of the Reaction by VPC and IR Spectroscopy  Elie Stephan
Procedure for the Baeyer-Villiger oxidation of indane-1-ones.
Stephan, Elie. J. Chem. Educ. 1995, 72, 1142.
IR Spectroscopy |
Synthesis |
Mechanisms of Reactions |
Oxidation / Reduction |
Aldehydes / Ketones
Synthesis of a Bromohydrin: An Experiment Demonstrating Markovnikov Addition  Diane J. Porter, Andrea T. Stewart, and Carl T. Wigal
Microscale procedure that demonstrates Markovnikov addition without the production of noxious products (i.e. mercury).
Porter, Diane J.; Stewart, Andrea T.; Wigal, Carl T. J. Chem. Educ. 1995, 72, 1039.
Mechanisms of Reactions |
Synthesis |
Microscale Lab |
Microscale Lab
Diastereospecific Synthesis of an Epoxide: An Introductory Experiment in Organic Synthetic and Mechanistic Chemistry  James A. Ciaccio
A two-step epoxide synthesis that can be presented to students in the form of two mechanistic "puzzles" that probe the stereoselectivity of two important reactions: halohydrin formation from alkenes and epoxide formation via intramolecular Williamson ether synthesis.
Ciaccio, James A. J. Chem. Educ. 1995, 72, 1037.
Stereochemistry |
Molecular Properties / Structure |
Mechanisms of Reactions |
Synthesis |
Epoxides |
Alkenes
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
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
Electrophilic Aromatic Substitution Discovery Lab  Jarret, Ronald M.; New, Jamie; Patraitis, Cynthia
An organic chemistry lab for introductory chemistry in which students must determine the reaction mechanism of an organic synthesis; includes sample data and analysis.
Jarret, Ronald M.; New, Jamie; Patraitis, Cynthia J. Chem. Educ. 1995, 72, 457.
Synthesis |
Mechanisms of Reactions |
Electrophilic Substitution
Acetylation of Ferrocene: A Study of the Friedel-Crafts Acylation Mechanism as Measured by HPLC Using an Internal Standard  Newirth, Terry L.; Srouji, Nadine
An experimental procedure that allows students to reach conclusions about the mechanism of an organic reaction (Friedel-Crafts acylation) based on their own data analysis; includes sample data and analysis.
Newirth, Terry L.; Srouji, Nadine J. Chem. Educ. 1995, 72, 454.
Mechanisms of Reactions |
Synthesis |
Chromatography |
HPLC
GC/MS experiments for the organic chemistry laboratory: I. E2 elimination of 2-bromo-2-methyloctane   Novak, Michael; Heinrich, Julie; Martin, Kristy A.; Green, John; Lytle, Scott
Two capillary GC/MS experiments that were designed for and tested in a sophomore organic laboratory course.
Novak, Michael; Heinrich, Julie; Martin, Kristy A.; Green, John; Lytle, Scott J. Chem. Educ. 1993, 70, A103.
Gas Chromatography |
Alkenes |
Alkanes / Cycloalkanes |
Alcohols |
Elimination Reactions |
Synthesis
The synthesis of urea: An undergraduate laboratory experiment   Tanski, Stephanie; Petro, Janeen; Ball, David W.
This paper presents a laboratory experiment for the production of urea from silver cyanate and ammonium chloride.
Tanski, Stephanie; Petro, Janeen; Ball, David W. J. Chem. Educ. 1992, 69, A128.
Synthesis |
Reactions
The synthesis of E-beta-bromostyrene: An experiment illustrating the use of IR bending modes to distinguish E and Z isomers and the concept of kinetic and thermodynamic controlled reactions.  Strom, Laura A.; Anderson, James R.; Gandler, Joseph R.
An experiment illustrating the concept of thermodynamic and kinetically controlled reactions to produce E and Z isomers (respectively); the use of IR to distinguish E and Z isomers; and the different properties of E and Z isomers (only the E isomer has a pleasant odor).
Strom, Laura A.; Anderson, James R.; Gandler, Joseph R. J. Chem. Educ. 1992, 69, 588.
Synthesis |
IR Spectroscopy |
Stereochemistry |
Kinetics |
Thermodynamics |
Alkenes |
Diastereomers |
Mechanisms of Reactions |
Molecular Properties / Structure
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
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
Industrial chemistry in the organic laboratory: C4 alkylations  Teegarden, David M.; Varco-Shea, Theresa C.; Conklin, Karen T.; Markle, Cynthia A.; Anderson, Scott D.
A set of experiments to illustrate reactions of the tertiary-butyl group; the products are all compounds that occur in consumer products and have received considerable attention in the popular press (BHT, BHA, TBHQ, and MTBE).
Teegarden, David M.; Varco-Shea, Theresa C.; Conklin, Karen T.; Markle, Cynthia A.; Anderson, Scott D. J. Chem. Educ. 1990, 67, 619.
Industrial Chemistry |
Aromatic Compounds |
Phenols |
Synthesis |
Mechanisms of Reactions
A simple procedure for the base-catalyzed cleavage of benzopinacolone to triphenylmethane: An undergraduate experiment  Stranberg, Michael; Anselme, J. -P.
A simple procedure for the base-catalyzed cleavage of benzopinacolone to triphenylmethane: An undergraduate experiment.
Stranberg, Michael; Anselme, J. -P. J. Chem. Educ. 1990, 67, 616.
Catalysis |
Aldehydes / Ketones |
Mechanisms of Reactions |
Synthesis
The use of fluoromethanes in organic synthesis  Everett, T. Stephen
A review of advances in selective fluorination; mechanisms and applications of fluoromethanes in organic synthesis.
Everett, T. Stephen J. Chem. Educ. 1987, 64, 143.
Synthesis |
Mechanisms of Reactions
The synthesis of 5,5'-diphenylhydantoin: A novel benzil-benzilic acid rearrangement  Pankaskie, Marvin C.; Small, Laverne
A novel benzil-benzilic acid rearrangement.
Pankaskie, Marvin C.; Small, Laverne J. Chem. Educ. 1986, 63, 650.
Synthesis |
Heterocycles |
Mechanisms of Reactions |
Amines / Ammonium Compounds
Phase-transfer-catalyzed alkylation of ethyl acetoacetate and diethyl malonate  Thompson, Douglas L.; Reeves, Perry C.
Improved method that requires shorter reaction times and safer reagents than traditional procedures.
Thompson, Douglas L.; Reeves, Perry C. J. Chem. Educ. 1985, 62, 907.
Catalysis |
Mechanisms of Reactions |
Synthesis
Teaching of chemical reactions and syntheses  Basolo, Fred
We are obliged to teach students some fundamental reactions that all chemists should know.
Basolo, Fred J. Chem. Educ. 1984, 61, 520.
Reactions |
Synthesis
Organic chemicals from carbon monoxide  Kolb, Kenneth E.; Kolb, Doris
Looking at organic chemicals and their reactions with carbon monoxide has a great pedagogical value.
Kolb, Kenneth E.; Kolb, Doris J. Chem. Educ. 1983, 60, 57.
Synthesis |
Reactions
Systematic inorganic reaction chemistry: Inorganic reaction types, general methods of synthesis, and the periodic table  Basolo, Fred
It is possible to teach inorganic reactions and syntheses without students having to memorize specific reactions and without the lectures being dull.
Basolo, Fred J. Chem. Educ. 1980, 57, 761.
Reactions |
Synthesis |
Periodicity / Periodic Table |
Descriptive 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
Synthesis of 4-methyl-3-heptanol and 4-methyl-3-heptanone. Two easily synthesized insect pheromones  Einterz, Robert M.; Ponder, Jay W.; Lenox, Ronald S.
A two step reaction sequence involving the Grignard synthesis of an alcohol followed by oxidation of this alcohol to the corresponding ketone.
Einterz, Robert M.; Ponder, Jay W.; Lenox, Ronald S. J. Chem. Educ. 1977, 54, 382.
Natural Products |
Synthesis |
Applications of Chemistry |
Grignard Reagents |
Mechanisms of Reactions |
Stereochemistry |
Alcohols |
Aldehydes / Ketones
Grignard dehydration reactions. An undergraduate organic experiment.  Duty, Robert C.; Ryder, Bernard L.
In this laboratory, the authors have incorporated the Grignard reaction in a step-wise synthesis that has been successful in demonstrating several experimental and instrumental techniques.
Duty, Robert C.; Ryder, Bernard L. J. Chem. Educ. 1976, 53, 457.
Grignard Reagents |
Reactions |
Synthesis |
Alkenes
Synthesis of a photochromic benzothiazolinic spiropyran  Guglielmetti, R.; Meyer, R.; Dupuy, C.
The purpose of this type of experiment is to elucidate structure of the different compounds gradually prepared starting from reaction mechanisms and chiefly from spectroscopic data given perviously to students.
Guglielmetti, R.; Meyer, R.; Dupuy, C. J. Chem. Educ. 1973, 50, 413.
Photochemistry |
Synthesis |
Mechanisms of Reactions |
Molecular Properties / Structure
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
The synthesis of 2-nitroresorcinol: An experiment with sulfonic acids  Schaffrath, Robert E.
This synthesis is an ideal example using the -SO3H as a blocking group.
Schaffrath, Robert E. J. Chem. Educ. 1970, 47, 224.
Synthesis |
Reactions |
Mechanisms of Reactions |
Molecular Properties / Structure
The Hantzsch pyridine synthesis: A factorial design experiment for the introductory organic laboratory  Norcross, B. E.; Clement, G.; Weinstein, M.
Students carry out the two-step Hantzsch pyridine synthesis; students are required to select the oxidizing agent and conditions for the second reaction step.
Norcross, B. E.; Clement, G.; Weinstein, M. J. Chem. Educ. 1969, 46, 694.
Synthesis |
Oxidation / Reduction |
Heterocycles |
Mechanisms of Reactions
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
3-Sulfolene: A butadiene source for a Diels-Alder synthesis: An undergraduate laboratory experiment  Sample, Thomas E., Jr.; Hatch, Lewis F.
By selecting a suitable diene cyclic sulfone, the common complication in performing a Diels-Alder experiment can be avoided.
Sample, Thomas E., Jr.; Hatch, Lewis F. J. Chem. Educ. 1968, 45, 55.
Alkenes |
Synthesis |
Mechanisms of Reactions
Bromination of alkanes: Experiment illustrating relative reactivities and synthetic utility  Warkentin, J.
The radical halogenation of alkanes lend themselves well to the teaching of basic material such as bond dissociation energies, potential energy profiles, enthalpy of reaction, activation energy, and reaction rate.
Warkentin, J. J. Chem. Educ. 1966, 43, 331.
Electrochemistry |
Alkanes / Cycloalkanes |
Rate Law |
Kinetics |
Synthesis |
Alkenes |
Mechanisms of Reactions |
Free Radicals
1-bromo-3-chloro-5-iodobenzene: An eight-step synthesis from benzene  Ault, Addison; Kraig, Raymond
Presents an eight-step synthesis of 1-bromo-3-chloro-5-iodobenzene from benzene.
Ault, Addison; Kraig, Raymond J. Chem. Educ. 1966, 43, 213.
Synthesis |
Aromatic Compounds |
Mechanisms of Reactions
A three-step synthesis: 2,4-Dinitrophenylhydrazine from benzene  Ault, Addison
Presents a synthetic sequence for use in the introductory organic chemistry laboratory: the synthesis of 2,4-dinitrophenylhydrazine from benzene by way of bromobenzene and 2,4-dinitrobromobenzene.
Ault, Addison J. Chem. Educ. 1965, 42, 267.
Synthesis |
Aromatic Compounds |
Mechanisms of Reactions |
Reactions
Polymer synthesis in the undergraduate organic laboratory  Sorenson, Wayne R.
Presents a series of experiments on polymer synthesis for the undergraduate organic laboratory.
Sorenson, Wayne R. J. Chem. Educ. 1965, 42, 8.
Synthesis |
Polymerization |
Reactions |
Mechanisms of Reactions
Constitutional Problems in Organic Chemistry (Watson, M. B.; Youngson, G. W.)  Haynes, LeRoy W.

Haynes, LeRoy W. J. Chem. Educ. 1964, 41, 691.
Reactions |
Synthesis
Principles of chemical reaction  Sanderson, R. T.
The purpose of this paper is to examine the nature of chemical change in the hope of recognizing and setting forth the basic principles that help us to understand why they occur.
Sanderson, R. T. J. Chem. Educ. 1964, 41, 13.
Reactions |
Thermodynamics |
Mechanisms of Reactions |
Kinetics |
Synthesis |
Covalent Bonding |
Ionic Bonding |
Metallic Bonding
PolystyreneA multistep synthesis  Wilen, S. H.
Suggestions for research to accompany a previously published article.
Wilen, S. H. J. Chem. Educ. 1963, 40, A463.
Undergraduate Research |
Reactions |
Polymerization |
Synthesis
Apparatus for the Friedel-Crafts reaction  Kremer, C. B.
Suggestions for research to accompany a previously published article.
Kremer, C. B. J. Chem. Educ. 1963, 40, A463.
Undergraduate Research |
Reactions |
Synthesis
Friedel-Crafts alkylation  Marsi, Kenneth L.; Wilen, Samuel H.
Some organic textbooks state that n-alkyl derivatives cannot be synthesized by the Friedel-Crafts reaction, or that they are formed in only minor amounts, though this is not the case.
Marsi, Kenneth L.; Wilen, Samuel H. J. Chem. Educ. 1963, 40, 214.
Reactions |
Synthesis
The decarboxylation of organic acid  March, Jerry
Simple aliphatic acids (except for acetic) do not give good yields of the corresponding alkanes through decarboxylation, although many organic chemistry textbooks cite this as a general method for the preparation of alkanes.
March, Jerry J. Chem. Educ. 1963, 40, 212.
Acids / Bases |
Reactions |
Synthesis |
Alkanes / Cycloalkanes |
Carboxylic Acids
The acylation of aliphatic unsaturated hydrocarbons  Sharefkin, Jacob G.
Introductory organic chemistry textbooks discuss the Friedel-Crafts synthesis of aromatic ketones but usually do not treat the corresponding reaction in the aliphatic series.
Sharefkin, Jacob G. J. Chem. Educ. 1962, 39, 206.
Aromatic Compounds |
Aldehydes / Ketones |
Reactions |
Synthesis |
Mechanisms of Reactions
A sequence of synthesis in the general organic laboratory class  Lange, Erwin F.; Teranishi, Roy; Christensen, Bert E.
This synthesis involves the oxidation of p-xylene, nitration and esterfication of terephthalic acid, reduction of nitroterephthalic acid, and the preparation of 4-quinazolone-7-carboxylic acid.
Lange, Erwin F.; Teranishi, Roy; Christensen, Bert E. J. Chem. Educ. 1955, 32, 40.
Synthesis |
Aromatic Compounds |
Reactions |
Oxidation / Reduction
The Friedel-Crafts reaction in elementary organic laboratories  Wright, Oscar L.; Fuhlhage, Donald; Sheridan, Earl
Presents a modification of the Perrier ketone synthesis.
Wright, Oscar L.; Fuhlhage, Donald; Sheridan, Earl J. Chem. Educ. 1952, 29, 620.
Reactions |
Aldehydes / Ketones |
Synthesis