| Journal Articles: 45 results |
|
|
Developing and Disseminating NOP: An Online, Open-Access, Organic Chemistry Teaching Resource To Integrate Sustainability Concepts in the Laboratory Johannes Ranke, Müfit Bahadir, Marco Eissen, and Burkhard König
Describes a project that identifies parameters for sustainable practices in organic chemistry laboratories, including the atom economy and energy efficiency of chemical transformations, questions of waste and renewable feedstocks, toxicity and ecotoxicity, and safety measures.
Ranke, Johannes; Bahadir, Müfit; Eissen, Marco; König, Burkhard. J. Chem. Educ. 2008, 85, 1000.
Green Chemistry |
Synthesis |
Toxicology
|
Synthesis and Characterization of 9-Hydroxyphenalenone Using 2D NMR Techniques Benjamin Caes and Dell Jensen Jr.
The synthesis of 9-Hydroxyphenalenone produces a planar multicyclic beta-ketoenol, the tautomerization of which results in C2v symmetry on the NMR time scale, thus simplifying the spectra and providing a unique structure for teaching 2D NMR spectroscopy.
Caes, Benjamin; Jensen, Dell, Jr. J. Chem. Educ. 2008, 85, 413.
Alcohols |
Aldehydes / Ketones |
Aromatic Compounds |
IR Spectroscopy |
NMR Spectroscopy |
Synthesis
|
Acylation of Ferrocene: A Greener Approach Kurt R. Birdwhistell, Andy Nguyen, Eric J. Ramos, and Robert Kobelja
This article describes an acylation of ferrocene that is more eco-friendly than the conventional experiment, which has been modified by replacing mineral acid with a polymeric acid catalyst and using microwave instead of conventional heating.
Birdwhistell, Kurt R.; Nguyen, Andy; Ramos, Eric J.; Kobelja, Robert. J. Chem. Educ. 2008, 85, 261.
Catalysis |
Chromatography |
Green Chemistry |
Organometallics |
Synthesis |
Transition Elements |
Brønsted-Lowry Acids / Bases
|
Chemical Aspects of Local and Regional Anesthesia Robert Brunsvold and Daryl L. Ostercamp
The chemistry that underlies the development of local and regional anesthesia is explored. Emphasis is placed upon the importance of acidity constants and lipophilic versus hydrophilic character in interpreting what affect a particular compound has upon biological processes.
Brunsvold, Robert; Ostercamp, Daryl L. J. Chem. Educ. 2006, 83, 1816.
Acids / Bases |
Bioorganic Chemistry |
Chirality / Optical Activity |
Drugs / Pharmaceuticals |
Medicinal Chemistry |
Synthesis |
Applications of Chemistry
|
Fluorous Compounds and Their Role in Separation Chemistry Maria Angeles Ubeda and Roman Dembinski
Reviews fluorous technology and outlines strategies towards organic synthesis.
Ubeda, Maria Angeles; Dembinski, Roman. J. Chem. Educ. 2006, 83, 84.
Amino Acids |
Catalysis |
Esters |
Green Chemistry |
Separation Science |
Synthesis
|
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 FriedelCrafts 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 FriedelCrafts 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
|
A Solvent-Free Claisen Condensation Reaction for the Organic Laboratory John J. Esteb and Matthew B. Stockton
An experiment involving the Claisen condensation reaction for a first-year organic chemistry laboratory is presented. In this experiment, potassium tert-butoxide and ethyl phenylacetate are heated to 100 C for 30 minutes under solvent-free conditions to produce 2,4-diphenyl acetoacetate in 80% yield.
Esteb, John J.; Stockton, Matthew B. J. Chem. Educ. 2003, 80, 1446.
Synthesis |
Esters
|
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
|
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
|
Preparing Students for Research: Synthesis of Substituted Chalcones as a Comprehensive Guided-Inquiry Experience James R. Vyvyan, Donald L. Pavia, Gary M. Lampman, and George S. Kriz Jr.
An aldol condensation of substituted benzaldehydes with substituted acetophones to produce substituted benzalacetophenones (chalcones) in a guided-inquiry approach.
Vyvyan, James R.; Pavia, Donald L.; Lampman, Gary M.; Kriz, George S., Jr. J. Chem. Educ. 2002, 79, 1119.
Medicinal Chemistry |
Microscale Lab |
Natural Products |
NMR Spectroscopy |
Synthesis |
Aromatic Compounds |
Aldehydes / Ketones
|
Organic Reaction Mechanisms. Selected Problems and Solutions, 1st Edition by William C. Groutas Richard Pagni
Mastering the fundamental principles of organic chemistry by using critical reasoning skills to solve a large number of mechanistic problems.
Pagni, Richard. J. Chem. Educ. 2001, 78, 33.
Mechanisms of Reactions |
Reactions
|
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
|
The Preparation of Lidocaine Thomas J. Reilly
The widely used local anesthetic Lidocaine is synthesized in two steps from 2,6-dimethylaniline. In the first step, the amine is acylated with chloroacetyl chloride. In the second step, the amide is subjected to nucleophilic substitution by diethylamine to give the final product.
Reilly, Thomas J. J. Chem. Educ. 1999, 76, 1557.
Synthesis |
Medicinal Chemistry
|
The Preparation of a UV-Light-Absorbing Polymer: A Project-Oriented Laboratory Experiment for the Introductory Organic Chemistry Curriculum Thomas Poon, Jean P. McIntyre, Andrea Dorigo, Drew J. Davis, Matthew A. Davis, Crystal F. Eller, Leah R. Eller, Heather K. Izumi, Kenya M. Jones, Kurt H. Kelley, William Massello, Megan L. Melamed, Cynthia M. Norris, Jeffrey A. Oelrich, Thomas A. Pluim, Sarah E. Poplawski, Jason M. St. Clair, Matthew P. Stokes, Wells C. Wheeler, and Erin E. Wilkes
A laboratory experiment is described that combines organic synthesis, spectroscopy, and polymer chemistry and is suitable for the sophomore organic chemistry curriculum. In this three-week sequence, students synthesize and characterize the UV-absorber 2-(2',4'-dimethylbenzoyl)benzoic acid and incorporate it into films of polymethylmethacrylate.
Poon, Thomas; McIntyre, Jean P.; Dorigo, Andrea; Davis, Drew J.; Davis, Matthew A.; Eller, Crystal F.; Eller, Leah R.; Izumi, Heather K.; Jones, Kenya M.; Kelley, Kurt H.; Massello, William; Melamed, Megan L.; Norris, Cynthia M.; Oelrich, Jeffrey A.; Pluim, Thomas A.; Poplawski, Sarah E.; St. Clair, Jason M.; Stokes, Matthew P.; Wheeler, Wells C.; Wilkes, Erin E. J. Chem. Educ. 1999, 76, 1523.
Synthesis |
UV-Vis Spectroscopy |
NMR Spectroscopy |
IR Spectroscopy |
Free Radicals
|
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
|
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
|
The Diels-Alder Reaction of 2,4-Hexadien-1-ol with Maleic Anhydride: A Novel Preparation for the Undergraduate Organic Chemistry Laboratory Course Keith F. McDaniel and R. Matthew Weekly
The reaction of 2,4-hexadien-1-ol with maleic anhydride provides an excellent exercise for undergraduate laboratory courses. In addition to the expected Diels-Alder reaction, which takes place readily in refluxing toluene, subsequent intramolecular cleavage of the resulting bicyclic anhydride by the pendant hydroxy group generates a lactone. Thus, two important organic reactions can be carried out in a single laboratory session.
McDaniel, Keith F.; Weekley, R. Matthew. J. Chem. Educ. 1997, 74, 1465.
Synthesis |
NMR Spectroscopy |
Molecular Properties / Structure |
Alcohols
|
Protecting Groups in Carbohydrate Chemistry Sigthór Pétursson
The most important protecting groups in carbohydrate chemistry are reviewed. The paper is aimed at those beginning to specialize in synthetic carbohydrate chemistry and at teachers with other specialties who wish to go beyond the content of general organic chemistry textbooks.
Petursson, Sigthor. J. Chem. Educ. 1997, 74, 1297.
Carbohydrates |
Molecular Properties / Structure |
Synthesis
|
An Efficient Microscale Procedure for the Preparation of 3,5-Dinitrobenzoates Smith, Richard F.; Cristalli, Gaetano M.
Efficient and simple microscale preparation of 3,5-dinitrobenzoates.
Smith, Richard F.; Cristalli, Gaetano M. J. Chem. Educ. 1995, 72, A164.
Synthesis |
Qualitative Analysis |
Laboratory Management |
Microscale Lab |
Aromatic Compounds |
Esters
|
Microscale Electrophilic Aromatic Substitution of p-Toluidine Kady, Ismail O.
Experimental procedure for first-year organic chemistry students to apply the principles of group protection and study the effect of ring substituents on reaction orientation.
Kady, Ismail O. J. Chem. Educ. 1995, 72, A9.
Synthesis |
Mechanisms of Reactions |
Aromatic Compounds |
Microscale Lab |
Electrophilic Substitution
|
Microscale Preparation of AlCl3 Arnaiz, Francisco J.
Experimental procedure for producing anhydrous AlCl3 (aluminum chloride).
Arnaiz, Francisco J. J. Chem. Educ. 1995, 72, A8.
Synthesis |
Laboratory Management |
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
|
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
|
A mnemonic for the Krebs cycle: Using letter additions, letter deletions, and anagrams to trace the acylation, decarboxylations, and other changes Williams, John P.
A mnemonic for the Krebs cycle.
Williams, John P. J. Chem. Educ. 1992, 69, 985.
Reactions
|
A synthesis of indane musk Celestolide Kagabu, Shinzo; Kojima, Yuka
This convenient operation using only a calculated amount of tetrahydrofuran will help students understand that one of the real operative species in Grignard reaction is a complex of alkylmagnesium halogenide with ether molecules.
Kagabu, Shinzo; Kojima, Yuka J. Chem. Educ. 1992, 69, 420.
Synthesis |
Grignard Reagents
|
Preparation of 1-phenyl-3-phenylaminopyrrolidine-2,5-dione: An organic laboratory experiment on the Michael addition Ram, Ram N.; Varsha, Kiran
Acylation of aniline with maleic anhydride to give maleanilic acid followed by Michael addition of aniline and cyclization to yield 1-phenyl-3-phenylaminopyrrolidine-2,5-dione.
Ram, Ram N.; Varsha, Kiran J. Chem. Educ. 1990, 67, 985.
Addition Reactions |
Aldehydes / Ketones |
Synthesis
|
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
|
Friedel Crafts acylation and alkylation with acid chlorides Jarret, Ronald M.; Keil, Nora; Allen, Susan; Cannon, Lisa; Coughlan, Julie; Cusumano, Leonarda; Nolan, Brian
A shortened Friedel-Crafts experiment; the extra time available allows for additional experiments designed to illustrate the finer points of the reaction, such as electrophile rearrangements and decarbonylation of acyl cations.
Jarret, Ronald M.; Keil, Nora; Allen, Susan; Cannon, Lisa; Coughlan, Julie; Cusumano, Leonarda; Nolan, Brian J. Chem. Educ. 1989, 66, 1056.
Electrophilic Substitution |
Aromatic Compounds |
Mechanisms of Reactions |
Microscale Lab
|
Friedel Crafts alkylation using elemental aluminum catalyst: An undergraduate laboratory experiment Meeks, B. Spencer; Lucas, Anita R.
This experiment uses aluminum metal as a catalyst for the synthesis of sec-butyltoluene by Friedel-Crafts alkylation of toluene.
Meeks, B. Spencer; Lucas, Anita R. J. Chem. Educ. 1989, 66, 176.
Alkylation |
Catalysis |
Synthesis
|
Aromatic substitution reactions: when you've said ortho, meta, and para you haven't said it all Traynham, James G.
The author presents a range of examples for nucleophilic, electrophilic, and free-radical reactions where the ipso is an important, predominant, or even exclusive site of reaction.
Traynham, James G. J. Chem. Educ. 1983, 60, 937.
Nucleophilic Substitution |
Electrophilic Substitution |
Free Radicals |
Diastereomers |
Stereochemistry |
Reactions
|
The synthesis of 4,6,8-trimethylazulene: an organic laboratory experiment Garst, Michael E.; Hochlowski, Jill; Douglass, III, James G.; Sasse, Scott
A procedure for a two-step synthesis of 4,6,8-trimethylazulene.
Garst, Michael E.; Hochlowski, Jill; Douglass, III, James G.; Sasse, Scott J. Chem. Educ. 1983, 60, 510.
Synthesis |
Heterocycles |
Aromatic Compounds |
Resonance Theory |
Chromatography
|
3-Ketoesters by malonic synthesis Pollet, Patrick L.
This essay reviews a synthesis strategy.
Pollet, Patrick L. J. Chem. Educ. 1983, 60, 244.
Synthesis |
Carboxylic Acids |
Aldehydes / Ketones |
Alkylation
|
Drugs in the chemistry laboratory: The conversion of acetaminophen into phenacetin Volker, Eugene J.; Pride, Ernest; Hough, Charles
The phenolic alcohol group of acetaminophen is alkylated with ethyl iodide using the basic catalyst K2CO3.
Volker, Eugene J.; Pride, Ernest; Hough, Charles J. Chem. Educ. 1979, 56, 831.
Nonmajor Courses |
Applications of Chemistry |
Medicinal Chemistry |
Drugs / Pharmaceuticals |
Synthesis |
Catalysis |
Phenols |
Alcohols
|
A student synthesis of the housefly sex attractant Cormier, Russell A.; Duc Phan, M.; Graddis, Thomas; Singer, Richard
This multi-step synthetic sequence illustrates several important laboratory techniques, including ir and nmr spectroscopy, thin-layer and column chromatography, rotary evaporation, recrystallization, and vacuum distillation.
Cormier, Russell A.; Duc Phan, M.; Graddis, Thomas; Singer, Richard J. Chem. Educ. 1979, 56, 345.
Synthesis |
Natural Products |
IR Spectroscopy |
NMR Spectroscopy |
Chromatography |
Thin Layer Chromatography
|
The scope of the Haworth synthesis Agranat, Israel; Shih, Yu-Shan
The duality of the Haworth synthesis as revealed most conspicuously in the preparation of both anthracene and phenanthrene, widens the scope of the method. On the basis of the reversibility of Friedel-Crafts acylation in PPA, the Haworth synthesis may serve as a route to linearly annelated-as well as to angularly annelated polynuclear aromatic hydrocarbons.
Agranat, Israel; Shih, Yu-Shan J. Chem. Educ. 1976, 53, 488.
Synthesis |
Catalysis |
Aromatic Compounds |
Aldehydes / Ketones
|
Aromatic nitro musk synthesis Nash, E. Gary; Nienhouse, Everett J.; Silhavy, Thomas A.; Humbert, Dale E.; Mish, Mary Jo
This synthesis involves the preparation of the nitro-musks, musk xylene and/or musk ketone, from readily available m-xylene.
Nash, E. Gary; Nienhouse, Everett J.; Silhavy, Thomas A.; Humbert, Dale E.; Mish, Mary Jo J. Chem. Educ. 1970, 47, 705.
Aromatic Compounds |
Synthesis
|
Enamine reactions for the undergraduate organic laboratory: A student water separator Darling, S. D.
This note describes the design and efficiency of a device that facilitates the removal of water in reactions such as enamine preparation or esterfications.
Darling, S. D. J. Chem. Educ. 1966, 43, 665.
Laboratory Equipment / Apparatus |
Amines / Ammonium Compounds |
Esters |
Synthesis |
Separation Science
|
Reaction mechanisms in organic chemistry. II. The reaction intermediate Caserio, Marjorie C.
This paper describes the more important methods that have been used to identify the various intermediates that are formed in complex reactions.
Caserio, Marjorie C. J. Chem. Educ. 1965, 42, 627.
Mechanisms of Reactions |
Reactive Intermediates
|
The Friedel-Crafts alkylation of benzene: A first year organic laboratory experiment Dunathan, H. C.
This experiment involves the alkylation of benzene with each of the four butyl chlorides and aluminum chloride; the monobutylbenzenes from each reaction are then analyzed by vapor phase chromatography and IR spectroscopy.
Dunathan, H. C. J. Chem. Educ. 1964, 41, 278.
Aromatic Compounds |
Reactions |
Mechanisms of Reactions |
IR Spectroscopy
|
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
|
PolystyreneA multistep synthesis: For the undergraduate organic chemistry laboratory Wilen, Samuel H.; Kremer, Chester B.; Waltcher, Irving
Describes a multistep synthesis in which polystyrene is synthesized from benzene.
Wilen, Samuel H.; Kremer, Chester B.; Waltcher, Irving J. Chem. Educ. 1961, 38, 304.
Polymerization |
Synthesis
|
The laboratory preparation of a simple vitamin: p-aminobenzoic acid Kremer, Chester B.
Describes the laboratory preparation of a simple vitamin, p-aminobenzoic acid, with beneficial physiological activity.
Kremer, Chester B. J. Chem. Educ. 1956, 33, 71.
Vitamins |
Synthesis
|
The orientation and mechanism of electrophilic aromatic substitution Ferguson, Lloyd N.
Electrophilic aromatic substitution apparently takes place by the formation of an intermediate pentadienate cation, +ArG, where Ar is an aromatic molecule and G is a portion of the reagent.
Ferguson, Lloyd N. J. Chem. Educ. 1955, 32, 42.
Electrophilic Substitution |
Reactions |
Mechanisms of Reactions |
Aromatic Compounds
|
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
|
|
