TIGER

Journal Articles: 29 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
Study of Molecular-Shape Selectivity of Zeolites by Gas Chromatography  Pei-Yu Chao, Yao-Yuan Chuang, Grace Hsiuying Ho, Shiow-Huey Chuang, Tseng-Chang Tsai, Chi-Young Lee, Shang-Tien Tsai, and Jun-Fu Huang
This analytical or physical chemistry sorption experiment uses hexane isomers as probe molecules to demonstrate the "molecular-shape selectivity" behavior of zeolites. Students can also modify the sorption protocol to build their own experiments.
Chao, Pei-Yu; Chuang, Yao-Yuan; Ho, Grace Hsiuying; Chuang, Shiow-Huey; Tsai, Tseng-Chang; Lee, Chi-Young; Tsai, Shang-Tien; Huang, Jun-Fu. J. Chem. Educ. 2008, 85, 1558.
Alkanes / Cycloalkanes |
Constitutional Isomers |
Gas Chromatography |
Molecular Properties / Structure |
Physical Properties |
Separation Science |
Solid State Chemistry |
Molecular Recognition
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
Gas Clathrate Hydrates Experiment for High School Projects and Undergraduate Laboratories  Melissa P. Prado, Annie Pham, Robert E. Ferazzi, Kimberly Edwards, and Kenneth C. Janda
Presents a procedure for preparing and studying propane clathrate hydrate. This experiment introduces students to this unusual solid while stimulating a discussion of the interplay of intermolecular forces, thermodynamics, and solid structure.
Prado, Melissa P.; Pham, Annie; Ferazzi, Robert E.; Edwards, Kimberly; Janda, Kenneth C. J. Chem. Educ. 2007, 84, 1790.
Alkanes / Cycloalkanes |
Applications of Chemistry |
Calorimetry / Thermochemistry |
Gases |
Phases / Phase Transitions / Diagrams |
Thermodynamics |
Water / Water Chemistry |
Hydrogen Bonding
The Aromaticity of Pericyclic Reaction Transition States  Henry S. Rzepa
Presents an approach that combines two fundamental concepts in organic chemistry, chirality and aromaticity, into a simple rule for stating selection rules for pericyclic reactions in terms of achiral Hckel-aromatic and chiral Mbius-aromatic transition states.
Rzepa, Henry S. J. Chem. Educ. 2007, 84, 1535.
Alkanes / Cycloalkanes |
Alkenes |
Aromatic Compounds |
Mechanisms of Reactions |
Stereochemistry
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
A Template-Controlled Solid-State Reaction for the Organic Chemistry Laboratory  Tomislav Friscic, Tamara D. Hamilton, Giannis S. Papaefstathiou, and Leonard R. MacGillivray
Describes a laboratory experiment that employs linear hydrogen-bond templates to direct [2 + 2] photodimerization in the solid state. The experiment introduces undergraduates to supramolecular and solid-state chemistry, as well as aspects of green chemistry.
Friscic, Tomislav; Hamilton, Tamara D.; Papaefstathiou, Giannis S.; MacGillivray, Leonard R. J. Chem. Educ. 2005, 82, 1679.
Green Chemistry |
Solid State Chemistry |
Crystals / Crystallography |
Alkenes |
Alkanes / Cycloalkanes |
Hydrogen Bonding |
Materials Science |
NMR Spectroscopy
Fractional Distillation and GC Analysis of Hydrocarbon Mixtures  Craig J. Donahue
Separating and identifying the components of a three-hydrocarbon mixture through fractional distillation and gas chromatography.
Donahue, Craig J. J. Chem. Educ. 2002, 79, 721.
Chromatography |
Gas Chromatography |
Separation Science |
Alkanes / Cycloalkanes |
Alkenes |
Aromatic Compounds |
IR Spectroscopy |
NMR Spectroscopy |
Qualitative Analysis
A Safe Simple Halogenation Experiment  Hilton M. Weiss and Lara Ganz
This experiment is designed to be a safe and experimentally simple procedure appropriate to the early weeks of a course when halogenation is the only reaction which has been discussed in the lecture. It can also provide some early experience with simple interpretation of NMR spectra.
Weiss, Hilton M.; Ganz, Lara. J. Chem. Educ. 1999, 76, 534.
Synthesis |
Free Radicals |
Reactions |
NMR Spectroscopy
S. M. Tanatar and His Contribution to the Field of Thermal Rearrangements  Ludmila Birladeanu
Thermal rearrangements constitute an important chapter in organic chemistry. Surprisingly, the name of its discoverer remains unknown. The present article is meant to remedy this situation by describing some of the work of the 19th century Russian chemist S. M. Tanatar (1849 - 1917) who, based on the thermochemical data provided by Berthelot, envisaged the possibility of transforming cyclopropane into propene under the influence of heat alone.
Birladeanu, Ludmila. J. Chem. Educ. 1998, 75, 603.
Gases |
Thermodynamics |
Synthesis |
Alkanes / Cycloalkanes |
Alkenes
Selective and Quantitative Catalytic Hydrogenation: A Safe, Inexpensive Experiment for Large Classes  John A. Landgrebe
A catalytic hydrogenation experiment suitable for large classes.
Landgrebe, John A. J. Chem. Educ. 1995, 72, A220.
Catalysis |
Synthesis |
Laboratory Equipment / Apparatus |
Microscale Lab
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
Synthesis of a bicyclo[2.2.1]heptene Diels-Alder adduct: An organic chemistry experiment utilizing NMR spectroscopy to assign endo stereochemistry  Harrison, Ernest A., Jr.
An organic chemistry experiment utilizing NMR spectroscopy to assign endo stereochemistry via synthesis of a bicyclo[2.2.1]heptene Diels-Alder adduct.
Harrison, Ernest A., Jr. J. Chem. Educ. 1991, 68, 426.
Alkanes / Cycloalkanes |
Synthesis |
Alkenes |
Aromatic Compounds |
NMR Spectroscopy |
Thin Layer Chromatography
Polarity and selectivity of ionic stationary phases used in gas chromatography: Evaluation of commercial detergents containing anionic surfactants as column packings  Furton, Kenneth G.; Mantilla, Adriana
Evaluation of commercial detergents containing anionic surfactants as column packings.
Furton, Kenneth G.; Mantilla, Adriana J. Chem. Educ. 1991, 68, 74.
Consumer Chemistry |
Gas Chromatography |
Physical Properties |
Alkanes / Cycloalkanes |
Quantitative Analysis |
Covalent Bonding |
Solutions / Solvents
An integrated first-year laboratory experiment involving synthesis, spectroscopy, and chromatography of metal acetylacetonates  Glidewell, Christopher; McKenchnic, James S.
This article presents a comprehensive experiment, involving synthesis, thin-layer chromatography, interpretation of two types of NMR and mass spectra.
Glidewell, Christopher; McKenchnic, James S. J. Chem. Educ. 1988, 65, 1015.
NMR Spectroscopy |
Mass Spectrometry |
Synthesis |
Separation Science |
Thin Layer Chromatography
Chemical dominos: How NOT to get lost in the shuffle  Garrett, James M.
A game for teaching introductory retrosynthetic analysis.
Garrett, James M. J. Chem. Educ. 1985, 62, 1102.
Enrichment / Review Materials |
Synthesis
Chemical properties of commonly available hydrocarbons  Perina, Ivo
Studying the properties of saturated hydrocarbons using natural gas.
Perina, Ivo J. Chem. Educ. 1985, 62, 864.
Alkanes / Cycloalkanes
An introduction to conformational analysis of ethane and butane  Flash, Patrick J.
60. Bits and pieces, 23. Introduces students to some conventions for drawing molecules and provides a brief tutorial and extensive drill work on the conformations of ethane and butane.
Flash, Patrick J. J. Chem. Educ. 1985, 62, 412.
Conformational Analysis |
Alkanes / Cycloalkanes |
Enrichment / Review Materials
Preparation of 2-bromopentane  Howell, B. A.; Kohrman, R. E.
The conversion of 2-pentanol to 2-bromopentane offers a good illustration of the problems associated with substitution in secondary systems.
Howell, B. A.; Kohrman, R. E. J. Chem. Educ. 1984, 61, 932.
Synthesis |
Alkanes / Cycloalkanes
Guidebook to organic synthesis (Mackie, R.K.;Smith, D.M.)  Wade, L. G., Jr.
A review of a text that was designed as a text for an advanced undergraduate course in organic synthesis.
Wade, L. G., Jr. J. Chem. Educ. 1983, 60, A320.
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
A Dramatic and relevant demonstration of ring strain  Kelly, T. Ross
Addition of the cyclobutane alpha-pinene to crystalline iodine results in an exceptionally exothermic reaction.
Kelly, T. Ross J. Chem. Educ. 1977, 54, 228.
Molecular Properties / Structure |
Alkanes / Cycloalkanes |
Reactions
Some reflections on the topological structure of covalent molecules  Rouvray, D. H.
Presents a method that involves a description of the possible topological structures a chemical species may adopt, subject to the constraints imposed by the valence.
Rouvray, D. H. J. Chem. Educ. 1975, 52, 768.
Molecular Properties / Structure |
Alkanes / Cycloalkanes
Conversions from cyclohexanol. An undergraduate laboratory project  Hanna, Samir B.; Wrobleski, James T.; Bohanon, Joseph T.; Peace, Bab W.
A procedure for a laboratory in conversions from cyclohexanol.
Hanna, Samir B.; Wrobleski, James T.; Bohanon, Joseph T.; Peace, Bab W. J. Chem. Educ. 1971, 48, 556.
Alkanes / Cycloalkanes |
Alcohols
The stereospecific synthesis of trans-1,4-disubstituted cyclohexanes. An organic chemistry laboratory experiment  Monson, Richard S.
The authors present a synthetic experiment suitable for the introductory organic chemistry laboratory which the introductory organic chemistry laboratory which allows for the unambiguous preparation of trans-1,4-disubstituted cyclohexane derivatives from readily available starting materials.
Monson, Richard S. J. Chem. Educ. 1971, 48, 197.
Alkanes / Cycloalkanes |
Stereochemistry |
Reactions
Preparation of the proteins by micro-organisms  Dieteren, H. M. L.; Schouteten, A. P. H.
Yeast are used to generate proteins from tetradecane in a controlled vessel.
Dieteren, H. M. L.; Schouteten, A. P. H. J. Chem. Educ. 1970, 47, 663.
Proteins / Peptides |
Synthesis
The preparation of naphthalene-alpha-d: An experiment in organic chemistry  Ziegler, Gene R.
This procedure involves the preparation of a hydrocarbon via the Grignard reagent from the corresponding bromide.
Ziegler, Gene R. J. Chem. Educ. 1967, 44, 609.
Synthesis |
Grignard Reagents |
Alkanes / Cycloalkanes
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
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