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Phenols and Quinones Ferric chloride test for phenols, nitration of acetaminophen, extraction of dichloroindophenol, oxidation of phenols with sodium periodate, nucleophilic addition to quinones, "purple benzene", oxidation of 2,6-Dit-butlhydoquinone, decolorization of crystal violet, and chameleon emulsion are demonstrated.
Alcohols |
Aromatic Compounds |
Phenols
Aromatic Compounds A molecular model of benzene, the reactions of bromine with cylohexane, cyclohexene, benzene, phenol, and toluene, the effect of substituents and number of methyl groups on the electron density of aromatic rings, and chlorination reactions of methyl benzenes are demonstrated.
Aromatic Compounds
TNT Detonation TNT is stable in the presence of shock, but can be detonated by adding a chemical priming agent.
The Comparative Nucleophilicity of Naphthoxide Derivatives in Reactions with a Fast-Red TR DyeCheryl M. Mascarenhas In this experiment, organic chemistry students perform reactions between three naphthyl acetate derivatives and the diazonium salt Fast-Red TR. Students discover under what conditions the hydrolysis and electrophilic aromatic substitution is fastest and slowest, allowing them to conclude that latter, rather than the former, is rate-limiting. Mascarenhas, Cheryl M. J. Chem. Educ.2008, 85, 1271.
Alcohols |
Aromatic Compounds |
Dyes / Pigments |
Esters |
IR Spectroscopy |
NMR Spectroscopy |
Synthesis |
Thin Layer Chromatography |
UV-Vis Spectroscopy
Construction of a Polyaniline Nanofiber Gas SensorShabnam Virji, Bruce H. Weiller, Jiaxing Huang, Richard Blair, Heather Shepherd, Tanya Faltens, Philip C. Haussmann, Richard B. Kaner, and Sarah H. Tolbert The objectives of this lab are to synthesize different diameter polyaniline nanofibers and compare them as sensor materials. Its advantages include simplicity and low cost, making it suitable for both high school and college students, particularly in departments with modest means. Virji, Shabnam; Weiller, Bruce H.; Huang, Jiaxing; Blair, Richard; Shepherd, Heather; Faltens, Tanya; Haussmann, Philip C.; Kaner, Richard B.; Tolbert, Sarah H. J. Chem. Educ.2008, 85, 1102.
Acids / Bases |
Aromatic Compounds |
Conductivity |
Hydrogen Bonding |
Oxidation / Reduction |
Oxidation State |
pH |
Polymerization |
Synthesis
"Greening Up" the Suzuki ReactionEvangelos Aktoudianakis, Elton Chan, Amanda R. Edward, Isabel Jarosz, Vicki Lee, Leo Mui, Sonya S. Thatipamala, and Andrew P. Dicks This article describes the green synthesis of a biaryl compound via a Pd(0)-catalyzed Suzuki cross-coupling reaction in water. The methodology exposes students to purely aqueous microscale organic reactivity and showcases topical research regarding an industrial process. Aktoudianakis, Evangelos; Chan, Elton; Edward, Amanda R.; Jarosz, Isabel; Lee, Vicki; Mui, Leo; Thatipamala, Sonya S.; Dicks, Andrew P. J. Chem. Educ.2008, 85, 555.
Aromatic HydrocarbonsEd Vitz, John W. Moore A section of ChemPrime, the Chemical Educations Digital Library's free General Chemistry textbook.
Aromatic Compounds
Conjugated SystemsEd Vitz, John W. Moore A section of ChemPrime, the Chemical Educations Digital Library's free General Chemistry textbook.
Aromatic Compounds
Coumarin, Naphthalene, and Additional Polycyclic Aromatic HydrocarbonsWilliam F. Coleman The featured molecules this month are drawn from two papers. The first, "One-Pot Synthesis of 7-Hydroxy-3-carboxycoumarin in Water", is a Green Chemistry feature by Fringuelli, Piermatti, and Pizzo. The three-dimensional versions of the molecules in the synthesis of the coumarin derivative are directly tied to the reaction scheme included in the paper, opening the possibility of showing large numbers of complex synthetic pathways in this manner.The second paper is "Determining the Carbon-Carbon Distance in an Organic Molecule with a Ruler" by Simoni, Tubino, and Ricchi. This article describes an experiment to determine the size of a naphthalene molecule, using an extension of classic experiments for determining molecular size and Avogadro's number. While the structure of naphthalene will come as no surprise to most students, the molecule collection also includes additional polycyclic aromatic hydrocarbons (PAHs) that can be used to introduce students to the environmental and health issues related to these molecules.
