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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
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.
The Anomalous Reactivity of Fluorobenzene in Electrophilic Aromatic Substitution and Related PhenomenaJoel Rosenthal and David I. Schuster Extensive analysis of the reactivity of fluorobenzene (electrophilic substitution); includes resonance and other inductive effects, acidities of fluorinated aromatic compounds, and properties of other organofluorine compounds. Rosenthal, Joel; Schuster, David I. J. Chem. Educ.2003, 80, 679.
Molecular Orbital Animations for Organic ChemistrySteven 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.
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.
