2.14. Aromatic Hydrocarbons: Physical Properties and Sources
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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.
Alcohols |
Aromatic Compounds |
Phenols
TNT Detonation TNT is stable in the presence of shock, but can be detonated by adding a chemical priming agent.
BiphenylJay A. Young Safe handling and laboratory use of biphenyl are discussed. Young, Jay A. J. Chem. Educ.2008, 85, 1486.
Aromatic Compounds |
Laboratory Management
Probing the Rate-Determining Step of the Claisen–Schmidt Condensation by Competition ReactionsKendrew 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 ClaisenSchmidt 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
Synthesis of Triarylmethane and Xanthene Dyes Using Electrophilic Aromatic Substitution ReactionsJames V. McCullagh and Kelly A. Daggett In this experiment, electrophilic aromatic substitution reactions are used to synthesize several triarylmethane and xanthene dyes (fluorescein, erythrosin B, thymolphthalein, and rhodamine B) using common equipment while avoiding often troublesome, hydroscopic Lewis acids. Subsequent UVvis analysis produce spectra that match commercially available dye samples. McCullagh, James V.; Daggett, Kelly A. J. Chem. Educ.2007, 84, 1799.
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.
