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Nucleophilic Substitution Reactions Solvolysis of secondary versus tertiary halides, effects of leaving groups, solvolysis of/and reactions of sodium iodide and silver nitrate with isomers of bromobutane, SN1 and SN2 mechanisms, and hydrolysis of tert-butyl chloride are demonstrated.
Nucleophilic Substitution
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.
Assessing Nitration Products of Benzene Derivatives Using TLC AnalysisRita K. Hessley Thin layer chromatography is applied to an earlier published, guided discovery experiment using GCMS analyses to identify isomers formed by the nitration of mono-substituted benzenes. Hessley, Rita K. J. Chem. Educ.2008, 85, 1623.
Thin Layer Chromatography |
Gas Chromatography |
Mass Spectrometry |
Aromatic Compounds
A More Challenging Interpretative Nitration Experiment Employing Substituted Benzoic Acids and AcetanilidesEdward M. Treadwell and Tung-Yin Lin An experiment is described involving the nitration of ortho or meta, monosubstituted benzoic acids and monochlorinated acetanilides with nitric acid to evaluate the regioselectivity of addition through computational methods and 1H NMR spectroscopy. Treadwell, Edward M.; Lin, Tung-Yin. J. Chem. Educ.2008, 85, 1541.
Aromatic Compounds |
Computational Chemistry |
Electrophilic Substitution |
Molecular Modeling |
NMR Spectroscopy |
Synthesis
BiphenylJay A. Young Safe handling and laboratory use of biphenyl are discussed. Young, Jay A. J. Chem. Educ.2008, 85, 1486.
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.
