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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.
Electronic Structure Principles and AromaticityP. K. Chattaraj, U. Sarkar, and D. R. Roy Electronic structure principles dictate that aromatic molecules are associated with low energy, polarizability, and electrophilicity but high hardness values, while antiaromatic molecules possess the opposite characteristics. These relationships are demonstrated through B3LYP/6-311G** calculations on benzene and cyclobutadiene. Chattaraj, P. K.; Sarkar, U.; Roy, D. R. J. Chem. Educ.2007, 84, 354.
Aromatic Compounds |
Molecular Properties / Structure |
Quantitative Analysis |
Theoretical Chemistry |
Alkenes |
Quantum Chemistry
Quantitative Thermodynamic Descriptions of Aromaticity. A Computational Exercise for the Organic Chemistry LaboratoryTerrence Gavin This article describes an exercise that enables students to establish a quantitative scale of aromaticity via computer-driven quantum mechanical calculations using Spartan software. The method utilizes a group of analogous isodesmic reactions from which the energy difference between two isomeric cyclic polyenes is calculated from their optimized geometries. The energy differences found are used to characterize structures as aromatic, nonaromatic, or antiaromatic depending on the value obtained. A representative group of structures, including hydrocarbons, hydrocarbon ions, and heterocycles are studied. Gavin, Terrence. J. Chem. Educ.2005, 82, 953.
Aromatic Compounds |
Computational Chemistry |
Heterocycles |
Molecular Modeling |
Thermodynamics
A Unified Approach to Electron Counting in Main-Group ClustersJohn E. McGrady A unified approach to electron counting in main-group cluster chemistry is presented, wherein the different classes, electron-rich, electron-precise, and electron-deficient, are viewed simply as different regions of a continuum defined by two variables, vertex count and valence electron count. McGrady, John E. J. Chem. Educ.2004, 81, 733.
Interactive Molecular OrbitalsWilliam F. Coleman The majority of Introductory Chemistry texts provide students with an adequate introduction to the visual aspects of the molecular orbital model for homonuclear diatomic molecules. The treatment of heteronuclear diatomic and polyatomic molecules is less uniform. Heteronuclear diatomics, when mentioned, are invariably treated as being derived from homonuclear diatomics. While the atomic orbital energy level differences in heteronuclear diatomics is sometimes pictured, the consequences of those differences for the resultant molecular orbitals are rarely discussed. The discussion of polyatomic molecular orbitals in these texts is limited to showing that parallel p-orbitals produce delocalized pi molecular orbitals. The molecules typically mentioned in this context are benzene, nitrate ion and carbonate ion. However, It is rarely pointed out that the six p-orbitals in benzene would form 6 pi molecular orbitals, and that only one of these orbitals would look like the picture in the text.These interactive modules are designed to clarify this subject.
MO Theory
Molecular OrbitalsEd Vitz, John W. Moore A section of ChemPrime, the Chemical Educations Digital Library's free General Chemistry textbook.
MO Theory |
Magnetic Properties
Delocalized ElectronsEd Vitz, John W. Moore A section of ChemPrime, the Chemical Educations Digital Library's free General Chemistry textbook.
