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Carboxylic Acids and Derivatives Conductivity of carboxylic acids, pH of acetic acid derivatives, hydrophobic effect, and soap emulsions of hydrocarbons are demonstrated.
Entropy and the Shelf Model: A Quantum Physical Approach to a Physical PropertyArnd H. Jungermann A quantum physical approach relying on energy quantization leads to three simple rules which are the key to understanding the physical property described by molar entropy values. Jungermann, Arnd H. J. Chem. Educ.2006, 83, 1686.
Alcohols |
Alkanes / Cycloalkanes |
Carboxylic Acids |
Covalent Bonding |
Ionic Bonding |
Physical Properties |
Quantum Chemistry |
Thermodynamics
Application of ChemDraw NMR Tool: Correlation of Program-Generated 13C Chemical Shifts and pKa Values of para-Substituted Benzoic AcidsHongyi Wang An application of ChemDraw NMR Tool was demonstrated by correlation of program-generated 13C NMR chemical shifts and pKa values of para-substituted benzoic acids. Experimental 13C NMR chemical shifts were analyzed in the same way for comparison. The project can be used as an assignment at the end of the first-year organic chemistry course to review topics or explore new techniques: Hammett equation, acidbase equilibrium theory, electronic nature of functional groups, inductive and resonance effects, structurereactivity relationship, NMR spectroscopy, literature search, database search, and ChemDraw software. Wang, Hongyi. J. Chem. Educ.2005, 82, 1340.
Acids / Bases |
Equilibrium |
NMR Spectroscopy |
Aqueous Solution Chemistry |
Carboxylic Acids
Stearic AcidJay A. Young Properties, hazards, and storage requirements for stearic acid. Young, Jay A. J. Chem. Educ.2004, 81, 25.
Molecular Models of Reactants and Products from an Asymmetric Synthesis of a Chiral Carboxylic AcidWilliam F. Coleman Our JCE Featured Molecules for this month come from the paper by Thomas E. Smith, David P. Richardson, George A. Truran, Katherine Belecki, and Megumi Onishi (1). The authors describe the use of a chiral auxiliary, 4-benzyl-2-oxazolidinone, in the synthesis of a chiral carboxylic acid. The majority of the molecules used in the experiment, together with several of the pharmaceuticals mentioned in the paper, have been added to our molecule collection. In many instances multiple enantiomeric and diastereomeric forms of the molecules have been included. This experiment could easily be extended to incorporate various aspects of computation for use in an advanced organic or integrated laboratory. Here are some possible exercises using the R and S forms of the 4-benzyl-2-oxazolidinone as the authors point out that both forms are available commercially. Calculation of the optimized structures and energies of the enantiomers at the HF/631-G(d) level using Gaussian03 (2) produces the results shown in Table 1. Evaluation of the vibrational frequencies results in no imaginary frequencies and the 66 real frequencies are identical for the two forms. Examination of the computed IR spectra also shows them to be identical. Additionally, the Raman and NMR spectra can be calculated for the enantiomers and compared to experimental values and spectral patterns. A tool that is becoming increasingly important for assigning absolute configuration is vibrational circular dichroism (VCD). Although the vibrational spectra of an enantiomeric pair are identical, the VCD spectra show opposite signs, as shown in Figure 1. One can imagine a synthesis, using an unknown enantiomer of the chiral auxiliary, followed by calculations of the electronic and vibrational properties of all of the intermediates and the product, and determination of absolute configuration of reactants and products by comparison of experimental and computed VCD spectra. Using a viewer capable of displaying two molecules that can be moved independently, students could more easily visualize the origin of the enantiomeric preference in the reaction between the chelated enolate and allyl iodide.
Green Chemistry
Carboxylic AcidsEd Vitz, John W. Moore A section of ChemPrime, the Chemical Educations Digital Library's free General Chemistry textbook.
Carboxylic Acids
Carboxylic Acids in EntomologyRobert Hetue A section of ChemPrime, the Chemical Educations Digital Library's free General Chemistry textbook.