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  Home > JCE Print > Journal of Chemical Education > Issues > 2009  > April  >
In the Laboratory
Investigation of Unexpected Reaction Intermediates in the Alkaline Hydrolysis of Methyl 3,5-Dinitrobenzoate
Clésia C. Silva, Ricardo O. Silva, Daniela M. A. F. Navarro, and Marcelo Navarro
Departamento de Química Fundamental - CCEN, Universidade Federal de Pernambuco, Cidade Universitária 50740-901, Recife (PE), Brazil
Cover
April 2009
Vol. 86 No. 4
p. 484
Abstract
An experimental project aimed at identifying stable reaction intermediates is described. Initially, the studied reaction appears to involve the simple hydrolysis, by aqueous sodium hydroxide, of methyl 3,5-dinitrobenzoate dissolved in dimethyl sulfoxide. On mixing the substrates, however, the reaction mixture unexpectedly turns an intense red in color, a phenomenon that is explained by the generation of stable Meisenheimer complexes following aromatic nucleophilic attack by the hydroxide ion. UV–vis and 1H NMR spectroscopic techniques are employed as analytical tools to follow the reactions and to identify both the intermediates and the final end product. Kinetic and thermodynamic effects associated with the concurrent reactions involving aromatic nucleophilic attack and carbonyl attack (hydrolysis) are invoked to explain the time course of formation of the intermediates and the final product (sodium 3,5-dinitrobenzoate). At the conclusion of the project, students should be able to construct a working hypothesis concerning the mechanism of the reaction sequence.
Supplement
Student handouts; Instructor notes with questions and answers; Additional NMR spectra
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Contents
  JCE2009p0484W.pdf
 
 
More Information
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Citation
Silva, Clésia C.; Silva, Ricardo O.; Navarro, Daniela M. A. F.; Navarro, Marcelo. J. Chem. Educ. 2009, 86, 484.
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Keywords
Addition Reactions; Aromatic Compounds; Hands-On Learning / Manipulatives; Kinetics; Laboratory Instruction; Mechanisms of Reactions; NMR Spectroscopy; Organic Chemistry; Problem Solving / Decision Making; Reactive Intermediates; Upper-Division Undergraduate; UV-Vis Spectroscopy
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History
Created:
Last Updated:
2/20/2009
3/4/2009
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  Home > JCE Print > Journal of Chemical Education > Issues > 2009  > April  > Page 484


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