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ERIC Number: EJ832503
Record Type: Journal
Publication Date: 2009-Apr
Pages: 4
Abstractor: As Provided
Reference Count: 11
ISSN: ISSN-0021-9584
Investigation of Unexpected Reaction Intermediates in the Alkaline Hydrolysis of Methyl 3,5-Dinitrobenzoate
Silva, Clesia C.; Silva, Ricardo O.; Navarro, Daniela M. A. F.; Navarro, Marcelo
Journal of Chemical Education, v86 n4 p484-487 Apr 2009
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 [superscript 1]H 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. (Contains 2 schemes and 2 figures.)
Division of Chemical Education of the American Chemical Society. Subscription Department, P.O. Box 1267, Bellmawr, NJ 08099-1267. Tel: 800-691-9846; Tel: 856-931-5825; Fax: 856-931-4115; e-mail:; Web site:
Publication Type: Journal Articles; Reports - Descriptive
Education Level: Higher Education
Audience: Teachers
Language: English
Sponsor: N/A
Authoring Institution: N/A