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ERIC Number: EJ814860
Record Type: Journal
Publication Date: 2008-Nov
Pages: 3
Abstractor: As Provided
Reference Count: 4
ISSN: ISSN-0021-9584
A More Challenging Interpretative Nitration Experiment Employing Substituted Benzoic Acids and Acetanilides
Treadwell, Edward M.; Lin, Tung-Yin
Journal of Chemical Education, v85 n11 p1541-1543 Nov 2008
An experiment is described involving the nitration of ortho or meta monosubstituted benzoic acids (XC[subscript 6]H[subscript 4]CO[subscript 2]H, X = Halogen, Me, OH, or OMe) and monochlorinated acetanilides with nitric acid to determine the regioselectivity of addition by [superscript 1]H NMR spectroscopy and molecular modeling. Students were able to interpret the [superscript 1]H NMR spectra regardless of the formation of multiple products or contamination from the starting materials. With one exception, both the [superscript 1]H NMR spectroscopy and computational methods agreed with the theoretical expectation and provided a nice demonstration of regioselectivity of nitration on substituted benzene. (Contains 2 tables, 1 figure and 1 note.)
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 - Evaluative
Education Level: Higher Education
Audience: N/A
Language: English
Sponsor: N/A
Authoring Institution: N/A