NotesFAQContact Us
Collection
Advanced
Search Tips
Peer reviewed Peer reviewed
Direct linkDirect link
ERIC Number: EJ826609
Record Type: Journal
Publication Date: 2008-Apr
Pages: 3
Abstractor: As Provided
Reference Count: 17
ISBN: N/A
ISSN: ISSN-0021-9584
A Nitration Reaction Puzzle for the Organic Chemistry Laboratory
Wieder, Milton J.; Barrows, Russell
Journal of Chemical Education, v85 n4 p549-551 Apr 2008
Treatment of phenylacetic acid with 90% HNO[subscript 3] yields a product, I, whose observed melting point is 175-179 degrees C and whose equivalent weight is approximately 226 grams. Treatment of phenylacetic acid with 70% HNO[subscript 3] yields a product, II, whose observed melting point is 106-111 degrees C and whose equivalent weight is approximately 181 grams. Based on these data and 1H NMR and infrared spectral data, students are asked to deduce the structures of nitration products I and II. The above nitration experiment illustrates fundamental electrophilic aromatic substitution concepts while posing an interesting structure elucidation puzzle for organic chemistry students. The nitration of phenylacetic acid requires students to ponder the directing ability of the carboxymethyl group. Given that nitric acid is a powerful oxidizing agent, students must also ponder whether the carboxymethyl group is subject to oxidation under the reaction conditions employed. Lastly, students must determine what impact, if any, the concentration of the nitric acid used will have on the structures of the nitration products obtained. (Contains 3 figures 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: jchemed@egpp.com; Web site: http://www.jce.divched.org
Publication Type: Journal Articles; Reports - Descriptive
Education Level: Higher Education
Audience: Students; Teachers
Language: English
Sponsor: N/A
Authoring Institution: N/A