An experiment involving the nitration of salicylic acid and subsequent separations, reactions, and analysis

CHED 100

William D. Korte, wkorte@csuchico.edu, Department of Chemistry /Emeritus Professor, California State University, Chico, 1590 Borman Way, Chico, CA 95926
The nitration of salicylic acid gives two isomers, 3-nitrosalicylic acid and 5-nitrosalicylic acid. In this experiment the two isomers are formed using a small scale reaction under mild conditions, quantitatively analyzed by HPLC, and separated and isolated by fractional crystallization. Identification is confirmed by mp, UV-VIS, and NMR analysis. Subsequent reduction, salt formation, and diazotization reactions can demonstrate synthetic applications of the nitro compounds. Selection of various components of these manipulations can make the experiment suitable for either elementary, full-year, or advanced organic chemistry classes. In my one-year organic class, students collaborate after the initial synthesis by performing experiments on either of the two isomers. Subsequent comparison of the two sets of results makes the experiment more extensive, interesting, and meaningful for the students. The small scale reactions are relatively safe, however, the nitration reaction must be carefully performed in a hood or other ventilation system.
 

General Posters
7:30 PM-9:30 PM, Sunday, April 6, 2008 Morial Convention Center -- Hall A, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, April 7, 2008 Morial Convention Center -- Hall A, Sci-Mix

Division of Chemical Education

The 235th ACS National Meeting, New Orleans, LA, April 6-10, 2008