io8 PRACTICAL ORGANIC CHEMISTRY compounds and primary and secondary amines, by obtaining crystalline acetyl derivatives. This applies particularly to aromatic compounds, since aliphatic compounds are often liquid, and frequently soluble in water; (2) to protect a primary or secondary amino group during a chemical reaction, as in the pre-paration of />-nitro-aniline by the nitration of acetanilide, followed by hydrolysis (p. 167), and in the preparation of sulphanilamide (p. 181). Acetanilide. C 6 H 5 NHCOCH 3 . (Method i.) Required: Acetic acid/anhydride mixture, 20 ml.; aniline, io ml. Add 20 ml. of a mixture of equal volumes of acetic anhydride and glacial acetic acid to io ml. (10-3 g.) of aniline contained in a 150 ml. conical flask. Fit a reflux water-condenser to the flask, and boil the mixture gently for io minutes. Then pour the hot liquid into 200 ml. of cold water, stirring the latter well C 6 H 6 NH 2 + O(OCCH 3 ) 2 = C 6 H 5 NHCOCH 3 + CH 3 COOH during the addition. The acetanilide rapidly crystallises. Filter
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This note was uploaded on 09/19/2011 for the course CHM 2211 taught by Professor Castalleano during the Fall '06 term at University of Florida.