HYDROXAMIC ACIDS .3. KINETICS OF ACETOHYDROXAMIC ACID FORMATION FROM ETHYL ACETATE

At pH 9.5, 40°, ethyl acetate simultaneously undergoes hydrolysis and hydroxyaminolysis to yield acetic acid and acetohydroxamic acid (N‐hydroxyacetamide), respectively. The pseudo first‐order rate constants for the overall reaction have been calculated from data based on the colorimetric determination of the hydroxamic acid‐iron complex and by the pH‐stat method. Yields of both products have been determined. Both O‐ and N‐attack by NH2OH on ethyl acetate has been postulated to explain the observed reaction yields. In the case of the O‐attack the resulting O‐acetylhydroxylamine is a reactive intermediate which undergoes further hydrolysis and hydroxyaminolysis to yield acetic acid and acetohydroxamic acid, respectively. Copyright © 1969 Wiley‐Liss, Inc., A Wiley Company