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Vol. 61 acid and water has been measured at 80°in dilute aqueous solution using hydrochloric acid as a catalyst. The reaction was followed by decomposing into benzene and carbon dioxide samples of benzoic acid crystallized from the reaction mixture and analyzing the carbon dioxide in the mass spectrometer. The rate is first order in the difference of O18 content of the reactants, first order in hydrogen ion, independent of the concentration of benzoic acid, and free of salt effects. New York, N. Y.

There has been much discussion as to which linkages are broken in the two reactions: (a) the saponification of an ester, and (b) the esterification of a carboxylic acid. The first of these was studied by Polanyi and Szabo,1 who demonstrated that the saponification of amyl acetate in heavy oxygen water results in amyl alcohol of ordinary isotopic composition. The solution of the second problem, for which evidence has been inconclusive up to the present, is the subject of this paper.The formation of water by the acid-catalyzed esterification of benzoic acid with methyl alcohol may be represented by either of the equations

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