The hydrolysis of
2-acetyloxybenzoic acid in the pH range 6-12 has been studied in the presence
of micelles of cetyltrimethylammonium bromide (ctab) and cetylpyridinium
chloride (cpc). In the plateau region (pH 6-8) the
hydrolysis is inhibited by the presence of micelles, while in the region where
the normal BAC2 hydrolysis (pH > 9) occurs the reaction is
catalysed by micelles of ctab and cpc. The mechanism of hydrolysis in the
plateau region is shown to involve general base catalysis by the adjacent
ionized carboxy group both in the presence and
absence of micelles. This reaction is inhibited in the presence of micelles
because the substrate molecules are solubilized into
the micelle and water is less available in this environment than in normal
aqueous solution.