Abstract
Rate coefficients and kinetic parameters have been determined for the acid-catalyzed hydrolysis of 2-, 3-, 4-, and 6- O-methyl derivatives of methyl β- D-glucopyranoside and of gentiobiose. All of the monomethyl ethers were hydrolyzed somewhat more slowly than the unsubstituted compounds, the rate decreasing for both series in the order 3- O-methyl > 2- O-methyl > 4- O-methyl > 6- O methyl. The results are in agreement with those to be expected if the unimolecular hydrolysis proceeds via a cyclic, carbonium ion; they thus offer additional evidence in favor of this mechanism.
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