Abstract
Carbonyl carbon, carbonyl oxygen, and nucleophile oxygen isotope effects were measured for the alkaline hydrolysis of methyl formate in water at 25 o C. The carbonyl carbon isotope effect is k 12 /k 13 =1.0338, the isotope effect for the carbonyl oxygen is k 16 /k 18 =0.999, and that for the oxygen nucleophile is k 16 /k 18 =1.023. These isotope effects are consistent with a stepwise mechanism in which the formation of the tetrahedral intermediate is largely rate-determining. The isotope effect on the oxygen nucleophile suggests that the attacking nucleophile in aqueous alkali is water with general base assistance from hydroxide
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