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Solvated metal hydroxide model. The concentration of metal hydroxide coordinated to the pro-R oxygen depends upon the pKa of a water molecule coordinated to the metal ion. Use of hydrated metal ions with lower pKa values would produce a larger Keq,1 but would also result in a smaller Keq,2. Because the active nucleophile in the rate limiting step is the 2′-alkoxide and not the metal hydroxide, the observed pKa correlation is not supported by a solvated metal hydroxide model.
