Acid-and base-catalysed hydrolysis of carbonates of 2,2-dialkylpropane-1,3-diol in H,180 proceeds with CO-0 bond-fission a t both stages. Under both conditions oxygen exchange occurs during the hydrolysis, in all the cases studied, between the exocyclic oxygen atom and the solvent. These facts are interpreted in terms of a possibly non-cyclic intermediate in which the carbonyl-oxygen atom participates in a reversible fashion.* Formerly Shalom Israelashvili.
The rates of the acid-catalysed hydrolysis of ethylene, trimethylene, and tetramethylene carbonate have been measured a t two temperatures, and the energies and entropies of activation have been calculated. I n the hydrolysis of propylene carbonate in > 1 M-hydrochloric acid the rates are not proportional to the acidity measured by Hammett's acidity function, h,. The large negative entropies of activation indicate that all the cyclic carbonates are hydrolysed by the same A-2 mechanism. The relative order of reactivities for acidcatalysed hydrolysis of homologous cyclic carbonates at temperatures investigated are 6-> 5-> 7-membered.
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