Organic carbonates. Part VIII.¹ the acid-catalysed hydrolysis of ethylene, trimethylene, and tetramethylene carbonate

The rates of the acid-catalysed hydrolysis of ethylene, trimethylene, and tetramethylene carbonate have been measured at two temperatures, and the energies and entropies of activation have been calculated. In the hydrolysis of propylene carbonate in > 1 M-hydrochloric acid the rates are not proportional to the acidity measured by Hammett's acidity function, h₀. 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 acid-catalysed hydrolysis of homologous cyclic carbonates at temperatures in-vestigated are 6- > 5- > 7-membered.