Aliphatic epoxides acid-catalyzed hydrolysis

Kinetic and isotopic labeling studies by Long and Pritchard on the hydrolyses of ethylene oxide, propylene oxide and isobutylene oxide to their corresponding glycols provide additional insight on the hydrolysis mechanisms of simple aliphatic epoxides.23 In each case, three kinetically distinct mechanisms for their reactions in water solutions were observed acid-catalyzed hydrolysis, pH-independent hydrolysis and hydroxide-catalyzed hydrolysis. Thus, the rate law for hydrolyses of these simple... 

ACID-CATALYZED HYDROLYSIS OF ALIPHATIC EPOXIDES Simple primary and secondary epoxides... 

In general, K-region arene oxides behave rather like aliphatic epoxides and thus readily undergo hydration reactions, whereas benzene oxides and non-K-region arene oxides form dihydrodiols much more reluctantly. Kinetic studies of the mechanism of solvolysis of phenanthrene 9,10-oxide 2 have been carried out in several laboratories.Below pH 7 the hydrolysis reaction was acid-catalyzed and the products included the trans- and c/s-9,10-dihydrodiols along with a preponderance of 9-phenanthrol, while above pH 7 the reaction proceeded via the spontaneous mechanism ( o) mainly the frans-dihydrodiol. 

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