Compare the base-promoted hydrolysis reaction of a thioester with that of an oxygen

Chapter 21, Problem 21.45

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Compare the base-promoted hydrolysis reaction of a thioester with that of an oxygen ester, and decide how each of the following factors affects the relative rate of the two reactions. R C SEt O (a) resonance stabilization of the carbonyl compound (b) polar stabilization of the transition state (The hydrolysis of thioesters is discussed in Sec. 25.5A.)

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