A comparison of the rates of SN1 solvolysis of the

Chapter 9, Problem 9.36

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A comparison of the rates of SN1 solvolysis of the bicyclic compounds (1) and (2) in acetic acid shows that compound (1) reacts 1011 times faster than compound (2). Furthermore, solvolysis of (1) occurs with complete retention of confi guration: the nucleophile occupies the same position on the one-carbon bridge as did the leaving 2OSO2Ar group. OSO2Ar (1) OSO2Ar (2) (a) Draw structural formulas for the products of solvolysis of each compound.(b)Account for the difference in rate of solvolysis of (1) and (2).(c) Account for complete retention of confi guration in the solvolysis of (1).

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