A comparison of the rates of Sy1 solvolysis of the bicyclic compounds (1) and (2) in acetic acid shows that compound (1) reacts 10" times faster than compound (2). Furthermore, solvolysis of (1) occurs with complete retention of configuration: the nucleophile occu- pies the same position on the one-carbon bridge as did the leaving -OSO,Ar group. LOSO,Ar OSO,Ar (1) (2)

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Account for the difference in rate of solvolysis of (1) and (2).

A comparison of the rates of Sy1 solvolysis of the bicyclic compounds (1) and (2) in acetic
acid shows that compound (1) reacts 10" times faster than compound (2). Furthermore,
solvolysis of (1) occurs with complete retention of configuration: the nucleophile occu-
pies the same position on the one-carbon bridge as did the leaving -OSO,Ar group.
LOSO,Ar
OSO,Ar
(1)
(2)
Transcribed Image Text:A comparison of the rates of Sy1 solvolysis of the bicyclic compounds (1) and (2) in acetic acid shows that compound (1) reacts 10" times faster than compound (2). Furthermore, solvolysis of (1) occurs with complete retention of configuration: the nucleophile occu- pies the same position on the one-carbon bridge as did the leaving -OSO,Ar group. LOSO,Ar OSO,Ar (1) (2)
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