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)

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)

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter24: Catalytic Carbon-carbon Bond Formation

Section: Chapter Questions

Problem 24.37P

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