Not all tertiary haloalkanes undergo S,1 reactions readily. For example, the bicyclic com- pound shown below is very unreactive under Sy1 conditions. What feature of this mol- ecule is responsible for such lack of reactivity? You will find it helpful to examine a model of this compound. 1-lodobicyclooctane

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
Chapter9: Nucleophilic Substitution And Β-elimination
Section: Chapter Questions
Problem 9.27P
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Not all tertiary haloalkanes undergo S,1 reactions readily. For example, the bicyclic com-
pound shown below is very unreactive under Sy1 conditions. What feature of this mol-
ecule is responsible for such lack of reactivity? You will find it helpful to examine a model
of this compound.
1-lodobicyclooctane
Transcribed Image Text:Not all tertiary haloalkanes undergo S,1 reactions readily. For example, the bicyclic com- pound shown below is very unreactive under Sy1 conditions. What feature of this mol- ecule is responsible for such lack of reactivity? You will find it helpful to examine a model of this compound. 1-lodobicyclooctane
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