When toluene is treated with bromine (shown), the bromine doesn't react with the double bond to form a viscinal dihalide, but instead a substitution of one of the benzylic hydrogens takes place. Why?

Chemistry by OpenStax (2015-05-04)
1st Edition
ISBN:9781938168390
Author:Klaus Theopold, Richard H Langley, Paul Flowers, William R. Robinson, Mark Blaser
Publisher:Klaus Theopold, Richard H Langley, Paul Flowers, William R. Robinson, Mark Blaser
Chapter18: Representative Metals, Metalloids, And Nonmetals
Section: Chapter Questions
Problem 53E: In drawing Lewis structures, we learn that a hydrogen atom forms only one bond in a covalent...
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When toluene is treated with bromine (shown), the bromine doesn't react with the double bond to form a viscinal dihalide, but instead a substitution of one of the benzylic hydrogens takes place. Why?

Br₂
Br...
Br
NOT FORMED
Br
Major Product
Transcribed Image Text:Br₂ Br... Br NOT FORMED Br Major Product
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Chemistry by OpenStax (2015-05-04)
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ISBN:
9781938168390
Author:
Klaus Theopold, Richard H Langley, Paul Flowers, William R. Robinson, Mark Blaser
Publisher:
OpenStax