Draw the sigma complex for the formation of the bromonium electrophile with proper resonance forms for the meta bromination of toluene and for the para bromination of toluene. Which resonance structure places the (+) next to the methyl group? Will either one (i.e. para and meta sigma complex) yield a fourth resonance structure? Given that alkyl groups such as CH3 are electron rich (i.e. no attached electronegative atoms), which sigma complex in part (A) would be more stable?

Chemistry for Today: General, Organic, and Biochemistry
9th Edition
ISBN:9781305960060
Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen
Publisher:Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen
Chapter12: Unsaturated Hydrocarbons
Section: Chapter Questions
Problem 12.67E
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Draw the sigma complex for the formation of the bromonium electrophile with proper resonance forms for the meta bromination of toluene and for the para bromination of toluene. Which resonance structure places the (+) next to the methyl group? Will either one (i.e. para and meta sigma complex) yield a fourth resonance structure? Given that alkyl groups such as CH3 are electron rich (i.e. no attached electronegative atoms), which sigma complex in part (A) would be more stable?
Br₂
CH3
FeBr3
CH3
HBr and
Br
.CH3
HBr
Br
Which one places the (+) next the methyl group? Will
Transcribed Image Text:Br₂ CH3 FeBr3 CH3 HBr and Br .CH3 HBr Br Which one places the (+) next the methyl group? Will
Expert Solution
Step 1

Given that,

Chemistry homework question answer, step 1, image 1

We have to draw the structure of the Sigma complex form from the above two products.

Also, we have to tell which one will generate the positive charge next two the methyl group.

And, also we have to determine which one is the most stable sigma complex.

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