A publication from this century generated the I+ cation via oxidation of I2. The researchers then studied the most effective (yield and regioselectivity) experimental conditions in which a variety of benzenes underwent electrophilic aromatic substitution to generate iodobenzenes. The researchers found that adding dimethoxyethane (CH3OCH2CH2OCH3) improved regioselectivity. This means the para:ortho ratio was higher when dimethoxyethane was used as a cosolvent. 1) When dimethoxyethane reacts with I+, it forms a Lewis acid-base complex in which both oxygens bond to the iodine. a) What is the electron group geometry (from VSEPR theory) of the complex?  b) Make a good Lewis drawing of the Lewis complex, using dash-wedge notation and correctly showing formal charges and the location of the lone pairs.

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
Chapter21: Benzene And The Concept Of Aromaticity
Section: Chapter Questions
Problem 21.63P
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A publication from this century generated the I+ cation via oxidation of I2.
The researchers then studied the most effective (yield and regioselectivity)
experimental conditions in which a variety of benzenes underwent
electrophilic aromatic substitution to generate iodobenzenes.

The researchers found that adding dimethoxyethane (CH3OCH2CH2OCH3)
improved regioselectivity. This means the para:ortho ratio was higher when
dimethoxyethane was used as a cosolvent.

1) When dimethoxyethane reacts with I+, it forms a Lewis acid-base complex
in which both oxygens bond to the iodine.

a) What is the electron group geometry (from VSEPR theory) of the
complex? 

b) Make a good Lewis drawing of the Lewis complex, using dash-wedge
notation and correctly showing formal charges and the location of the lone
pairs. 

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