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.
Reactions of Ethers
Ethers (R-O-R’) are compounds formed by replacing hydrogen atoms of an alcohol (R-OH compound) or a phenol (C6H5OH) by an aryl/ acyl group (functional group after removing single hydrogen from an aromatic ring). In this section, reaction, preparation and behavior of ethers are discussed in the context of organic chemistry.
Epoxides
Epoxides are a special class of cyclic ethers which are an important functional group in organic chemistry and generate reactive centers due to their unusual high reactivity. Due to their high reactivity, epoxides are considered to be toxic and mutagenic.
Williamson Ether Synthesis
An organic reaction in which an organohalide and a deprotonated alcohol forms ether is known as Williamson ether synthesis. Alexander Williamson developed the Williamson ether synthesis in 1850. The formation of ether in this synthesis is an SN2 reaction.
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
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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