In cationic rearrangements like the pinacol reaction, migrating hydrogens and alkyl groups are shown moving in one step from carbon to carbon as pictured below. This reaction is also classified as a [1,2]-sigmatropic rearrangement. R R R -C+-R R .C+ -R OH R OH R But for migration of phenyl groups (benzene rings), the rearrangement proceeds by a two step process as pictured below: R C+ -R R OH R он R H -R R-C+ OH R -R Relative the to benzene ring and considering the center intermediate, phenyl migration is a(n) a. acyl substitution b. SN2 c. nucleophilic aromatic d. benzyne e. free radical f. electrophilic aromatic g. carbonyl h. SN1 Clear my choice substitution?

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
Chapter19: Enolate Anions And Enamines
Section19.9: Crossed Enolate Reactions Using Lda
Problem JQ
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In cationic rearrangements like the pinacol reaction, migrating hydrogens and alkyl groups are shown moving in one step from carbon to carbon as pictured below. This reaction is also
classified as a [1,2]-sigmatropic rearrangement.
R
R
R
-C+-R
R
.C+
-R
OH
R
OH
R
But for migration of phenyl groups (benzene rings), the rearrangement proceeds by a two step process as pictured below:
R
C+ -R
R
OH
R
он
R
H
-R
R-C+
OH
R
-R
Relative the to benzene ring and considering the center intermediate, phenyl migration is a(n)
a. acyl substitution
b. SN2
c. nucleophilic aromatic
d. benzyne
e. free radical
f.
electrophilic aromatic
g. carbonyl
h. SN1
Clear my choice
substitution?
Transcribed Image Text:In cationic rearrangements like the pinacol reaction, migrating hydrogens and alkyl groups are shown moving in one step from carbon to carbon as pictured below. This reaction is also classified as a [1,2]-sigmatropic rearrangement. R R R -C+-R R .C+ -R OH R OH R But for migration of phenyl groups (benzene rings), the rearrangement proceeds by a two step process as pictured below: R C+ -R R OH R он R H -R R-C+ OH R -R Relative the to benzene ring and considering the center intermediate, phenyl migration is a(n) a. acyl substitution b. SN2 c. nucleophilic aromatic d. benzyne e. free radical f. electrophilic aromatic g. carbonyl h. SN1 Clear my choice substitution?
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