3. N,N-Dimethylaniline is an extremely reactive aromatic substrate and readily reacts with even very weak electrophiles. This reactivity is greatly diminished by introduction of alkyl substituents in the ortho position, as in o-methyl-N,N-dimethylaniline. Considering what you know about the theory of aromaticity, conjugation, pi bonding, as well as electron- withdrawing and electron-donating groups, explain this difference in reactivity. Н HIC H-C-H H N,N-Dimethylaniline HH H H H H H o-Methyl-N,N-Dimethylaniline

Organic Chemistry
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Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
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Chapter23: Amines
Section: Chapter Questions
Problem 23.58P
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3.
N,N-Dimethylaniline is an extremely reactive aromatic substrate and readily reacts with
even very weak electrophiles. This reactivity is greatly diminished by introduction of alkyl
substituents in the ortho position, as in o-methyl-N,N-dimethylaniline. Considering what
you know about the theory of aromaticity, conjugation, pi bonding, as well as electron-
withdrawing and electron-donating groups, explain this difference in reactivity.
Н
HIC
H-C-H
H
N,N-Dimethylaniline
HH
H
H
H
H H
o-Methyl-N,N-Dimethylaniline
Transcribed Image Text:3. N,N-Dimethylaniline is an extremely reactive aromatic substrate and readily reacts with even very weak electrophiles. This reactivity is greatly diminished by introduction of alkyl substituents in the ortho position, as in o-methyl-N,N-dimethylaniline. Considering what you know about the theory of aromaticity, conjugation, pi bonding, as well as electron- withdrawing and electron-donating groups, explain this difference in reactivity. Н HIC H-C-H H N,N-Dimethylaniline HH H H H H H o-Methyl-N,N-Dimethylaniline
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