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
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
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
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](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2Fe71f7bea-94c0-494e-933b-0ddb8363a678%2Fa37cc8ee-4c01-45e3-b81e-4b2ae1a8bed5%2Frct68y_processed.png&w=3840&q=75)
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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