he amide 4 has a nitrogen attached to the benzene ring, and a chlorine attached to a primary arbon. Yet, it doesn't react with itself in a nucleophilic displacement. Why is the nitrogen in the mide not nucleophilic? Give your answer in terms of the resonance forms of amides in general: ? R NH2
he amide 4 has a nitrogen attached to the benzene ring, and a chlorine attached to a primary arbon. Yet, it doesn't react with itself in a nucleophilic displacement. Why is the nitrogen in the mide not nucleophilic? Give your answer in terms of the resonance forms of amides in general: ? R NH2
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
Section: Chapter Questions
Problem 19.69P
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![4. The amide 4 has a nitrogen attached to the benzene ring, and a chlorine attached to a primary
carbon. Yet, it doesn't react with itself in a nucleophilic displacement. Why is the nitrogen in the
amide not nucleophilic? Give your answer in terms of the resonance forms of amides in general:
?
RT
`NH2](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F16030cd3-6f82-495c-ab93-3422ea8080ff%2Fb4343214-8a3d-4f6c-b3de-4031f7fe9588%2F31xgpv_processed.png&w=3840&q=75)
Transcribed Image Text:4. The amide 4 has a nitrogen attached to the benzene ring, and a chlorine attached to a primary
carbon. Yet, it doesn't react with itself in a nucleophilic displacement. Why is the nitrogen in the
amide not nucleophilic? Give your answer in terms of the resonance forms of amides in general:
?
RT
`NH2
![REFER TO THE SCHEME FOR THE SYNTHESIS OF LIDOCAINE SHOWN BELOW
NO2 SnCl,/ HCI
NH3 CI
NH2
Кон
CH,COOH
CH;COOH
1
2
3
2,6-Dimethy-
2,6-Dimethy-
nitrobenzene
aniline
H
toluene
5
a-Chloro-2,6-
Lidocaine
dimethylacetanilide](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F16030cd3-6f82-495c-ab93-3422ea8080ff%2Fb4343214-8a3d-4f6c-b3de-4031f7fe9588%2Fbutis49v_processed.png&w=3840&q=75)
Transcribed Image Text:REFER TO THE SCHEME FOR THE SYNTHESIS OF LIDOCAINE SHOWN BELOW
NO2 SnCl,/ HCI
NH3 CI
NH2
Кон
CH,COOH
CH;COOH
1
2
3
2,6-Dimethy-
2,6-Dimethy-
nitrobenzene
aniline
H
toluene
5
a-Chloro-2,6-
Lidocaine
dimethylacetanilide
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