Could you help me with this question? I don't know where to start. All the information has been provided. 4. The amide 4 has a nitrogen attached to the benzene ring, and a chlorine attached to a primarycarbon. Yet, it doesn't react with itself in a nucleophilic displacement. Why is the nitrogen in theamide 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 BELOWNO2 SnCl,/ HCINH3 CINH2КонCH,COOHCH;COOH1232,6-Dimethy-2,6-Dimethy-nitrobenzeneanilineHtoluene5a-Chloro-2,6-Lidocainedimethylacetanilide

The explanation of the organic reaction is given below

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

Chapter23: Amines

Section: Chapter Questions

Problem 23.68P: Show how the synthetic scheme developed in Problem 23.67 can be modified to synthesize this...

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Question

Could you help me with this question? I don't know where to start. All the information has been provided.

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

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