5. In the reaction below, what factors come into play to favor attack of the aniline 3 on the carbonyl carbon of the acid chloride (carbon 1 in red), rather than at the a-carbon (carbon 2 in red)? „NH2 3

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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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
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
5. In the reaction below, what factors come into play to favor attack of the aniline 3 on the carbonyl
carbon of the acid chloride (carbon 1 in red), rather than at the a-carbon (carbon 2 in red)?
LNH2
2
Transcribed Image Text:5. In the reaction below, what factors come into play to favor attack of the aniline 3 on the carbonyl carbon of the acid chloride (carbon 1 in red), rather than at the a-carbon (carbon 2 in red)? LNH2 2
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