Draw out a complete mechanism for imine formation from the reaction of 4-iodoaniline will be 4-nitrobenzaldehyde. Be sure to include all

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
Chapter18: Functional Derivatives Of Carboxylic Acids
Section: Chapter Questions
Problem 18.42P
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Chemistry
Draw out a complete mechanism for imine
formation from the reaction of 4-iodoaniline will
be 4-nitrobenzaldehyde. Be sure to include all
appropriate arrows. This aryl imine synthesis
was performed using 95:5 ethyl lactate: water
(v/v) solvent the pH of the solvent is ~ 5.
With knowledge of the mechanism of imine
formation answer the following:
a) if the reaction was performed in an HCl: ethyl
lactate: water solvent system with a pH = 0 what
would occur? Why?
b) if the reaction was performed in an NaOH:
ethyl lactate: water solvent system at pH = 10
what would occur? Why?
c) if the reaction was performed in a 100% water
solvent system would it work? Why or why not?
Transcribed Image Text:Chemistry Draw out a complete mechanism for imine formation from the reaction of 4-iodoaniline will be 4-nitrobenzaldehyde. Be sure to include all appropriate arrows. This aryl imine synthesis was performed using 95:5 ethyl lactate: water (v/v) solvent the pH of the solvent is ~ 5. With knowledge of the mechanism of imine formation answer the following: a) if the reaction was performed in an HCl: ethyl lactate: water solvent system with a pH = 0 what would occur? Why? b) if the reaction was performed in an NaOH: ethyl lactate: water solvent system at pH = 10 what would occur? Why? c) if the reaction was performed in a 100% water solvent system would it work? Why or why not?
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