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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Question
![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?](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2Fc418f0cd-165a-4ea5-9a24-6d9fb76e817b%2F3d9ea1b1-f3b9-4c26-b9b7-ffa8575322ea%2Fceye66g_processed.jpeg&w=3840&q=75)
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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