During the decarboxylation of acetoacetate, what is the nucleophile and what is the electrophile? Is the formation of a schiff base simply a preparation step or is the formation of a schiff base formed also by nucleophile/electrophile interaction?

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter20: Carboxylic Acids And Nitriles
Section20.8: Spectroscopy Of Carboxylic Acids And Nitriles
Problem 15P: Cyclopentanecarboxylic acid and 4-hydroxycyclohexanone have the same formula (C6H10O2), and both...
icon
Related questions
Question

During the decarboxylation of acetoacetate, what is the nucleophile and what is the electrophile? Is the formation of a schiff base simply a preparation step or is the formation of a schiff base formed also by nucleophile/electrophile interaction?

 

CO₂
H+
Love 2 [onfron] I ow-t-ons
[CH₂]
ci
CH3-C-CH₂
CH3-C=
CH3-C-CH3
Acetoacetate
OH
-RNH₂
CH3-C-CH2
0:
Enolate
Acetoacetate decarboxylase
CO₂
H+
Figure 11-11
©2013 John Wiley & Sons, Inc. All rights reserved.
R
CH3-C=CH₂
in
Schiff base Electrophile
(imine)
RNH2
Acetone
-OH
H
CH3-C-CH3
Transcribed Image Text:CO₂ H+ Love 2 [onfron] I ow-t-ons [CH₂] ci CH3-C-CH₂ CH3-C= CH3-C-CH3 Acetoacetate OH -RNH₂ CH3-C-CH2 0: Enolate Acetoacetate decarboxylase CO₂ H+ Figure 11-11 ©2013 John Wiley & Sons, Inc. All rights reserved. R CH3-C=CH₂ in Schiff base Electrophile (imine) RNH2 Acetone -OH H CH3-C-CH3
Expert Solution
trending now

Trending now

This is a popular solution!

steps

Step by step

Solved in 3 steps

Blurred answer
Knowledge Booster
Aldehydes and Ketones
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Similar questions
  • SEE MORE QUESTIONS
Recommended textbooks for you
Organic Chemistry
Organic Chemistry
Chemistry
ISBN:
9781305080485
Author:
John E. McMurry
Publisher:
Cengage Learning
Introduction to General, Organic and Biochemistry
Introduction to General, Organic and Biochemistry
Chemistry
ISBN:
9781285869759
Author:
Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:
Cengage Learning