(d) When a primary amine is combined with a ketone, both an imine and an enamine can be obtained. With most ketones, the major product is the imine, as shown: H3C NH2 -N -CH3 -CH3 imine: major product enamine: minor product However, in some cases, like the one shown below, the major product is the enamine. CO₂Et CO₂Et CO₂Et H H3C NH2 -CH3 imine: minor product -CH3 enamine: major product Referring to specific features of the starting materials, intermediates, or products, explain why.
(d) When a primary amine is combined with a ketone, both an imine and an enamine can be obtained. With most ketones, the major product is the imine, as shown: H3C NH2 -N -CH3 -CH3 imine: major product enamine: minor product However, in some cases, like the one shown below, the major product is the enamine. CO₂Et CO₂Et CO₂Et H H3C NH2 -CH3 imine: minor product -CH3 enamine: major product Referring to specific features of the starting materials, intermediates, or products, explain why.
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 23.36P
Related questions
Question
![(d) When a primary amine is combined with a ketone, both an imine and an enamine can be
obtained. With most ketones, the major product is the imine, as shown:
H3C
NH2
-N
-CH3
-CH3
imine:
major product
enamine:
minor product
However, in some cases, like the one shown below, the major product is the enamine.
CO₂Et
CO₂Et
CO₂Et
H
H3C
NH2
-CH3
imine:
minor product
-CH3
enamine:
major product
Referring to specific features of the starting materials, intermediates, or products, explain why.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2Fe30c5dfd-22e5-43e4-a344-ec8c335a1df7%2F46b8287c-a558-4b8f-814e-cba6b6417367%2Fdx4c1lr_processed.png&w=3840&q=75)
Transcribed Image Text:(d) When a primary amine is combined with a ketone, both an imine and an enamine can be
obtained. With most ketones, the major product is the imine, as shown:
H3C
NH2
-N
-CH3
-CH3
imine:
major product
enamine:
minor product
However, in some cases, like the one shown below, the major product is the enamine.
CO₂Et
CO₂Et
CO₂Et
H
H3C
NH2
-CH3
imine:
minor product
-CH3
enamine:
major product
Referring to specific features of the starting materials, intermediates, or products, explain why.
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