Question
Draw the kinetic and thermodynamic enolates formed when 3-methylbutan-2-one (methyl isopropyl ketone) is treated with base. Include charges. Draw the oxyanion species; do not draw carbanion resonance forms.
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Concepts and reason

Kinetic Enolates

The base deprotonates the less hindered alpha hydrogen at low temperature, giving the kinetic enolate anion with less substituted C=C double bond as the major product. This enolate is less stable but it is formed very fast.

Thermodynamic Enolates

The base deprotonates the highly hindered alpha hydrogen, giving the thermodynamic enolate anion with a more substituted C=C double bond as the major product. This enolate is more thermodynamically stable.

Fundamentals

Formation of the Kinetic Enolates (Oxyanion)

Consider an unsymmetrical ketone containing two different alpha hydrogen atoms (chemically nonequivalent hydrogen atoms):

H3C
НЫС,
Base
7.
H7
-H
ketone
enolate
less substituted C=C double bond

Formation of Thermodynamic Enolates (Oxyanion)

Consider an unsymmetrical ketone containing two different alpha hydrogen atoms:

H3C、
Base
H3C、
人:
HTT
CH3 CH3
*
不
-
H
CH3
CH3
ketone
enolate
more substituted C=C double bond

Formation of the Kinetic Enolate Ion

00
Нас
I
HC
base
I
CH3
CH3
3-methylbutan-2-one
kinetic enolate ion

The Formation of Thermodynamic Enolate Ion

0
H₃C-
I
H3C
base
II
H
Η
|
н
-H
CH3
CH3
H
3-methylbutan-2-one
thermodynamic enolate ion

Ans:

kinetic enolate
thermodynamic enolate
H3C
H3C
H
CH3
H.
CH3
H

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