CHEM 2312 Exam 3

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Enols/Enolates, Aldol + Condensations, Imines + Enamines, Amines

Last updated 3:55 AM on 4/10/26
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16 Terms

1
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Ketone/Enol tautomerization is ___ catalyzed

acid (H3O+) or base (-OH)

2
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Acid Catalyzed enol/ketone tautomerization mechanism

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Base Catalyzed enol/ketone tautomerization mechanism

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Enolate structure and properties

  • deprotonated version of an enol

  • can attack from the oxygen or carbon position

<ul><li><p>deprotonated version of an enol</p></li><li><p>can attack from the oxygen or carbon position</p></li></ul><p></p>
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When unsymmetrical ketones tautomerize to enols, which types of enols are favored?

the more substituted enol

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Ketone vs Enol preference

  • usually ketone is favored unless hydrogen bonding can occur (diketone) or connected group is aromatic in enol form

<ul><li><p>usually ketone is favored unless hydrogen bonding can occur (diketone) or connected group is aromatic in enol form</p></li></ul><p></p>
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<p>Ketone → Enolate</p>

Ketone → Enolate

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<p>Ketone → Enolate</p>

Ketone → Enolate

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<p>Ketone → Enolate</p>

Ketone → Enolate

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