Chapter 22: Carbonyl Alpha-Substitution Reactions

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Last updated 12:46 PM on 4/8/26
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4 Terms

1
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alpha substitution

occurs at position adjacent to a carbonyl

  • replacement of a hydrogen atom with another group through an enol or enolate intermediate

2
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tautomerism

spontaneous interconversion between two isomers (keto —> enol)

  • favors keto form normally

  • enolization is catalyzed by acid + base

3
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acidity of alpha protons

only protons adjacent to the carbonyl are acidic

  • corresponding anion is resonance stabilized

4
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reactivity of enols

double bond of an enol is electron rich

  • behave as nucleophiles but are more reactive