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Tautomerization definitions

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  • Alpha Carbon
    A carbon atom directly adjacent to a carbonyl group, notable for its enhanced acidity compared to typical alkanes.
  • pKa
    A logarithmic measure of acidity; lower values indicate stronger acids, with alpha carbons showing much lower values than alkanes.
  • Tautomerization
    A process where a pi bond and a hydrogen atom exchange positions, creating constitutional isomers in equilibrium.
  • Ketone
    A carbonyl-containing compound that can undergo tautomerization, forming equilibrium with its enol form.
  • Aldehyde
    A carbonyl compound capable of tautomerization, forming tautomers with distinct structural features.
  • Constitutional Isomer
    Molecules with the same formula but different connectivity, as seen in tautomers formed during tautomerization.
  • Keto Tautomer
    The form of a tautomer that retains the original carbonyl structure, predominant in equilibrium with enol.
  • Enol Tautomer
    A tautomer featuring a hydroxyl group bonded to a double-bonded carbon, also known as a vinyl alcohol.
  • Vinyl Alcohol
    A structure with a hydroxyl group directly attached to a carbon-carbon double bond, characteristic of the enol tautomer.
  • Acid Catalysis
    A mechanism where protonation of the carbonyl initiates tautomerization, leading to the formation of enol.
  • Base Catalysis
    A mechanism where deprotonation of the alpha proton triggers tautomerization, often forming an enolate intermediate.
  • Enolate Ion
    A negatively charged intermediate formed during base-catalyzed tautomerization, highly reactive in organic reactions.
  • Conjugate Base
    The species formed after an acid donates a proton, stabilized in alpha carbons due to tautomerization.
  • Equilibrium
    A dynamic state where keto and enol tautomers interconvert, maintaining constant proportions in solution.