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Directed Condensations definitions

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  • Aldol Condensation
    A reaction where an enolate attacks an electrophilic carbonyl, forming a β-hydroxy carbonyl compound.
  • Asymmetrical Ketone
    A molecule with two different groups attached to the carbonyl carbon, allowing formation of two distinct enolates.
  • Enolate
    A resonance-stabilized anion formed by deprotonation of a carbon adjacent to a carbonyl group.
  • Directed Reaction
    A process used to selectively generate a specific enolate from a molecule with multiple possible sites.
  • Thermodynamic Enolate
    The more substituted, stable enolate formed under equilibrium conditions, favored by small bases.
  • Kinetic Enolate
    The less substituted, rapidly formed enolate favored by bulky bases and low temperatures.
  • Thermodynamic Control
    A condition where product distribution is determined by relative stability, typically using small bases.
  • Kinetic Control
    A condition where product distribution is determined by the rate of formation, typically using bulky bases.
  • Small Base
    A reagent like NaOH that can access more hindered positions, favoring formation of the more substituted enolate.
  • Bulky Base
    A large, sterically hindered base such as LDA, favoring deprotonation at less hindered positions.
  • LDA
    A non-nucleophilic, bulky base commonly used to generate kinetic enolates selectively.
  • Tert Butoxide
    A bulky base that can also be used to favor formation of kinetic enolates by deprotonating less hindered sites.
  • Non-nucleophilic Base
    A base that removes protons without adding to electrophilic centers, preventing side reactions.
  • Electrophile
    A species with an electron-deficient center that reacts with nucleophiles like enolates.