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Conjugate Addition definitions

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  • Enone
    Alpha, beta-unsaturated carbonyl compound formed from aldol condensation, featuring two electrophilic regions due to resonance.
  • Aldol Reaction
    Process forming beta-hydroxy carbonyls, which upon dehydration yield enones capable of further nucleophilic or conjugate additions.
  • Conjugate Addition
    Nucleophilic attack at the beta carbon (4 position) of an enone, typically leading to loss of the double bond at that site.
  • Nucleophilic Addition
    Attack by a strong nucleophile at the carbonyl carbon (2 position) of an enone, producing a substituted alcohol with a double bond.
  • Resonance Structure
    Alternative electron arrangements in enones that reveal multiple electrophilic sites, influencing reactivity.
  • Grignard Reagent
    Strong organomagnesium nucleophile favoring 1,2-addition to enones, resulting in alcohols with retained double bonds.
  • Organolithium
    Highly reactive organometallic nucleophile that prefers 1,2-addition to enones, similar to Grignard reagents.
  • Gilman Reagent
    Lithium dialkylcuprate, a weaker organometallic nucleophile, favoring conjugate (1,4) addition to enones.
  • Michael Reaction
    Conjugate addition of an enolate to an enone, forming a 1,5-dicarbonyl compound capable of further cyclization.
  • Stork Enamine Synthesis
    Conjugate addition of an enamine to an enone, also yielding a 1,5-dicarbonyl intermediate.
  • Enolate
    Resonance-stabilized anion derived from deprotonation of a carbonyl compound, acting as a nucleophile in Michael reactions.
  • Enamine
    Nitrogen-containing nucleophile with a double bond, used in Stork synthesis for conjugate addition to enones.
  • 1,5-Dicarbonyl
    Product of Michael or Stork reactions, featuring two carbonyl groups separated by three carbons, prone to cyclization.
  • Electrophilic Region
    Site within an enone susceptible to nucleophilic attack, determined by resonance and position relative to the carbonyl.
  • Cyclization
    Transformation where a linear 1,5-dicarbonyl intermediate forms a six-membered ring, often following conjugate addition.