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Imine vs Enamine definitions

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  • Imine
    Compound resembling a carbonyl but with a nitrogen double-bonded to carbon, formed from a primary amine and a carbonyl under acidic conditions.
  • Enamine
    Molecule with a nitrogen atom bonded to a carbon-carbon double bond, produced by reacting a secondary amine with a carbonyl in acid.
  • Iminium Cation
    Positively charged intermediate featuring a nitrogen double-bonded to carbon and carrying a formal positive charge, crucial in imine and enamine formation.
  • Primary Amine
    Nitrogen-containing group bonded to one carbon, reacts with carbonyls to yield imines in the presence of acid.
  • Secondary Amine
    Nitrogen atom bonded to two carbons, often cyclic, reacts with carbonyls to form enamines under acidic conditions.
  • Protonation
    Initial step where a proton is added to a carbonyl oxygen, increasing its electrophilicity for subsequent nucleophilic attack.
  • Nucleophilic Attack
    Step where an amine's lone pair forms a bond with the electrophilic carbon of a protonated carbonyl.
  • Proton Transfer
    Movement of a proton within the reaction intermediate, facilitating the departure of a leaving group or stabilization.
  • Elimination
    Step where a leaving group, such as water, is expelled, often forming a double bond in the process.
  • Alpha Hydrogen
    Hydrogen atom attached to the carbon adjacent to a carbonyl, removed during enamine formation to create a double bond.
  • Asymmetrical Ketone
    Ketone with two different alkyl groups, leading to multiple possible enamine products depending on double bond placement.
  • Resonance Structure
    Alternative Lewis structure showing electron delocalization, used to depict charge distribution in intermediates.
  • Leaving Group
    Atom or group, such as water, that departs from a molecule during a reaction, enabling double bond formation.
  • Conjugate Acid
    Species formed when a base gains a proton, often present as NH4+ in these mechanisms to facilitate proton transfers.
  • Catalytic Acid
    Acid used to accelerate the reaction without being consumed, typically regenerated at the end of the mechanism.