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Gabriel Synthesis definitions

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  • Gabriel Synthesis
    A method using potassium thalidomide to efficiently produce primary amines, avoiding polyalkylation and unwanted by-products.
  • Potassium Thalidomide
    A secondary diamide anion formed by deprotonation, acting as a strong nucleophile in the synthesis of primary amines.
  • Primary Amine
    A compound with a nitrogen atom bonded to one alkyl group and two hydrogens, the main product of this synthesis.
  • KOH
    A strong base used to deprotonate thalidomide, generating the nucleophilic species needed for the reaction.
  • Alkyl Halide
    A molecule containing a halogen attached to a primary carbon, serving as the electrophile in the SN2 step.
  • Hydrazine
    A nucleophilic reagent (NH2NH2) that cleaves the nitrogen from thalidomide, enabling release of the primary amine.
  • SN2 Mechanism
    A one-step nucleophilic substitution involving backside attack, leading to inversion of configuration at the electrophilic carbon.
  • Nucleophile
    A species with a lone pair or negative charge, capable of attacking electrophilic centers in organic reactions.
  • Nucleophilic Acyl Substitution
    A mechanism where a nucleophile replaces a leaving group on a carbonyl compound, forming a tetrahedral intermediate.
  • Tetrahedral Intermediate
    A transient structure formed during nucleophilic attack on a carbonyl, featuring four groups attached to the central carbon.
  • Proton Transfer
    A step where a hydrogen ion moves between atoms, often stabilizing intermediates or facilitating leaving group departure.
  • Polyalkylation
    An undesired process where multiple alkyl groups attach to a nitrogen, leading to mixtures rather than a single primary amine.
  • Leaving Group
    An atom or group that departs with a pair of electrons during a substitution or elimination reaction.
  • Carboxylic Acid Derivative
    A compound structurally related to carboxylic acids, such as amides, which can undergo nucleophilic substitution.
  • Diamide
    A molecule containing two amide groups, as seen in thalidomide, which influences its reactivity in synthesis.