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Baeyer-Villiger Oxidation definitions

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  • Baeyer-Villiger Oxidation
    A reaction converting ketones to esters and aldehydes to carboxylic acids by inserting an oxygen atom using a peroxy acid.
  • Peroxy Acid
    An oxidizing agent containing an extra oxygen atom, commonly used to insert oxygen into carbonyl compounds.
  • MCPBA
    A widely used peroxy acid, meta-chloroperoxybenzoic acid, notable for its efficiency in oxygen insertion reactions.
  • Migratory Aptitude
    A ranking of groups based on their tendency to shift during oxygen insertion, following the trend: H > tertiary > secondary > aromatic > primary.
  • Ketone
    A carbonyl compound that, when oxidized in this reaction, forms an ester via oxygen insertion.
  • Aldehyde
    A carbonyl compound that, upon oxidation, yields a carboxylic acid through oxygen insertion.
  • Ester
    A functional group produced from a ketone after oxygen is inserted between the carbonyl and the migrating group.
  • Carboxylic Acid
    A functional group formed from an aldehyde after oxygen insertion, increasing the oxidation state.
  • Migration
    A key mechanistic step where a group shifts from the carbonyl carbon to an adjacent oxygen atom during the reaction.
  • Stereochemistry
    The spatial arrangement of atoms, which remains unchanged throughout this oxidation process.
  • Absolute Configuration
    The R/S designation of a chiral center, preserved during the reaction, ensuring product and reactant share the same configuration.
  • Protonation
    The initial step where a carbonyl oxygen gains a proton, activating the molecule for further reaction.
  • Nucleophilic Addition
    A mechanistic step where a nucleophile attacks the carbonyl carbon, forming a new bond and setting up migration.
  • Deprotonation
    The final step where a proton is removed, yielding a neutral product and a carboxylic acid byproduct.
  • Regioselectivity
    The preference for oxygen insertion at the position adjacent to the group with the highest migratory aptitude.