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Ozonolysis Full Mechanism definitions

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  • Ozonolysis
    Oxidative cleavage of alkenes using ozone, producing carbonyl compounds via unstable cyclic intermediates.
  • Ozonide
    Unstable, three-membered cyclic intermediate with three oxygens, formed after ozone adds to an alkene.
  • Molozonide
    First unstable intermediate in the reaction, formed immediately after ozone adds to an alkene double bond.
  • Reductive Workup
    Process using agents like DMS or zinc/acetic acid to convert ozonides into aldehydes and ketones.
  • Oxidative Workup
    Treatment with hydrogen peroxide that transforms ozonides into carboxylic acids and ketones.
  • Dimethyl Sulfide
    Common reducing agent in the reaction, attacking ozonides to yield DMSO and carbonyl products.
  • Hydrogen Peroxide
    Oxidizing agent used to convert aldehyde intermediates into carboxylic acids during the reaction.
  • Aldehyde
    Product formed from ozonolysis under reductive conditions, containing a carbonyl group bonded to hydrogen.
  • Ketone
    Product of both reductive and oxidative workups, featuring a carbonyl group bonded to two carbons.
  • Carboxylic Acid
    Compound produced from aldehydes during oxidative workup, containing a carbonyl and hydroxyl group.
  • Sigma Bond
    Single covalent bond formed by direct overlap of orbitals, broken and formed during the mechanism.
  • Pi Bond
    Bond formed by sideways overlap of p orbitals, present in alkenes and broken during the reaction.
  • Nucleophile
    Species with a negative charge or lone pair, attacking electrophilic centers in the mechanism.
  • Electrophile
    Atom or group with partial positive charge, attracting nucleophiles during bond formation.
  • Stereochemistry
    Spatial arrangement of atoms retained during the syn addition of ozone to the alkene.