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Monosaccharides - Wohl Degradation definitions

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  • Wohl Degradation
    A chain-shortening process for aldoses that removes one carbon per cycle, retaining stereochemistry at all chiral centers.
  • Kiliani-Fischer Synthesis
    A chain-lengthening method for aldoses that adds a carbon, often resulting in multiple epimers.
  • Aldehyde
    A functional group in aldoses that undergoes reactions enabling both chain shortening and lengthening.
  • Cyanohydrin
    An intermediate formed by adding a cyano group to a carbonyl, which can be reversibly removed in base.
  • Base
    A reagent, often methoxide, used to eliminate the cyanohydrin and reform the carbonyl, shortening the chain.
  • Stereochemistry
    The spatial arrangement of atoms in a molecule, preserved during chain shortening in this reaction.
  • Epimer
    A sugar differing in configuration at one stereocenter; only one is produced in this chain-shortening process.
  • Oxime
    An imine derivative formed from the reaction of an aldehyde with hydroxylamine, serving as a key intermediate.
  • Hydroxylamine
    A primary amine with an -OH group, used to convert an aldehyde into an oxime.
  • Beckmann Rearrangement
    A transformation converting an oxime into a cyanohydrin using an anhydride, crucial for chain shortening.
  • Anhydride
    A dehydrating agent used to facilitate the rearrangement of an oxime to a cyanohydrin.
  • Alpha Elimination
    A reaction where two single bonds on the same carbon are replaced by a double bond, eliminating a group.
  • D-Glucose
    A common starting monosaccharide for chain shortening, converted stepwise to a shorter sugar.
  • D-Arabinose
    A monosaccharide product formed after chain shortening, with retained chirality at all centers.
  • Chiral Center
    A carbon atom bonded to four different groups, whose configuration is preserved except at the removed position.