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Monosaccharides - Kiliani-Fischer definitions

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  • Kiliani-Fischer Synthesis
    A method for extending monosaccharide chains by one carbon using cyanohydrin formation, selective reduction, and hydrolysis.
  • Monosaccharide
    A simple sugar molecule containing a single polyhydroxy aldehyde or ketone unit, serving as a building block for carbohydrates.
  • Cyanohydrin
    A functional group formed by nucleophilic addition of HCN to an aldehyde, introducing a cyano and a hydroxyl group to the same carbon.
  • Nucleophilic Addition
    A reaction where a nucleophile attacks an electrophilic carbonyl carbon, commonly seen in carbonyl and saccharide chemistry.
  • Aldehyde
    A carbonyl-containing functional group at the end of a carbon chain, highly reactive toward nucleophiles like cyanide.
  • Imine
    A functional group with a carbon-nitrogen double bond, formed by partial reduction of a nitrile during chain extension.
  • Hydrolysis
    A reaction involving water that cleaves chemical bonds, such as converting imines back to carbonyl groups in sugars.
  • Poisoned Catalyst
    A catalyst intentionally weakened, such as palladium on barium sulfate, to prevent over-reduction during selective transformations.
  • Diastereomer
    A stereoisomer that is not a mirror image, often resulting from new chiral centers formed during chain extension.
  • Chirality
    A property where a carbon atom has four different groups, leading to non-superimposable mirror images and stereoisomerism.
  • Catalytic Hydrogenation
    A process using hydrogen gas and a metal catalyst to reduce multiple bonds, but can over-reduce unless a poisoned catalyst is used.
  • Palladium on Barium Sulfate
    A specific poisoned catalyst used to selectively reduce nitriles to imines without full reduction to amines.
  • Chain Extension
    The process of increasing the carbon count in a monosaccharide, typically by one, through sequential chemical reactions.
  • Functional Group
    A specific group of atoms within molecules responsible for characteristic chemical reactions, such as carbonyl, cyano, or imine.
  • Yield
    The amount of product obtained from a chemical reaction, with modern methods improving this in the Kiliani-Fischer process.