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Monosaccharides - Aldose-Ketose Rearrangement quiz

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  • What is the aldose-ketose rearrangement also known as?
    The aldose-ketose rearrangement is also known as the indial rearrangement or the Lobry de Bruyn Van Eckenstein reaction.
  • What intermediate is crucial for the aldose-ketose rearrangement?
    The enediol intermediate is crucial for the aldose-ketose rearrangement.
  • What transformation can occur at C2 through the enediol mechanism?
    Epimerization at C2 can occur through the enediol mechanism.
  • What is the result of the aldose-ketose rearrangement of glucose?
    The aldose-ketose rearrangement of glucose results in the conversion of glucose into fructose.
  • What is the role of base in the aldose-ketose rearrangement?
    The base removes an alpha hydrogen from the monosaccharide, forming an enediol intermediate.
  • What happens to the stereochemical information during the formation of the enediol intermediate?
    The stereochemical information is lost from carbon 2 during the formation of the enediol intermediate.
  • What can happen if the base removes a proton from carbon 2 instead of the top proton?
    If the base removes a proton from carbon 2, it can lead to the formation of a ketohexose like fructose.
  • What is required for epimerization at C3 to occur?
    Very strongly basic conditions are required for epimerization at C3 to occur.
  • Why is the aldose-ketose rearrangement considered inefficient?
    The aldose-ketose rearrangement is considered inefficient because it produces a mixture of isomers.
  • What is the significance of the enediol intermediate beyond epimerization?
    The enediol intermediate is significant for rearrangement, allowing the conversion of an aldose to a ketose.