D & L Glucose: Haworth Formula Explained

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SUMMARY

The discussion clarifies the representation of D and L glucose in the Haworth formula, specifically addressing the stereochemistry of carbon 5. It confirms that both representations of D glucose are valid despite the apparent contradiction regarding the positioning of hydrogen and hydroxyl groups. The conversation emphasizes the rapid rotation around the C4-C5 bond, which allows for the interchangeability of the D and L forms without altering their stereochemistry. The participants express a shared frustration with the D/L convention, indicating a need for clearer understanding.

PREREQUISITES
  • Understanding of carbohydrate chemistry
  • Familiarity with stereochemistry concepts
  • Knowledge of the Haworth projection for cyclic sugars
  • Basic grasp of molecular rotation and conformational analysis
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  • Study the Haworth projection of carbohydrates in detail
  • Explore stereochemical conventions in organic chemistry
  • Learn about conformational analysis of cyclic compounds
  • Investigate the implications of D/L nomenclature in biochemical contexts
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Chemistry students, organic chemists, and anyone studying carbohydrate structures and their stereochemical representations.

gracy
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It is a rotation around the axis defined by the C4-C5 bond by 60°. Bonds are allowed to rotate, and do so very quickly without changing stereochemistry. Imagine the three substituents on C5 as the legs of a tripod, with the camera or whatnot as the rest of the molecule, and you may be able to see it better.

Refer to this link for an idea about D/L. For what it's worth, I agree with that author about the whole D/L convention. It always annoyed me and I never retained that information beyond whatever exam I needed to know it for.
 

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