Fischer Projection to Haworth/Chair Conformation

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SUMMARY

The conversion from Fischer projection to Haworth and chair conformations cannot definitively indicate whether the resulting ring structure will be in the alpha or beta form without prior knowledge. This is due to the phenomenon of mutarotation, where the C-1 to C-2 bond rotates during the interconversion between open and closed forms of glucose. In aqueous solution, glucose exists in equilibrium between its open and closed forms, with the beta anomer being more predominant than the alpha anomer. This equilibrium is a key factor in understanding the behavior of monosaccharides.

PREREQUISITES
  • Understanding of Fischer projections
  • Knowledge of Haworth projections
  • Familiarity with chair conformations
  • Concept of mutarotation in carbohydrates
NEXT STEPS
  • Study the mechanism of mutarotation in detail
  • Learn about the structural differences between alpha and beta anomers
  • Explore the equilibrium dynamics of monosaccharides in solution
  • Investigate the role of solvent in carbohydrate conformation
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Chemistry students, organic chemists, and anyone studying carbohydrate chemistry will benefit from this discussion.

ngu9997
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Can you tell if the ring will be beta or alpha in the haworth projection, chair conformation by just looking at the Fischer projection, or must you be told first before creating the two from the Fischer? If so, could someone explain how? I've seen a bunch of websites and they all seem to say that you won't be able to tell from a Fischer alone.
 
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In aqueous solution, glucose exists in both the open and closed forms. These two forms always exist in equilibrium. In the process of converting from closed to open form and then back to closed form, the C-1→ C-2 bond rotates. This rotation produces either of the two anomers. We term this phenomenon of opening of the ring, rotation of the C-1→ C-2 bond and the subsequent closing of the ring as mutarotation. So as a result of mutarotation, both the α and β anomers are present in equilibrium in solution. In the case of glucose, β anomer is more predominant than α anomer. This may not be the case with all the monosaccharides.
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https://www.khanacademy.org/test-pr...d-ketones/a/cyclic-hemiacetals-and-hemiketals
 

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