Planar representation to chair conformation

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SUMMARY

The discussion centers on the chair conformation of carbohydrates, specifically \beta-D-glucose. It is established that in a Fischer projection, the \alpha position is represented to the right and down, while in chair conformation, the hydroxyl (OH) groups in \beta-D-glucose can be arranged in both axial and equatorial positions. However, the optimal arrangement for minimizing steric strain is the equatorial configuration, as it allows for a lower energy state. The axial arrangement, while theoretically possible, is less favorable due to increased steric hindrance.

PREREQUISITES
  • Understanding of Fischer projections in carbohydrate chemistry
  • Knowledge of chair conformations in cyclohexane derivatives
  • Familiarity with the concepts of axial and equatorial positions
  • Basic principles of steric strain and energy minimization in molecular structures
NEXT STEPS
  • Study the chair conformation of other carbohydrates to compare steric effects
  • Learn about the energy implications of different conformations in cyclohexane derivatives
  • Explore the concept of stereochemistry in organic compounds
  • Investigate the role of steric hindrance in molecular stability and reactivity
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Chemistry students, organic chemists, and researchers focusing on carbohydrate chemistry and molecular conformations.

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For carbohydrates, the \alpha position is to the right in a Fischer projection and down in a planar representation. Is it axial or equatorial in a chair conformation?

My book also says that all the OH groups in \beta-D-glucose are in axial positions. Is this true?
 
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leopard said:
For carbohydrates, the \alpha position is to the right in a Fischer projection and down in a planar representation. Is it axial or equatorial in a chair conformation?

My book also says that all the OH groups in \beta-D-glucose are in axial positions. Is this true?

You will note that in \beta-D-glucose the OH groups alternate left and right. This is the perfect alignment to have all of the OH groups in an equatorial arrangement. It is also the perfect alignment to have all of the OH groups (and the CH2OH group) in an axial arrangement. Which arrangement would be of lowest energy?
 

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