Planar representation to chair conformation

In summary, in a Fischer projection, the \alpha position for carbohydrates is to the right and down in a planar representation. In a chair conformation, the OH groups in \beta-D-glucose are in an equatorial arrangement, which is also the lowest energy arrangement. Therefore, the statement in the book that all the OH groups in \beta-D-glucose are in axial positions is not true.
  • #1
leopard
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For carbohydrates, the [tex]\alpha[/tex] 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 [tex]\beta[/tex]-D-glucose are in axial positions. Is this true?
 
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  • #2
leopard said:
For carbohydrates, the [tex]\alpha[/tex] 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 [tex]\beta[/tex]-D-glucose are in axial positions. Is this true?

You will note that in [tex]\beta[/tex]-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?
 
  • #3


In a chair conformation, the alpha position of a carbohydrate is considered to be in the equatorial position. This is because the equatorial position is more stable and allows for better interaction with neighboring groups. In contrast, the axial position is less stable and can lead to steric hindrance. Therefore, in a chair conformation, the alpha position is typically found in the equatorial position.

Regarding the statement about all OH groups in beta-D-glucose being in axial positions, this is not entirely accurate. In a beta-D-glucose molecule, the OH groups at the C2, C3, and C5 positions are in axial positions, while the OH group at the C4 position is in an equatorial position. This is due to the fact that in a beta-D-glucose molecule, the OH group at the C4 position is pointing down in a planar representation, while the other OH groups are pointing up. It is important to note that the positions of these OH groups can vary depending on the specific conformation of the molecule.
 

1. What is a planar representation of a chair conformation?

A planar representation of a chair conformation is a simplified way of visualizing the three-dimensional structure of a cyclohexane molecule. It represents the molecule as a flat, two-dimensional drawing with alternating single and double bonds, rather than the three-dimensional structure it actually has.

2. Why is a planar representation used for chair conformations?

A planar representation is used because it allows for a clearer and simpler visualization of the molecule's structure. It also helps to highlight the alternating single and double bonds, which are important for understanding the stability and reactivity of the molecule.

3. How is a planar representation converted to a chair conformation?

A planar representation can be converted to a chair conformation by imagining the molecule as a flat hexagon with the alternating single and double bonds. The two ends of the hexagon can then be bent upwards to form the chair shape, with the single bonds becoming the "legs" of the chair and the double bonds becoming the "arms".

4. What is the advantage of using a chair conformation over other conformations?

The chair conformation is the most stable and energetically favorable conformation for cyclohexane molecules. It also allows for maximum bond angles and minimizes steric hindrance between substituents, making it an ideal conformation for reactions to occur.

5. Can a molecule have multiple chair conformations?

Yes, a molecule can have multiple chair conformations depending on the orientation of the substituents on the cyclohexane ring. These different conformations can also interconvert through ring-flipping, in which the molecule flips from one chair conformation to another while maintaining the same overall structure.

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