In the conformation labeled 'Chair B', a hydrogen bonding interaction is possible between the two hydroxyl groups. One orientation of this interaction is shown below. Draw a differ... In the conformation labeled 'Chair B', a hydrogen bonding interaction is possible between the two hydroxyl groups. One orientation of this interaction is shown below. Draw a different hydrogen bonding orientation (trade which OH is the H-bond donor vs. acceptor). Additionally, explain why this intramolecular hydrogen-bonding interaction is not possible in the conformation labeled 'Chair A'.
Understand the Problem
The question is asking to illustrate a different orientation of hydrogen bonding between hydroxyl groups in Chair B and to explain why this bonding is not feasible in Chair A conformation. This involves understanding molecular structures and hydrogen bonding interactions.
Answer
Switch the donor and acceptor roles. In Chair A, hydrogen bonds can't form due to spatial constraints.
To reverse the donor and acceptor roles, swap which hydroxyl group donates the hydrogen and which one accepts it. In Chair A, the spatial arrangement of the hydroxyl groups makes it so that they are not in the correct positions to form a stable hydrogen bond.
Answer for screen readers
To reverse the donor and acceptor roles, swap which hydroxyl group donates the hydrogen and which one accepts it. In Chair A, the spatial arrangement of the hydroxyl groups makes it so that they are not in the correct positions to form a stable hydrogen bond.
More Information
Intramolecular hydrogen bonding can only occur if the donor and acceptor are properly oriented and in close proximity. Chair conformations influence the spatial arrangement of substituents.
Sources
- Hydrogen bonding (video) | Khan Academy - khanacademy.org
- 1.2.2: Hydrogen Bonding - Chemistry LibreTexts - chem.libretexts.org
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