Question
Download Solution PDFThe structure that corresponds to the most stable conformation of the following compound is
Answer (Detailed Solution Below)
Detailed Solution
Download Solution PDFConcept:
- In a 6-membered heterocyclic system, the electronegative group joined with the adjacent carbon of hetero-atom prefers a more sterically hindered axial configuration over a less steric equatorial position.
- The reason behind this is anomeric effect as shown by the picture given below:
- As we can see in axial conformation the antibonding orbital of the adjacent group is parallel to the non-bonding orbitals of oxygen. The lone pairs can be shared to the antibonding orbital, providing them extra stability. This is called Anomeric effect.
- No such effect can be seen in equatorial configuration.
Explanation:
The given structure is:
As we can see two of the chlorine groups on the either left or right side of O are trans to each other. Therefore, option (2) and (3) are incorrect.
Now, the possible configurations are :
and
considering the arrangement of Cl and anomeric effect the correct and more stable configuration will be the with axial C-Cl bonds, that is:
Conclusion:
Hence, the correct option is (4).
Last updated on Jun 5, 2025
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