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Q.

The most stable conformation of 3-fluorobutan-2-ol is

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a

Anti form

b

Gauche form

c

Fully eclipsed form

d

Partially eclipsed form

answer is C.

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Detailed Solution

Question Image

The most stable conformation of 3-fluorobutan-2-ol is the one where the –OH group at C-2 and the fluorine atom at C-3 are gauche to each other.

Explanation:

  1.  

  2. Structure:

    • Butan-2-ol has the –OH group attached to C-2.

    • In 3-fluorobutan-2-ol, a fluorine atom is attached to C-3.

  3. Conformational analysis:

    • Around the C-2–C-3 bond, there can be anti or gauche conformations between –OH and –F.

    • Normally, anti would be favored to minimize steric repulsion.

  4.  

  5. Gauche effect:

    • In molecules with electronegative substituents on adjacent carbons, a gauche conformation is stabilized.

    • Here, stabilization arises from hyperconjugation and orbital interactions:

      • The lone pair on oxygen overlaps with the σ* orbital of C–F bond, giving extra stabilization.

  6.  

  7. Conclusion:

    • Due to this gauche effect, the most stable conformation of 3-fluorobutan-2-ol is the one where –OH and –F are gauche to each other (dihedral angle ≈ 60°).

    •  

Final Answer:
The most stable conformation of 3-fluorobutan-2-ol is the gauche conformation, where the hydroxyl group at C-2 and the fluorine atom at C-3 are gauche to each other.

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