JEE Challenger
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Number of Stable Conformers with Non-Zero Dipole Moment

Find the total number of stable\textbf{stable} conformations having a non-zero\textbf{non-zero} dipole moment for the compound shown below:

Question Diagram 1
Official Numerical Answer3

Step-by-Step Solution

To determine the total number of stable conformers with a non-zero dipole moment, we analyze the molecular structure and stereochemistry given in the Fischer projection.

1. Determination of Stereochemistry

The given compound is 2,3-dibromo-2,3-dichlorobutane: CH3−C(Br)(Cl)−C(Br)(Cl)−CH3\text{CH}_3-\text{C}(\text{Br})(\text{Cl})-\text{C}(\text{Br})(\text{Cl})-\text{CH}_3

Assigning priorities to the substituents at both chiral carbons (C2\text{C}_2 and C3\text{C}_3) using the Cahn-Ingold-Prelog (CIP) priority rules:

  1. −Br-\text{Br} (Priority 1)
  2. −Cl-\text{Cl} (Priority 2)
  3. −C(Br)(Cl)CH3-\text{C}(\text{Br})(\text{Cl})\text{CH}_3 (Priority 3)
  4. −CH3-\text{CH}_3 (Priority 4)

From the given Fischer projection:

  • At C2\text{C}_2: The path 1→2→31 \to 2 \to 3 goes clockwise with the lowest priority group (−CH3-\text{CH}_3) on a horizontal bond, giving the (2S)(2S) configuration.
  • At C3\text{C}_3: The path 1→2→31 \to 2 \to 3 goes counterclockwise with the lowest priority group (−CH3-\text{CH}_3) on a vertical bond, giving the (3S)(3S) configuration.

Thus, the given molecule is the chiral (2S,3S)(2S, 3S)-isomer (active form).


2. Analysis of Conformational Stability

  • Stable conformers correspond to local potential energy minima, which are the 3 staggered conformations around the C2−C3\text{C}_2-\text{C}_3 single bond.
  • Eclipsed conformations are energy maxima and are thus unstable.

3. Dipole Moment (μ\mu) Analysis

For a conformer to have a net dipole moment of zero (μ=0\mu = 0), it must possess a center of inversion (ii). In 2,3-disubstituted butane systems, a center of inversion requires identical groups on adjacent carbons to be in anti-positions relative to each other (Br\text{Br} anti to Br\text{Br}, Cl\text{Cl} anti to Cl\text{Cl}, and CH3\text{CH}_3 anti to CH3\text{CH}_3).

This centrosymmetric arrangement can only exist in the optically inactive meso form (2R,3S)(2R, 3S).

Since the given compound is the (2S,3S)(2S, 3S) chiral stereoisomer:

  1. It lacks a center of inversion (ii) in all of its conformations.
  2. The bond dipole vectors do not cancel out completely in any of the staggered forms.
  3. Therefore, all 33 staggered (stable) conformers possess a non-zero dipole moment (μ≠0\mu \neq 0).

Final Answer:

The total number of stable conformers with a non-zero dipole moment is 3.