Number of Stable Conformers with Non-Zero Dipole Moment
Find the total number of conformations having a dipole moment for the compound shown below:

Topics & Concepts
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:
Assigning priorities to the substituents at both chiral carbons ( and ) using the Cahn-Ingold-Prelog (CIP) priority rules:
- (Priority 1)
- (Priority 2)
- (Priority 3)
- (Priority 4)
From the given Fischer projection:
- At : The path goes clockwise with the lowest priority group () on a horizontal bond, giving the configuration.
- At : The path goes counterclockwise with the lowest priority group () on a vertical bond, giving the configuration.
Thus, the given molecule is the chiral -isomer (active form).
2. Analysis of Conformational Stability
- Stable conformers correspond to local potential energy minima, which are the 3 staggered conformations around the single bond.
- Eclipsed conformations are energy maxima and are thus unstable.
3. Dipole Moment () Analysis
For a conformer to have a net dipole moment of zero (), it must possess a center of inversion (). 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 ( anti to , anti to , and anti to ).
This centrosymmetric arrangement can only exist in the optically inactive meso form .
Since the given compound is the chiral stereoisomer:
- It lacks a center of inversion () in all of its conformations.
- The bond dipole vectors do not cancel out completely in any of the staggered forms.
- Therefore, all staggered (stable) conformers possess a non-zero dipole moment ().
Final Answer:
The total number of stable conformers with a non-zero dipole moment is 3.