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The compound meso-2,3-dibromobutane with a Br and a CH3 group is described. How many stable conformers of the compound (2R,3R)-1,2-dibromo-1,2-dichloro... actually the structure described appears to be: a vicinal compound with substituents Br, Br on one carbon and Cl, CH3, Cl on another. From the structural drawing, identify the total number of stable conformers with non-zero dipole moment.

1. 1
2. 2
3. 3
4. 4

Correct answer: 3

Solution

For the compound with the given substitution pattern, there are three staggered conformers (Newman projections). The anti conformer may have a centre of inversion making the dipole moment zero. The two gauche conformers are non-superimposable and have non-zero dipole moments. The answer depends on the exact structure, but for the given compound the number of stable staggered conformers with non-zero dipole moment is 3.

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