Disubstituted Cyclo Hexanes.pptx - Disubstituted...

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Disubstituted CycloHexanes 1,1-dibromocyclohexane = achiral Trans 1,2-dibromo … chiral or achiral? There are 7 isomers to consider. Which are chiral?
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Cis, 1,2-dibromocyclohexane Ring flip Note axial Br is now equatorial and the equatorial Br is now axial Note: the axial Br is (S) and the equatorial Br is (R) Same conformation generated by a ring flip
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Cis-1,2 dibromocyclohexane - continued Enantiomers are interconverted by a ring flip Therefore not chiral, but conformational racemates due to fast interconversion between the two chair structures at equilibrium. Each chiral carbon has the same 4 groups attached and they have opposite R/S conformations. Why isn’t it meso? Although it looks like it should be meso, the compound exists overwhelmingly in the chair conformation and in this conformation there is NO Plane of Symmetry. Consider the following conformation .
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