Conformational Analysis of Mono substituted Cyclohexane | Stereochemistry | Organic Chemistry

Cyclohexane is the most stable alicyclic ring system. The cyclohexane ring exists in the non-planar conformation to avoid the angle strain.

When a hydrogen atom in cyclohexane is replaced by some substituent R like CH3, OH or Br and which is larger than hydrogen, then substituent can either be axial or in equatorial position in the chair conformation.

Accurate measurements have shown that an axial substitution at 1 is closer to the two axial hydrogen atoms at 3 and 5 positions as compared to the other hydrogen atoms. Thus 1a, 3a interaction will be greater than 1a, 2e or 1e, 2a interaction. The steric repulsion between the axial groups at 1,3-positions in the ring is called 1,3-diaxial interaction. Therefore, a monosubstituted cyclohexane will assume the conformation in which the substituent occupies an equatorial position to avoid the 1,3-diaxial interactions.

It has been calculated that the equatorial conformation of methyl-cyclohexane is more stable than the axial conformation by about 1.7 kcal/mole.

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