transcyclohexanol

Transcyclohexanol is an organic chemical compound with the molecular formula C6H12O. It is a stereoisomer of cyclohexanol, meaning it has the same chemical formula and connectivity but a different spatial arrangement of atoms. Specifically, in trans-cyclohexanol, the hydroxyl group (-OH) and the hydrogen atom on the adjacent carbon atom are on opposite sides of the cyclohexane ring's plane. This contrasts with cis-cyclohexanol, where these two groups are on the same side.

The cyclohexane ring typically exists in a chair conformation, which is the most stable arrangement. In trans-cyclohexanol, the two substituents (the hydroxyl group and the hydrogen atom) are in equatorial positions, or one is axial and the other equatorial. However, due to ring flipping, both configurations are possible and interconvert. The equatorial-equatorial conformation is generally more stable.

Trans-cyclohexanol is a colorless solid at room temperature and is soluble in organic solvents and moderately soluble in water. It is produced through the reduction of cyclohexanone. The stereochemistry of the reduction process, using different reducing agents, can favor the formation of either the cis or trans isomer. For example, catalytic hydrogenation often yields a mixture, while some chemical reducing agents can selectively produce the trans isomer. Trans-cyclohexanol can be used as a chemical intermediate in the synthesis of other organic compounds.