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A monosubstituted cyclohexane is one in which there is one non-hydrogen substituent in the cyclohexane ring. The most energetically favorable conformation for a monosubstituted cyclohexane is the chair conformation with the non-hydrogen substituent in the equatorial position because it prevents high steric strain from 1,3 diaxial interactions. [11]
Another conformation of cyclohexane exists, known as boat conformation, but it interconverts to the slightly more stable chair formation. If cyclohexane is mono-substituted with a large substituent , then the substituent will most likely be found attached in an equatorial position, as this is the slightly more stable conformation .
A-values help predict the conformation of cyclohexane rings. The most stable conformation will be the one which has the substituent or substituents equatorial. When multiple substituents are taken into consideration, the conformation where the substituent with the largest A-value is equatorial is favored.
Cyclohexane-1,2,3,4,5,6-hexol is a family of chemical compounds with formula C 6 H 12 O 6, whose molecule consists of a ring of six carbon atoms, each bound to one hydrogen atom and one hydroxyl group (–OH). There are nine stereoisomers, that differ by the position of the hydroxyl groups relative to the mean plane of the ring.
Eclipsing of hydrogen atoms is an important destabilizing effect, as well. The strain energy of a cycloalkane is the increase in energy caused by the compound's geometry, and is calculated by comparing the experimental standard enthalpy change of combustion of the cycloalkane with the value calculated using average bond energies. Molecular ...
Thus, B is the most stable conformation. With certain polar substituents, hydrogen bonding can occur in the allylic system between the substituents. Rather than the strain that would normally occur in the close group proximity, the hydrogen bond stabilizes the conformation and makes it energetically much more favorable.
The repulsion between an axial t-butyl group and hydrogen atoms in the 1,3-diaxial position is so strong that the cyclohexane ring will revert to a twisted boat conformation. The strain in cyclic structures is usually characterized by deviations from ideal bond angles ( Baeyer strain ), ideal torsional angles ( Pitzer strain ) or transannular ...
They have been used as models for analyzing the effects of different geometric positions of the large atoms with dipolar bonds on the stability of the cyclohexane conformation. [1] The isomers are poisonous, pesticidal, and persistent organic pollutants, to varying degrees. Hexachlorocyclohexane was dimerized to produce mirex, a banned pesticide.