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A steroid molecule is shown in the attachment
A steroid molecule is shown in the attachment. I have to explain which of the two is oxidised faster using Cr(VI) reagents.
I've drawn the molecule in 3D and can say that the equatorial OH is more easily attacked than the axial one because the axial OH has axial interaction with Me causing steric hindrance to the incoming reactant. Are there any more reasons?
Expert Solution
It is clear from the 3D structure that the axial hydroxyl group is hindered more by the Me group as compared to the equatorial hydroxyl group.
When a compound is oxidised, the equatorial group is oxidised faster compared to the axial one as the axial attack is very sensitive to steric hidrance with rate constants reduced significantly as a result of increased substitution.
Equatorial attack is also impeded but to a lower extent. This stereoselectivity is mainly enthalpy controlled with axial attack requiring more activation energy than the equatorial attack.
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