The enzymatic oxidation of alkanes to produce alcohols is a simplified version of the reactions that produce the adrenocortical steroid hormones. In the biosynthesis of corticosterone from progesterone (Section 4-7), two such oxidations take place successively (a, b). It is thought that the monooxygenase enzymes act as complex oxygen-atom donors in these reactions.
A suggested mechanism, as applied to cyclohexane, consists of the two steps shown below the biosynthesis.

Calculate ˆ†H° for each step and for the overall oxidation reaction of cyclohexane. Use the following DH° values: cyclohexane C-H bond, 98.5 kcal mol-1; bond in O-H radical, 102.5 kcal mol-1; cyclohexanol C-O bond, 96 kcal mol-1.

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HOCH CH HO CH3 Steroid CH O, O) Progesterone Corticosterone O (atom)Enye OH