= Solution
\b[Product 5 is 1-methylcyclohexan-1-ol.] The tertiary ring C–H bond of methylcyclohexane is replaced by C–OH. This is a single constitutional product; the two ring paths at that carbon are equivalent, so no new <stereocenter> is created there.
The manganese–oxo species abstracts the relatively weak tertiary hydrogen, then hydroxyl rebound converts the carbon radical into the tertiary <alcohol>. The unfunctionalized <catalyst> has no crown-ether receptor to preassociate the ammonium substrate. Its selectivity therefore mainly follows intrinsic C–H reactivity: the tertiary site of methylcyclohexane outcompetes the secondary C–H sites of the linear chain. The cationic ammonium group also electronically deactivates nearby sites. This explains the dominant product under the idealized selectivity described in the question.
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