Problem: On catalytic hydrogenation over a rhodium catalyst, the compound shown gave a mixture containing cis-1-tert-butyl-4-methylcyclohexane (88%) and trans-1-tert-butyl- 4-methylcyclohexane (12%). With this stereochemical result in mind, consider the reactions in (a) and (b).(b) What two products are formed in the hydroboration–oxidation of this compound? Which one do you think will predominate?

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On catalytic hydrogenation over a rhodium catalyst, the compound shown gave a mixture containing cis-1-tert-butyl-4-methylcyclohexane (88%) and trans-1-tert-butyl- 4-methylcyclohexane (12%). With this stereochemical result in mind, consider the reactions in (a) and (b).

(b) What two products are formed in the hydroboration–oxidation of this compound? Which one do you think will predominate?