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