Which of the following reagent sequences convert the alkene shown mainly into the tertiary alcohol (Markovnikov hydration product)?

A $H X_{2} O$ , catalytic $H X_{2} SO X_{4}$
B(i) $Hg (OAc) X_{2}$ , $H X_{2} O$ ; (ii) $NaBH X_{4}$
C(i) $BH X_{3}$ in THF; (ii) $H X_{2} O X_{2}$ , $NaOH$
D(i) $HBr$ , $ROOR$ ; (ii) aqueous $NaOH$

Answer: A, B

The alkene is 2-methylbut-2-ene; the tertiary alcohol is 2-methylbutan-2-ol. Acid-catalysed hydration and oxymercuration-demercuration both place OH on the more substituted carbon. Hydroboration-oxidation gives 3-methylbutan-2-ol, and the peroxide-HBr route gives 2-bromo-3-methylbutane, which substitutes to 3-methylbutan-2-ol, so options C and D are wrong.

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Which of the following reagent sequences convert the alkene shown mainly into the tertiary alcohol (Markovnikov hydration product)?

Answer: A, B

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