Hydroboration-oxidation of propene yields which product, and what is the regioselectivity?

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Multiple Choice

Hydroboration-oxidation of propene yields which product, and what is the regioselectivity?

Hydroboration-oxidation adds the boron atom to the less substituted carbon of the double bond and hydrogen to the more substituted carbon, giving anti-Markovnikov regioselectivity. For propene, the terminal carbon is the less substituted one, so boron attaches there and, after oxidation, is replaced by OH on that same carbon. This yields 1-propanol, not 2-propanol. The process proceeds without carbocation rearrangements, unlike acid-catalyzed hydration which gives Markovnikov (2-propanol).

Hydroboration-oxidation adds the boron atom to the less substituted carbon of the double bond and hydrogen to the more substituted carbon, giving anti-Markovnikov regioselectivity. For propene, the terminal carbon is the less substituted one, so boron attaches there and, after oxidation, is replaced by OH on that same carbon. This yields 1-propanol, not 2-propanol. The process proceeds without carbocation rearrangements, unlike acid-catalyzed hydration which gives Markovnikov (2-propanol).

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