Oxymercuration-demercuration of propene yields which product and why is it special?

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Multiple Choice

Oxymercuration-demercuration of propene yields which product and why is it special?

The key idea is that oxymercuration-demercuration adds water to alkenes in a way that follows Markovnikov control but avoids carbocation rearrangements. The mechanism forms a mercurinium ion, not a free carbocation, so the second step (water attack) occurs on the more substituted carbon without any rearrangement happening before demercuration. For propene, the more substituted carbon is the middle carbon, so the hydroxyl group ends up on that carbon after demeruration, giving 2-propanol. This is the special feature: you get the Markovnikov alcohol without any rearrangement, unlike acid-catalyzed hydration where a carbocation could rearrange. The option claiming 1-propanol via anti-Markovnikov hydration is incorrect for this reaction. Anti-Markovnikov hydration is associated with hydroboration-oxidation, not oxymercuration-demercuration.

The key idea is that oxymercuration-demercuration adds water to alkenes in a way that follows Markovnikov control but avoids carbocation rearrangements. The mechanism forms a mercurinium ion, not a free carbocation, so the second step (water attack) occurs on the more substituted carbon without any rearrangement happening before demercuration.

For propene, the more substituted carbon is the middle carbon, so the hydroxyl group ends up on that carbon after demeruration, giving 2-propanol. This is the special feature: you get the Markovnikov alcohol without any rearrangement, unlike acid-catalyzed hydration where a carbocation could rearrange.

The option claiming 1-propanol via anti-Markovnikov hydration is incorrect for this reaction. Anti-Markovnikov hydration is associated with hydroboration-oxidation, not oxymercuration-demercuration.

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