What will be the major product obtained from the acid-catalysed hydration of pent-1-ene?

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Multiple Choice

What will be the major product obtained from the acid-catalysed hydration of pent-1-ene?

The major product comes from Markovnikov hydration, where the hydrogen adds to the carbon of the double bond that has more hydrogens, forming the more stable carbocation, which is then attacked by water. For pent-1-ene, the double bond is between C1 and C2. Protonation at C1 gives a secondary carbocation at C2, which is more stable than the primary alternative if protonation occurred at C2. Water attack followed by deprotonation yields an alcohol on the more substituted carbon, so the OH ends up on C2. That gives pentan-2-ol as the product. The other possibilities would require oxidation (giving pentanal), complete reduction (giving pentane), or an anti-Markovnikov outcome (which acid-catalyzed hydration doesn’t provide).

The major product comes from Markovnikov hydration, where the hydrogen adds to the carbon of the double bond that has more hydrogens, forming the more stable carbocation, which is then attacked by water. For pent-1-ene, the double bond is between C1 and C2. Protonation at C1 gives a secondary carbocation at C2, which is more stable than the primary alternative if protonation occurred at C2. Water attack followed by deprotonation yields an alcohol on the more substituted carbon, so the OH ends up on C2. That gives pentan-2-ol as the product. The other possibilities would require oxidation (giving pentanal), complete reduction (giving pentane), or an anti-Markovnikov outcome (which acid-catalyzed hydration doesn’t provide).

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