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Example · Example 3

Q.But-1-ene is treated with dilute H2SO4\text{H}_2\text{SO}_4/H2O\text{H}_2\text{O}. Give the structure of the major alcohol formed and name the mechanism/rule that decides which alcohol is major.

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✓ Free question

But-1-ene, CH2=CHCH2CH3\text{CH}_2{=}\text{CHCH}_2\text{CH}_3, protonates at C-1 (the terminal carbon, which already carries two hydrogens) because this generates the more stable secondary carbocation at C-2, rather than a primary carbocation at C-1. Water then attacks this secondary carbocation at C-2, and loss of a proton gives the alcohol: H+\text{H}^+ effectively adds to C-1 and −OH-\text{OH} to C-2, exactly as Markovnikov's rule predicts (the electrophile's H goes to the carbon already bearing more hydrogens).

✓Final answer

The major product is butan-2-ol, since the mechanism proceeds through the more stable secondary carbocation at C-2 (Markovnikov's rule).

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