Example · Example 3
Q.But-1-ene is treated with dilute /. 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, , 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: effectively adds to C-1 and 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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