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Hydration of 3-phenylbut-1-ene in dilute `H_(3)SO_(4)` forms 2-pheylbutan -2-ol and not 3-phenylbutan-2-ol. Why ? |
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Answer» Correct Answer - `H_(2)C=CH-underset(Ph)underset(|)CH-CH_(3)overset(H^(+))rarrH_(3)C-overset(+)CH-underset(Ph)underset(|)CH-CH_(3)overset(-H)rarrH_(3)C-CH_(2)-underset(Ph)overset(+)C-CH_(3)` `underset(-H^(+))overset(H_(2)O)rarrCH_(3)CH_(2)-underset(Ph)underset(|)overset(OH)overset(|)C-CH_(3)` (Hydration gives an intermediate `2^(@)C`, which undergoes a hydride shift Although phenyl is a better migrator than `H`, migration of H oC Curs leading to a more stable `3^(@)` benzylic carbocation.) |
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