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JEE Advanced levelSingle correct optionDifficulty 3 of 3ap183

An alkene C5H10 gives 2-methylbutan-1-ol on hydroboration-oxidation (/THF, then /), but gives 2-methylbutan-2-ol on acid-catalysed hydration. The alkene is

  1. A2-methylbut-1-ene
  2. B3-methylbut-1-ene
  3. C2-methylbut-2-ene
  4. Dpent-1-ene

Answer: A

For 2-methylbut-1-ene, , anti-Markovnikov addition puts OH on the terminal (2-methylbutan-1-ol) and Markovnikov addition puts OH on C-2 (2-methylbutan-2-ol). 3-Methylbut-1-ene would give 3-methylbutan-1-ol, 2-methylbut-2-ene would give 3-methylbutan-2-ol, and pent-1-ene would give pentan-1-ol.
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