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JEE Main levelSingle correct optionDifficulty 2 of 3g3137

The first step of the acid-catalysed hydration of propene is addition of to the double bond to give a carbocation. The proton goes to the terminal carbon because

  1. Athe step is endothermic and its transition state resembles the carbocation, so the more stable secondary cation is reached through the lower transition state
  2. Bthe primary cation is more stable than the secondary one
  3. Cthe transition state resembles propene itself, so cation stability is irrelevant
  4. Da secondary cation has fewer hyperconjugating C-H bonds

Answer: A

Protonation of an alkene is endothermic, so the transition state is late and cation-like (Hammond postulate). The secondary carbocation is more stable than the primary one, and the transition state leading to it is lower in energy. Markovnikov addition follows.
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