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NEET levelSingle correct optionDifficulty 1 of 3o2174

Oxymercuration-demercuration of alkenes is generally free from rearrangement because

  1. Athe intermediate is a free radical
  2. Bthe intermediate is a carbanion
  3. Cthe intermediate is a bridged mercurinium ion rather than a free carbocation
  4. Dthe reaction occurs by SN2 attack of water on the alkene

Answer: C

Hg(OAc)+ adds to the alkene to give a three-membered mercurinium ion. Water opens it at the more substituted carbon. No discrete carbocation is formed, so no hydride or methyl shift occurs.
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