Epoxide Opening with Organometallics (Grignard / RLi): Mechanism + Exam Traps

Open epoxides with Grignards/RLi under basic conditions: attack the less substituted carbon (SN2), invert stereochemistry, then protonate to alcohol.

  • Reaction: Epoxide Opening with Organometallics (Grignard / RLi)
  • What it does: Open epoxides with Grignards/RLi under basic conditions: attack the less substituted carbon (SN2), invert stereochemistry, then protonate to alcohol.
  • Typical reagents: 1) CH3MgBr 2) H3O+
  • Key intermediate: Epoxide / oxonium
  • Driving force: Formation of strong C=O / oxidation state stabilization
  • Exam type: Predict major product
  • Exam type: Mechanism choice

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