Michael Addition: The 1,4‑Addition You’ll See in Orgo II

Master the Michael addition: enolate (soft nucleophile) 1,4‑adds to an α,β‑unsaturated carbonyl, then protonation gives a 1,5‑dicarbonyl. Learn 1,2 vs 1,4 rules and practice.

  • Electrophile: α,β‑unsaturated carbonyl (enone/enal)
  • Nucleophile: Stabilized enolate (e.g., 1,3‑dicarbonyl enolate)
  • Key bond formed: Nu–Cβ (conjugate addition)
  • Product pattern: 1,5‑dicarbonyl (often)
  • Big exam contrast: Hard nucleophiles (e.g., Grignard) often give 1,2-addition
  • Exam type: Predict the major product
  • Exam type: Choose the mechanism
  • Exam type: Regiochemistry (1,2 vs 1,4)

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