Quick Recap — Electronic Effects & Intermediate Stability

  • Carbocation stability: 3>2>1>3^\circ>2^\circ>1^\circ> methyl; benzyl/allyl are resonance-stabilised.
  • Free radicals: 3>2>13^\circ>2^\circ>1^\circ; carbanions: stabilised by I-I/M-M (so CCl3>CH3>3CCl_3^->CH_3^->3^\circ).
  • Resonance (mesomeric): +M+M donors (OH-OH, NH2-NH_2, OR-OR, X-X lone pairs) enrich ortho/para; M-M acceptors (NO2-NO_2, CN-CN, CHO-CHO, COOH-COOH) withdraw.
  • Hyperconjugation (no-bond resonance): more α\alpha-H \Rightarrow greater stability of the cation/alkene.