Part of JOC-01 — GOC: Hybridization, Isomerism & Effects (I, M, H, R)

Carbocation Stability & Rearrangements

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Stability order: 3 degrees > 2 degrees > 1 degrees > CH3+

Special carbocations (extra stable):

  • Benzylic: Resonance with aromatic ring
  • Allylic: Resonance with C=C
  • Tropylium (C7H7+): Aromatic, 6 pi electrons
  • Cyclopropenyl (C3H3+): Aromatic, 2 pi electrons

Rearrangements: Less stable carbocations rearrange to more stable ones via:

  • 1,2-hydride shift: H migrates with its bonding electrons
  • 1,2-methyl shift: CH3 migrates with bonding electrons
  • Ring expansion: Cyclobutyl to cyclopentyl

JEE favorite: Neopentyl system — primary carbocation rearranges to tertiary via 1,2-methyl shift. This explains unexpected products in SN1/E1 reactions.

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