Part of OC-03 — Aromatic Hydrocarbons

Aromatic Hydrocarbons: 5-Bullet Rapid Revision

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  • Benzene: All C-C bonds equal (1.39 Å), 6 delocalized pi electrons, planar; Huckel's Rule: (4n+2) pi ee^{-} + planar + cyclic + conjugated = aromatic; COT (8 pi ee^{-}) is non-aromatic (non-planar), not anti-aromatic.

  • EAS Mechanism: E+E^{+} generation → arenium ion (sigma complex, RDS, aromaticity lost) → H+H^{+} loss (rearomatization); substitution not addition because of 36 kcal/mol resonance driving force.

  • 5 EAS Reactions: Halogenation (X+X^{+}/Lewis acid), Nitration (NO2+NO_{2}^{+}/H2SO4H_{2}SO_{4}), Sulfonation (SO3SO_{3}, REVERSIBLE), FC Alkylation (R+R^{+}, rearranges + polyalkylates), FC Acylation (RCO+CO^{+}, no rearrangement, no polyacylation).

  • Halogen Anomaly: -Cl, -Br etc. are o/p directors (via +M) but deactivating (via dominant -I) — the ONLY deactivating o/p directors; all other deactivators are meta.

  • Meta Directors: -NO2NO_{2}, -CN, -CHO, -COOH, -COR — all withdraw by -M; FC reactions fail on these deactivated rings.

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