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Benzene: All C-C bonds equal (1.39 Å), 6 delocalized pi electrons, planar; Huckel's Rule: (4n+2) pi + planar + cyclic + conjugated = aromatic; COT (8 pi ) is non-aromatic (non-planar), not anti-aromatic.
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EAS Mechanism: generation → arenium ion (sigma complex, RDS, aromaticity lost) → loss (rearomatization); substitution not addition because of 36 kcal/mol resonance driving force.
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5 EAS Reactions: Halogenation (/Lewis acid), Nitration (/), Sulfonation (, REVERSIBLE), FC Alkylation (, rearranges + polyalkylates), FC Acylation (R, no rearrangement, no polyacylation).
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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.
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Meta Directors: -, -CN, -CHO, -COOH, -COR — all withdraw by -M; FC reactions fail on these deactivated rings.
Part of OC-03 — Aromatic Hydrocarbons
Aromatic Hydrocarbons: 5-Bullet Rapid Revision
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