Electrophilic Aromatic Substitution (EAS): Mechanism and Directing Effects

Master EAS with a step-by-step mechanism (sigma complex) and a clear directing effects framework. Predict products for nitration, sulfonation, halogenation, and Friedel–Crafts reactions with practice.

  • Mechanism core: Attack → sigma complex → deprotonation restores aromaticity
  • Rate-determining: Formation of sigma complex (loss of aromaticity)
  • Directing effects: EDG donate → ortho/para + activation; EWG withdraw → meta + deactivation
  • Exception: Halogens are deactivating but ortho/para directing
  • Exam type: Predict the major product
  • Exam type: Choose conditions
  • Exam type: Failure modes / distractors

Related Resources

All 194 Mechanisms — Aromatic & Pericyclic (High-Yield Orgo II) Mechanism Flashcards AI Reaction Predictor Ask the AI Tutor