有机化学（加州大学伯克利分校）CHAPTER13.pdf

ELECTROPHILIC ATTACK ON ELECTROPHILIC ATTACK ON DERIVATIVES OF BENZENE DERIVATIVES OF BENZENE R E+ ? What are the effects of the substituent? What are the effects of the substituent? a. Reactivity of the benzene ring a. Reactivity of the benzene ring b. Regiochemistry of EAS: ortho, meta, para b. Regiochemistry of EAS: ortho, meta, para Donors and Acceptors Donors and Acceptors Donors Acceptors Donors Acceptors activate deactivate activate deactivate Deactivators: Direct Activators: Direct Deactivators: Direct Activators: Direct electrophilic attack to electrophilic attack electrophilic attack to electrophilic attack the meta positions to the ortho and the meta positions to the ortho and para positions para positions Induction and Resonance Induction and Resonance Both can operate, not always in the same direction Both can operate, not always in the same direction Inductive effect: Inductive effect: -Occurs through the -Occurs through the σframework σframework - Tapers off rapidly - Tapers off rapidly with distance