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Chemistry

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Organic Chemistry

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Reactions of Aromatic Compounds

Meisenheimer Complex in Aromatic Substitution

Description

Nucleophilic aromatic substitution can happen on aromatic compounds that carry strong electron-withdrawing groups. These groups must be placed ortho or para to the leaving group. The reaction follows an addition–elimination path and depends on the ring being activated for substitution.

The reacti...

Transcript

Recall that nucleophiles attack only those aryl halides that comprise strong electron-withdrawing substituents placed ortho or para to the leaving group. 

The reaction proceeds via nucleophilic aromatic substitution, involving two steps—the addition of the nucleophile and the elimination of the leaving group.

In t...

Tags

Addition Elimination MechanismElectron Withdrawing GroupsMeisenheimer Complex FormationAromaticity RestorationOrtho Para SubstitutionLeaving Group DepartureNucleophile AttackPi Electron DelocalizationResonance Stabilization