Nucleophilic aromatic substitution involves the formation of a resonance-stabilized carbanion intermediate called a Meisenheimer complex as the nucleophile attacks the ring carbon carrying the eventual leaving group; electron-withdrawing groups ortho and/or para to the site of attack help to stabilize this structure via resonance. For the reaction below, draw the structure of the stabilized reaction intermediate in the box below. CI F3C CF3 NO₂ F3C N CF3 NO₂ • You do not have to consider stereochemistry. • Draw the Meisenheimer complex with a formal charge of 0 on the nucleophilic atom. If more than one resonance structure is possible, only draw the most important one.

Nucleophilic aromatic substitution involves the formation of a resonance-stabilized carbanion intermediate called a Meisenheimer complex as the nucleophile attacks the ring carbon carrying the eventual leaving group; electron-withdrawing groups ortho and/or para to the site of attack help to stabilize this structure via resonance. For the reaction below, draw the structure of the stabilized reaction intermediate in the box below. CI F3C CF3 NO₂ F3C N CF3 NO₂ • You do not have to consider stereochemistry. • Draw the Meisenheimer complex with a formal charge of 0 on the nucleophilic atom. If more than one resonance structure is possible, only draw the most important one.

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter18: Functional Derivatives Of Carboxylic Acids

Section: Chapter Questions

Problem 18.70P

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