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.

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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.
Transcribed Image Text: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.
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