CONCEPT: SNAr ADDITION-ELIMINATION MECHANISM Unlike EAS ...
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CONCEPT: SNAr ADDITION-ELIMINATION MECHANISM Unlike EAS ...
CONCEPT: SNAr ADDITION-ELIMINATION MECHANISM. Unlike EAS, where addition is initiated by the presence of a strong electr
CONCEPT: SNAr ADDITION-ELIMINATION MECHANISM Unlike EAS, where addition is initiated by the presence of a strong electrophile, addition-elimination can also be initiated by a strong nucleophile in the presence of a good aryl leaving group. ● Reaction has similarities to SN2 but it is not _____________________ ● Known as Addition-Elimination Nucleophilic Aromatic Substitution, SNAr or ipso-substitution.
An early method of preparing phenol called the Dow Process used chlorobenzene, NaOH and high heat to force S NAr.
.
CONCEPT: THE MEISENHEIMER COMPLEX The Dow Process, a typical SNAr reaction, requires tons of heat and pressure to proceed forward. ● This is due to the instability of the anionic sigma-complex ● Withdrawing groups or Heteroatoms to the Ortho or Para positions (WHOP) stabilize the intermediate
□ A classical trinitrobenzene Meisenheimer Complex can proceed in room temperature
EXAMPLE: Use resonance structures to determine which of the following ipso-substitutions is more favored.
EXAMPLE: Which of the following compounds will most readily undergo nucleophilic aromatic substitution in the additionelimination pathway?
