Nucleophilic aromatic substitution reaction

Nucleophilic aromatic substitution reaction - from those of...

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Nucleophilic Aroma/c Subs/tu/on A typical nucleophilic aroma/c subs/tu/on reac/on has an oxygen, nitrogen, or cyanide nucleophile a halide for a leaving group a carbonyl, nitro, or cyanide group ortho or para to the leaving group Two EWGs are be±er than one A meta anion-stabilizing group does not work.
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Examples
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13 C NMR of EAS, S N Ar intermediates The shifts of the meta carbons in both ions are very slightly different
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Unformatted text preview: from those of benzene itself (about 130 ppm). But the ortho and para carbons in the cation have gone downfield to much larger shifts while the ortho and para carbons in the anion have gone upfield to much smaller shifts. This means that stabilizing groups, such as nitro or carbonyl in the case of the anion, must be on the ortho or para carbons to have any effect....
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This note was uploaded on 01/12/2012 for the course CHEM 335 taught by Professor Dr.yan during the Winter '11 term at Portland State.

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Nucleophilic aromatic substitution reaction - from those of...

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