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Nucleophilic substitution in aromatic compounds is feasible in substrates bearing strong electron-withdrawing substituents positioned ortho or para to the leaving group. The reaction proceeds via two steps: the addition of the nucleophile and the elimination of the leaving group.

The reaction beginswith an attack of the nucleophile on the carbon that holds the leaving group. This results in the delocalization of the π electrons over the ring carbons. The resonance interaction between the delocalized electron pair and the electron-withdrawing group further stabilizes the intermediate through the formation of Meisenheimer complexes. Finally, the electron-withdrawing group releases the electron back into the ring, facilitatingthe departure of the leaving group and restoringaromaticity.

Tags
Nucleophilic Aromatic SubstitutionSNArAddition eliminationElectron withdrawing SubstituentsMeisenheimer ComplexAromaticity

Del capítulo 18:

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18.18 : Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)

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18.1 : Espectroscopía de RMN de derivados del benceno

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18.2 : Reacciones en la posición bencílica: oxidación y reducción

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18.3 : Reacciones en la posición bencílica: halogenación

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18.4 : Sustitución aromática electrofílica: descripción general

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18.5 : Sustitución aromática electrofílica: cloración y bromación del benceno

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18.6 : Sustitución aromática electrofílica: fluoración y yodación del benceno

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18.7 : Sustitución aromática electrofílica: nitración del benceno

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18.8 : Sustitución aromática electrofílica: sulfonación del benceno

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18.9 : Sustitución aromática electrofílica: Friedel-Crafts alquilación de benceno

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18.10 : Sustitución aromática electrofílica: acilación de benceno de Friedel-Crafts

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18.11 : Limitaciones de las reacciones de Friedel-Crafts

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18.12 : Efecto Directivo de los Sustituyentes: Grupos Orto-Para-Directores

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18.13 : Efecto Directivo de los Sustituyentes: Grupos Meta-Directores

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18.14 : Activadores orto-para-direccionamientos: –CH3, –OH, –⁠NH2, –OCH3

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