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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.

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Nucleophilic Aromatic SubstitutionSNArAddition eliminationElectron withdrawing SubstituentsMeisenheimer ComplexAromaticity

장에서 18:

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

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18.1 : 벤젠 유도체의 NMR 분광법

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18.2 : 벤질산 위치에서의 반응: 산화 및 환원

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18.3 : 벤질산 위치에서의 반응 : 할로겐화

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18.4 : 친전자성 방향족 대체: 개요

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18.5 : 친전자성 방향족 치환: 벤젠의 염소화 및 브롬화

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18.6 : 친전자성 방향족 치환: 벤젠의 불소화 및 요오드화

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18.7 : 친전자성 방향족 치환: 벤젠의 질화

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18.8 : 친전자성 방향족 치환: 벤젠의 설폰화

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18.9 : 친전자성 방향족 치환: Friedel–Crafts 벤젠의 알킬화

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18.10 : 친전자성 방향족 치환: Friedel–Crafts 벤젠의 아실화

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18.11 : Friedel-Crafts 반응의 한계

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18.12 : 치환의 지시 효과: ortho-para-directing groups

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18.13 : 치환의 지시 효과: 메타 지시 그룹

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18.14 : 직교-파라-디렉팅 활성제: -CH3, -OH, -⁠NH2, -OCH3

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