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All meta-directing substituents are deactivating groups. These substituents withdraw electrons from the aromatic ring, making the ring less reactive toward electrophilic substitution. For example, the nitration of nitrobenzene is 100,000 times slower than that of benzenebecause of thedeactivating effect of the nitro group. The first step in an electrophilic aromatic substitution is the addition of an electrophile to form a resonance-stabilized carbocation. The energy diagrams for the nitration of benzene and nitrobenzeneshowthat the electron-withdrawing nitro group destabilizes the carbocation intermediate and increases the transition state energy. The higher activation energy barrier for nitrobenzene, compared to that for benzene,makes the reactionslower. Whilemeta-directing groups deactivatethe ring at all positions,deactivation at the ortho and para positions is stronger, resulting inmeta-substituted products.

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Meta directingDeactivatingNitro GroupElectrophilic Aromatic SubstitutionCarbocationActivation EnergyMeta substitution

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18.16 : meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H

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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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