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Orthopara directors are substituent groups attached to the benzene ring and direct the addition of an electrophile to the positions ortho or para to the substituent. All electron-donating groups are considered orthopara directors. They donate electrons to the ring and make the ring more electron-rich. The ring is therefore susceptible to the addition of electrophiles. Substituents such as amino, hydroxy, or alkoxy, containing lone pairs on the atom adjacent to the ring, donate electrons through resonance. For instance, phenol can undergo nitration at either ortho, meta, or para positions. However, the ortho and para carbocation intermediates are more stable than the meta intermediate because they have more resonance forms. Moreover, a particular favorable form in ortho and para carbocation intermediates exists—the one arising from the donation of oxygen’s nonbonding electrons.

Alkyl substituents without lone pairs also function as orthopara directors. They donate electrons through an inductive effect. The carbocation intermediates involved in the orthopara attack are more stable than meta. The orthopara directors function by stabilizing a positive charge directly on the methyl-substituted carbon. Since it is a tertiary position, the positive charge can be stabilized by the electron-donating inductive effect of the methyl group.

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Ortho para DirectingElectron donatingElectrophilic Aromatic SubstitutionResonance StabilizationInductive EffectCarbocation IntermediatePhenol NitrationAlkyl Substituents

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18.12 : Directing Effect of Substituents: ortho–para-Directing Groups

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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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18.13 : 치환의 지시 효과: 메타 지시 그룹

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

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18.15 : ortho-para-directing Deactivators: 할로겐

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