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Chlorination and bromination are important classes of electrophilic aromatic substitutions, where benzene reacts with chlorine or bromine in the presence of a Lewis acid catalyst to give halogenated substitution products. A Lewis acid such as aluminium chloride or ferric chloride catalyzes the chlorination, and ferric bromide catalyzes the bromination reactions. During the bromination of alkenes, bromine polarizes and becomes electrophilic. However, in the bromination of benzene, the bromine molecule reacts with ferric bromide by donating a pair of electrons to the Lewis acid, which creates a more polar Br–Br bond and forming a more reactive electrophile.

Figure1

The benzene attacks this electrophile to generate the arenium ion, which is resonance stabilized.

Figure2

A proton transfer from arenium ion forms bromobenzene, thereby restoring aromaticity and regenerating the catalyst.

Figure3

The mechanism of chlorination of benzene proceeds in the same manner as bromination of benzene.

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Electrophilic Aromatic SubstitutionChlorinationBrominationBenzeneLewis Acid CatalystAluminium ChlorideFerric ChlorideFerric BromideElectrophileArenium IonResonance StabilizationBromobenzeneProton TransferMechanism

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18.5 : Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene

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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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18.7 : 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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18.15 : ortho-para-directing Deactivators: 할로겐

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