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Chapter 19: Benzene and Aromatic Substitution Reactions

Chapter 19: Benzene and Aromatic Substitution Reactions [Sections: , ; ]Nomenclature of Substituted Benzenesi. Monosubstituted BenzenesClCH2CH3NO2ii. Disubstituted BenzenesXXXYYYCH3 ClNO2iii. Polysubstituted Benzenes with more than 2 substituents, locant values MUST be used Minimize value of locants Name alphabeticallyCH2CH3 BrCliv. IUPAC Accepted Common NamesOHCH3NH2 OHOOHCH3 Brv. Benzene ring as a substituent is a "phenyl" groupPhCl with 2 substituents, either the ortho, meta, para-terminology OR locant values may be usedProblems: 1 if a continuous chain attached to a Benzene ring exceeds 6 carbons, the Benzene ring becomes a substituent off of the parent alkyl chainSubstitution versus Addition ReactionsBr2 BrBrBr2 FeBr3Br Substitution Reactions are favored by Aromatic compounds since aromaticity is retained addition Reactions (typical of alkenes) would result in loss of aromaticityBrBrFeBr3 BrBrFeBr3 HHHHHHFeFeBr3 HHHHHHBrHHHHHHBrBrHHHHHHHHHHHBrHHHHHHBr arenium ion (or sigma complex) intermediate is formed resonance stabilization means it has a reasonable activation barrierfor formation since aromaticity is temporarily lostarenium ion(sigma complex)Mechanism for Electrophilic Aromatic Substitution Process the net result is Substitution on the aromati

Chapter 19: Benzene and Aromatic Substitution Reactions [Sections: 18.2, 18.6; 19.1-19.12] Nomenclature of Substituted Benzenes i. Monosubstituted Benzenes Cl CH 2CH3 NO ii. Disubstituted Benzenes X Y Y Y CH3 Cl NO2 iii. Polysubstituted Benzenes • with more than 2 substituents, locant values MUST be used • Minimize value of locants • Name ...

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  Aromatic, Reactions, Benzene, Substitution, Benzene and aromatic substitution reactions

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Transcription of Chapter 19: Benzene and Aromatic Substitution Reactions

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