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17: Reactions of Aromatic Compounds

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  • Page ID
    183074

    • learning objectives

    After reading this chapter and completing ALL the exercises, a student can be able to

    • propose mechanisms for Electrophilic Aromatic Substitution Reactions (EAS): halogenation, nitration, sulfonation, and Friedel-Crafts Alkylation & Acylation (sections 18.1 to 18.5)
    • predict products and specify reagents for Electrophilic Aromatic Substitution Reactions (EAS): halogenation, nitration, sulfonation, and Friedel-Crafts Alkylation & Acylation (sections 18.1 to 18.5)
    • draw resonance structures of the sigma complexes resulting from EAS rxns of substituted aromatic rings (sections 18.1 to 18.5)
    • draw reaction energy diagrams for EAS reactions (sections 18.1 to 18.5)
    • explain why substituents are activating or deactivating and o,p-directors or m-directors (section 18.6)
    • list the major substituents in their EAS activation “pecking order” (section 18.6)
    • predict the products of side chain reactions:  oxidation of catechols and alkyl substituents, bromination of benzylic carbons, SN1 and SN2 rxns at the benzylic carbon, reduction of carbonyls, and reduction of nitro groups (sections 18.7 and 18.12)
    • design multiple step syntheses that use substituent effects to create the desired isomers of multi-substituted aromatic compounds (sections 18.8 and 18.9)
    • predict the products of Nucleophilic Aromatic Substitution Reactions (NAS):  addition-elimination and elimination-addition (benzyne) (sections 18.10 and 18.11)
    • propose mechanisms for Nucleophilic Aromatic Substitution Reactions (NAS):  addition-elimination and elimination-addition (benzyne) (sections 18.10 and 18.11)