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  • Chapter 16:substituent Effects in Aromatic Substitution

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    Chris_Barber09
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    This document provides an overview of substitution reactions that can occur on aromatic rings, including bromination, chlorination, nitration, Friedel-Crafts alkylation and acylation, nitro group reduction, sulfonation, benzyne intermediate formation, addition/elimination reactions on activated aryl halides, benzylic bromination of alkylbenzenes, Clemmensen reduction of dialkyl ketones, oxidation of alkylbenzene side chains, reduction of aryl alkyl ketones, and catalytic hydrogenation. It notes factors that influence the reactivity and substrate scope of these reactions such as deactivation effects and the need for at least a halobenzene substrate in some cases.

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    Organic Chemistry

    Originaltitel

    Aromatic Notes 1

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    This document provides an overview of substitution reactions that can occur on aromatic rings, including bromination, chlorination, nitration, Friedel-Crafts alkylation and acylation, nitro group reduction, sulfonation, benzyne intermediate formation, addition/elimination reactions on activated aryl halides, benzylic bromination of alkylbenzenes, Clemmensen reduction of dialkyl ketones, oxidation of alkylbenzene side chains, reduction of aryl alkyl ketones, and catalytic hydrogenation. It notes factors that influence the reactivity and substrate scope of these reactions such as deactivation effects and the need for at least a halobenzene substrate in some cases.

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    104 Ansichten2 Seiten

    Chapter 16:substituent Effects in Aromatic Substitution

    Hochgeladen von

    Chris_Barber09
    This document provides an overview of substitution reactions that can occur on aromatic rings, including bromination, chlorination, nitration, Friedel-Crafts alkylation and acylation, nitro group reduction, sulfonation, benzyne intermediate formation, addition/elimination reactions on activated aryl halides, benzylic bromination of alkylbenzenes, Clemmensen reduction of dialkyl ketones, oxidation of alkylbenzene side chains, reduction of aryl alkyl ketones, and catalytic hydrogenation. It notes factors that influence the reactivity and substrate scope of these reactions such as deactivation effects and the need for at least a halobenzene substrate in some cases.

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    © All Rights Reserved
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    von 2

    Chapter 16:Substituent Effects in Aromatic Substitution

    Chapter 16 Overview:
    Bromination
    Br2, FeBr3

    Iodination
    I2, CuCl2

    Br

    Chlorination
    Cl2, FeCl3

    Nitration

    Friedel-Crafts Alkylation
    RCl, AlCl3

    SO3H

    Friedel-Crafts Acylation
    AlCl3

    Nitro Reduction to an Amine


    NO2

    SnCl2, H3O

    OH

    NaOH

    NH2

    OH

    Alkali Fusion of Aromatic Sulfonates


    SO3H

    R group may rearrange


    Substrate must be at least as reactive as a halobenzene
    Deactivated rings don't react

    O
    Cl

    NO2

    HNO3, H2SO4

    Sulfonation
    SO3, H2SO4

    Cl

    Benzyne Intermediate for Amination

    H3O

    Br

    NH2

    NH2

    NH3

    Addition/Elimination to an Activated Aryl Halide


    OH

    Br
    O2N

    NO2

    OH
    H3O

    O2N

    NO2

    CH3

    Benzylic Bromination of Alkylbenzenes with NBS


    CH3

    NBS

    CH2Br

    CCl4
    Clemeson Reduction of Dialkyl Ketones
    O

    Zn(Hg)/HCl

    Oxidation of Alkylbenzene Side Chains


    KMnO4

    COOH

    H2O
    reaction doesn't work with tertriary alkanes
    Reduction of Aryl Alkyl Ketones
    O
    C

    CH3

    H2, Pd

    only works with benzylic ketones


    Catalytic Hydrogenation
    H2/Rh/C

    H2
    C

    CH3

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