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    NOTES-Aromatic Substituents-Directing & Activating Trends

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    Hanin Latpi
    1. Electrophilic aromatic substitution reactions are accelerated by electron donating groups (EDGs) and retarded by electron withdrawing groups (EWGs) due to differences in the transition state energies of the reactions. 2. The transition state for reactions with EDG substituents resembles the starting materials more closely than the transition state for reactions with EWG substituents. 3. Ortho/para directing substituents such as EDGs and weakly deactivating halogens lead to substitution at the ortho and para positions, while strongly deactivating EWGs lead to substitution at the meta position.

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    NOTES-Aromatic Substituents-Directing & Activating Trends

    Uploaded by

    Hanin Latpi
    28 views4 pages
    1. Electrophilic aromatic substitution reactions are accelerated by electron donating groups (EDGs) and retarded by electron withdrawing groups (EWGs) due to differences in the transition state energies of the reactions. 2. The transition state for reactions with EDG substituents resembles the starting materials more closely than the transition state for reactions with EWG substituents. 3. Ortho/para directing substituents such as EDGs and weakly deactivating halogens lead to substitution at the ortho and para positions, while strongly deactivating EWGs lead to substitution at the meta position.

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    NOTES-Aromatic_Substituents-Directing_&_Activating_Trends

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    1. Electrophilic aromatic substitution reactions are accelerated by electron donating groups (EDGs) and retarded by electron withdrawing groups (EWGs) due to differences in the transition state energies of the reactions. 2. The transition state for reactions with EDG substituents resembles the starting materials more closely than the transition state for reactions with EWG substituents. 3. Ortho/para directing substituents such as EDGs and weakly deactivating halogens lead to substitution at the ortho and para positions, while strongly deactivating EWGs lead to substitution at the meta position.

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    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    28 views4 pages

    NOTES-Aromatic Substituents-Directing & Activating Trends

    Uploaded by

    Hanin Latpi
    1. Electrophilic aromatic substitution reactions are accelerated by electron donating groups (EDGs) and retarded by electron withdrawing groups (EWGs) due to differences in the transition state energies of the reactions. 2. The transition state for reactions with EDG substituents resembles the starting materials more closely than the transition state for reactions with EWG substituents. 3. Ortho/para directing substituents such as EDGs and weakly deactivating halogens lead to substitution at the ortho and para positions, while strongly deactivating EWGs lead to substitution at the meta position.

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    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    of 4

    Rationalizing Substituent Effects for Electrophilic

    Aromatic Substitution Reactions


    RDS
    EWG
    EWG
    RDS
    A + E
    RDS
    E

    free energy
    H
    H

    the intermediate
    TS≠ resembles
    B + E

    E
    A B C
    EDG starting A B C
    EDG substrates products
    progress of reaction
    C + E
    Since the benzene ring is the
    nucleophile the reaction is
    __________,
    E accelerated by EDGs
    Comparing Intermediates
    For Rings with an EWG vs. EDG
    EWG O H O H
    O H
    deactivating
    A + E

    E H E H

    EDG activating CH3 CH3 CH3 CH3


    CH3 CH3 N N
    N

    C + E

    E H E H all atoms have a


    complete octet
    Substituents and Regiochemistry in
    Electrophilic Aromatic Substitution
    X
    X X X
    H E
    + E or or

    E
    E
    X is EWG
    or EDG ortho meta para

    •  All activating substituents (EDG) and weakly


    ortho / para directors
    deactivating halogens are __________
    •  All substituents more deactivating than the
    halogens are meta
    ____ directors (i.e., the EWGs)
    Substituent - Reactivity Correlation Chart

    Ortho / para
    directing

    From P. Y. Bruice
    Organic Chemistry (5th Ed.)

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