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    PDA104T - 38 Electrophilic Aromatic Substitution Reactions

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    Prince Pavan
    The document discusses electrophilic aromatic substitution reactions. It defines aromaticity and provides examples of aromatic and non-aromatic compounds. The mechanism of electrophilic aromatic substitution is described as the addition of an electrophile to form a carbocation followed by loss of a proton to form the substituted product.

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    PDA104T - 38 Electrophilic Aromatic Substitution Reactions

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    Prince Pavan
    122 views18 pages
    The document discusses electrophilic aromatic substitution reactions. It defines aromaticity and provides examples of aromatic and non-aromatic compounds. The mechanism of electrophilic aromatic substitution is described as the addition of an electrophile to form a carbocation followed by loss of a proton to form the substituted product.

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    PDA104T_38 Electrophilic Aromatic Substitution Reactions

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    The document discusses electrophilic aromatic substitution reactions. It defines aromaticity and provides examples of aromatic and non-aromatic compounds. The mechanism of electrophilic aromatic substitution is described as the addition of an electrophile to form a carbocation followed by loss of a proton to form the substituted product.

    Copyright:

    © All Rights Reserved
    Download as PPT, PDF, TXT or read online from Scribd
    Download as ppt, pdf, or txt
    122 views18 pages

    PDA104T - 38 Electrophilic Aromatic Substitution Reactions

    Uploaded by

    Prince Pavan
    The document discusses electrophilic aromatic substitution reactions. It defines aromaticity and provides examples of aromatic and non-aromatic compounds. The mechanism of electrophilic aromatic substitution is described as the addition of an electrophile to form a carbocation followed by loss of a proton to form the substituted product.

    Copyright:

    © All Rights Reserved
    Download as PPT, PDF, TXT or read online from Scribd
    Download as ppt, pdf, or txt
    of 18

    Lecture No.

    38
    Electrophilic Aromatic Substitution
    At the end of thisReactions
    lecture, student will be able
    to
    Discuss the concept of aromaticity and Huckels
    rule
    Differentiate aromatic and nonaromatic
    compounds
    Explain the general mechanism of electrophilic
    aromatic substitution reaction
    List out examples for EAS reactions

    1
    Faculty of Pharmacy

    M. S. Ramaiah

    Structure of Benzene
    It contains a six-membered ring and three additional
    degrees of unsaturation
    It is planar
    All C C bond lengths are equal
    Resonance
    Benzene is conjugated

    2
    Faculty of Pharmacy

    M. S. Ramaiah

    Structure of Benzene Contd

    Benzenes six -electrons make it electron rich and so


    it readily reacts with electrophiles
    Overlap of six adjacent p orbitals creates two rings of
    electron density
    Delocalisation of electrons
    Clouds of electrons above and below the plane of
    benzene ring
    3
    Faculty of Pharmacy

    M. S. Ramaiah

    Nomenclature of Benzene Derivatives


    Monosubstituted Benzenes

    4
    Faculty of Pharmacy

    M. S. Ramaiah

    Nomenclature of Benzene Derivatives


    Disubstituted benzenes

    5
    Faculty of Pharmacy

    M. S. Ramaiah

    Nomenclature of Benzene Derivatives


    Arrange the substituents in alphabetical order

    6
    Faculty of Pharmacy

    M. S. Ramaiah

    Nomenclature of Benzene Derivatives


    Polysubstituted benzenes

    7
    Faculty of Pharmacy

    M. S. Ramaiah

    Nomenclature of Benzene Derivatives


    Phenyl and benzyl group

    8
    Faculty of Pharmacy

    M. S. Ramaiah

    Criteria for Aromaticity


    A molecule must have uninterrupted cyclic cloud of electrons
    For the cloud to be cyclic, the molecule must be cyclic
    For the cloud to be uninterrupted, every atom in the ring must have a porbital
    For the cloud to form, each p orbital must overlap with the p orbitals on
    either side of it
    Therefore, the molecule must be planar
    Odd number of pairs of electrons
    Huckels rule or 4n + 2 rule states that for a planar, cyclic compound to
    be aromatic its uninterrupted cloud must contain (4n+2) electrons,
    where n is any whole number (0,1,2,)

    9
    Faculty of Pharmacy

    M. S. Ramaiah

    Criteria for Aromaticity Contd


    Example 1
    Benzene 3 pairs of electrons aromatic
    Cyclobutadiene & cyclooctatetraene non aromatic

    10
    Faculty of Pharmacy

    M. S. Ramaiah

    Criteria for Aromaticity Contd


    Example 2

    Cyclopropene non aromatic


    Cyclopropenyl cation aromatic
    Cyclopropenyl anion non aromatic

    11
    Faculty of Pharmacy

    M. S. Ramaiah

    Criteria for Aromaticity Contd


    Example 3
    Naphthalene 5 pairs of electrons aromatic
    Phenanthrene 7 pairs of electrons non aromatic

    12
    Faculty of Pharmacy

    M. S. Ramaiah

    Electrophilic Aromatic Substitution


    Reactions

    13
    Faculty of Pharmacy

    M. S. Ramaiah

    Electrophilic Aromatic Substitution


    Reactions Contd
    Benzene - does not undergo addition reactions
    like unsaturated hydrocarbons
    Typical reactions of benzene - substitution

    14
    Faculty of Pharmacy

    M. S. Ramaiah

    Electrophilic Aromatic Substitution


    Reactions Contd

    15
    Faculty of Pharmacy

    M. S. Ramaiah

    Electrophilic Aromatic Substitution


    Reactions Contd

    Mechanism
    Step 1
    Addition of electrophile to form a carbocation
    Rate determining step
    Step 2
    Loss of a proton to form the substituted product

    16
    Faculty of Pharmacy

    M. S. Ramaiah

    Electrophilic Aromatic Substitution


    Reactions Contd

    How to draw resonance structures for carbocation?

    17
    Faculty of Pharmacy

    M. S. Ramaiah

    Summary
    Benzene planar and resonance stabilized
    Huckels rule states that for a planar, cyclic compound
    to be aromatic its uninterrupted cloud must contain
    (4n+2) electrons, where n is any whole number
    (0,1,2,)
    Benzene
    undergoes
    electrophilic
    aromatic
    substitution reactions
    Sigma complex is formed which is resonance
    stabilized
    Nitration, sulphonation, halogenation, Friedel Crafts
    alkylation and Friedel Crafts acylation of benzene are
    electrophilic substitution reactions
    18
    Faculty of Pharmacy

    M. S. Ramaiah

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