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    L4 - Aromatic

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    SUBHAM SAGAR
    The document provides a brief overview of addition reactions of benzene derivatives and aromatic compounds. It discusses the addition of chlorine to benzene to form benzene hexachloride, catalytic hydrogenation of benzene to form cyclohexane, and the Birch reduction of aromatic compounds. It also mentions side chain halogenation, oxidation of side chains with potassium permanganate, addition to double bonds of side chains, and common methods for preparing aromatic compounds.

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    L4 - Aromatic

    Uploaded by

    SUBHAM SAGAR
    28 views36 pages
    The document provides a brief overview of addition reactions of benzene derivatives and aromatic compounds. It discusses the addition of chlorine to benzene to form benzene hexachloride, catalytic hydrogenation of benzene to form cyclohexane, and the Birch reduction of aromatic compounds. It also mentions side chain halogenation, oxidation of side chains with potassium permanganate, addition to double bonds of side chains, and common methods for preparing aromatic compounds.

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    The document provides a brief overview of addition reactions of benzene derivatives and aromatic compounds. It discusses the addition of chlorine to benzene to form benzene hexachloride, catalytic hydrogenation of benzene to form cyclohexane, and the Birch reduction of aromatic compounds. It also mentions side chain halogenation, oxidation of side chains with potassium permanganate, addition to double bonds of side chains, and common methods for preparing aromatic compounds.

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    28 views36 pages

    L4 - Aromatic

    Uploaded by

    SUBHAM SAGAR
    The document provides a brief overview of addition reactions of benzene derivatives and aromatic compounds. It discusses the addition of chlorine to benzene to form benzene hexachloride, catalytic hydrogenation of benzene to form cyclohexane, and the Birch reduction of aromatic compounds. It also mentions side chain halogenation, oxidation of side chains with potassium permanganate, addition to double bonds of side chains, and common methods for preparing aromatic compounds.

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    Aromatic 11th

    1. Side Chain Reactions


    2. Name Reactions
    3. Preparation of benzene
    Paaras Thakur
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    Addition reactions of Benzene Derivatives

    When benzene is treated with an excess of chlorine under heat and pressure (or with
    irradiation by light), six chlorine atoms add to form 1,2,3,4,5,6-hexachlorocyclohexane.
    This product is often called benzene hexachloride (BHC)
    Addition reactions of Benzene Derivatives

    Catalytic hydrogenation of benzene to cyclohexane takes place at elevated temperatures


    and pressures, often catalyzed by ruthenium or rhodium-based catalysts.
    Birch Reduction

    Partial reduction of aromatic compounds

    The reduction of aromatic compounds by alkali metals in liquid ammonia in the presence
    of an alcohol is called the Birch reduction, and yields selectively the 1,4-hydrogenated
    product.
    A carbon bearing an electron-withdrawing carbonyl group is reduced

    A carbon bearing an electron-releasing alkoxy group is not reduced


    Birch Reduction

    Mechanism
    Side Chain Halogenation
    Oxidation of Side Chain with KMnO4

    An aromatic ring imparts extra stability to the nearest carbon atom of its side chains.
    The aromatic ring and one carbon atom of a side chain can survive a vigorous
    permanganate oxidation.
    Oxidation of Side Chain with KMnO4

    Side-chain oxidation is not restricted to alkyl groups. Alkenyl, alkynyl, and acyl
    groups are also oxidized by hot alkaline potassium permanganate.
    Oxidation of Side Chain with KMnO4

    tert-Butylbenzene is resistant to side-chain oxidation. Why?


    Addition to double bond of side chain
    Preparation of Arenes
    Preparation of Arenes
    Use of Protecting and Blocking Groups

    Very powerful activating groups such as amino groups and hydroxyl groups cause
    the benzene ring to be so reactive that undesirable reactions may take place.
    Use of Protecting and Blocking Groups
    Example The major product obtained in the following reaction:
    Example
    Example
    Reaction in Naphthalene

    Naphthalene is an organic compound with formula C10H8. It is the simplest polycyclic


    aromatic hydrocarbon.
    Reaction in Naphthalene

    Polycyclic aromatic hydrocarbons are generally more reactive than benzene in


    electrophilic substitution reactions

    Electrophilic attack at naphthalene occurs preferentially at C1 to form an intermediate


    naphthalenium ion which is more stable than the one formed by attack at C2
    Reaction in Naphthalene

    ● Naphthalenium ion formed by electrophilic addition to C1:


    Reaction in Naphthalene

    ● Naphthalenium ion formed by electrophilic addition to C2:


    Example

    Which statement is correct?

    (a) i form in large quantity


    (b) ii form in large quantity
    (c) i, ii form in equal quantity
    (d) naphthalene does not show nitration
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