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    Benzene

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    SANJAY S SHEKAR
    The document discusses the orbital and resonance structure of benzene. It describes how benzene is a flat molecule with sp2 hybridized carbons forming six delocalized pi electrons around the ring. It also discusses Huckel's rule for aromaticity and how benzene meets the 4n+2 criteria to be aromatic.

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    Benzene

    Uploaded by

    SANJAY S SHEKAR
    13 views9 pages
    The document discusses the orbital and resonance structure of benzene. It describes how benzene is a flat molecule with sp2 hybridized carbons forming six delocalized pi electrons around the ring. It also discusses Huckel's rule for aromaticity and how benzene meets the 4n+2 criteria to be aromatic.

    Original Title

    Benzene-converted(1)

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    The document discusses the orbital and resonance structure of benzene. It describes how benzene is a flat molecule with sp2 hybridized carbons forming six delocalized pi electrons around the ring. It also discusses Huckel's rule for aromaticity and how benzene meets the 4n+2 criteria to be aromatic.

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    13 views9 pages

    Benzene

    Uploaded by

    SANJAY S SHEKAR
    The document discusses the orbital and resonance structure of benzene. It describes how benzene is a flat molecule with sp2 hybridized carbons forming six delocalized pi electrons around the ring. It also discusses Huckel's rule for aromaticity and how benzene meets the 4n+2 criteria to be aromatic.

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    of 9

    Orbital and resonance structure of Benzene

    • Benzene is a flat molecule, with every carbon and hydrogen lying in


    the same plane these bonds are designated as a sigma (σ) bonds.

    • Each sp2 hybridized C in the ring has an unhybridized p orbital


    perpendicular to the ring which overlaps around the ring.

    • The six pi (π) electrons are delocalized over the six carbons.

    Aromatic character: The Huckel 4n + 2 rule


    In 1931, German chemist and physicist Erich Hückel proposed a theory to
    help determine if a planar ring molecule would have aromatic properties.

    Four Criteria for Aromaticity


    • The molecule is cyclic (a ring of atoms)
    • The molecule is planar (all atoms in the molecule lie in the same
    plane)
    • The molecule is fully conjugated (p orbitals at every atom in the ring)
    • The molecule has 4n+2 π-electrons (n=0 or any positive integer)

    Why 4n+2 π-Electrons?


    • According to Hückel's Molecular Orbital Theory, a compound is
    particularly stable if all of its bonding molecular orbitals are filled
    with paired electrons.

    • In benzene, each double bond (π bond) always contributes 2 π


    electrons. Benzene has 3 double bonds, so it has 6 π electrons.

    • To apply the 4n+2 rule, first count the number of π electrons in the
    molecule.
    • Then, set this number equal to 4n+2 and solve for n. If is 0 or any
    positive integer (1, 2, 3,...), the rule has been met. For example, benzene
    has six π electrons:
    • 4n+2=6
    n=1
    4X1+2=6
    For benzene, we find that n=1, which is a positive integer, so the rule is
    met. Benzene is aromatic compound.
    • 4n+2=8
    n=1 becomes 6
    n=2 becomes 10 but cyclooctatetraene has 8 electrons.
    For cyclooctatetraene, we cannot find an integer1,2.. so the rule will not
    meet. Cyclooctatetraene is not aromatic compound.
    Substituted Derivatives of Benzene and their Nomenclature

    Benzenes with two or more substituents:


    • Choose numbers to get lowest possible values
    • List substituents alphabetically with hyphenated numbers
    • Non-systematic names, such as “toluene” can serve as parent
    Preparation of benzene
    (i) industrial preparation of benzene from coal tar :

    Coal tar is a viscous liquid obtained by the pyrolysis of coal. During fractional
    distillation, coal tar is heated and distills away its volatile compounds namely benzene,
    toluene, xylene in the temperature range of 350 to 443 K. These vapours are collected
    at the upper part of the fractionating column

    (ii) from acetylene.


    (iii) Decarboxylaation Of Aromatic Acid.

    (iv) Wurtz – Fittig Reaction:

    Reactions of Benzene
    Electrophilic Aromatic Substitution:
    Aromatic compounds undergo electrophilic aromatic substitution
    (EAS) and the Electrophile has a full or partial positive charge.

    Benzene undergoes Halogenation, Nitration, Sulfonation,


    Friedalcraft’s Acylation and Alkylation
    General mechanism of Electrophilic Aromatic Substitution
    Step I: Formation of Electrophile
    Catalyst
    H+ E E + H- Catalyst

    Step II: Attack of Electrophile:

    The electrophile reacts with two p electrons from the aromatic


    ring
    Step III: Removal of proton:

    The energy diagram of this reaction shows that thJe first step is highly
    endothermic and has a large DG‡ (1).
    The second step is highly exothermicand has a small DG‡ (2).

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