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    The Chemistry of Benzene: A Guide For A Level Students

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    The Chemistry of Benzene: A Guide For A Level Students

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    jules blanco
    59 views23 pages
    chm

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    chm

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    Download as ppt, pdf, or txt
    59 views23 pages

    The Chemistry of Benzene: A Guide For A Level Students

    Uploaded by

    jules blanco
    chm

    Copyright:

    © All Rights Reserved
    Download as PPT, PDF, TXT or read online from Scribd
    Download as ppt, pdf, or txt
    of 23

    THE CHEMISTRY

    OF BENZENE
    A guide for A level students

    KNOCKHARDY PUBLISHING
    2008
    SPECIFICATIONS
    CONTENTS
    • Prior knowledge
    • Structure of benzene
    • Delocalisation
    • RESONANCE HYBRID
    Before you start it would be helpful to…

    • know the arrangement of bonds around carbon atoms


    (Hybridization)
    HYBRIDISATION OF ORBITALS - REVISION

    2p
    The electronic configuration of a 2
    carbon atom is 1s22s22p2 2s

    1 1s
    HYBRIDISATION OF ORBITALS - REVISION

    2p
    The electronic configuration of a 2
    carbon atom is 1s22s22p2 2s

    1 1s

    If you provide a bit of energy you 2p


    2
    can promote (lift) one of the s 2s
    electrons into a p orbital. The
    configuration is now 1s22s12p3
    1 1s

    The process is favourable because of the arrangement of


    electrons; four unpaired and with less repulsion is more stable
    HYBRIDISATION OF ORBITALS - REVISION

    The four orbitals (an s and three p’s) combine or HYBRIDISE


    to give four new orbitals. All four orbitals are equivalent.

    2s22p2 2s12p3 4 x sp3


    HYBRIDISE

    sp3
    HYBRIDISATION
    HYBRIDISATION OF ORBITALS - REVISION

    Alternatively, only three orbitals (an s and two p’s) combine or


    HYBRIDISE to give three new orbitals. All three orbitals are
    equivalent. The remaining 2p orbital is unchanged.

    2s22p2 2s12p3 3 x sp2 2p


    HYBRIDISE

    sp2
    HYBRIDISATION
    STRUCTURE OF ALKENES - REVISION

    In ALKANES, the four sp3 orbitals


    repel each other into a tetrahedral
    arrangement.

    In ALKENES, the three


    sp2 orbitals repel each
    other into a planar
    arrangement and the
    2p orbital lies at right
    angles to them
    STRUCTURE OF ALKENES - REVISION

    Covalent bonds are formed An sp2 orbital from each carbon


    by overlap of orbitals. overlaps to form a single C-C bond.

    The resulting bond is called


    a SIGMA (δ) bond.
    STRUCTURE OF ALKENES - REVISION

    The two 2p orbitals also overlap. This forms a second bond; it


    is known as a PI (π) bond.

    For maximum overlap and hence the strongest bond, the 2p


    orbitals are in line.

    This gives rise to the planar arrangement around C=C bonds.


    ORBITAL OVERLAP IN ETHENE - REVIEW

    two sp2 orbitals overlap to form a sigma two 2p orbitals overlap to form a pi
    bond between the two carbon atoms bond between the two carbon atoms

    s orbitals in hydrogen overlap with the the resulting shape is planar


    sp2 orbitals in carbon to form C-H bonds with bond angles of 120º
    STRUCTURE OF BENZENE

    Primary analysis revealed benzene had...

    an empirical formula of CH and

    a molecular mass of 78 and

    a molecular formula of C6H6


    STRUCTURE OF BENZENE

    Primary analysis revealed benzene had...

    an empirical formula of CH and

    a molecular mass of 78
    a molecular formula of C6H6

    Kekulé suggested that benzene was...

    PLANAR
    CYCLIC and
    HAD ALTERNATING DOUBLE AND SINGLE BONDS
    STRUCTURE OF BENZENE

    It was suggested that the structure oscillated


    between the two forms but was represented by neither of
    them. It was a RESONANCE HYBRID.
    STRUCTURE OF BENZENE - DELOCALISATION
    The theory suggested that instead of three localised (in one position) double bonds,
    the six p (p) electrons making up those bonds were delocalised (not in any one
    particular position) around the ring by overlapping the p orbitals. There would be no
    double bonds and all bond lengths would be equal. It also gave a planar structure.

    6 single bonds
    STRUCTURE OF BENZENE - DELOCALISATION
    The theory suggested that instead of three localised (in one position) double bonds,
    the six p (p) electrons making up those bonds were delocalised (not in any one
    particular position) around the ring by overlapping the p orbitals. There would be no
    double bonds and all bond lengths would be equal. It also gave a planar structure.

    6 single bonds one way to overlap


    adjacent p orbitals
    STRUCTURE OF BENZENE - DELOCALISATION
    The theory suggested that instead of three localised (in one position) double bonds,
    the six p (p) electrons making up those bonds were delocalised (not in any one
    particular position) around the ring by overlapping the p orbitals. There would be no
    double bonds and all bond lengths would be equal. It also gave a planar structure.

    6 single bonds one way to overlap another


    adjacent p orbitals possibility
    STRUCTURE OF BENZENE - DELOCALISATION
    The theory suggested that instead of three localised (in one position) double bonds,
    the six p (p) electrons making up those bonds were delocalised (not in any one
    particular position) around the ring by overlapping the p orbitals. There would be no
    double bonds and all bond lengths would be equal. It also gave a planar structure.

    6 single bonds one way to overlap another delocalised pi


    adjacent p orbitals possibility orbital system
    STRUCTURE OF BENZENE - DELOCALISATION
    The theory suggested that instead of three localised (in one position) double bonds,
    the six p (p) electrons making up those bonds were delocalised (not in any one
    particular position) around the ring by overlapping the p orbitals. There would be no
    double bonds and all bond lengths would be equal. It also gave a planar structure.

    6 single bonds one way to overlap another delocalised pi


    adjacent p orbitals possibility orbital system
    STRUCTURE OF BENZENE
    STRUCTURE OF BENZENE
    ANIMATION
    THE CHEMISTRY
    OF ARENES
    THE END

    © 2009 KNOCKHARDY PUBLISHING

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