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    The Structure of Benzene in Powerpoint

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    danielmahsa
    1) This document discusses the structure of benzene, which was a mystery when it was first isolated in 1825. 2) In 1865, Kekulé suggested benzene has a ring structure with alternating single and double bonds. However, this did not explain its unusual stability and reactivity. 3) It is now understood that benzene has a delocalized pi electron cloud above and below the ring, with equal carbon-carbon bond lengths. This delocalization makes benzene highly stable.

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    The Structure of Benzene in Powerpoint

    Uploaded by

    danielmahsa
    492 views16 pages
    1) This document discusses the structure of benzene, which was a mystery when it was first isolated in 1825. 2) In 1865, Kekulé suggested benzene has a ring structure with alternating single and double bonds. However, this did not explain its unusual stability and reactivity. 3) It is now understood that benzene has a delocalized pi electron cloud above and below the ring, with equal carbon-carbon bond lengths. This delocalization makes benzene highly stable.

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    benzene and chemical reaction electrophilic substitution

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    The Structure of Benzene in powerpoint

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    1) This document discusses the structure of benzene, which was a mystery when it was first isolated in 1825. 2) In 1865, Kekulé suggested benzene has a ring structure with alternating single and double bonds. However, this did not explain its unusual stability and reactivity. 3) It is now understood that benzene has a delocalized pi electron cloud above and below the ring, with equal carbon-carbon bond lengths. This delocalization makes benzene highly stable.

    Copyright:

    © All Rights Reserved
    Download as PPT, PDF, TXT or read online from Scribd
    Download as ppt, pdf, or txt
    492 views16 pages

    The Structure of Benzene in Powerpoint

    Uploaded by

    danielmahsa
    1) This document discusses the structure of benzene, which was a mystery when it was first isolated in 1825. 2) In 1865, Kekulé suggested benzene has a ring structure with alternating single and double bonds. However, this did not explain its unusual stability and reactivity. 3) It is now understood that benzene has a delocalized pi electron cloud above and below the ring, with equal carbon-carbon bond lengths. This delocalization makes benzene highly stable.

    Copyright:

    © All Rights Reserved
    Download as PPT, PDF, TXT or read online from Scribd
    Download as ppt, pdf, or txt
    of 16

    The structure of benzene

    The electron
    config of
    carbon

    This new hydrocarbon isolated by Michael Faraday in 1825


    presented a huge problem.
    .

    The % of carbon was 92% Carbon (C= 12) . Its


    relative molecular mass was 78.
    Calculate the molecular formula

    The molecular formula is C6H6 suggesting that the molecule


    contained a large number of double bonds.
    Benzene did not, it was surprisingly unreactive
    All the chemistry they knew suggested that any substance
    with a double or triple bond would be very reactive and react
    readily with HBr in the dark.

    In 1865 after a dream about a snake biting its own tale, Kekul
    suggested the following structure for benzene.

    This did not explain why the structure was so unreactive, the
    chemists of the time were convinced that it should react with
    bromine in the dark at room temperature. This does not happen
    with benzene.

    This does not fit with Kekuls idea of alternating double and
    single bonds.
    Another problem was the energy of hydrogenation (addition of
    hydrogen).
    The hydrogenation of cyclohexane is well known.

    So if three double bonds are present as in benzene, then the


    comparable reaction should liberate 3 times that of cyclohexane.
    -(3 120) = - 360 kJ mol-1

    But the actual value for benzene was found to be different. -208kJ
    mol-1
    So benzene is (360-208) = 152 kJ mol-1 more stable than
    otherwise expected, or if it contained 3 ordinary C=C bonds.

    -360kJ/mol (3
    X 120)

    -208kJ/mol

    progress

    This is a better all round model than the Kekul


    structure which shows 2 extremes of the same
    thing. The circle in the middle shows the
    delocalisation of the aromatic system.

    The bond length of C-C bonds in benzene are found


    someway between that of an alkane and an alkene.
    Bond Lengths

    /nm

    C-C
    cyclohexane

    0.154

    C=C
    cyclohexane

    0.134

    C-C in benzene

    0.140

    Evidence for delocalisation in benzene


    Hydrogenation energies are lower than expected
    Delocalised systems are highly saturated, but their
    reactions are of substitution rather than addition..
    Carbon-Carbon bond lengths are equal in the delocalised system.

    Benzene is a flat
    molecule, with all atoms
    in the same plane,( bond
    angle 120)

    Any compound
    where the ratio of
    C:H is about 1:1 is
    likely to contain a
    benzene ring.

    When the benzene ring is


    attached to an aliphatic
    skeleton, it is called the
    phenyl group. The formula
    of a phenyl group id C6H5.

    There are several methods of displaying the formula of


    benzene, the standard A2 method is:

    This represents the delocalised electrons, and is


    probably the best way of representing the delocalisation
    during mechanisms

    Exam points
    Benzene is a flat molecule with 6 carbons bonded in a
    Planar ring
    Each carbon is covalently joined to two other carbons
    and one hydrogen. A total of three covalent bonds
    The remaining outer electron of each carbon is shared
    with the other carbons in the ring. The six electrons are
    delocalised around the ring system, giving stability
    All bond lengths are the same.

    Never draw benzene as a


    simple hexagon. This would
    be a molecule of cyclohexane
    this has no delocalised
    electrons, and is not flat like
    benzene.

    Also unless drawing


    mechanisms, never include
    the hydrogens attached
    directly to the benzene ring.
    This is bad chemistry.

    Naming benzene molecules

    1.2-dimethyl
    benzene

    1,4-dimethyl benzene
    1,3dimethylbenzene

    2-hydroxybenzoic
    acid
    benzene-1,4-dicarboxylic
    acid
    phenyamine
    chlorobenzene
    nitrobenzene
    Methyl 3-nitrobenzoate
    2,4,6-trichlorophenol
    phenyl ethanoate
    phenylethanone
    phenol
    Benzoic acid
    phenylethene

    Fused ring systems

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