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  • Chemistry Benzene

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    Yasmin Yehia
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    1. Benzene has a planar ring structure of 6 carbon atoms with delocalized pi bonding rather than localized double bonds as depicted by Kekule's model. 2. Evidence against Kekule's model includes the unusual reactivity of benzene which does not behave as a normal alkene, and the thermodynamic stability of benzene upon hydrogenation which is better explained by delocalized bonding than separate carbon-carbon double bonds. 3. The delocalized model of benzene with a cloud of pi electrons above and below the ring plane provides greater stability compared to Kekule's separate double bond representation.

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    1. Benzene has a planar ring structure of 6 carbon atoms with delocalized pi bonding rather than localized double bonds as depicted by Kekule's model. 2. Evidence against Kekule's model includes the unusual reactivity of benzene which does not behave as a normal alkene, and the thermodynamic stability of benzene upon hydrogenation which is better explained by delocalized bonding than separate carbon-carbon double bonds. 3. The delocalized model of benzene with a cloud of pi electrons above and below the ring plane provides greater stability compared to Kekule's separate double bond representation.

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    8 views1 page

    Chemistry Benzene

    Uploaded by

    Yasmin Yehia
    1. Benzene has a planar ring structure of 6 carbon atoms with delocalized pi bonding rather than localized double bonds as depicted by Kekule's model. 2. Evidence against Kekule's model includes the unusual reactivity of benzene which does not behave as a normal alkene, and the thermodynamic stability of benzene upon hydrogenation which is better explained by delocalized bonding than separate carbon-carbon double bonds. 3. The delocalized model of benzene with a cloud of pi electrons above and below the ring plane provides greater stability compared to Kekule's separate double bond representation.

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    of 1

    Qwhy notaccurate

    GHG
    simplestarene
    BENZENE
    1 L I V L L IV L All e to C bonds samelength
    Explaindirtarranger e
    aliphatic straight1branchedchainorgsubs 1716 e of C Ddoc
    aromatic i haveplanar unsat ring pleasentsmell inbenzene
    arene 31 ring 6C atoms w delocalised bonding
    aromatichydrocarbon

    STRUCTURE
    CGH6 Actualstruct
    6 C atoms hex ring oneH bondedeachC
    planarMol deloc e system

    e delocaroundring overlap porbitals H C C bond angle9 1200


    Kekule model evidence to prove WRONG
    Kbenz
    ring large nonpolar
    hydrophobic

    delocalised model
    Gp e deloc in ring above t below
    p plane carbon ring
    6 orbitals overlap 317 bonds
    17bonds clouds deloc e
    e constant move shared equally bet 6 C atoms
    stability
    EVIDENCE AGAINST KEKULE
    1 x decor 13hwater Clackreactivity ofbenzene as not normalalkene
    than
    giverforbenzene exp
    2 Thermodyn stability OHhydrogenation delocalization is stable ordecoct
    f E req break bonds in benzene
    t Hz
    cyclohexane
    f OH 120KJmol kendo texovalue

    If Kekule correct OHF benzene SHOULD be 3X 360


    BUT NET is 208
    benzene stable by152KTmol
    G n e deloc not as 3 C c
    Benzene stableby15215mi
    difference delocalisationenthalpy onbonde Deloc
    sub rxns insteadaddn
    maintains delocsyst

    Ivexo than expected


    due delocstabring fromring e

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