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  • Organic Chemistry - Unit 5

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    RUGRLN
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    The document discusses the structure and properties of benzene. It begins by explaining that benzene's structure is not accurately depicted by Kekule's proposed structure, as evidenced by experimental data showing its carbon bonds are equal in length and delocalized pi electrons. The key aspects are that benzene's carbon atoms are in a flat ring with each carbon contributing one p orbital, forming a delocalized system of 6 pi electrons through sideways overlap. This pi bonding system makes benzene unusually stable. The document also briefly outlines benzene's physical properties as a liquid with a characteristic smell and discusses its carcinogenicity, and describes nitration as an example of benzene undergoing electrophilic substitution while maintaining its pi electron system.

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    The document discusses the structure and properties of benzene. It begins by explaining that benzene's structure is not accurately depicted by Kekule's proposed structure, as evidenced by experimental data showing its carbon bonds are equal in length and delocalized pi electrons. The key aspects are that benzene's carbon atoms are in a flat ring with each carbon contributing one p orbital, forming a delocalized system of 6 pi electrons through sideways overlap. This pi bonding system makes benzene unusually stable. The document also briefly outlines benzene's physical properties as a liquid with a characteristic smell and discusses its carcinogenicity, and describes nitration as an example of benzene undergoing electrophilic substitution while maintaining its pi electron system.

    Copyright:

    Attribution Non-Commercial (BY-NC)
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    212 visualizzazioni4 pagine

    Organic Chemistry - Unit 5

    Caricato da

    RUGRLN
    The document discusses the structure and properties of benzene. It begins by explaining that benzene's structure is not accurately depicted by Kekule's proposed structure, as evidenced by experimental data showing its carbon bonds are equal in length and delocalized pi electrons. The key aspects are that benzene's carbon atoms are in a flat ring with each carbon contributing one p orbital, forming a delocalized system of 6 pi electrons through sideways overlap. This pi bonding system makes benzene unusually stable. The document also briefly outlines benzene's physical properties as a liquid with a characteristic smell and discusses its carcinogenicity, and describes nitration as an example of benzene undergoing electrophilic substitution while maintaining its pi electron system.

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    Benzene

    Thursday, January 13, 2011


    7:01 PM

    Benzene was originally thought to have Kekule's structure, however the following evidence showed that that
    structure was not possible:
    - Benzene doesn't undergo electrophilic addition (as alkenes do) but electrophilic substitution
    - X-ray diffraction data shows all the bonds in benzene are of the same length, however they are of a length
    between that of C-C bonds and C=C
    - Thermochemical analysis disagrees with benzene's structure:

    - From IR spectra analysis:


    Alkene 2952-2853 cm-1 Benzene 3050 and 750 cm-1
    Due to CH of CH2, CH3
    C=C is below 1700 cm-1

    Structure of Benzene

    Organic Chemistry - Unit 5 Page 1


    Pi (π) Bonds
    Pi (π) bonds are formed by the
    sideways overlap of 2 p
    orbitals.

    The 6 carbon atoms in benzene are all in the same plane. Each carbon has a p electron. Due to the planar structure of
    benzene, the p-orbitals of benzene now overlap sideways leading to a delocalised system of 6 π electrons. This does
    not lead to any distinct π bonds but the overlap between the p orbitals is throughout the whole ring, above and below
    it.
    Molecules with delocalised electrons are more stable, than those whose electrons are not delocalised.

    In benzene this accounts for the compound being 152 kJmol-1 more stable than expected for the Kekule structure.

    Physical Properties of Benzene


    - It is a liquid
    - It has a nice smell since it is volatile
    - It is one of the most carcinogenic compounds that we have
    - It causes leukemia.

    Organic Chemistry - Unit 5 Page 2


    Reactions of Benzene
    Friday, January 14, 2011
    11:02 AM

    Addition reaction

    When it undergoes substitution, it retains its 6π cloud of electrons, so it retains its stability.

    Nitration of Benzene
    Electrophilic Substitution

    ‫ܱܰܪ‬ଷ + 2‫ܪ‬ଶ ܱܵସ → ܱܰଶା + ‫ܪ‬ଷ ܱା + 2‫ܱܵܪ‬ସି


    nitration mixture ↘ nitroneum ion (electrophile)

    ‫ܱܰܪ‬ଷ + ‫ܪ‬ଶ ܱܵସ → ‫ܪ‬ଶ ܱ + ܱܰଶା + ‫ܱܵܪ‬ସି


    ‫ܪ‬ଶ ܱ + ‫ܪ‬ଶ ܱܵସ → ‫ܪ‬ଷ ܱା + ‫ܱܵܪ‬ସି
    = ‫ܱܰܪ‬ଷ + 2‫ܪ‬ଶ ܱܵସ → ܱܰଶା + ‫ܪ‬ଷ ܱା + 2‫ܱܵܪ‬ସି

    Organic Chemistry - Unit 5 Page 3


    At the end the 6π delocalised electron cloud is restored.

    Organic Chemistry - Unit 5 Page 4

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