Chemistry > Hydrocarbons > 14.0 Chemical Properteis

  Hydrocarbons
    1.0 Introduction
    2.0 Alkanes
    3.0 Methods of Preparation Alkanes
    4.0 Physical Proparties
    5.0 Chemical Properties
    6.0 Alkenes
    7.0 Methods of Preparation Alkenes
    8.0 Physical Proparties
    9.0 Chemical Properties
    10.0 Mechanism Of Some Important Reaction Of Alkenes
    11.0 Alkynes
    12.0 Methods of Preparation Alkynes
    13.0 Physical Properties
    14.0 Chemical Properteis
    15.0 Modern Concept
    16.0 Properteis
    17.0 Mechanism of Electrophilic Substitution Reactions
    18.0 Toluene
    19.0 Alkenyl Benzene

14.4 Structure of Benzene
Benzene has been known since 1825 when it was first isolated by Michel Faraday. Form elemental analysis and molecular mass determination, it was found that the molecular formula of benzene is ${C_6}{H_6}$ indicating high unsaturation. However, benzene does undergo addition reactions in contrast to unsaturated hydrocarbons, although it mainly undergoes substitution reactions.
In 1865 Friedrich August Kekule proposed a ring structure for benzene (I). However, many alternative structures have been proposed from time to time by different workers. (II-IV).
Then main objection against Kekule structure was that it should yield two ortho disubstituted products when it reacts with bromine. However, experimentally benzene was found to yield only one product.

Kekule removed this objection by proposing that the double bonds in benzene are continuously oscillating back and forth between two adjacent positions. Since positions of double bonds are not fixed, only one product is formed. This structure came to be known as Kekule’s dynamic formula, which formed the basis for the present electronic structure of benzene.


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