Benzene is an important organic chemical compound with the chemical formula C6H6. The benzene molecule is composed of 6 carbon atoms joined in a ring with 1 hydrogen atom attached to each. Because it contains only carbon and hydrogen atoms, benzene is classed as a hydrocarbon.
Benzene is a natural constituent of crude oil and is one of the elementary petrochemicals. Because of the cyclic continuous pi bond between the carbon atoms, benzene is classed as an aromatic hydrocarbon, the second [n]-annulene ([6]-annulene. It is sometimes abbreviated Ph–H. Benzene is a colorless and highly flammable liquid with a sweet smell. It is used primarily as a precursor to the manufacture of chemicals with more complex molecules, such as ethylbenzene and cumene, of which billions of kilograms are produced. Because benzene has a high octane number, it is an important component of gasoline.
Because benzene is a human carcinogen, most non-industrial applications have been limited.
The empirical formula for benzene was long known, but its highly polyunsaturated structure, with just one hydrogen atom for each carbon atom, was challenging to determine. Archibald Scott Couper in 1858 and Joseph Loschmidt in 1861[28] suggested possible structures that contained multiple double bonds or multiple rings, but too little evidence was then available to help chemists decide on any particular structure.
In 1865, the German chemist Friedrich August Kekulé published a paper in French (for he was then teaching in Francophone Belgium) suggesting that the structure contained a ring of six carbon atoms with alternating single and double bonds. The next year he published a much longer paper in German on the same subject.[29][30] Kekulé used evidence that had accumulated in the intervening years—namely, that there always appeared to be only one isomer of any monoderivative of benzene, and that there always appeared to be exactly three isomers of every disubstituted derivative—now understood to correspond to the ortho, meta, and para patterns of arene substitution—to argue in support of his proposed structure.[31] Kekulé's symmetrical ring could explain these curious facts, as well as benzene's 1:1 carbon-hydrogen ratio.[32]
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