CH 2536 Lecture 03 Arom 14.1 - 14.7

CH 2536 Lecture 03 Arom 14.1 - 14.7 - Lecture 3 Aromaticity...

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Lecture 3 Aromaticity & Reactions of Benzene Sections 14.1-5
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Aromatic Compounds: Benzene Benzene was discovered in 1825 (Michael Faraday) Its composition was correctly determined as C 6 H 6 in 1834. Its structure was not finally settled until the 1930’s, over 100 years after its discovery. Why did it take so long?
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The structure of benzene Degrees of unsaturation for a hydrocarbon or an oxygen-containing compound C n H m O p can be calculated by the formula DOS = (2n + 2 – m)/2 (the number of oxygens can be ignored) For benzene DOS = (12+2-6)/2 = 4 Each DOS is equivalent to a ring or a double bond. So benzene has four double bonds, or one ring plus three double bonds, or two rings and two double bonds.
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The stability of benzene Compounds with many double bonds are usually quite unstable and quite reactive. For example: Br 2 , room temp very fast Br Br + Br Br (3 degrees of unsaturation)
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The stability of benzene Benzene, on the other hand, is very unreactive: Br 2 , room temp No reaction Benzene (4 degrees of unsaturation) The reason for this is that benzene has delocalized electrons and a resonance- stabilized structure.
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This note was uploaded on 05/06/2008 for the course CHEM 2536 taught by Professor Berg during the Spring '08 term at Virginia Tech.

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CH 2536 Lecture 03 Arom 14.1 - 14.7 - Lecture 3 Aromaticity...

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