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SCAN0002 - CHAPTER 11 Arenes and Aromaticity I History The...

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Unformatted text preview: CHAPTER 11: Arenes and Aromaticity I. History The history of benzene and aromatic compounds: Ch. 11.1 and 11.2 Benzene (CeHs) was synthesized in 1834 fiom benzoic acid. Benzene was an unusual compound because it had the same number of H's as C's. Usually there were twice as many hydrogens. Therefore, this molecule was highly unsaturated. It was soon found that a large number of compounds contained a six-carbon fragment related to benzene. These compounds were called aromatic because many of them had distinctive smells, to distinguish them with aliphatic compounds with larger numbers of hydrogens. In 1834, very little was known about the structure of organic molecules, so figuring out the structure of benzene was a difficult problem. ‘ p i . . l C5H5002H + 0230 heat H “l CBHB + C3003 Known reactions of unsaturated compounds: Bremineis decohrized ‘1‘ i ‘ .5 i C: Pemanganaie is demierized ‘ Q 1 OH 3: B: H H Reactivity of benzene No reaction No reaction Benzene — CSHS No reaction C5H12 Reaction is extremely slow at high temperature and pressure 1 The reactivity of benzene was unlike the other unsaturated compounds that were known at the time. Benzene could react with bromine in the presence of F e3+ (rusty iron wire), but did not give a dibromination product. Fe3+ CeHe + Br2 ~———>— CeHsBr +HBr u..— wl 3‘ Only a single monosubstitutioniproduct was formed. What can that tell us about the structure of benzene? ...
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