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Quick Overview of Aromatic Compounds

Quick Overview of Aromatic Compounds - Aromatic Compounds...

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Aromatic Compounds and Aromaticity Solomons 6 th Edition Chapter 14 p 614 – 654 Chapter 15 p 655 – 703 (Reactions) You will by now be familiar with the structure of benzene C 6 H 6 or Discovered in 1825 by Michael Faraday (RI). Molecular formula deduced by Mitscherlich in 1834. The fragrant odour of benzene and its derivatives led them to being classed as “aromatic”. This classification now has a chemical meaning – “aromaticity” is associated with a special stability resulting from structure. Elucidation of the structure posed a problem – the molecular formula C 6 H 6 indicated a highly unsaturated compound (double and/or triple bonds) but benzene does not show this behaviour. Kekulé (1865) conceived a cyclic structure, C C C C C C H H H H H H but this would imply alternating single and double bonds (C-C = 1.47Å, C=C = 1.34Å). Kekulé suggested that two forms of benzene were in rapid equilibrium: Later spectroscopic evidence showed all bond lengths to be equal and intermediate between single and double bond lengths (1.39 Å). It was also found that benzene was a flat (planar) molecule. We now look at benzene using two different possible approaches to try to describe its stability.
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