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Aromatic Compounds Early in the history of …

Aromatic Compounds Early in the history of organic chemistry (late 18th, Early 19th century) chemists discovered a class of Compounds which were unusually stable A number of these Compounds had a distinct odor Hence these Compounds were called Aromatic Today the term Aromatic is used regardless of the odor of the compound Some Aromatic Compounds have little to no odor Benzene The parent Aromatic compound was discovered to have a molecular formula of C6H6 This 1:1 ratio of carbon to hydrogen is extremely low compared to other known Compounds It was also quickly discovered that these Aromatic Compounds did not react like other alkene Compounds Structure Before NMR and other spectroscopic tools it was hard to determine the structure of organic Compounds Ultimately the symmetry of the molecule revealed its structure All carbon atoms, and all carbon-carbon bonds, are symmetrically equivalent To account for these observations the proposed structure consisted of a cyclic compound stabilized by resonance Each resonance structure is equal in energy and thus each contributes equally to the overall structure Stability The resonance structures imply an extra stability, but the amount of stability in benzene is much more than a typical resonance structure Consider reactivity: RCO3H O.

Aromatic Compounds! Early in the history of organic chemistry (late 18 th, early 19 century) ! chemists discovered a class of compounds which were unusually stable! A number of these compounds had a distinct odor!

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