Dolbier HW Solutions 280

Dolbier HW Solutions 280 - 274 ARENES AND AROMATICITY (b)...

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( b ) This compound, called azonine, has 10 electrons in a completely conjugated planar mono- cyclic p system and therefore satis f es H ü ckel s rule for (4 n 1 2) p electrons where n 5 2. There are 8 p electrons from the conjugated tetraene and 2 electrons contributed by the nitro- gen unshared pair. ( c ) Borazole, sometimes called inorganic benzene, is aromatic. Six p electrons are contributed by the unshared pairs of the three nitrogen atoms. Each boron contributes a p orbital to main- tain the conjugated system but no electrons. ( d ) This compound has 8 p electrons and is not aromatic. 11.47 The structure and numbering system for pyridine are given in Section 11.21, where we are also told that pyridine is aromatic. Oxidation of 3-methylpyridine is analogous to oxidation of toluene. The methyl side chain is oxidized to a carboxylic acid. 11.48 The structure and numbering system for quinoline are given in Section 11.21.
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