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lecture 21.2

lecture 21.2 - 21-21-1Organic Organic H BrownWilliam H...

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Unformatted text preview: 21-21-1Organic Organic ChemistryChemistryWilliam H. BrownWilliam H. BrownChristopher S. FooteChristopher S. FooteBrent L. IversonBrent L. Iverson21-21-2Benzene andBenzene andand the Concept ofand the Concept ofAromaticityAromaticityChapter 21Chapter 2121-21-3Heterocyclic AromaticsHeterocyclic Aromatics◆Heterocyclic compound:Heterocyclic compound:a compound that contains more than one kind of atom in a ring •in organic chemistry, the term refers to a ring with one or more atoms are other than carbon◆Pyridine and pyrimidine are heterocyclic analogs of benzene; each is aromatic.PyridineNNNPyrimidine12345612345621-21-4PyridinePyridine•the nitrogen atom of pyridine is sp2 hybridized•the unshared pair of electrons lies in an sp2hybrid orbital and is not a part of the six pi electrons of the aromatic system•pyridine has a resonance energy of 134 kJ (32 kcal)/mol, slightly less than that of benzeneNthis orbital is perpendicularto the six 2p orbitals of thepi systemthis pair of electronsis not a part of the 4n + 2 pi electrons21-21-5FuranFuran•the oxygen atom of furan is sp2hybridized•one unshared pairs of electrons on oxygen lies in an unhybridized 2porbital and is a part of the aromatic sextet•the other unshared pair lies in an sp2hybrid orbital and is not a part of the aromatic system•the resonance energy of furan is 67 kJ (16 kcal)/molOthis pair of electronsis notthis pair of electronsis a part of the 4n + 2 pi electrons21-21-6Other HeterocyclicsOther HeterocyclicsPurineIndoleNNNNNHHNHCH2CH2NH2 Serotonin(a neurotransmitter)HOCaffeineNNNNOOH3CCH3CH321-21-7Aromatic Hydrocarbon Ions...
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lecture 21.2 - 21-21-1Organic Organic H BrownWilliam H...

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