lecture 21.2

lecture 21.2 - 21-21-1Organic Organic...

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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 AromaticsHeterocyclic 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 carbonPyridine and pyrimidine are heterocyclic analogs of benzene; each is aromatic.PyridineNNNPyrimidine12345612345621-21-4PyridinePyridinethe nitrogen atom of pyridine is sp2 hybridizedthe unshared pair of electrons lies in an sp2hybrid orbital and is not a part of the six pi electrons of the aromatic systempyridine 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 electrons21-21-5FuranFuranthe oxygen atom of furan is sp2hybridizedone unshared pairs of electrons on oxygen lies in an unhybridized 2porbital and is a part of the aromatic sextetthe other unshared pair lies in an sp2hybrid orbital and is not a part of the aromatic systemthe 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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This note was uploaded on 03/30/2008 for the course CHEM 262 taught by Professor Forbes during the Spring '08 term at UNC.

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lecture 21.2 - 21-21-1Organic Organic...

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