chapter5

chapter5 - 5-5-1Organic Organic ChemistryChemistryWilliam...

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Unformatted text preview: 5-5-1Organic Organic ChemistryChemistryWilliam H. BrownWilliam H. BrownChristopher S. FooteChristopher S. FooteBrent L. IversonBrent L. Iverson5-5-2Alkenes:Alkenes:Structure andStructure andNomenclatureNomenclatureChapter 5Chapter 55-5-3Unsaturated HydrocarbonsUnsaturated HydrocarbonsUnsaturated hydrocarbon:Unsaturated hydrocarbon:contains one or more carbon-carbon double or triple bondsAlkene:Alkene:contains a carbon-carbon double bond and has the general formula CnH2nAlkyne:Alkyne:contains a carbon-carbon triple bond and has the general formula CnH2n-2Ethylene(an alkene)HC CHH HAcetylene(an alkyne) .H-C C-H5-5-4Unsaturated HydrocarbonsUnsaturated HydrocarbonsArenes:Arenes:benzene and its derivatives (Ch 21-22)we do not study arenes until Chapters 21 & 22however, we show structural formulas of compounds containing the phenyl group before that timethe phenyl group is not reactive under any of the conditions we describe in Ch 6-20BenzeneAlternative representations for the phenyl groupCCCCCCC6H5-Ph-HHHHHH5-5-5Structure of AlkenesStructure of AlkenesA double bond consists of one sigma bond formed by the overlap of sp2hybrid orbitals and one pi bond formed by the overlap of parallel 2porbitalsthe two carbon atoms of a double bond and the four atoms bonded to them lie in a plane, with bond angles of approximately 1205-5-6Structure of AlkenesStructure of Alkenesit takes approximately 264 kJ (63 kcal)/mol to break the pi bond in ethylene; that is, to rotate one carbon by 90 with respect to the other so that there is no overlap between 2porbitals on adjacent carbons5-5-7Cis,TransCis,TransIsomerism in AlkenesIsomerism in AlkenesCis,transCis,transisomers:isomers:isomers that have the same connectivity but a different arrangement of their atoms in space due to the presence of either a ring or a carbon-carbon double bondcis-2-Butenemp -139 C, bp 4 Ctrans-2-Butenemp -106 C, bp 1 CCCCH3HH3CHCCHCH3H3CH5-5-8Index of Hydrogen DeficiencyIndex of Hydrogen DeficiencyIndex of hydrogen deficiency (IHD):Index of hydrogen deficiency (IHD):the sum of the number of rings and pi bonds in a moleculeTo determine IHD, compare the number of hydrogens in an unknown compound with the number in a reference hydrocarbon of the same number of carbons and with no rings or pi bondsthe molecular formula of the reference hydrocarbon is CnH2n+25-5-9Index of Hydrogen DeficiencyIndex of Hydrogen Deficiencyfor each atom of a Group 7 element (F, Cl, Br, I), add...
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chapter5 - 5-5-1Organic Organic ChemistryChemistryWilliam...

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