有机化学文课件chapter5.pptVIP

Organic Chemistry William H. Brown Christopher S. Foote Brent L. Iverson Unsaturated Hydrocarbons Unsaturated hydrocarbon: contains one or more carbon-carbon double or triple bonds Alkene: contains a carbon-carbon double bond and has the general formula CnH2n Alkyne: contains a carbon-carbon triple bond and has the general formula CnH2n-2 Unsaturated Hydrocarbons Arenes: benzene and its derivatives (Ch 21-22) we do not study arenes until Chapters 21 22 however, we show structural formulas of compounds containing the phenyl group before that time the phenyl group is not reactive under any of the conditions we describe in Ch 6-20 Structure of Alkenes A double bond consists of one sigma bond formed by the overlap of sp2 hybrid orbitals and one pi bond formed by the overlap of parallel 2p orbitals the two carbon atoms of a double bond and the four atoms bonded to them lie in a plane, with bond angles of approximately 120° Structure of Alkenes it 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 2p orbitals on adjacent carbons Cis,Trans Isomerism in Alkenes Cis,trans 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 bond Index of Hydrogen Deficiency Index of hydrogen deficiency (IHD): the sum of the number of rings and pi bonds in a molecule To 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 bonds the molecular formula of the reference hydrocarbon is CnH2n+2 Index of Hydrogen Deficiency for each atom of a Group 7 element (F, Cl, Br, I), add one H no correction is necessary for the addition of atoms of Group 6 elements (O,S) to the reference hydrocarbon for each atom of a Group 5 element (N, P), subtract