columbia大学有机化学课件 （十二）.pptVIP

1.15Bonding in Methane andOrbital Hybridization Structure of Methane tetrahedral bond angles = 109.5° bond distances = 110 pm but structure seems inconsistent withelectron configuration of carbon Electron configuration of carbon only two unpaired electrons should form s bonds to only two hydrogen atoms bonds should be at right angles to one another sp3 Orbital Hybridization Promote an electron from the 2s to the 2p orbital sp3 Orbital Hybridization sp3 Orbital Hybridization Mix together (hybridize) the 2s orbital and the three 2p orbitals sp3 Orbital Hybridization 4 equivalent half-filled orbitals are consistent with four bonds and tetrahedral geometry Shapes of orbitals Nodal properties of orbitals Shape of sp3 hybrid orbitals take the s orbital and place it on top of the p orbital Shape of sp3 hybrid orbitals reinforcement of electron wave in regions where sign is the same destructive interference in regions of opposite sign Shape of sp3 hybrid orbitals orbital shown is sp hybrid analogous procedure using three s orbitals and one p orbital gives sp3 hybrid shape of sp3 hybrid is similar Shape of sp3 hybrid orbitals hybrid orbital is not symmetrical higher probability of finding an electron on one side of the nucleus than the other leads to stronger bonds consistent with structure of methane allows for formation of 4 bonds rather than 2 bonds involving sp3 hybrid orbitals are stronger than those involving s-s overlap or p-p overlap  1.16sp3 Hybridization and Bonding in Ethane tetrahedral geometry at each carbon C—H bond distance = 110 pm C—C bond distance = 153 pm In-phase overlap of half-filled sp3 hybridorbital of one carbon with half-filled sp3hybrid orbital of another. Overlap is along internuclear axis to give a s bond. In-phase overlap of half-filled sp3 hybridorbital of one carbon with half-filled sp3hybrid orbital of another. Overlap is along internuclear axis to give a s bond. 1.17sp2 Hybridization and Bonding in Ethylene Struct