HYBRIDIZATION Hybridization is the mixing together of "atomic orbitals" (i.e., s-, p-) to form new, hybridizedatomic orbitals. These new, hybridized, atomic orbitals overlap to form σand πbonds. Carbon, oxygen and nitrogen valence atomic orbitals hybridize to form sp3, sp2 or sp hybridized orbitals. For neutral (no formal charge)C, O, and N atoms, the following guidelines in the table below can be used to predict the hybridization of these atoms in organic molecules. CARBON Valence atomic orbitals Hybridized atomic orbitals Bonding Pattern, geometry and bond angles in molecules sp3 2s + 2px + 2py + 2pz All fourof carbon's valence orbitals mix to form four new hybridized orbitals sp3 + sp3 + sp3 + sp3 Four new, degenerate (equal energy) orbitals are generated after hybridization. Each orbital is used to form a sigma bond (methane) Tetrahedral geometry(Td) 109°bond angles Four σbondssp2 2s + 2px + 2py + 2pz Threeof carbon's four valence orbitals mix(in box) to form three new hybridized orbitals. The unhbridized p-orbital is used for πbondingsp2 + sp2 + sp2 + p Three new degenerate orbitals are formed after hybridization. The p orbital remains unhybridized. The sp2 orbitals are used to form σbonds and the p orbital is used to form a πbond. (ethylene) Trigonal planar geometry 120°bond angles Three σbonds, one π bond sp 2s + 2px + 2py + 2pz Twoof carbon's four valence orbitals mix(in box) to form two new hybridized orbitals. The unhbridized p-orbitals are used for πbondingsp + sp + p + p Two new degenerate orbitals are generated after hybridization. The two p orbitals remain unhybridized. The sp orbitals are used to form σbonds and the p orbitals are used to form πbonds. (acetylene) Linear geometry 180°bond angles Two σbonds, two π bonds
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