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Organic Chemistry Text Book (CHEM 3401 and 3402)

1.4 Atomic Orbitals

Atomic Orbitals


A more detailed model of covalent bonding requires a consideration of valence shell atomic orbitals. For second period elements such as carbon, nitrogen and oxygen, these orbitals have been designated 2s, 2px, 2py & 2pz. The spatial distribution of electrons occupying each of these orbitals is shown in the diagram below. 
Very nice displays of orbitals may be found at the following sites: 
J. Gutow, Univ. Wisconsin Oshkosh
R. Spinney, Ohio State 
M. Winter, Sheffield University

The valence shell electron configuration of carbon is 2s2, 2px1, 2py1 & 2pz0. If this were the configuration used in covalent bonding, carbon would only be able to form two bonds. In this case, the valence shell would have six electrons- two shy of an octet. However, the tetrahedral structures of methane and carbon tetrachloride demonstrate that carbon can form four equivalent bonds, leading to the desired octet. In order to explain this covalent bonding, Linus Pauling proposed an orbital hybridization model in which all the valence shell electrons of carbon are reorganized.

Hybrid Orbitals
In order to explain the structure of methane (CH4), the 2s and three 2p orbitals are converted to four equivalent hybrid atomic orbitals, each having 25% s and 75% p character, and designated sp3. These hybrid orbitals have a specific orientation, and the four are naturally oriented in a tetrahedral fashion. Thus, the four covalent bonds of methane consist of shared electron pairs with four hydrogen atoms in a tetrahedral configuration, as predicted by VSEPR theory.