By Valerie Coulter
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Extra info for Advanced Organic Chemistry
The inversion involves a change of hybridisation where the nitrogen becomes sp 2 hybridised rather than sp3 hybridised. Because of this, the molecule becomes planar and the lone pair of electrons occupy a p orbital. Once the hybridisation reverts back to sp3, the molecule can either revert back to its original shape or invert. Although the enantiomers of chiral amines cannot be separated, such amines can be alkylated to form quaternary ammonium salts where the enantiomers can be separated. Once the lone pair of electrons is locked up in a σ bond, pyramidal inversion becomes impossible and the enantiomers can no longer interconvert.
According to Hund’s rule, all the four hybridised orbitals are half filled with electrons thus there are four unpaired electrons. Four bonds are now possible. A. sp3 Hybridisation. The Organisation 39 Geometry Each of the sp3 hybridised orbitals has the same shape. e. one lobe is larger as compared to other lobe: Fig. sp3 Hybridised orbital. Each sp3 orbital occupies a space as far apart from each other as possible by pointing to the concerns of tetrahedron. 5°. This is what is meant by the expression tetrahedral carbon.
After hybridisation, it will have one half-filled sp3 orbital and will form one bond. Fig. (a) Geometry of sp3 hybridised nitrogen; (b) geometry of sp3 hybridised oxygen. e. N, O and Cl) form a tetrahedral arrangement having one or more of the hybridised orbitals occupied by a lone pair of electrons. 5° (c. (a). This compression of the bond angles is because of the orbital containing the lone The Organisation 41 pair of electrons, which requires a slightly greater amount of space than a bond. (b)]: Alcohols, amines, alkyl halides, and ethers all contain sigma bonds that involve nitrogen, oxygen, or chlorine.
Advanced Organic Chemistry by Valerie Coulter