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Additional resources for Advanced Organic Chemistry
Properties The nitrile group (CN) is linear in shape with both the carbon and the nitrogen atoms being sp hybridised. The triple bond linking the two atoms consists of one σ bond and two π bonds. Nitriles are strongly polarised. The nitrogen is a nucleophilic centre and the carbon is an electrophilic centre. ). Generally, the nucleophile will form a bond to the electrophilic carbon resulting in simultaneous breaking of one of the π bonds. The π electrons end up on the nitrogen to form an sp2 hybridised imine anion which then react further to give different products depending on the reaction conditions used.
The energy of each hybridised orbital is greater than that of the original s orbital but less than that of the original p orbitals. The remaining 2p orbital (in this case the 2py orbital) remains at its original energy level: Fig. sp2 Hybridisation. e. 2s22px1 2p p ) to fit into the three hybridised sp2 orbitals and the remaining 2p orbital. The first three electrons are fitted into each of the hybridised orbitals according to Hund’s rule and they are all halffilled this leaves one electron still to place.
38 Organic Chemistry • The 2s orbital is mixed with one of the 2p orbitals. This is called as sp hybridisation. The other types of hybridisation observed in some other compounds are: (i) dsp2: In it one (n – 1)d orbital and one ns orbital and 2 np orbitals combine to form 4 hybridised orbitals. (ii) d2sp3 or sp3d2: The six hybridised orbitals are formed by mixing up of two λ(n – 1)d orbitals, or two nd orbitals with one ns and three np orbitals. sp3 Hybridisation Definition: The sp3 hybridisation of carbon involves mixing up of the 2s orbitals with all three of the 2p orbitals to give a set of four sp3 hybrid orbitals.