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Potassium cyanide (KCN) is a predominantly ionic salt of alkali metal and gives cyanide ion on solution under SN2 reaction. Although both carbon and nitrogen atoms can donate electrons, the reaction takes place through the carbon atom since the C−C bond is stronger than the C−N bond. On the other hand, Silver cyanide (AgCN), is predominantly covalent in nature. Therefore, only nitrogen electron pair is available for bond formation. As a result, alkyl isocyanides are obtained as major products.Similarly, the Nitrite ion is an ambident nucleophile because it has two sites - oxygen and nitrogen - through which an attack can take place. Potassium nitrite (KNO2) is predominantly ionic and one of the oxygen atoms has a negative charge (O=N−O−K+). Nucleophilic attack through this negatively charged oxygen atom mainly gives alkyl nitrite. Silver nitrite (AgNO2), on the other hand, is predominantly covalent and both oxygen and nitrogen atoms have lone pairs of electrons. Since nitrogen is less electronegative than oxygen, the lone pair of electrons on nitrogen are more easily available for bond formation. In short, the nucleophilic attack takes place through nitrogen; hence, nitroalkanes are obtained as major products.
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