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Haloalkanes And Haloarenes

Question
CBSEENCH12007886

Write the mechanism of the following reaction:

bold n bold space bold BuBr bold space bold plus bold space bold KCN bold space bold rightwards arrow with bold space bold space bold space bold space bold EtOH bold space bold minus bold space bold H subscript bold 2 bold O bold space bold space bold space bold space on top bold space bold n bold space bold BuCN bold.

Solution

The given reaction is SN2 reaction. The nucleophile, Nu approaches the carbon atom on the side opposite from the halogen and forms new covalent bond with the carbon. This is because KCN is an ionic compound, K+ [C ≡ N]. Since carbon carrying a lone pair of electrons is more reactive than nitrogen carrying a lone pair, the transition state is formed by the carbon of the cyanide ion forming band with the carbon halogen bond thus,