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Haloalkanes And Haloarenes

Question
CBSEENCH12007986

How do the products differ when ethyl bromide reacts separately with KCN and AgCN?

Solution

KCN is predominantly , ionic and therefore , both C and N atoms is available for the electron donation but the reaction occurs through carbon as C-C bonds are stronger than C- N bond, therefore the attack occurs through the carbon atom of the cyanide group forming alkyl cyanides as the main product.
C2H5Br +KCN --> C2H5CN +KBr

On the other hand ,AgCN is predominantly covalent in nature and nitrogen is free to donate electron pair forming isocyanides as the main product.
C2H5Br + AgCN ---> C2H5NC