Answer to Question #313750 in Organic Chemistry for swarnajeet kumar

Question

Explain following: Reaction of silver cyanide with bromopropane gives 1-propylisonitile not npropyl cyanide. 

Answer 1

Ethylbromide on treatment with silver cyanide gives Ethyl isocyanide because AgCN is covalent in nature. Ag+ has very strong affinity for Br- , hence the formation of CH3-CH2+ take place and only N is free to donates the electron pair, hence reaction proceeds through SN1 mechanism.

CH3-CH2-Br + AgCN → CH3-CH2-NC +AgBr

Ethylbromide on treatment with silver cyanide gives CH3 - CH2 - N C