Which of the followings reagents forms an isonitrile when reacted with an alkyl halide?

K C N

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A g C N

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K N O_{2}

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(a) and (b) above.

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Solution

The correct option is B $A g C N$
$C N^{-}$ is the ambident nucleophile and can form different product with same substrate.
$C H_{3} - C H_{2} - B r + N a C N \to C H_{3} - C H_{2} - C N + C H_{3} - C H_{2} + N \equiv C^{-} + N a B r Ethyl cyanide Ethyl isocyanide Major Minor$

$C H_{3} C H_{2} - B r + A g C N \to C H_{3} C H_{2} C N + C H_{3} C H_{2} N^{-} C^{+} + N a B r Ethyl cyanide Ethyl isocyanide Minor Major$
Hence, cyanide ion gives the different substitution product with $C H_{3} C H_{2} B r$ when their sodium and silver salts are used.

$K N O_{2}$ is predominantly ionic. It exists as free ions in solution. O site is more nucleophilic than N site and available to attack the ethyl chloride. Hence, the major product will be ethyl nitrite.

$C_{2} H_{5} C l + K N O_{2} \to C_{2} H_{5} O N O Ethylnitrite + C_{2} H_{5} N O_{2} Nitroethane$

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