Which of the following gives the different substitution product with $C H_{3} C H_{2} B r$ when their sodium and silver salts are used?

C N^{-}

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O H^{-}

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R O H

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None of the above

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Solution

The correct option is A $C N^{-}$
$C N^{-}$ 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.

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