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We need to identify which reagent converts an alkyl halide into an alkyl isocyanide. The key distinction lies in the ambident nature of the cyanide ion ($$CN^-$$), which can bond through either the carbon atom or the nitrogen atom. Bonding through carbon ($$C$$) gives an alkyl cyanide (nitrile) $$R-CN$$, while bonding through nitrogen ($$N$$) yields an alkyl isocyanide $$R-NC$$.
According to the HSAB (Hard-Soft Acid-Base) principle, $$NaCN$$ and $$KCN$$ are ionic cyanides that provide free $$CN^-$$ ions in solution; these ions attack preferentially through the carbon end, forming alkyl cyanides (nitriles). By contrast, $$AgCN$$ is a covalent cyanide in which silver is bonded to the carbon end of $$CN$$, leaving the nitrogen end free to attack the alkyl halide and form an alkyl isocyanide.
The reaction with $$AgCN$$ is:
$$R-X + AgCN \rightarrow R-NC + AgX$$
This pathway produces an alkyl isocyanide because the nitrogen atom of $$CN$$ attacks the carbon of the alkyl halide. Therefore, the correct answer is Option 4: AgCN.
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