Explain, in terms of the ionic vs. covalent character of the two reagents, why $\text{KCN}$ reacts with a haloalkane through carbon (giving an alkyl cyanide) while $\text{AgCN}$ reacts through nitrogen (giving an alkyl isocyanide).

Cyanide is an ambident nucleophile whose negative charge is shared between carbon and nitrogen, and which end reacts is decided by the character of the counter-cation. Potassium, a hard, weakly polarising cation, leaves $\text{CN}^-$ essentially free and ionic in solution, so …

Explain, in terms of the ionic vs. covalent charac

Example · Example 30

\text{KCN}

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Concept understanding — Preparation and Reactions of Cyanides and Isocyanides

A haloalkane reacts with the same $\text{CN}^-$ ambident ion to give two different

products depending on the metal: ionic $\text{KCN}$ attacks through carbon (giving the

cyanide), while covalent $\text{AgCN}$ -- its carbon end tied up by the strongly …

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Q.Explain, in terms of the ionic vs. covalent character of the two reagents, why KCN\text{KCN}KCN reacts with a haloalkane through carbon (giving an alkyl cyanide) while AgCN\text{AgCN}AgCN reacts through nitrogen (giving an alkyl isocyanide).

Concept understanding — Preparation and Reactions of Cyanides and Isocyanides

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Q.Explain, in terms of the ionic vs. covalent character of the two reagents, why $\text{KCN}$ reacts with a haloalkane through carbon (giving an alkyl cyanide) while $\text{AgCN}$ reacts through nitrogen (giving an alkyl isocyanide).

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