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Q6.22(vi):
What happens when (vi) methyl chloride is treated with ( KCN )?

Solution :

1. Chemical Reaction Setup

The reaction involves the nucleophilic substitution of methyl chloride ($CH_{3}Cl$) with potassium cyanide ($KCN$). $KCN$ is an ionic compound that dissociates in aqueous or alcoholic media to provide cyanide ions ($CN^{-}$).

The chemical equation for the reaction is:

$CH_{3}Cl + KCN \xrightarrow{\text{alcohol/water}} CH_{3}CN + KCl$

2. Reaction Mechanism Analysis

The reaction follows the $S_{N}2$ (Substitution Nucleophilic Bimolecular) mechanism because methyl chloride is a primary alkyl halide, which is highly susceptible to backside attack by the nucleophile due to minimal steric hindrance [Per the Kinetics of $S_{N}2$ Reactions].

  • Nucleophile: The cyanide ion ($CN^{-}$) acts as an ambident nucleophile, meaning it has two nucleophilic centers (Carbon and Nitrogen).
  • Mode of Attack: In $KCN$, the bond between $K^{+}$ and $CN^{-}$ is primarily ionic. In an ionizing solvent, the $CN^{-}$ ion is free. The carbon atom of the cyanide ion is more nucleophilic and attacks the electrophilic carbon of methyl chloride [Per Hard-Soft Acid-Base Theory].
  • Transition State: The reaction proceeds through a concerted, single-step process involving a pentacoordinate transition state where the incoming $CN^{-}$ ion forms a bond simultaneously as the $Cl^{-}$ ion departs.

3. Visualization of Molecular Geometry

CH₃Cl CN⁻ CH₃CN (Methyl Cyanide/Acetonitrile) + KCl Sₙ2 Substitution

4. Summary of Products

Reactant Reagent Major Product By-product
Methyl Chloride ($CH_{3}Cl$) $KCN$ Methyl cyanide (Acetonitrile) Potassium chloride ($KCl$)

Note: If the reagent had been $AgCN$ (Silver Cyanide), which is predominantly covalent, the nitrogen atom would have acted as the nucleophile, leading to the formation of methyl isocyanide ($CH_{3}NC$) instead [Per the Ambident Nucleophile Reactivity Rule].

Final Solution: Methyl chloride reacts with $KCN$ to form methyl cyanide (acetonitrile) and potassium chloride.


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