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Question
When CH3CH2Br is treated with aqueous NaCN, CH3CH2CN is formed while CH3CH2NC is formed when AgCN is used in the similar reaction. It is due to
When CH3CH2Br is treated with aqueous NaCN, CH3CH2CN is formed while CH3CH2NC is formed when AgCN is used in the similar reaction. It is due to
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Solution
The correct option is B Covalent nature of Ag-C bond in AgCN
CN− is the ambident nucleophile and can form different product with same substrate.
CH3−CH2−Br+NaCN→CH3−CH2−CN+ CH3−CH2+N≡C−+NaBr Ethyl cyanide Ethyl isocyanide Major Minor
Here, NaCN is predominantly ionic and exist as free ions in solution. C site is more nucleophilic than N site and available to attack the ethyl bromide. Hence, the major product will be ethyl cyanide.
AgCN is predominantly covalent. Although C site is more nucleophilic than N site but not available in case of AgCN. Hence, lone pair of N attacks the ethyl chloride and isocyanide is formed as the major product. Hence, the major product will be ethylisocyanide.
CH3CH2−Br+NaCN→CH3CH2CN+CH3CH2NC+NaBr Ethyl cyanide Ethyl isocyanide Minor Major
CN− is the ambident nucleophile and can form different product with same substrate.
CH3−CH2−Br+NaCN→CH3−CH2−CN+ CH3−CH2+N≡C−+NaBr Ethyl cyanide Ethyl isocyanide Major Minor
Here, NaCN is predominantly ionic and exist as free ions in solution. C site is more nucleophilic than N site and available to attack the ethyl bromide. Hence, the major product will be ethyl cyanide.
AgCN is predominantly covalent. Although C site is more nucleophilic than N site but not available in case of AgCN. Hence, lone pair of N attacks the ethyl chloride and isocyanide is formed as the major product. Hence, the major product will be ethylisocyanide.
CH3CH2−Br+NaCN→CH3CH2CN+CH3CH2NC+NaBr Ethyl cyanide Ethyl isocyanide Minor Major
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