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Example · Example 33

Q.Methyl isocyanide (CH3NC\text{CH}_3\text{NC}) is hydrolysed under acidic aqueous conditions. Name the two products formed, and explain how this outcome differs from the hydrolysis of the isomeric methyl cyanide.

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Acidic hydrolysis of methyl isocyanide breaks the molecule so that nitrogen (still bonded to the methyl group) is retained as the amine, while the terminal carbon is expelled as a one-carbon acid: CH3NC+2H2O→H+,ΔCH3NH2+HCOOH\text{CH}_3\text{NC} + 2\text{H}_2\text{O} \xrightarrow{\text{H}^+, \Delta} \text{CH}_3\text{NH}_2 + \text{HCOOH}. This is the exact reverse pattern of methyl cyanide's hydrolysis (Example 30's family): there, nitrogen leaves as ammonia and carbon is retained in the acid; here, carbon leaves as fo …

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