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Q. Hydrolysis of phenyl isocyanide forms

NTA AbhyasNTA Abhyas 2020Amines

Solution:

Solution

Note: Isocyanides are hydrolyzed only by acids, but not by alkalies. It is because negative charge present on the carbon atom in isocyanides initially attracts electrophile (i.e., $H^{+}$ ).

$R-\overset{+}{N}\equiv \overset{-}{C}:+H^{+} \rightarrow R-\overset{+}{N}\equiv CH\overset{H_{2} O}{ \rightarrow }R-N=\overset{H}{\overset{\left|\right.}{C}}-OH$

$\overset{T a u t o m e r i s m}{ \rightarrow }R-NH-\overset{O}{\overset{\left|\right. \left|\right.}{C}}-H\overset{H^{+} / H_{2} O}{ \rightarrow }R-NH_{2}+HCOOH$