Question

Hydrolysis of phenyl isocyanide forms

• A. benzoic acid
• B. formic acid
• C. acetanilide
• D. acetic acid

Answer 1

Answer: (B)

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., $H^{+}$ ).
$R-\stackrel{+}{N}\equiv \stackrel{-}{C}:+H^{+}\to R-\stackrel{+}{N}\equiv CH\stackrel{H_{2}O}{\to }R-N=\stackrel{H}{\stackrel{|}{C}}-OH$
$\stackrel{Tautomerism}{\to }R-NH-\stackrel{O}{\stackrel{||}{C}}-H\stackrel{H^{+}/H_{2}O}{\to }R-N{H}_2+HCOOH$