Question

How will you convert nitromethane to methyl isocyanide?

Hint:

Conversion trick: Nitro → Amine (Reduction) Primary amine + CHCl\(_3\)/KOH → Isocyanide

Answer 1

Concept: Nitroalkanes can be reduced to primary amines, and primary amines can be converted into isocyanides via the
carbylamine reaction.
Step 1: Reduction of nitromethane to methylamine. Nitromethane is reduced using reducing agents such as:

• \( H_2 / Ni \)
• \( Sn/HCl \)
• \( Fe/HCl \)

\[ CH_3NO_2 \xrightarrow{[H]} CH_3NH_2 \]
Step 2: Convert methylamine to methyl isocyanide. Use carbylamine reaction: \[ CH_3NH_2 + CHCl_3 + 3KOH \rightarrow CH_3NC + 3KCl + 3H_2O \]
Step 3: Overall conversion. \[ CH_3NO_2 \xrightarrow{Reduction} CH_3NH_2 \xrightarrow[\text{KOH}]{CHCl_3} CH_3NC \]
Final Answer: Nitromethane → Methylamine (reduction) → Methyl isocyanide (carbylamine reaction).