Lithium aluminium hydride (LiAlH4) is a strong reducing agent that affects nitrogen-containing functional groups differently:
- Isocyanides (R−NC): Reduction yields secondary amines (R−NH−CH3). Specifically, methyl isocyanide (CH3NC) is reduced to dimethylamine (CH3−NH−CH3), which is a secondary amine .
- Amides (R−CONH2): Reduction yields primary amines (R−CH2−NH2). Acetamide (CH3CONH2) gives ethylamine .
- Cyanides/Nitriles (R−CN): Reduction yields primary amines (R−CH2−NH2). Methyl cyanide (CH3CN) gives ethylamine .
- Nitroalkanes (R−NO2): Reduction yields primary amines (R−NH2). Nitroethane gives ethylamine .
Therefore, only Methyl isocyanide yields a secondary amine.