Question

what happens when phenyl isocyanide is treated with LiAlH4​

Answer 1

Answer:

Methyl isocyanide is reduced by lialh4 (aka LiAlH4, LAH) with the formation of dimethylamine as shown below. Personally, I would not make dimethyl amine, I would buy it, it will be much less expensive than the cost of materials (MIC, LAH, and the solvent plus whatever it costs to isolate).

Answer 2

Phenyl isocyanide is an organic compound with the chemical formula $C_{6} H_{5} NC$ . When it is treated with LiAl$H_{4}$ (lithium aluminum hydride), a reducing agent, it undergoes reduction to produce a primary amine, phenyl methylamine ($C_{6} H_{5} CH_{2} NH_{2}$).

The reaction between phenyl isocyanide and LiAl$H_{4}$ occurs through a nucleophilic addition-elimination mechanism. The mechanism involves the following steps:

• Nucleophilic attack: The LiAl$H_{4}$ acts as a nucleophile and attacks the carbon atom of the isocyanide group, which is electron deficient due to the presence of the triple bond.
• Proton transfer: After nucleophilic attack, the hydrogen atom of LiAl$H_{4}$ is transferred to the nitrogen atom of the isocyanide group, forming an intermediate alkyl aluminum species.
• Elimination: The intermediate species then undergoes elimination of the aluminum atom and formation of a primary amine, phenyl methylamine.
• The overall reaction can be represented as follows:
• $C_{6} H_{5} NC$ + 4 LiAl$H_{4}$ → $C_{6} H_{5} CH_{2} NH_{2}$ + 4 LiAl$O_{2}$ + 2 $H_{2}$
• In summary, when phenyl isocyanide is treated with LiAl$H_{4}$ , it undergoes nucleophilic addition-elimination mechanism to produce a primary amine, phenyl methylamine. This reaction is a useful method for the synthesis of primary amines from isocyanides.

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