Question

How do we prepare a primary amine from a nitrile?

Answer 1

To get to the primary amine I think you need an aggressive reducing agent.....

Explanation:

And `LiAlH_4` is such a reagent; mind you it has to be deployed in ether or THF, and when you work it up (with water) you have to be very careful as the unreacted `"lithal"` reacts.... In principle `LiAlH_4` can deliver 4 equiv of hydride...certainly it will deliver three equiv.....

Acidic hydrolysis of a nitrile should deliver the carboxylic acid and ammonium salt....

`R-C-=N + 2H_2O stackrel(H_3O^+)rarrRCO_2H + NH_4^+`

Just as an edit....the formal oxidation state of the ipso carbon in `R-C-=N` is `+III`....the formal oxidation of carbon in `R-CH_2NH_2` is `-I`, i.e. nitrile to amine is a FOUR electron reduction....

`R-C-=N + 4e^(-) +4H^+ rarr RCH_2NH_2`