What is the mechanism for this reaction, and what is it called?

Question

NH2–R –> CH3COO–R

Is this reaction an oxidative deamination and an O-acetylation or is there a simpler way for it to occur, and if so, what is the reaction called? What should be the mechanism of this reaction?

R is a hydrocarbon chain.

Answer 1

Unfortunately, there is no simple direct reaction to convert an amine directly to an alcohol. While some precedent exists for doing such a transformation via transition metal catalysis (see below), we can assume this method to be not applicable for standard lecture class or lab procedure. The best way to afford this transformation would be either to make the ammonium by using acid (risk of elimination) or a diazonium intermediate. Reaction of the amine with sodium nitrite and acetic acid could afford this reaction in one step, as the sodium nitrate plus acetic acid would yield you a diazonium salt with an acetate anion which could subsequently preform substitution. However, this Sandmeyer type reaction generally requires an aromatic amine and stronger acid, so it will likely require quite forcing conditions, if it goes at all.