Chemical Properties of Cyanides

(1) HYDROLYSIS: boiling a cyanide with alkali or dilute mineral acid hydrolyses it to a carboxylic acid, via a two-stage mechanism -- PARTIAL hydrolysis (H2O2/OH-) stops at the amide (e.g. ethanenitrile gives acetamide), while COMPLETE hydrolysis (2H2O/H+) carries all the way to the carboxylic acid (ethanenitrile gives acetic acid). (2) REDUCTION: LiAlH4 (or Ni/H2) reduces an alkyl cyanide to a PRIMARY amine, e.g. ethanenitrile + 2H2 (Ni) gives ethanamine -- this is the same reduction route already introduced under amine preparation. (3) CONDENSATION REACTIONS: (a) THORPE NITRILE CONDENSATION -- two molecules of an alkyl nitrile carrying an alpha-hydrogen self-condense in the presence of sodium metal (ether solvent) to form an imino-nitrile, e.g. propanenitrile self-condenses to 3-imino-2-methylpentanenitrile. (b) the LEVINE-HAUSER ACETYLATION (also called CYANOMETHYLATION): a nitrile carrying an alpha-hydrogen condenses with an ester, in the presence of sodamide (NaNH2) in ether, replacing the ester's ethox …