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Cyanide is unstable in water, but the reaction is slow until about 170 °C. It undergoes hydrolysis to give ammonia and formate, which are far less toxic than cyanide: [14] CN − + 2 H 2 O → HCO − 2 + NH 3. Cyanide hydrolase is an enzyme that catalyzes this reaction.
Cyanogen is typically generated from cyanide compounds. One laboratory method entails thermal decomposition of mercuric cyanide: . 2 Hg(CN) 2 → (CN) 2 + Hg 2 (CN) 2 Or, one can combine solutions of copper(II) salts (such as copper(II) sulfate) with cyanides; an unstable copper(II) cyanide is formed which rapidly decomposes into copper(I) cyanide and cyanogen.
Asymmetric reaction of benzaldehyde with (R)–Binol–lithium(i-propyloxy) gives (S)-acetonitrile with 98% ee The chemist Urech in 1872 was the first to synthesize cyanohydrins from ketones with alkali cyanides and acetic acid [ 2 ] and therefore this reaction also goes by the name of Urech cyanohydrin method .
The general formula is R 2 C(OH)CN, where R is H, alkyl, or aryl. Cyanohydrins are industrially important precursors to carboxylic acids and some amino acids . Cyanohydrins can be formed by the cyanohydrin reaction , which involves treating a ketone or an aldehyde with hydrogen cyanide (HCN) in the presence of excess amounts of sodium cyanide ...
Benzyl cyanide (abbreviated BnCN) is an organic compound with the chemical formula C 6 H 5 CH 2 CN. This colorless oily aromatic liquid is an important precursor to numerous compounds in organic chemistry. [2] It is also an important pheromone in certain species. [3]
Nitriles can also be converted to aldehydes by reduction and hydrolysis. The Stephen aldehyde synthesis uses Tin(II) chloride and hydrochloric acid to yield an aldehyde via the hydrolysis of a resulting iminium salt. Aldehydes can also form using a hydrogen donor followed by in-situ hydrolysis of an imine.
The most important industrial application is the nickel-catalyzed synthesis of adiponitrile (NC−(CH 2) 4 −CN) synthesis from buta-1,3-diene (CH 2 =CH−CH=CH 2). Adiponitrile is a precursor to hexamethylenediamine (H 2 N−(CH 2) 6 −NH 2), which is used for the production of certain kinds of Nylon. The DuPont ADN process to give ...
Stephen aldehyde synthesis, a named reaction in chemistry, was invented by Henry Stephen (OBE/MBE).This reaction involves the preparation of aldehydes (R-CHO) from nitriles (R-CN) using tin(II) chloride (SnCl 2), hydrochloric acid (HCl) and quenching the resulting iminium salt ([R-CH=NH 2] + Cl −) with water (H 2 O).