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The Rosenmund–von Braun synthesis is an 
organic reaction
Organic reactions are chemical reactions involving organic compounds. The basic organic chemistry reaction types are addition reactions, elimination reactions, substitution reactions, pericyclic reactions, rearrangement reactions, mechanistic organ ...
in which an aryl halide
In organic chemistry, an aryl halide (also known as a haloarene) is an aromatic compound in which one or more hydrogen atoms directly bonded to an aromatic ring are replaced by a halide ion (such as fluorine F''−'', chlorine Cl−1,−3,−5, br ...
reacts with cuprous cyanide to yield an aryl
In organic chemistry, an aryl is any functional group or substituent derived from an aromatic ring, usually an aromatic hydrocarbon, such as phenyl and naphthyl. "Aryl" is used for the sake of abbreviation or generalization, and "Ar" is used ...
nitrile
In organic chemistry, a nitrile is any organic compound that has a functional group. The name of the compound is composed of a base, which includes the carbon of the , suffixed with "nitrile", so for example is called " propionitrile" (or pr ...
.
:
The reaction was named after Karl Wilhelm Rosenmund
Karl Wilhelm Louis Rosenmund (15 December 1884 – 8 February 1965) was a German chemist. He was born in Berlin and died in Kiel.
Rosenmund studied chemistry and received his Ph.D. 1906 from University of Berlin for his work with Otto Diels. H ...
who together with his Ph.D. student Erich Struck discovered in 1914 that aryl halide reacts with alcohol water solution of potassium cyanide
Potassium cyanide is a compound with the formula KCN. It is a colorless salt, similar in appearance to sugar, that is highly soluble in water. Most KCN is used in gold mining, organic synthesis, and electroplating. Smaller applications include ...
and catalytic amounts of cuprous cyanide at 200 °C. The reaction yields the carboxylic acid
In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group () attached to an Substituent, R-group. The general formula of a carboxylic acid is often written as or , sometimes as with R referring to an organyl ...
, not the nitrile, but Rosenmund speculated that the intermediate should be the nitrile, since nitriles on aromatic rings can react to form carboxylic acids. Independently Alfred Pongratz and improved the reaction by changing the reaction conditions to higher temperatures and used no solvent for the reaction. Further improvement of the reaction was done in the following years, for example the use of ionic liquid
An ionic liquid (IL) is a salt (chemistry), salt in the liquid state at ambient conditions. In some contexts, the term has been restricted to salts whose melting point is below a specific temperature, such as . While ordinary liquids such as wate ...
s as solvent for the reaction.
:
See also
*Kolbe nitrile synthesis
The Kolbe nitrile synthesis is a method for the preparation of alkyl nitriles by reaction of the corresponding organohalide, alkyl halide with a metal cyanide. A side product for this reaction is the formation of an isonitrile because the cyanide i ...
a similar reaction for the synthesis of alkyl nitrile
* Sandmeyer reaction
* Von Braun reaction
References
{{DEFAULTSORT:Rosenmund-von Braun reaction Substitution reactions Name reactions