The Hunsdiecker reaction (also called the Borodin reaction or the Hunsdiecker–Borodin reaction) is a
name reaction A name reaction is a chemical reaction named after its discoverers or developers. Among the tens of thousands of organic reactions that are known, hundreds of such reactions are well-known enough to be named after people. Well-known examples include ...
in
organic chemistry
Organic chemistry is a subdiscipline within chemistry involving the scientific study of the structure, properties, and reactions of organic compounds and organic materials, i.e., matter in its various forms that contain carbon atoms.Clayden, J.; ...
whereby
silver
Silver is a chemical element with the Symbol (chemistry), symbol Ag (from the Latin ', derived from the Proto-Indo-European wikt:Reconstruction:Proto-Indo-European/h₂erǵ-, ''h₂erǵ'': "shiny" or "white") and atomic number 47. A soft, whi ...
salts of
carboxylic acid
In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group () attached to an R-group. The general formula of a carboxylic acid is or , with R referring to the alkyl, alkenyl, aryl, or other group. Carboxylic ...
s react with a
halogen
The halogens () are a group in the periodic table consisting of five or six chemically related elements: fluorine (F), chlorine (Cl), bromine (Br), iodine (I), astatine (At), and tennessine (Ts). In the modern IUPAC nomenclature, this group is ...
to produce an
organic halide
Halocarbon compounds are chemicals in which one or more carbon atoms are linked by covalent bonds with one or more halogen atoms ( fluorine, chlorine, bromine or iodine – ) resulting in the formation of organofluorine compounds, organoch ...
.
It is an example of both a
decarboxylation
Decarboxylation is a chemical reaction that removes a carboxyl group and releases carbon dioxide (CO2). Usually, decarboxylation refers to a reaction of carboxylic acids, removing a carbon atom from a carbon chain. The reverse process, which is t ...
and a
halogenation
In chemistry, halogenation is a chemical reaction that entails the introduction of one or more halogens into a compound. Halide-containing compounds are pervasive, making this type of transformation important, e.g. in the production of polymers, ...
reaction as the product has one fewer carbon atoms than the starting material (lost as
carbon dioxide
Carbon dioxide (chemical formula ) is a chemical compound made up of molecules that each have one carbon atom covalently double bonded to two oxygen atoms. It is found in the gas state at room temperature. In the air, carbon dioxide is transpar ...
) and a halogen atom is introduced its place. The reaction was first demonstrated by
Alexander Borodin
Alexander Porfiryevich Borodin ( rus, link=no, Александр Порфирьевич Бородин, Aleksandr Porfir’yevich Borodin , p=ɐlʲɪkˈsandr pɐrˈfʲi rʲjɪvʲɪtɕ bərɐˈdʲin, a=RU-Alexander Porfiryevich Borodin.ogg, ...
in his 1861 reports of the preparation of
methyl bromide
Bromomethane, commonly known as methyl bromide, is an organobromine compound with formula C H3 Br. This colorless, odorless, nonflammable gas is produced both industrially and biologically. It has a tetrahedral shape and it is a recognized ozon ...
() from
silver acetate
Silver acetate is an coordination compound with the empirical formula CH3CO2Ag (or AgC2H3O2). A photosensitive, white, crystalline solid, it is a useful reagent in the laboratory as a source of silver ions lacking an oxidizing anion.
Synthesis an ...
().
Shortly after, the approach was applied to the degradation of
fatty acid
In chemistry, particularly in biochemistry, a fatty acid is a carboxylic acid with an aliphatic chain, which is either saturated or unsaturated. Most naturally occurring fatty acids have an unbranched chain of an even number of carbon atoms, fr ...
s in the laboratory of
Adolf Lieben
Adolf Lieben (3 December 1836 – 6 June 1914) was an Austrian Jewish chemist. He was born in Vienna the son of Ignatz Lieben. He studied at the University of Vienna, University of Heidelberg (Ph.D. 1856 with Robert Wilhelm Bunsen), and Paris ...
.
However, it is named for
Cläre Hunsdiecker and her husband
Heinz Hunsdiecker
Heinz Hunsdiecker (22 January 1904 – 22 November 1981) was a German chemist who together with his wife Claire Hunsdiecker (1903–1995) improved a reaction of Alexander Borodin now known as the Hunsdiecker reaction.
References