Wilhelm Rudolph Fittig
Encyclopedia
Wilhelm Rudolph Fittig was a German
chemist
. Fittig discovered the pinacol coupling reaction
, mesitylene
, diacetyl
and biphenyl
. He studied the action of sodium
on ketone
s and hydrocarbon
s. He discovered the Fittig reaction or Wurtz-Fittig reaction
for the synthesis of alkylbenzenes, he proposed a diketone structure for benzoquinone and isolated phenanthrene
from coal tar
. He discovered and synthesized the first lactone
s and investigated structures of piperine
naphthalene
and fluorene
.
with a dissertation on acetone
in 1858, under the supervision of Heinrich Limpricht
and Friedrich Wöhler
. He subsequently held several appointments at Göttingen, becoming privatdozent
in 1860 and extraordinary professor in 1870. In 1870 he was made the chair at University of Tübingen and in 1876 at Strassburg, where the laboratories were erected from his designs.
Fittig's research covered wide areas of organic chemistry
. The aldehyde
s and ketone
s provided material for his earlier work. He observed that aldehydes and ketones may suffer reduction
in neutral
, alkaline, and sometimes acid solution to secondary and tertiary glycols, substances which he named pinacones; and also that certain pinacones when distilled with dilute sulfuric acid
gave compounds, which he named pinacolines. The unsaturated acids also received much attention, and he discovered the internal anhydrides of oxyacids, termed lactone
s. In 1863 he introduced the reaction known by his name. In 1855 Charles-Adolphe Wurtz
had shown that when sodium acted upon alkyl iodides, the alkyl residues combined to form more complex hydrocarbon
s; Fittig developed this method by showing that a mixture of an aromatic and alkyl haloid, under similar treatment, yielded homologues
of benzene
. His investigations on Perkins reaction led him to an explanation of its mechanism which appeared to be more in accordance with the facts. The question, however, is one of much difficulty, and the exact course of the reaction appears to await solution. These researches incidentally solved the constitution of coumarin
, the odoriferous principle of woodruff
. Fittig and Erdmann's observation that phenyl isocrotonic acid readily yielded α-naphthol by loss of water was of much importance, since it afforded valuable evidence as to the constitution of naphthalene
. They also investigated certain hydrocarbons occurring in the high boiling point fraction of the coal tar
distillate and solved the constitution of phenanthrene
. We also owe much of our knowledge of the alkaloid piperine
to Fittig, who in collaboration with Ira Remsen
established its constitution in 1871.
Fittig has published two widely used textbooks; be edited several editions of Wohler's Grundriss der organischen Chemie (11th ed., 1887) and wrote an Unorganische Chemie (1st ed., 1872; 3rd, 1882). His researches have been recognized by many scientific societies and institutions, the Royal Society awarding him the Davy medal in 1906.
Germany
Germany , officially the Federal Republic of Germany , is a federal parliamentary republic in Europe. The country consists of 16 states while the capital and largest city is Berlin. Germany covers an area of 357,021 km2 and has a largely temperate seasonal climate...
chemist
Chemist
A chemist is a scientist trained in the study of chemistry. Chemists study the composition of matter and its properties such as density and acidity. Chemists carefully describe the properties they study in terms of quantities, with detail on the level of molecules and their component atoms...
. Fittig discovered the pinacol coupling reaction
Pinacol coupling reaction
A pinacol coupling reaction is an organic reaction in which a carbon–carbon covalent bond is formed between the carbonyl groups of an aldehyde or a ketone in presence of an electron donor in a free radical process . The reaction product is a vicinal diol...
, mesitylene
Mesitylene
Mesitylene or 1,3,5-trimethylbenzene is an aromatic hydrocarbon with three methyl substituents attached to the benzene ring. It is prepared by distillation of acetone with sulfuric acid or by trimerization of propyne in sulfuric acid, which, in both cases, acts as a catalyst and dehydrating agent....
, diacetyl
Diacetyl
Diacetyl is a natural byproduct of fermentation. It is a vicinal diketone with the molecular formula C4H6O2...
and biphenyl
Biphenyl
Biphenyl is an organic compound that forms colorless crystals. It has a distinctively pleasant smell. Biphenyl is an aromatic hydrocarbon with a molecular formula 2...
. He studied the action of sodium
Sodium
Sodium is a chemical element with the symbol Na and atomic number 11. It is a soft, silvery-white, highly reactive metal and is a member of the alkali metals; its only stable isotope is 23Na. It is an abundant element that exists in numerous minerals, most commonly as sodium chloride...
on ketone
Ketone
In organic chemistry, a ketone is an organic compound with the structure RCR', where R and R' can be a variety of atoms and groups of atoms. It features a carbonyl group bonded to two other carbon atoms. Many ketones are known and many are of great importance in industry and in biology...
s and hydrocarbon
Hydrocarbon
In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. Hydrocarbons from which one hydrogen atom has been removed are functional groups, called hydrocarbyls....
s. He discovered the Fittig reaction or Wurtz-Fittig reaction
Wurtz-Fittig reaction
The Wurtz-Fittig reaction is the chemical reaction of aryl halides with alkyl halides and sodium metal to give substituted aromatic compounds....
for the synthesis of alkylbenzenes, he proposed a diketone structure for benzoquinone and isolated phenanthrene
Phenanthrene
Phenanthrene is a polycyclic aromatic hydrocarbon composed of three fused benzene rings. The name phenanthrene is a composite of phenyl and anthracene. In its pure form, it is found in cigarette smoke and is a known irritant, photosensitizing skin to light...
from coal tar
Coal tar
Coal tar is a brown or black liquid of extremely high viscosity, which smells of naphthalene and aromatic hydrocarbons. Coal tar is among the by-products when coal iscarbonized to make coke or gasified to make coal gas...
. He discovered and synthesized the first lactone
Lactone
In chemistry, a lactone is a cyclic ester which can be seen as the condensation product of an alcohol group -OH and a carboxylic acid group -COOH in the same molecule...
s and investigated structures of piperine
Piperine
Piperine is the alkaloid responsible for the pungency of black pepper and long pepper, along with chavicine . It has also been used in some forms of traditional medicine and as an insecticide. Piperine forms monoclinic needles, is slightly soluble in water and more so in alcohol, ether or...
naphthalene
Naphthalene
Naphthalene is an organic compound with formula . It is a white crystalline solid with a characteristic odor that is detectable at concentrations as low as 0.08 ppm by mass. As an aromatic hydrocarbon, naphthalene's structure consists of a fused pair of benzene rings...
and fluorene
Fluorene
Fluorene, or 9H-fluorene, is a polycyclic aromatic hydrocarbon. It forms white crystals that exhibit a characteristic, aromatic odor similar to that of naphthalene. It is combustible. It has a violet fluorescence, hence its name. For commercial purposes it is obtained from coal tar...
.
Career
Fittig studied chemistry at the University of Göttingen, graduating as Ph.D.Ph.D.
A Ph.D. is a Doctor of Philosophy, an academic degree.Ph.D. may also refer to:* Ph.D. , a 1980s British group*Piled Higher and Deeper, a web comic strip*PhD: Phantasy Degree, a Korean comic series* PhD Docbook renderer, an XML renderer...
with a dissertation on acetone
Acetone
Acetone is the organic compound with the formula 2CO, a colorless, mobile, flammable liquid, the simplest example of the ketones.Acetone is miscible with water and serves as an important solvent in its own right, typically as the solvent of choice for cleaning purposes in the laboratory...
in 1858, under the supervision of Heinrich Limpricht
Heinrich Limpricht
Heinrich Limpricht was a German chemist. Limpricht was a pupil of Friedrich Wöhler; he worked on the chemistry of furans and pyrroles, discovering furan in 1870....
and Friedrich Wöhler
Friedrich Wöhler
Friedrich Wöhler was a German chemist, best known for his synthesis of urea, but also the first to isolate several chemical elements.-Biography:He was born in Eschersheim, which belonged to aau...
. He subsequently held several appointments at Göttingen, becoming privatdozent
Privatdozent
Privatdozent or Private lecturer is a title conferred in some European university systems, especially in German-speaking countries, for someone who pursues an academic career and holds all formal qualifications to become a tenured university professor...
in 1860 and extraordinary professor in 1870. In 1870 he was made the chair at University of Tübingen and in 1876 at Strassburg, where the laboratories were erected from his designs.
Fittig's research covered wide areas of organic chemistry
Organic chemistry
Organic chemistry is a subdiscipline within chemistry involving the scientific study of the structure, properties, composition, reactions, and preparation of carbon-based compounds, hydrocarbons, and their derivatives...
. The aldehyde
Aldehyde
An aldehyde is an organic compound containing a formyl group. This functional group, with the structure R-CHO, consists of a carbonyl center bonded to hydrogen and an R group....
s and ketone
Ketone
In organic chemistry, a ketone is an organic compound with the structure RCR', where R and R' can be a variety of atoms and groups of atoms. It features a carbonyl group bonded to two other carbon atoms. Many ketones are known and many are of great importance in industry and in biology...
s provided material for his earlier work. He observed that aldehydes and ketones may suffer reduction
Redox
Redox reactions describe all chemical reactions in which atoms have their oxidation state changed....
in neutral
PH
In chemistry, pH is a measure of the acidity or basicity of an aqueous solution. Pure water is said to be neutral, with a pH close to 7.0 at . Solutions with a pH less than 7 are said to be acidic and solutions with a pH greater than 7 are basic or alkaline...
, alkaline, and sometimes acid solution to secondary and tertiary glycols, substances which he named pinacones; and also that certain pinacones when distilled with dilute sulfuric acid
Sulfuric acid
Sulfuric acid is a strong mineral acid with the molecular formula . Its historical name is oil of vitriol. Pure sulfuric acid is a highly corrosive, colorless, viscous liquid. The salts of sulfuric acid are called sulfates...
gave compounds, which he named pinacolines. The unsaturated acids also received much attention, and he discovered the internal anhydrides of oxyacids, termed lactone
Lactone
In chemistry, a lactone is a cyclic ester which can be seen as the condensation product of an alcohol group -OH and a carboxylic acid group -COOH in the same molecule...
s. In 1863 he introduced the reaction known by his name. In 1855 Charles-Adolphe Wurtz
Charles-Adolphe Wurtz
Adolphe Wurtz was an Alsatian French chemist. He is best remembered for his decades-long advocacy for the atomic theory and for ideas about the structures of chemical compounds, against the skeptical opinions of chemists such as Marcellin Berthelot and Etienne Henri Sainte-Claire Deville...
had shown that when sodium acted upon alkyl iodides, the alkyl residues combined to form more complex hydrocarbon
Hydrocarbon
In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. Hydrocarbons from which one hydrogen atom has been removed are functional groups, called hydrocarbyls....
s; Fittig developed this method by showing that a mixture of an aromatic and alkyl haloid, under similar treatment, yielded homologues
Homologous series
In chemistry, a homologous series is a series of compounds with a similar general formula, possessing similar chemical properties due to the presence of the same functional group, and showing a gradation in physical properties as a result of increase in molecular size and mass...
of benzene
Benzene
Benzene is an organic chemical compound. It is composed of 6 carbon atoms in a ring, with 1 hydrogen atom attached to each carbon atom, with the molecular formula C6H6....
. His investigations on Perkins reaction led him to an explanation of its mechanism which appeared to be more in accordance with the facts. The question, however, is one of much difficulty, and the exact course of the reaction appears to await solution. These researches incidentally solved the constitution of coumarin
Coumarin
Coumarin is a fragrant chemical compound in the benzopyrone chemical class, found in many plants, notably in high concentration in the tonka bean , vanilla grass , sweet woodruff , mullein , sweet grass , cassia cinnamon and sweet clover...
, the odoriferous principle of woodruff
Woodruff
Galium odoratum is a perennial plant in the family Rubiaceae, native to Europe, North Africa and Western Asia.A herbaceous plant, it grows to 30-50 cm long, often lying flat on the ground or supported by other plants...
. Fittig and Erdmann's observation that phenyl isocrotonic acid readily yielded α-naphthol by loss of water was of much importance, since it afforded valuable evidence as to the constitution of naphthalene
Naphthalene
Naphthalene is an organic compound with formula . It is a white crystalline solid with a characteristic odor that is detectable at concentrations as low as 0.08 ppm by mass. As an aromatic hydrocarbon, naphthalene's structure consists of a fused pair of benzene rings...
. They also investigated certain hydrocarbons occurring in the high boiling point fraction of the coal tar
Coal tar
Coal tar is a brown or black liquid of extremely high viscosity, which smells of naphthalene and aromatic hydrocarbons. Coal tar is among the by-products when coal iscarbonized to make coke or gasified to make coal gas...
distillate and solved the constitution of phenanthrene
Phenanthrene
Phenanthrene is a polycyclic aromatic hydrocarbon composed of three fused benzene rings. The name phenanthrene is a composite of phenyl and anthracene. In its pure form, it is found in cigarette smoke and is a known irritant, photosensitizing skin to light...
. We also owe much of our knowledge of the alkaloid piperine
Piperine
Piperine is the alkaloid responsible for the pungency of black pepper and long pepper, along with chavicine . It has also been used in some forms of traditional medicine and as an insecticide. Piperine forms monoclinic needles, is slightly soluble in water and more so in alcohol, ether or...
to Fittig, who in collaboration with Ira Remsen
Ira Remsen
Ira Remsen was a chemist who, along with Constantin Fahlberg, discovered the artificial sweetener saccharin. He was the second president of Johns Hopkins University.-Biography:...
established its constitution in 1871.
Fittig has published two widely used textbooks; be edited several editions of Wohler's Grundriss der organischen Chemie (11th ed., 1887) and wrote an Unorganische Chemie (1st ed., 1872; 3rd, 1882). His researches have been recognized by many scientific societies and institutions, the Royal Society awarding him the Davy medal in 1906.