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Lobry-de Bruyn-van Ekenstein transformation

 

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Lobry-de Bruyn-van Ekenstein transformation



 
 
The Lobry-de Bruyn-van Ekenstein transformation also known as the Lobry-de Bruyn-van-Alberda-van-Ekenstein transformation is a base
Base (chemistry)

In chemistry, a base is most commonly thought of as an aqueous substance that can accept protons. A base is also often referred to as an alkali if OH- ions are involved....
 catalyzed
Catalysis

Catalysis is the process in which the reaction rate of a chemical reaction is either increased or decreased by means of a chemical substance known as a catalyst....
 Aldose
Aldose

An aldose is a monosaccharide containing one aldehyde group per molecule and having a chemical formula of the form Cnn....
-Ketose
Ketose

A ketose is a sugar containing one ketone group per molecule.With 3 carbon atoms, dihydroxyacetone is the simplest of all ketoses and is the only one having no optical activity....
-Isomerization
Isomer

In chemistry, isomers are compounds with the same molecular formula but different structural formulae. Isomers do not necessarily share similar properties unless they also have the same functional groups....
 in carbohydrate chemistry
Carbohydrate chemistry

Carbohydrate chemistry is a subdiscipline of chemistry primarily concerned with the synthesis, structure, and function of carbohydrate structures....
  . A typical rearrangement reaction
Rearrangement reaction

A rearrangement reaction is a broad class of organic reactions where the carbon skeleton of a molecule is rearranged to give a structural isomer of the original molecule ....
 is that between glyceraldehyde
Glyceraldehyde

Glyceraldehyde is a triose monosaccharide with chemical formula Carbon3Hydrogen6Oxygen3. It is the simplest of all common aldoses....
 and dihydroxyacetone
Dihydroxyacetone

Dihydroxyacetone is a simple carbohydrate that is primarily used as an ingredient in sunless tanning products. It is often derived from plant sources such as sugar beets and sugar cane, by the fermentation of glycerin....
 in a chemical equilibrium
Chemical equilibrium

In a chemical process, chemical equilibrium is the state in which the Activity or concentrations of the reactants and products have no net change over time....
.

The reaction is relevant for the industrial production of certain ketose
Ketose

A ketose is a sugar containing one ketone group per molecule.With 3 carbon atoms, dihydroxyacetone is the simplest of all ketoses and is the only one having no optical activity....
s and was discovered in 1885 by Cornelis Adriaan Lobry van Troostenburg de Bruyn
Cornelis Adriaan Lobry van Troostenburg de Bruyn

Cornelis Adriaan Lobry van Troostenburg de Bruyn was a chemist from the Netherlands.De Bruyn studied natural sciences from 1875 until 1883 at the University of Leiden and obtained a PhD degree in chemistry in 1883....
 and Willem Alberda van Ekenstein
Willem Alberda van Ekenstein

Willem Alberda van Ekenstein was a Dutch chemist and discovered the Lobry-de Bruyn-van Ekenstein transformation together with Cornelis Adriaan Lobry van Troostenburg de Bruyn....
.

following scheme describes the reaction mechanism
Reaction mechanism

In chemistry, a reaction mechanism is the step by step sequence of elementary reactions by which overall chemical change occurs .Although only the net chemical change is directly observation for most chemical reactions, experiments can often be designed that suggest the possible sequence of steps in a reaction mechanism....
  where R is any organic
Organic chemistry

Organic chemistry is a discipline within chemistry which involves the science study of the structure, properties, composition, chemical reaction, and preparation of chemical compounds that contain carbon....
 residue.

The position of the equilibrium or the reactant to product ratio depends on concentration
Concentration

In chemistry, concentration is the measure of how much of a given chemical substance there is mixed with another substance. This can apply to any sort of chemical mixture, but most frequently the concept is limited to homogeneous solutions, where it refers to the amount of solute in the solvent....
, solvent
Solvent

A solvent is a liquid or gas that dissolves a solid, liquid, or gaseous solute, resulting in a solution.The most common solvent in everyday life is water....
,pH
PH

pH is a measure of the Acid or Base of a solution. It is defined as the cologarithm of the Activity of dissolved hydrogen ions . Hydrogen ion activity coefficients cannot be measured experimentally, so they are based on theoretical calculations....
 value and temperature
Temperature

In physics, temperature is a physical property of a Physical system that underlies the common notions of hot and cold; something that feels hotter generally has the greater temperature....
.






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The Lobry-de Bruyn-van Ekenstein transformation also known as the Lobry-de Bruyn-van-Alberda-van-Ekenstein transformation is a base
Base (chemistry)

In chemistry, a base is most commonly thought of as an aqueous substance that can accept protons. A base is also often referred to as an alkali if OH- ions are involved....
 catalyzed
Catalysis

Catalysis is the process in which the reaction rate of a chemical reaction is either increased or decreased by means of a chemical substance known as a catalyst....
 Aldose
Aldose

An aldose is a monosaccharide containing one aldehyde group per molecule and having a chemical formula of the form Cnn....
-Ketose
Ketose

A ketose is a sugar containing one ketone group per molecule.With 3 carbon atoms, dihydroxyacetone is the simplest of all ketoses and is the only one having no optical activity....
-Isomerization
Isomer

In chemistry, isomers are compounds with the same molecular formula but different structural formulae. Isomers do not necessarily share similar properties unless they also have the same functional groups....
 in carbohydrate chemistry
Carbohydrate chemistry

Carbohydrate chemistry is a subdiscipline of chemistry primarily concerned with the synthesis, structure, and function of carbohydrate structures....
  . A typical rearrangement reaction
Rearrangement reaction

A rearrangement reaction is a broad class of organic reactions where the carbon skeleton of a molecule is rearranged to give a structural isomer of the original molecule ....
 is that between glyceraldehyde
Glyceraldehyde

Glyceraldehyde is a triose monosaccharide with chemical formula Carbon3Hydrogen6Oxygen3. It is the simplest of all common aldoses....
 and dihydroxyacetone
Dihydroxyacetone

Dihydroxyacetone is a simple carbohydrate that is primarily used as an ingredient in sunless tanning products. It is often derived from plant sources such as sugar beets and sugar cane, by the fermentation of glycerin....
 in a chemical equilibrium
Chemical equilibrium

In a chemical process, chemical equilibrium is the state in which the Activity or concentrations of the reactants and products have no net change over time....
.

The reaction is relevant for the industrial production of certain ketose
Ketose

A ketose is a sugar containing one ketone group per molecule.With 3 carbon atoms, dihydroxyacetone is the simplest of all ketoses and is the only one having no optical activity....
s and was discovered in 1885 by Cornelis Adriaan Lobry van Troostenburg de Bruyn
Cornelis Adriaan Lobry van Troostenburg de Bruyn

Cornelis Adriaan Lobry van Troostenburg de Bruyn was a chemist from the Netherlands.De Bruyn studied natural sciences from 1875 until 1883 at the University of Leiden and obtained a PhD degree in chemistry in 1883....
 and Willem Alberda van Ekenstein
Willem Alberda van Ekenstein

Willem Alberda van Ekenstein was a Dutch chemist and discovered the Lobry-de Bruyn-van Ekenstein transformation together with Cornelis Adriaan Lobry van Troostenburg de Bruyn....
.

Reaction mechanism

The following scheme describes the reaction mechanism
Reaction mechanism

In chemistry, a reaction mechanism is the step by step sequence of elementary reactions by which overall chemical change occurs .Although only the net chemical change is directly observation for most chemical reactions, experiments can often be designed that suggest the possible sequence of steps in a reaction mechanism....
  where R is any organic
Organic chemistry

Organic chemistry is a discipline within chemistry which involves the science study of the structure, properties, composition, chemical reaction, and preparation of chemical compounds that contain carbon....
 residue.

The position of the equilibrium or the reactant to product ratio depends on concentration
Concentration

In chemistry, concentration is the measure of how much of a given chemical substance there is mixed with another substance. This can apply to any sort of chemical mixture, but most frequently the concept is limited to homogeneous solutions, where it refers to the amount of solute in the solvent....
, solvent
Solvent

A solvent is a liquid or gas that dissolves a solid, liquid, or gaseous solute, resulting in a solution.The most common solvent in everyday life is water....
,pH
PH

pH is a measure of the Acid or Base of a solution. It is defined as the cologarithm of the Activity of dissolved hydrogen ions . Hydrogen ion activity coefficients cannot be measured experimentally, so they are based on theoretical calculations....
 value and temperature
Temperature

In physics, temperature is a physical property of a Physical system that underlies the common notions of hot and cold; something that feels hotter generally has the greater temperature....
. At equilibrium the aldose and ketose form a mixture which in the case of the glyceraldehyde and dihydroxyacetone is also called glycerose.

Stereochemistry

The carbon atom at which the initial deprotonation
Deprotonation

Deprotonation is a chemistry term that refers to the removal of a proton from a molecule, forming the conjugate base. The relative ability for a molecule to give up a proton is measured by a pKa value....
 takes place is a stereocenter
Stereocenter

A stereocenter, or stereogenic center, is any point, though not necessarily an atom, in a molecule bearing groups such that an interchanging of any two groups leads to a stereoisomer ....
 and based on the equilibrium all reaction steps constitute a epimerization. For example, D-Glucose
Glucose

Glucose , a monosaccharide also known as grape sugar, blood sugar, or corn sugar, is a very important carbohydrate in biology....
 (an Aldose) rearranges to D-Fructose
Fructose

Fructose is a simple Reducing sugar sugar found in many foods and is one of the three important dietary monosaccharides along with glucose and galactose....
 the ketose. The stereochemical configuration is lost in this reaction in the enol
Enol

Enols are alkenes with a hydroxyl group affixed to one of the carbon atoms composing the double bond. Enols and carbonyl compounds are in fact isomers; this is called keto-enol tautomerism:...
 form. In the equilibrium the enol can be protonated from two faces resulting in the backformation of glucose and the formation of D-mannose
Mannose

Mannose is a sugar monomer of the hexose series of carbohydrates....
. The final product is a mix of D-glucose, D-fructose and D-mannose.