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Organic redox reaction

 

 
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Organic redox reaction
 
 
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Organic reductions or organic oxidations or organic redox reactions are redox reactions that take place with organic compound
Organic compound

An organic compound is any member of a large class of chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of compounds such as carbonates, simple oxides of carbon and cyanides, as well as the allotropes of carbon, are considered Inorganic compound....
s. In organic chemistry
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....
 oxidations and reductions are different from ordinary redox reactions because many reactions carry the name but do not actually involve electron transfer in the electrochemical
Electrochemistry

Electrochemistry is a branch of chemistry that studies chemical reactions which take place in a solution at the interface of an electron Electrical conductor and an ionic conductor , and which involve electron transfer between the electrode and the electrolyte or species in solution....
 sense of the word .

Following the rules for determining the oxidation number
Oxidation number

The oxidation number of a central atom in a complex is the charge that it would have if all the ligands were removed along with the electron pairs that were shared with the central atom....
 for an individual carbon atom leads to

Methane
Methane

Methane is a chemical compound with the molecular formula . It is the simplest alkane, and the principal component of natural gas. Methane's bond angles are 109.5 degrees....
 is oxidized to carbon dioxide
Carbon dioxide

Carbon dioxide is a chemical compound composed of two oxygen atoms covalent bond to a single carbon atom. It is a gas at standard temperature and pressure and exists in Earth's atmosphere in this state....
 because the oxidation number changes from -4 to +4.






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Organic reductions or organic oxidations or organic redox reactions are redox reactions that take place with organic compound
Organic compound

An organic compound is any member of a large class of chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of compounds such as carbonates, simple oxides of carbon and cyanides, as well as the allotropes of carbon, are considered Inorganic compound....
s. In organic chemistry
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....
 oxidations and reductions are different from ordinary redox reactions because many reactions carry the name but do not actually involve electron transfer in the electrochemical
Electrochemistry

Electrochemistry is a branch of chemistry that studies chemical reactions which take place in a solution at the interface of an electron Electrical conductor and an ionic conductor , and which involve electron transfer between the electrode and the electrolyte or species in solution....
 sense of the word .

Following the rules for determining the oxidation number
Oxidation number

The oxidation number of a central atom in a complex is the charge that it would have if all the ligands were removed along with the electron pairs that were shared with the central atom....
 for an individual carbon atom leads to
  • oxidation number -4 for alkane
    Alkane

    Alkanes, also known as paraffins, are chemical compounds that consist only of the elements carbon and hydrogen , wherein these atoms are linked together exclusively by single bonds without any cyclic structure ....
    s,
  • oxidation number -2 for alkene
    Alkene

    In organic chemistry, an alkene, olefin, or olefine is an Saturation chemical compound containing at least one carbon-to-carbon double bond....
    s, alcohol
    Alcohol

    In chemistry, an alcohol is any organic compound in which a hydroxyl Functional group is bound to a carbon atom of an alkyl or substituted alkyl group....
    s, alkyl halides, amine
    Amine

    Amines are organic compounds and functional groups that contain a base nitrogen atom with a lone pair. Amines are derivative s of ammonia, wherein one or more hydrogen atoms are replaced by organic substituents such as alkyl and aryl groups....
    s,
  • oxidation number 0 for alkyne
    Alkyne

    Alkynes are hydrocarbons that have at least one triple bond between two carbon atoms, with the formula CnH2n-2. The alkynes are traditionally known as acetylenes or the acetylene series, although the name acetylene is also used to refer specifically to the simplest member of the series, known as e...
    s, ketone
    Ketone

    In organic chemistry, a ketone is a type of organic compound which contains a carbonyl group bonded to two other carbon atoms in the form:Neither of the substituents R1 and R2 may be equal to hydrogen ....
    s, aldehyde
    Aldehyde

    An aldehyde is an organic compound containing a terminal carbonyl group. This functional group, which consists of a carbon atom bonded to a hydrogen atom and double bond to an oxygen atom , is called the aldehyde group....
    s, geminal
    Geminal

    In chemistry, the term geminal refers to the relationship between two functional groups that are attached to the same atom. The prefix gem is applied to a chemical name to denote this relationship, as in a gem-dibromide....
     diol
    Diol

    A diol or glycol is a chemical compound containing two hydroxyl groups Vicinal diols have hydroxyl groups attached to adjacent atoms. Examples of vicinal diol compounds are ethylene glycol and propylene glycol....
    s,
  • oxidation number +2 for carboxylic acid
    Carboxylic acid

    Carboxylic acids are organic acids characterized by the presence of a carboxyl group, which has the Chemical formula -COH, usually written -COOH or -CO2H....
    s, amide
    Amide

    In chemistry, an amide is one of three kinds of compounds:* the organic chemistry functional group characterized by a carbonyl group linked to a nitrogen atom , or a compound that contains this functional group ; or...
    s, chloroform
    Chloroform

    Chloroform, also known as trichloromethane and methyl trichloride, is a chemical compound with chemical formula CarbonHydrogenChlorine3....
     and
  • oxidation number +4 for carbon dioxide
    Carbon dioxide

    Carbon dioxide is a chemical compound composed of two oxygen atoms covalent bond to a single carbon atom. It is a gas at standard temperature and pressure and exists in Earth's atmosphere in this state....
    , tetrachloromethane.


Methane
Methane

Methane is a chemical compound with the molecular formula . It is the simplest alkane, and the principal component of natural gas. Methane's bond angles are 109.5 degrees....
 is oxidized to carbon dioxide
Carbon dioxide

Carbon dioxide is a chemical compound composed of two oxygen atoms covalent bond to a single carbon atom. It is a gas at standard temperature and pressure and exists in Earth's atmosphere in this state....
 because the oxidation number changes from -4 to +4. Classical reductions include alkene
Alkene

In organic chemistry, an alkene, olefin, or olefine is an Saturation chemical compound containing at least one carbon-to-carbon double bond....
 reduction to alkane
Alkane

Alkanes, also known as paraffins, are chemical compounds that consist only of the elements carbon and hydrogen , wherein these atoms are linked together exclusively by single bonds without any cyclic structure ....
s and classical oxidations include oxidation of alcohol
Alcohol

In chemistry, an alcohol is any organic compound in which a hydroxyl Functional group is bound to a carbon atom of an alkyl or substituted alkyl group....
s to aldehyde
Aldehyde

An aldehyde is an organic compound containing a terminal carbonyl group. This functional group, which consists of a carbon atom bonded to a hydrogen atom and double bond to an oxygen atom , is called the aldehyde group....
s with manganese dioxide. In oxidations electrons are removed and the electron density of a molecule is reduced. In reductions electron density increases when electrons are added to the molecule. This terminology is always centered around the organic compound. So a ketone
Ketone

In organic chemistry, a ketone is a type of organic compound which contains a carbonyl group bonded to two other carbon atoms in the form:Neither of the substituents R1 and R2 may be equal to hydrogen ....
 is always reduced by Lithium aluminium hydride
Lithium aluminium hydride

Lithium aluminium hydride , commonly abbreviated to LAH, is a reducing agent used in organic synthesis. It is more powerful than the related reagent sodium borohydride due to the weaker Al-H bond compared to the B-H bond....
 but it is bad form to have lithium aluminium hydride oxidized by a ketone. Many oxidations involve removal of proton
Hydrogen ion

Hydrogen ion is recommended by IUPAC as a general term for all ions of hydrogen and its isotopes. Depending on the charge of the ion, two different classes can be distinguished:...
s from the organic molecule and the reverse reduction adds protons to an organic molecule.

Many reactions classified as reductions also appear in other classes. For instance conversion of the ketone to an alcohol by Lithium aluminium hydride can be considered a reduction but the hydride is also a good nucleophile
Nucleophile

In chemistry, a nucleophile is a reagent that forms a chemical bond to its reaction partner by donating both bonding electrons. Because nucleophiles donate electrons, they are by definition Lewis bases ....
 in nucleophilic substitution
Nucleophilic substitution

In organic chemistry and inorganic chemistry, nucleophilic substitution is a fundamental class of substitution reaction in which an "electron rich" nucleophile selectively bonds with or attacks the positive or partially positive charge of an atom attached to a group or atom called the leaving group; the positive or partially positive atom...
. Many redox reactions in organic chemistry have coupling reaction
Coupling reaction

A coupling reaction in organic chemistry is a catch-all for a range of reactions in Organometallic chemistry where two hydrocarbon free radical are coupled with the aid of a metal containing catalyst....
 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....
 involving free radical intermediates. True organic redox chemistry can be found in electrochemical organic synthesis or electrosynthesis
Electrosynthesis

Electrosynthesis in organic chemistry is the organic synthesis of chemical compounds in a electrochemical cell The main advantage of electrosynthesis over an ordinary redox reaction is avoidance of the potential wasteful other half-reaction and the ability to precisely tune the required potential....
. Examples of organic reactions that can take place in an electrochemical cell
Electrochemical cell

An electrochemical cell is a device used for generating an electromotive force and current from electrochemistry, or the reverse, inducing a chemical reaction by a flow of current....
 are the Kolbe electrolysis
Kolbe electrolysis

Kolbe electolysis or Kolbe reaction is an organic reaction named after Adolph Wilhelm Hermann Kolbe. The Kolbe reaction is formally a decarboxylative dimerisation and proceeds by a free radical reaction mechanism....
 

In disproportionation
Disproportionation

Disproportionation or dismutation is used to describe two particular types of chemical reaction:* A chemical reaction of the type: 2A ? A' + A" where A, A' and A" are different chemical species....
 reactions the reactant is both oxidised and reduced in the same chemical reaction forming 2 separate compounds.

Asymmetric catalytic reduction
Asymmetric catalytic reduction

Asymmetric catalytic reduction is the use of various chiral catalysts to reduction a prochiral organic compound to obtain a chiral product. This is one of the several techniques used in chiral synthesis....
s and asymmetric catalytic oxidation
Asymmetric catalytic oxidation

Asymmetric catalytic oxidation is a technique of oxidation various substrate s to give an enantiopure product using a catalyst....
s are important in asymmetric synthesis.

Organic reductions


Several reaction mechanisms exist for organic reductions:
  • Direct electron transfer in one-electron reduction
    One-electron reduction

    A one-electron reduction in organic chemistry involves the transfer of an electron from a metal to an organic compound Substrate . It serves to differentiate between true organic reductions and other reductions such as hydride transfer reactions that actually involve two-electron species....
     with the Birch reduction
    Birch reduction

    The Birch reduction is the organic reduction of Aromatic_ring with sodium and an alcohol in liquid ammonia to form 1,4-Cyclohexadiene . The reaction was reported by the Australian chemist Arthur John Birch in 1944....
     as example
  • Hydride
    Hydride

    Hydride is the name given to the Electric charge ion of hydrogen, H-. Although this ion does not exist except in extraordinary conditions, the term hydride is widely applied to describe Chemical compound of hydrogen with other chemical element, particularly those of Periodic table group 1–16....
     transfer in reductions with for example lithium aluminium hydride
    Lithium aluminium hydride

    Lithium aluminium hydride , commonly abbreviated to LAH, is a reducing agent used in organic synthesis. It is more powerful than the related reagent sodium borohydride due to the weaker Al-H bond compared to the B-H bond....
     or a hydride shift as in the Meerwein-Ponndorf-Verley reduction
    Meerwein-Ponndorf-Verley reduction

    The Meerwein-Ponndorf-Verley Reduction in organic chemistry is the organic reduction of ketones to secondary alcohols with aluminumisopropylate catalysis in isopropanol solution ....
  • Hydrogen
    Hydrogen

    Hydrogen is the chemical element with atomic number 1. It is represented by the chemical symbol H. At standard temperature and pressure, hydrogen is a colorless, odorless, nonmetallic, tasteless, highly combustion and explosive Diatomic molecule gas with the molecular formula H2....
     reductions with a catalyst such as the Lindlar catalyst
    Lindlar catalyst

    A Lindlar catalyst is a heterogeneous catalyst that consists of palladium deposited on calcium carbonate and treated with various forms of lead....
     or the Adkins catalyst
    Adkins catalyst

    Copper chromite is a complex inorganic composition Cu2Cr2O5, but often containing barium oxide that is used to catalyse certain reactions in organic synthesis....
     or in specific reductions such as the Rosenmund reduction
    Rosenmund reduction

    The Rosenmund reduction is a chemical reaction that redox an acid halide to an aldehyde using hydrogen over palladium-on-carbon catalyst poisoning with barium sulfate....
    .
  • Disproportionation
    Disproportionation

    Disproportionation or dismutation is used to describe two particular types of chemical reaction:* A chemical reaction of the type: 2A ? A' + A" where A, A' and A" are different chemical species....
     reaction such as the Cannizzaro reaction
    Cannizzaro reaction

    The Cannizzaro reaction, named after its discoverer Stanislao Cannizzaro, is a chemical reaction that involves the base -induced disproportionation of an aldehyde lacking a hydrogen atom in the alpha position....


Reductions that do not fit in any reduction reaction mechanism and in which just the change in oxidation state is reflected include the Wolff-Kishner reaction.

Organic oxidations


Several reaction mechanisms exist for organic oxidations:
  • Single electron transfer
  • Oxidations through ester intermediates with chromic acid
    Chromic acid

    Chromic acid generally refers to a collection of chemical compound generated by the acidification of solutions containing chromate and dichromate ion or the dissolving of chromium trioxide in sulfuric acid....
     or manganese dioxide
  • Hydrogen atom transfer as in Free radical halogenation
    Free radical halogenation

    In organic chemistry, free radical halogenation is a type of halogenation. This chemical reaction is typical of alkanes and alkyl-substituted aromatics under application of heat or UV light....
  • Oxidation with oxygen
    Oxygen

    Oxygen no O2 produced; 2) O2 produced, but absorbed in oceans & seabed rock; 3) O2 starts to gas out of the oceans, but is absorbed by land surfaces and formation of ozone layer; 4-5) O2 sinks filled and the gas accumulates]]...
     (combustion
    Combustion

    Combustion or burning is a complex sequence of exothermic chemical reactions between a fuel and an oxidant accompanied by the production of heat or both heat and light in the form of either a glow or flames, appearance of light flickering....
    )
  • Oxidation involving ozone
    Ozone

    Ozone or trioxygen is a triatomic molecule, consisting of three oxygen atoms. It is an allotrope of oxygen that is much less stable than the diatomic O2....
     in ozonolysis
    Ozonolysis

    Ozonolysis is the cleavage of an alkene or alkyne with ozone to form organic compounds in which the multiple carbon-carbon bond has been replaced by a double bond to oxygen....
     and peroxide
    Peroxide

    A peroxide is a compound containing an oxygen-oxygen chemical bond. The simplest stable peroxide is hydrogen peroxide. Superoxides, dioxygenyls, ozones and ozonides compound are considered separately....
    s
  • Oxidations involving an elimination reaction
    Elimination reaction

    An elimination reaction is a type of organic reaction in which two substituents are removed from a molecule in either a one or two-step mechanism ....
     mechanism such as the Swern oxidation
    Swern oxidation

    The Swern oxidation, named after Daniel Swern, is a chemical reaction whereby a primary or secondary alcohol is redox to an aldehyde or ketone using oxalyl chloride, dimethyl sulfoxide and an organic base, such as triethylamine....
    , the Kornblum oxidation
    Kornblum oxidation

    The Kornblum oxidation is a chemical reaction of a primary halide with Dimethyl sulfoxide to form an aldehyde. Like all DMSO-based oxidations, the Kornblum oxidation creates an alkoxysulphonium ion, which, in the presence of a base, such as Triethylamine, will Elimination reaction to form the desired aldehyde....
     and with reagents such as IBX acid and Dess-Martin periodinane
    Dess-Martin periodinane

    Dess-Martin periodinane is a chemical reagent used to oxidation primary alcohols to aldehydes and secondary alcohols to ketones. This periodinane has several advantages over chromium- and dimethyl sulfoxide-based oxidants that include milder conditions, shorter reaction times, higher yields, and simplified workups....
    .
  • oxidation by nitroso
    Nitroso

    Nitroso refers to a functional group in organic chemistry which has the general formula RNO. Nitroso compounds can be prepared by the reduction of nitro compounds or by the oxidation of hydroxylamines....
     radicals
    Radical (chemistry)

    In chemistry, radicals are atoms, molecules or ions with unpaired electrons on an otherwise open shell configuration. These unpaired electrons are usually highly chemical reaction, so radicals are likely to take part in chemical reactions....
     Fremy's salt
    Fremy's salt

    Fr?my's salt, discovered in 1845 by Edmond Fr?my , is a chemical compound and a strong organic oxidation agent. The formal name is disodium nitrosodisulfonic acid or Na2NO2, but the expression "Fr?my's salt" refers equally well to potassium nitrosodisulfonate, also known as potassium peroxylamine disulfonate....
     or TEMPO
    Tempo

    In musical terminology, 'tempo' is the speed or pace of a given musical piece. It is an extremely crucial element of composition, as it can affect the mood and difficulty of a piece....