Organic reaction

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Organic reaction

Organic reactions are chemical reaction

Chemical reaction

A chemical reaction is a process that always results in the interconversion of chemical substances. The substance or substances initially involved in a chemical reaction are called reactants....
s involving 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. The basic 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....
reaction types are addition reaction

Addition reaction

An addition reaction, in organic chemistry, is in its simplest terms an organic reaction where two or more molecules combine to form a larger one....
s, 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 ....
s, substitution reaction

Substitution reaction

In a substitution reaction, a functional group in a particular chemical compound is replaced by another group . In organic chemistry, the electrophile and nucleophile substitution reactions are of prime importance....
s, pericyclic reaction

Pericyclic reaction

In organic chemistry, a pericyclic reaction is a type of organic reaction wherein the transition state of the molecule has a cyclic geometry, and the reaction progresses in a concerted reaction fashion....
s, 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 ....
s and redox reactions

Organic redox reaction

Organic reductions or organic oxidations or organic redox reactions are redox reactions that take place with organic compounds. In organic chemistry oxidations and reductions are different from ordinary redox reactions because many reactions carry the name but do not actually involve electron transfer in the electrochemistry sense...
. In organic synthesis

Organic synthesis

Organic synthesis is a special branch of chemical synthesis and is concerned with the construction of organic compounds via organic reactions. Organic_chemistry molecules can often contain a higher level of complexity compared to purely Inorganic_chemistry compounds, so the synthesis of organic compounds has developed into one of the most im...
, organic reactions are used in the construction of new organic molecules. The production of many man-made chemicals such as drugs, plastics, food additives, fabrics depend on organic reactions.

The oldest organic reactions are 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....
of organic fuels and saponification

Saponification

Saponification is the hydrolysis of an ester under base conditions to form an alcohol and the salt of a carboxylic acid . Saponification is commonly used to refer to the reaction of a metallic alkali with a fat or oil to form soap....
of fats to make soap.

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Encyclopedia

Organic reactions are chemical reaction

Chemical reaction

Organic compound

Organic chemistry

Addition reaction

An addition reaction, in organic chemistry, is in its simplest terms an organic reaction where two or more molecules combine to form a larger one....
s, 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 ....
s, substitution reaction

Substitution reaction

Pericyclic reaction

Rearrangement reaction

Organic redox reaction

Organic synthesis

Combustion

Saponification

Organic chemistry

Wöhler synthesis

The W?hler synthesis is the conversion of ammonium cyanate into urea . This chemical reaction was discovered in 1828 by Friedrich W?hler in an attempt to synthesize ammonium cyanate itself and is considered the starting point of modern organic chemistry....
in 1828. In the history of the Nobel Prize in Chemistry

Nobel Prize in Chemistry

The Nobel Prize in Chemistry is awarded annually by the Royal Swedish Academy of Sciences to scientists in the various fields of chemistry. It is one of the five Nobel Prizes established by the will of Alfred Nobel in 1895, awarded for outstanding contributions in chemistry, Nobel Prize in Physics, Nobel Prize in Literature, Nobel Peace Pri...
awards have been given for the invention of specific organic reactions such as the Grignard reaction

Grignard reaction

The Grignard reaction, named after the French chemist Fran?ois Auguste Victor Grignard, is an organometallic chemistry chemical reaction in which alkyl- or aryl-magnesium halides , act as nucleophiles, attack electrophilic carbon atoms that are present within polar bonds to yield a carbon-carbon bond , thus altering hybridization about the r...
in 1912, the Diels-Alder reaction

Diels-Alder reaction

The Diels-Alder reaction is an organic chemical reaction between a conjugated diene and a substituted alkene, commonly termed the dienophile, to form a substituted cyclohexene system....
in 1950, the Wittig reaction

Wittig reaction

The Wittig reaction is a chemical reaction of an aldehyde or ketone with a triphenyl #Wittig reagents to give an alkene and triphenylphosphine oxide....
in 1979 and olefin metathesis

Olefin metathesis

Olefin metathesis or transalkylidenation is an organic reaction that entails redistribution of alkylene fragments by the scission of carbon - carbon chemical bond in olefins....
in 2005.

Classifications

Organic chemistry has a strong tradition of naming a specific reaction to its inventor or inventors and a long list

List of organic reactions

This page aims to list well-known organic reaction and reagents in organic chemistry. It is organized in alphabetical order. You may also find it useful to browse :Category:Organic reactions....
of so-called named reactions exists, conservatively estimated at 1000. A very old named reaction is the Claisen rearrangement

Claisen rearrangement

The Claisen rearrangement is a powerful carbon-carbon chemical bond-forming chemical reaction discovered by Rainer Ludwig Claisen. The heating of an allyl vinyl ether will initiate a Sigmatropic reaction to give a ?,d-unsaturated carbonyl....
(1912) and a recent named reaction is the Bingel reaction

Bingel reaction

The Bingel reaction in fullerene chemistry is a fullerene cyclopropane to a methanofullerene first discovered by C. Bingel in 1993 with the bromo derivative of diethyl malonate in the presence of a base such as sodium hydride or DBU ....
(1993). When the named reaction is difficult to pronounce or very long as in the Corey-House-Posner-Whitesides reaction

Corey-House-Posner-Whitesides reaction

The Corey-House synthesis is an organic reaction that involves the reaction of a lithium dialkyl cuprate with an alkyl halide to form a new alkane....
it helps to use the abbreviation as in the CBS reduction

CBS reduction

The CBS reduction, in full the Corey-Bakshi-Shibata reduction, is an organic reaction which transforms ketones enantioselectively into alcohols....
. The number of reactions hinting at the actual process taking place is much smaller, for example the ene reaction

Ene reaction

The Ene reaction is a chemical reaction between an alkene with an allylic hydrogen and a multiple bond . It is a group transfer reaction. The product is a substituted alkene with the double bond shifted to the allylic position....
or aldol reaction

Aldol reaction

The aldol reaction is a carbon-carbon bond formation chemical reaction in organic chemistry. In its usual form, it involves the nucleophilic addition of a ketone enolate to an aldehyde to form a Hydroxy ketone, or "aldol" , a structural unit found in many biomolecule and pharmaceuticals....
.

Another approach to organic reactions is by type of organic reagent, many of them inorganic

Inorganic compound

Traditionally, inorganic compounds are considered to be of a mineral, not biological, origin. Complementarily, most organic compounds are traditionally viewed as being of biological origin....
, required in a specific transformation. The major types are oxidizing agent

Oxidizing agent

An oxidizing agent can be defined as either:#a chemical compound that readily transfers oxygen atoms, or#a substance that gains electrons in a redox chemical reaction...
s such as osmium tetroxide, reducing agent

Reducing agent

A reducing agent is the element or compound in a redox reaction that reduces another Chemical species. In doing so, it becomes oxidized, and is therefore the electron donor in the redox....
s such as 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....
, bases

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....
such as lithium diisopropylamide

Lithium diisopropylamide

Lithium diisopropylamide is the chemical compound with the formula [2CH]2NLi. Generally abbreviated LDA, it is a strong base used in organic chemistry for the deprotonation of weakly acidic compounds....
and acid

Acid

An acid is traditionally considered any chemical compound that, when dissolved in water, gives a solution with a hydrogen ion Activity greater than in pure water, i.e....
s such as sulfuric acid

Sulfuric acid

Sulfuric acid, hydrogen2sulfuroxygen4, is a strong mineral acid. It is soluble in water at all concentrations. Sulfuric acid has many applications, and is one of the top products of the chemical industry....
.

Fundamentals

Factors governing organic reactions are essentially the same as that of any chemical reaction

Chemical reaction

Conjugated system

A conjugated system occurs in an organic compound where atoms covalently Chemical bond with alternating single and multiple bonds and influence each other to produce a region called electron delocalization....
, hyperconjugation

Hyperconjugation

Hyperconjugation in organic chemistry is the stabilizing interaction that results from the interaction of the electrons in a sigma bond with an adjacent empty non-bonding p-orbital or antibonding pi bond or filled p orbital to give an extended molecular orbital that increases the stability of the system....
and aromaticity

Aromaticity

Aromaticity is a chemical property in which a conjugated system ring of unsaturated bonds, lone pairs, or empty orbitals exhibit a stabilization stronger than would be expected by the stabilization of conjugation alone....
and the presence and stability of reactive intermediates such as free radical

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....
s, carbocation

Carbocation

A carbocation is an ion with a positively-charged carbon atom. The charged carbon atom in a carbocation is a "sextet", i.e. it has only six electrons in its outer Electron shell#Valence shell instead of the eight valence electrons that ensures maximum stability ....
s and carbanion

Carbanion

A carbanion is an anion in which carbon has an unshared pair of electrons and bears a negative charge usually with three substituents for a total of eight valence electrons ....
s.

An organic compound may consist of many isomer

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....
s. Selectivity in terms of regioselectivity

Regioselectivity

In chemistry, regioselectivity is the preference of one direction of chemical bond making or breaking over all other possible directions . It can often apply to which of many possible positions a reagent will affect, such as which proton a strong Base will abstract from an organic molecule, or where on a substituted benzene ring a further s...
, diastereoselectivity and enantioselectivity is therefore an important criterion for many organic reactions. The stereochemistry

Stereochemistry

Stereochemistry, a subdiscipline of chemistry, involves the study of the relative spatial arrangement of atoms within molecules. An important branch of stereochemistry is the study of chirality molecules ....
of pericyclic reaction

Pericyclic reaction

Woodward-Hoffmann rules

The Woodward?Hoffmann rules devised by Robert Burns Woodward and Roald Hoffmann are a set of rules in organic chemistry predicting the stereochemistry of pericyclic reactions based on orbital symmetry....
and that of many 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 ....
s by the Zaitsev's rule

Zaitsev's rule

In chemistry, Zaitsev's rule, Saytzeff's rule or Saytsev's rule named after Alexander Mikhailovich Zaitsev is a rule that states that if more than one alkene can be formed by an elimination reaction, the more stable alkene is the major product....
.

Organic reactions are important in the production of pharmaceutical

Medication

A pharmaceutical drug, also referred to as medicine or medicament, can be loosely defined as any substance intended for use in the diagnosis, cure, mitigation, treatment, or prevention of disease....
s. In a 2006 review it was estimated that 20% of chemical conversions involved alkylation

Alkylation

Alkylation is the transfer of an alkyl group from one molecule to another. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion or a carbene ....
s on nitrogen and oxygen atoms, another 20% involved placement and removal of protective groups, 11% involved formation of new carbon-carbon bond

Carbon-carbon bond

A carbon-carbon bond is a covalent Chemical bond between two carbon atoms. The most common form is the single bond ? a bond composed of two electrons, one from each of the two atoms....
and 10% involved functional group interconversions.

Organic reactions by mechanism

There is no limit to the number of possible organic reactions and mechanisms. However, certain general patterns are observed that can be used to describe many common or useful reactions. Each reaction has a stepwise 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....
that explains how it happens, although this detailed description of steps is not always clear from a list of reactants alone. Organic reactions can be organized into several basic types. Some reactions fit into more than one category. For example, some substitution reactions follow an addition-elimination pathway. This overview isn't intended to include every single organic reaction. Rather, it is intended to cover the basic reactions.

Addition reaction
Addition reaction

An addition reaction, in organic chemistry, is in its simplest terms an organic reaction where two or more molecules combine to form a larger one....
s include such reactions as halogenation
Halogenation

Halogenation is a chemical reaction that incorporates a halogen atom into a molecule. More specific descriptions exist that specify the type of halogen: fluorination, chlorination, bromination, and iodination....
, hydrohalogenation
Hydrohalogenation

A hydrohalogenation reaction is the electrophilic addition of hydrohalic acids like hydrogen chloride or hydrogen bromide to alkenes to yield the corresponding haloalkanes ....
and hydration
Hydration reaction

In organic chemistry, a hydration reaction is a chemical reaction in which a hydroxyl group and a hydrogen cation are added to the two carbon atoms covalent bonded together in the carbon-carbon double bond which makes up an alkene functional group....
. The main addition reactions are:

electrophilic addition
Electrophilic addition

In organic chemistry, an electrophilic addition reaction is an addition reaction where, in a chemical compound, a pi bond is removed by the creation of two new covalent bonds....
or EA
nucleophilic addition
Nucleophilic addition

In organic chemistry, a nucleophilic addition reaction is an addition reaction where in a chemical compound a p bond is removed by the creation of two new covalent bonds by the addition of a nucleophile ....
or NA
radical addition or RA

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 ....
s include processes such as dehydration
Dehydration reaction

In chemistry, a dehydration reaction is usually defined as a chemical reaction that involves the loss of water from the reacting molecule. Dehydration reactions are a subset of elimination reactions....
and are found to follow an E1, E2 or E1cB
E1cB elimination reaction

The E1cB elimination reaction is a special type of elimination reaction in organic chemistry. This reaction mechanism explains the formation of alkenes from alkyl halides through a carbanion intermediate given specified reaction conditions and specified substrates....
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....

Substitution reaction
Substitution reaction

In a substitution reaction, a functional group in a particular chemical compound is replaced by another group . In organic chemistry, the electrophile and nucleophile substitution reactions are of prime importance....
s are divided into:

nucleophilic aliphatic 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...
with S_N1
SN1 reaction

The SN1 reaction is a substitution reaction in organic chemistry. "SN" stands for nucleophilic substitution and the "1" represents the fact that the rate-determining step is molecule....
, S_N2
SN2 reaction

The SN2 reaction is a type of nucleophilic substitution, where a lone pair from a nucleophile attacks an electron deficient electrophile center and covalent bond to it, expelling another group called a leaving group....
and S_Ni 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....
s
nucleophilic aromatic substitution
Nucleophilic aromatic substitution

A nucleophilic aromatic substitution is a substitution reaction in organic chemistry in which the nucleophile displaces a good leaving group, such as a halide on an aromatic ring....
or NAS
nucleophilic acyl substitution
Nucleophilic acyl substitution

Nucleophilic acyl substitution describes the substitution reaction involving nucleophiles and acyl compounds. Acyl compounds are carboxylic acid derivatives including esters, amides and acid halides....
electrophilic substitution
Electrophilic substitution

Electrophilic substitution reactions are chemical reactions in which an electrophile displaces another group, typically but not always hydrogen....
or ES
electrophilic aromatic substitution
Electrophilic aromatic substitution

Electrophilic aromatic substitution or EAS is an organic reaction in which an atom, usually hydrogen, appended to an aromatic ring is replaced by an electrophile....
or EAS
radical substitution
Radical substitution

In organic chemistry, a radical substitution reaction is a substitution reaction involving radical s as a reactive intermediate .The reaction always involves at least two steps, and possibly a third....
or RS

Organic redox reaction
Organic redox reaction

Organic reductions or organic oxidations or organic redox reactions are redox reactions that take place with organic compounds. In organic chemistry oxidations and reductions are different from ordinary redox reactions because many reactions carry the name but do not actually involve electron transfer in the electrochemistry sense...
s are redox reactions specific to 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 and are very common.

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 ....
s are divided into:

1,2-rearrangement
1,2-rearrangement

A 1,2-rearrangement or 1,2-migration or 1,2-shift or Frank C. Whitmore 1,2-shift is an organic reaction where a substituent moves from one atom to another atom in a chemical compound....
s
pericyclic reactions
metathesis
Olefin metathesis

Olefin metathesis or transalkylidenation is an organic reaction that entails redistribution of alkylene fragments by the scission of carbon - carbon chemical bond in olefins....

In Condensation reaction

Condensation reaction

A condensation reaction is a chemical reaction in which two molecules or moieties combine to form one single molecule, together with the loss of a small molecule....
s a small molecule, usually water

Water

Water is a common chemical substance that is essential for the survival of all known forms of life. In typical usage, water refers only to its liquid form or States of matter, but the substance also has a solid state, ice, and a gaseous state, water vapor or steam....
, is split off when two reactants combine in a chemical reaction. The opposite reaction, when water is consumed in a reaction, is called hydrolysis

Hydrolysis

Hydrolysis is a chemical reaction during which one or more water are split into hydrogen and hydroxide ions which may go on to participate in further reactions....
. Many Polymerization

Polymerization

In polymer chemistry, polymerization is a process of reacting monomer molecules together in a chemical reaction to form three-dimensional networks or polymer chains....
reactions are derived from organic reactions. They are divided into addition polymerization

Addition polymerization

Addition polymerisation, also called polyaddition or chain growth polymerisation, is a polymerisation technique where Unsaturated compound monomer molecules add on to a growing polymer chain one at a time ....
s and step-growth polymerization

Step-growth polymerization

Step-growth polymerization is a polymerization process that involves a chemical reaction between multifunctional monomer molecules. In a step-growth reaction, the growing chains may react with each other to form even longer chains....
s.

Organic reactions by functional groups

Organic reactions can be categorized based on the type of functional group

Functional group

In organic chemistry, functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules....
involved in the reaction as a reactant and the functional group that is formed as a result of this reaction. For example in the Fries rearrangement

Fries rearrangement

The Fries rearrangement, named for the German chemist Karl Theophil Fries, is a rearrangement reaction of a phenyl ester to a hydroxy aryl ketone by catalysis of lewis acids....
the reactant is an ester

Ester

An ester is an often Aroma compound organic chemistry or partially organic compound formed by the reaction between an acid and an alcohol or aromatic alcohol with the elimination of water....
and the reaction product an 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....
.

An overview of functional groups with their preparation and reactivity is presented on the right:

Other organic reaction classification

In heterocyclic chemistry, organic reactions are classified by the type of heterocycle formed with respect to ring-size and type of heteroatom. See for instance the chemistry of indole

Indole

Indole is an aromatic Heterocyclic compound organic compound. It has a bicyclic structure, consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring....
s.

Organic reactions can also be classified by the type of bond to carbon with respect to the element involved. More reactions are found in organosilicon chemistry

Organosilicon

Organosilicon compounds are Organic chemistry chemical compound containing carbon silicon chemical bond. Organosilicon chemistry is the corresponding science exploring their properties and reactivity....
, organosulfur chemistry, organophosphorus chemistry and organofluorine chemistry

Organofluorine chemistry

Organofluorine chemistry describes the chemistry of organofluorine compounds, organic compounds that contain the carbon?fluorine bond. The carbon?fluorine bond can confer different properties to different compounds, and organofluorine compounds have diverse properties, reflecting the diversity of their structures....
. With the introduction of carbon-metal bonds the field crosses over to organometallic chemistry

Organometallic chemistry

Organometallic chemistry is the study of chemical compounds containing chemical bonding between carbon and a metal. Since many compounds without such bonds are chemically similar, an alternative may be compounds containing metal-element bonds of a largely covalent character....
.

Organic reaction

Classifications

Fundamentals

Organic reactions by mechanism

Organic reactions by functional groups

Other organic reaction classification

See also

Further reading

External links