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Organic reaction
Organic reactions are chemical reactions inv olv ing organic
compounds. [1][2][3] The basic organic chemistry reaction
ty pes are addition reactions, elimination reactions,
substitution reactions, pericy clic reactions, rearrangement
reactions, photochemical reactions and redox reactions. In
organic sy nthesis, organic reactions are used in the
construction of new organic molecules. The production of
many man-made chemicals such as drugs, plastics, food
additiv es, fabrics depend on organic reactions.

The oldest organic reactions are combustion of organic fuels and saponification of fats to make soap. Modern organic chemistry
starts with the Wöhler sy nthesis in 1828. In the history of the Nobel Prize in Chemistry awards hav e been giv en for the inv ention
of specific organic reactions such as the Grignard reaction in 1912, the Diels-Alder reaction in 1950, the Wittig reaction in 197 9
and olefin metathesis in 2005.

Contents
Classifications
Fundamentals
By mechanism
By functional groups
Other classification
See also
References
External links

Classifications
Organic chemistry has a strong tradition of naming a specific reaction to its inv entor or inv entors and a long list of so-called
nam ed reactions exists, conserv ativ ely estimated at 1000. A v ery old named reaction is the Claisen rearrangement (1912) and
a recent named reaction is the Bingel reaction (1993). When the named reaction is difficult to pronounce or v ery long as in the
Corey -House-Posner-Whitesides reaction it helps to use the abbrev iation as in the CBS reduction. The number of reactions
hinting at the actual process taking place is much smaller, for example the ene reaction or aldol reaction.

Another approach to organic reactions is by ty pe of organic reagent, many of them inorganic, required in a specific
transformation. The major ty pes are oxidizing agents such as osmium tetroxide, reducing agents such as Lithium aluminium
hy dride, bases such as lithium diisopropy lamide and acids such as sulfuric acid.

Fundamentals
Factors gov erning organic reactions are essentially the same as that of any chemical reaction. Factors specific to organic
reactions are those that determine the stability of reactants and products such as conjugation, hy perconjugation and aromaticity
and the presence and stability of reactiv e intermediates such as free radicals, carbocations and carbanions.

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An organic compound may consist of many isomers. Selectiv ity in terms of regioselectiv ity , diastereoselectiv ity and
enantioselectiv ity is therefore an important criterion for many organic reactions. The stereochemistry of pericy clic reactions is
gov erned by the Woodward–Hoffmann rules and that of many elimination reactions by the Zaitsev 's rule.

Organic reactions are important in the production of pharmaceuticals. In a 2006 rev iew[4] it was estimated that 20% of chemical
conv ersions inv olv ed alky lations on nitrogen and oxy gen atoms, another 20% inv olv ed placement and remov al of protectiv e
groups, 11% inv olv ed formation of new carbon-carbon bond and 10% inv olv ed functional group interconv ersions.

By mechanism
There is no limit to the number of possible organic reactions and mechanisms. [5][6] Howev er, certain general patterns are
observ ed that can be used to describe many common or useful reactions. Each reaction has a stepwise reaction mechanism that
explains how it happens, although this detailed description of steps is not alway s clear from a list of reactants alone. Organic
reactions can be organized into sev eral basic ty pes. Some reactions fit into more than one category . For example, some
substitution reactions follow an addition-elimination pathway . This ov erv iew isn't intended to include ev ery single organic
reaction. Rather, it is intended to cov er the basic reactions.

Reaction type Subtype Comment

electrophilic addition

Addition reactions nucleophilic addition include such reactions as halogenation, hydrohalogenation and hydration.

radical addition

include processes such as dehydration and are found to follow an E1, E2 or E1cB
Elimination reaction
reaction mechanism

nucleophilic aliphatic
with SN1, SN2 and SNi reaction mechanisms
substitution

nucleophilic aromatic
substitution

Substitution nucleophilic acyl

reactions substitution

electrophilic substitution

electrophilic aromatic
substitution

radical substitution

Organic redox
are redox reactions specific to organic compounds and are very common.
reactions

1,2-rearrangements
Rearrangement
pericyclic reactions
reactions
metathesis

In condensation reactions a small molecule, usually water, is split off when two reactants combine in a chemical reaction. The
opposite reaction, when water is consumed in a reaction, is called hy droly sis. Many poly merization reactions are deriv ed from
organic reactions. They are div ided into addition poly merizations and step-growth poly merizations.

In general the stepwise progression of reaction mechanisms can be represented using arrow pushing techniques in which curv ed
arrows are used to track the mov ement of electrons as starting materials transition to intermediates and products.

By functional groups

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Organic reactions can be categorized based on the ty pe of functional group inv olv ed 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 the reactant is an ester and
the reaction product an alcohol.

An ov erv iew of functional groups with their preparation and reactiv ity is presented below:

Functional group Preparation Reactions

Acid anhydride preparation reactions

Acyl halides preparation reactions

Acyloins preparation reactions

Alcohols preparation reactions

Aldehydes preparation reactions

Alkanes preparation reactions

Alkenes preparation reactions

Alkyl halides preparation reactions

Alkyl nitrites preparation reactions

Alkynes preparation reactions

Amides preparation reactions

Amine oxide preparation reactions

Amines preparation reactions

Arene compounds preparation reactions

Azides preparation reactions

Aziridines preparation reactions

Carboxylic acids preparation reactions

Cyclopropanes preparation reactions

Diazo compounds preparation reactions

Diols preparation reactions

Esters preparation reactions

Ethers preparation reactions

Epoxide preparation reactions

Haloketones preparation reactions

Imines preparation reactions

Isocyanates preparation reactions

Ketones preparation reactions

Lactams preparation reactions

Nitriles preparation reactions

Nitro compounds preparation reactions

Phenols preparation reactions

Thiols preparation reactions

Other classification

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In heterocy clic chemistry , organic reactions are classified by the ty pe of heterocy cle formed with respect to ring-size and ty pe of
heteroatom. See for instance the chemistry of indoles. Reactions are also categorized by the change in the carbon framework.
Examples are ring expansion and ring contraction, homologation reactions, poly merization reactions, insertion reactions, ring-
opening reactions and ring-closing reactions.

Organic reactions can also be classified by the ty pe of bond to carbon with respect to the element inv olv ed. More reactions are
found in organosilicon chemistry , organosulfur chemistry , organophosphorus chemistry and organofluorine chemistry . With the
introduction of carbon-metal bonds the field crosses ov er to organometallic chemistry .

Compounds of carbon with other elements in the periodic table

CH He

CLi CBe CB CC CN CO CF Ne

CNa CMg CAl CSi CP CS CCl CAr

CK CCa CSc CTi CV CCr CMn CFe CCo CNi CCu CZn CGa CGe CAs CSe CBr CKr

CRb CSr CY CZr CNb CMo CTc CRu CRh CPd CAg CCd CIn CSn CSb CTe CI CXe

CCs CBa CHf CTa CW CRe COs CIr CPt CAu CHg CTl CPb CBi CPo CAt Rn

Fr CRa Rf Db CSg Bh Hs Mt Ds Rg Cn Nh Fl Mc Lv Ts Og
↓

CLa CCe CPr CNd CPm CSm CEu CGd CTb CDy CHo CEr CTm CYb CLu

Ac CTh CPa CU CNp CPu CAm CCm CBk CCf CEs Fm Md No Lr

Chemical bonds to carbon
Many uses in
Core organic chemistry
chemistry
Academic research, but no
Bond unknown
widespread use

See also
List of organic reactions
Other chemical reactions: inorganic reactions, metabolism, organometallic reactions, polymerization reactions.
Important publications in organic chemistry

References
1. Strategic Applications of Named Reactions in Organic Synthesis Laszlo Kurti, Barbara Czako Academic Press (March 4, 2005)
ISBN 0-12-429785-4
2. J. Clayden, N. Greeves & S. Warren "Organic Chemistry" (Oxford University Press, 2012)
3. Robert T. Morrison, Robert N. Boyd, and Robert K. Boyd, Organic Chemistry, 6th edition, Benjamin Cummings, 1992
4. Analysis of the reactions used for the preparation of drug candidate molecules John S. Carey, David Laffan, Colin Thomson and Mike
T. Williams Org. Biomol. Chem., 2006, 4, 2337–2347, doi:10.1039/b602413k (https://doi.org/10.1039%2Fb602413k)
5. Is This Reaction a Substitution, Oxidation–Reduction, or Transfer? / N.S.Imyanitov. J. Chem. Educ. 1993, 70(1), 14–16.
6. March, Jerry (1992), Advanced Organic Chemistry: Reactions, Mechanisms, and Structure (4th ed.), New York: Wiley, ISBN 0-471-
60180-2

External links
Organic reactions @ Synarchive.com (http://www.synarchive.com/named-reactions/)

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4/27/2018 Organic reaction - Wikipedia

Organic reaction flashcards from OSU (https://web.archive.org/web/20041210052445/http://www.chemistry.ohio-state.edu/organic/flas

hcards/)
list of named reactions from UConn (http://arquivo.pt/wayback/20091011112359/http://orgchem.chem.uconn.edu/namereact/named.ht
ml)
organic reactions (https://web.archive.org/web/20061107085444/http://www.organicworldwide.net/reaction/)
Organic chemistry help-Best of the Web 2008 (http://www.aceorganicchem.com/resources.html)
Organic chemistry help-Electronic Flashcards (http://www.aceorganicchem.com/organic_chemistry_flash_cards.html)
Study-Organic-Chemistry.com (http://www.study-organic-chemistry.com)
organic-reaction.com (http://www.organic-reaction.com)

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