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Latest revision as of 20:27, 4 September 2012
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Overview
Organic reactions are chemical reactions involving organic compounds.[1] The basic organic chemistry reaction types are addition reactions, elimination reactions, substitution reactions, pericyclic reactions, rearrangement reactions and redox reactions. In organic synthesis, 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 of organic fuels and saponification of fats to make soap. Modern organic chemistry starts with the Wöhler synthesis in 1828. In the history of the Nobel Prize in Chemistry awards have been given for the invention of specific organic reactions such as the Grignard reaction in 1912, the Diels-Alder reaction in 1950, the Wittig reaction in 1979 and olefin metathesis in 2005.
Classifications
Organic chemistry has a strong tradition of naming a specific reaction to its inventor or inventors and a long list of so-called named reactions exists, conservatively estimated at 1000. A very 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 very long as in the Corey-House-Posner-Whitesides reaction it helps to use the abbreviation 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 type of organic reagent, many of them inorganic, required in a specific transformation. The major types are oxidizing agents such as osmium tetroxide, reducing agents such as Lithium aluminium hydride, bases such as lithium diisopropylamide and acids such as sulfuric acid.
Fundamentals
Factors governing 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, hyperconjugation and aromaticity and the presence and stability of reactive intermediates such as free radicals, carbocations and carbanions.
An organic compound may consist of many isomers. Selectivity in terms of regioselectivity, diastereoselectivity and enantioselectivity is therefore an important criterion for many organic reactions. The stereochemistry of pericyclic reactions is governed 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 review [2] it was estimated that 20% of chemical conversions involved alkylations on nitrogen and oxygen atoms, another 20% involved placement and removal of protective groups, 11% involved formation of new carbon-carbon bond 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 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 reactions include such reactions as halogenation, hydrohalogenation and hydration. The main addition reactions are:
- electrophilic addition or EA
- nucleophilic addition or NA
- radical addition or RA
Elimination reactions include processes such as dehydration and are found to follow a E1, E2 or E1cB reaction mechanism
Substitution reactions are divided into:
- nucleophilic aliphatic substitution with SN1, SN2 and SNi reaction mechanisms
- nucleophilic aromatic substitution or NAS
- nucleophilic acyl substitution
- electrophilic substitution or ES
- electrophilic aromatic substitution or EAS
- radical substitution or RS
Organic redox reactions are redox reactions specific to organic compounds and are very common.
Rearrangement reactions are divided into:
- 1,2-rearrangements
- pericyclic 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 hydrolysis. Many Polymerization reactions are derived from organic reactions. They are divided into addition polymerizations and step-growth polymerizations.
Organic reactions by functional groups
Organic reactions can be categorized based on the type of functional group 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 the reactant is an ester and the reaction product an alcohol.
An overview of functional groups with their preparation and reactivity is presented below:
- Acyl halides: preparation - reactions
- Aldehydes: preparation - reactions
- Acyloins: preparation - reactions
- Alkanes: preparation - reactions
- Alkenes: preparation - reactions
- Alkynes: preparation - reactions
- Alkyl halides: preparation - reactions
- Alcohols: preparation - reactions
- Arene compounds: preparation - reactions
- Azides: preparation - reactions
- Aziridines: preparation - reactions
- Amides: preparation - reactions
- Amines: preparation - reactions
- Carboxylic acids: preparation - reactions
- Cyclopropanes: 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
- Nitrites: preparation - reactions
- Phenols: preparation - reactions
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 indoles.
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, organosulfur chemistry, organophosphorus chemistry and organofluorine chemistry. With the introduction of carbon-metal bonds the field crosses over to organometallic chemistry.
Template:ChemicalBondsToCarbon
See also
- List of organic reactions
- Other chemical reactions: inorganic reactions, biochemical reactions, organometallic reactions, polymerization reactions.
- Important publications in organic chemistry
- Metabolism
External links
References
- ↑ Strategic Applications of Named Reactions in Organic Synthesis Laszlo Kurti, Barbara Czako Academic Press (March 4, 2005) ISBN 0-12-429785-4
- ↑ 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
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