Organic reaction 172592 221218210 2008-06-23T15:48:22Z Loupeter 7217958 [[Image:Claisen Rearrangement Scheme.png|right|400px|The Claisen rearrangement]]'''Organic reactions''' are [[chemical reaction]]s involving [[organic compound]]s.<ref>''Strategic Applications of Named Reactions in Organic Synthesis'' Laszlo Kurti, Barbara Czako Academic Press (March 4, '''2005''') ISBN 0-12-429785-4 </ref> The basic [[organic chemistry]] reaction types are [[addition reaction]]s, [[elimination reaction]]s, [[substitution reaction]]s, [[pericyclic reaction]]s, [[rearrangement reaction]]s and [[organic redox reaction|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 organic reactions|'''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 compound|inorganic]], required in a specific transformation. The major types are [[oxidizing agent]]s such as [[osmium tetroxide]], [[reducing agent]]s such as [[Lithium aluminium hydride]], [[base (chemistry)|bases]] such as [[lithium diisopropylamide]] and [[acid]]s 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 [[Conjugated system|conjugation]], [[hyperconjugation]] and [[aromaticity]] and the presence and stability of [[reactive intermediate]]s such as [[radical (chemistry)|free radical]]s, [[carbocation]]s and [[carbanion]]s. An organic compound may consist of many [[isomer]]s. Selectivity in terms of [[regioselectivity]], [[diastereoselectivity]] and [[enantioselectivity]] is therefore an important criterion for many organic reactions. The [[stereochemistry]] of [[pericyclic reaction]]s is governed by the [[Woodward-Hoffmann rules]] and that of many [[elimination reaction]]s by the [[Zaitsev's rule]]. Organic reactions are important in the production of [[Medication|pharmaceutical]]s. In a 2006 review <ref>''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}}</ref> it was estimated that 20% of chemical conversions involved [[alkylation]]s on nitrogen and oxygen atoms, another 20% involved placement and removal of [[protective group]]s, 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 reaction]]s 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 reaction]]s include processes such as [[dehydration reaction|dehydration]] and are found to follow an E1, E2 or [[E1cB elimination reaction|E1cB]] [[reaction mechanism]] *[[Substitution reaction]]s are divided into: # [[Nucleophilic substitution|nucleophilic aliphatic substitution]] with [[SN1 reaction|SN1]], [[SN2 reaction|SN2]] and [[SNi]] [[reaction mechanism]]s # [[nucleophilic aromatic substitution]] or NAS # [[nucleophilic acyl substitution]] # [[electrophilic substitution]] or ES # [[electrophilic aromatic substitution]] or EAS # [[radical substitution]] or RS *[[Organic redox reaction]]s are [[redox reaction]]s specific to [[organic compound]]s and are very common. *[[Rearrangement reaction]]s are divided into: # [[1,2-rearrangement]]s # [[pericyclic|pericyclic reactions]] # [[olefin metathesis|metathesis]] In [[Condensation reaction]]s a small molecule, usually [[water]], is split off when two [[reactant]]s 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 polymerization]]s and [[step-growth polymerization]]s. == Organic reactions by functional groups == {|align="right" class="wikitable" |'''Functional group'''||'''Preparation'''||'''Reactions''' |- | [[Acyl halides]]: || [[Acyl halide#Acyl halide synthesis|preparation]] || [[Acyl halide#Acyl halide reactions|reactions]] |- | [[Aldehyde]]s: || [[Aldehyde#Preparation|preparation]] || [[Aldehyde#Common reactions|reactions]] |- | [[Acyloin]]s: || [[Acyloin#Synthesis of acyloins|preparation]] || [[Acyloin#Reactions of acyloins|reactions]] |- | *[[Alkane]]s: || [[Alkanes#Preparation|preparation]] || [[Alkanes#Reactions|reactions]] |- | [[Alkene]]s || [[Alkenes#Synthesis|preparation]] || [[Alkenes#Reactions|reactions]] |- | [[Alkyne]]s || [[Alkynes#Synthesis|preparation]] || [[Alkynes#Reactions|reactions]] |- | [[Alkyl halide]]s || [[Alkyl halide#Synthesis|preparation]] || [[Haloalkane#Reactions of haloalkanes|reactions]] |- | [[Alcohol]]s || [[Alcohol#Laboratory synthesis|preparation]] || [[Alcohol#Reactions|reactions]] |- | [[Arene compound]]s || [[Aromatic hydrocarbons#arene synthesis|preparation]] || [[Aromatic hydrocarbons#arene reactions|reactions]] |- | [[Azide]]s || [[Azide#Organic azides|preparation]] || [[Azide#Organic azides|reactions]] |- | [[Aziridine]]s || [[Aziridine#Synthesis|preparation]] || [[Aziridine#Reactions|reactions]] |- | [[Amide]]s || [[Amide#Amide synthesis|preparation]] || [[Amide#Amide reactions|reactions]] |- | [[Amine]]s || [[Amine#Synthesis|preparation]] || [[Amine#Reactions|reactions]] |- | [[Carboxylic acid]]s || [[Carboxylic acids#Synthesis|preparation]] || [[Carboxylic acids#Reactions|reactions]] |- | [[Cyclopropane]]s || [[Cyclopropane#Organic synthesis|preparation]] || [[Cyclopropane#Organic reactions|reactions]] |- | [[Diol]]s || [[Diol#Synthesis of diols|preparation]] || [[Diol#Reactions|reactions]] |- | [[Ester]]s || [[Ester#Ester synthesis|preparation]] || [[Ester#Ester reactions|reactions]] |- | [[Ether]]s || [[Ether#Synthesis|preparation]] || [[Ether#Reactions|reactions]] |- | [[Epoxide]]: || [[Epoxide#Synthesis|preparation]] || [[Epoxide#Reactions|reactions]] |- | [[Haloketone]]s || [[Haloketone#Haloketone synthesis|preparation]] || [[Haloketone#Haloketone reactions|reactions]] |- | [[Imine]]s || [[Imine#Imine synthesis|preparation]] || [[Imine#Imine reactions|reactions]] |- | [[Isocyanate]]s || [[Isocyanate#Isocyanate synthesis|preparation]] || [[Isocyanate#Isocyanate reactions|reactions]] |- | [[Ketone]]s || [[Ketone#Synthesis|preparation]] || [[Ketone#Reactions 2|reactions]] |- | [[Lactam]]s || [[Lactam#Synthesis|preparation]] || [[Lactam#Reactions|reactions]] |- | [[Nitrile]]s || [[Nitrile#Synthesis of nitriles|preparation]] || [[Nitrile#Reactions of Nitriles|reactions]] |- | [[Alkyl nitrites|Nitrites]] || [[Alkyl nitrites|preparation]] || [[Alkyl nitrites|reactions]] |- | [[Phenol]]s || [[Phenols#Synthesis of phenols|preparation]] || [[Phenols#Reactions of phenols|reactions]] |} 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 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]]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]], [[organosulfur chemistry]], [[organophosphorus chemistry]] and [[organofluorine chemistry]]. With the introduction of carbon-metal bonds the field crosses over to [[organometallic chemistry]]. {{ChemicalBondsToCarbon}} ==See also== * [[List of organic reactions]] * Other chemical reactions: [[Inorganic chemical reaction|inorganic reaction]]s, [[Metabolic pathway|biochemical reaction]]s, [[Organometallic chemistry|organometallic reaction]]s, [[polymerization reaction]]s. * [[List of publications in chemistry#Organic chemistry|Important publications in organic chemistry]] * [[Metabolism]] ==External links== * [http://www.chemistry.ohio-state.edu/organic/flashcards/ Organic reaction flashcards from OSU] * [http://orgchem.chem.uconn.edu/namereact/named.html list of named reactions from UConn] * [http://www.organicworldwide.net/reaction/ organic reactions] *[http://www.aceorganicchem.com/resources.html Organic chemistry help-Best of the Web 2008] *[http://www.aceorganicchem.com/organic_chemistry_flash_cards.html Organic chemistry help-Electronic Flashcards] ==References== {{reflist}} {{Organic reactions}} {{Organic chemistry}} [[Category:Organic chemistry]] [[Category:Organic reactions| ]] [[ar:تفاعل عضوي]] [[ca:Reacció orgànica]] [[de:Reaktionsmechanismus]] [[it:reazione organica]] [[nl:Organische synthese]] [[pt:Reação orgânica]] [[zh:有机反应]]