Chemical reaction in which one functional group in a compound is replaced by another
"Aromatic substitution" redirects here. For ortho/meta/para patterns, see Arene substitution pattern.
A substitution reaction (also known as single displacement reaction or single substitution reaction) is a chemical reaction during which one functional group in a chemical compound is replaced by another functional group.[1] Substitution reactions are of prime importance in organic chemistry. Substitution reactions in organic chemistry are classified either as electrophilic or nucleophilic depending upon the reagent involved, whether a reactive intermediate involved in the reaction is a carbocation, a carbanion or a free radical, and whether the substrate is aliphatic or aromatic. Detailed understanding of a reaction type helps to predict the product outcome in a reaction. It also is helpful for optimizing a reaction with regard to variables such as temperature and choice of solvent.
A good example of a substitution reaction is halogenation. When chlorine gas (Cl2) is irradiated, some of the molecules are split into two chlorine radicals (Cl•), whose free electrons are strongly nucleophilic. One of them breaks a C–H covalent bond in CH4 and grabs the hydrogen atom to form the electrically neutral HCl. The other radical reforms a covalent bond with the CH3• to form CH3Cl (methyl chloride).
chlorination of methane by chlorine
^March, Jerry (1985), Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 3rd edition, New York: Wiley, ISBN 9780471854722, OCLC 642506595
and 22 Related for: Substitution reaction information
A substitutionreaction (also known as single displacement reaction or single substitutionreaction) is a chemical reaction during which one functional...
In chemistry, a nucleophilic substitution (SN) is a class of chemical reactions in which an electron-rich chemical species (known as a nucleophile) replaces...
Electrophilic substitutionreactions are chemical reactions in which an electrophile displaces a functional group in a compound, which is typically, but...
Bimolecular nucleophilic substitution (SN2) is a type of reaction mechanism that is common in organic chemistry. In the SN2 reaction, a strong nucleophile...
Electrophilic aromatic substitution (SEAr) is an organic reaction in which an atom that is attached to an aromatic system (usually hydrogen) is replaced...
discoveries, established the mechanisms of substitutionreactions. The general characteristics of chemical reactions are: Evolution of a gas Formation of a...
A nucleophilic aromatic substitution (SNAr) is a substitutionreaction in organic chemistry in which the nucleophile displaces a good leaving group, such...
catalysts. It is an example of a radical-nucleophilic aromatic substitution. The Sandmeyer reaction provides a method through which one can perform unique transformations...
The unimolecular nucleophilic substitution (SN1) reaction is a substitutionreaction in organic chemistry. The Hughes-Ingold symbol of the mechanism expresses...
Nucleophilic acyl substitution (SNAcyl) describes a class of substitutionreactions involving nucleophiles and acyl compounds. In this type of reaction, a nucleophile...
Finkelstein reaction, named after the German chemist Hans Finkelstein, is a type of SN2 reaction (Substitution Nucleophilic Bimolecular reaction) that involves...
In chemistry, SNi (substitution nucleophilic internal) refers to a specific, regio-selective but not often encountered reaction mechanism for nucleophilic...
other Pd(0)-catalyzed cross-coupling reactions. The Heck reaction is a way to substitute alkenes. The original reaction by Tsutomu Mizoroki (1971) describes...
chemistry, a radical-substitutionreaction is a substitutionreaction involving free radicals as a reactive intermediate. The reaction always involves at...
halogen: this is called a substitutionreaction. An example is the conversion of methane to chloroform using a chlorination reaction. Halogenating a hydrocarbon...
up substitution in Wiktionary, the free dictionary. Substitution may refer to: Substitution (poetry), a variation in poetic scansion Substitution (theatre)...
"Catalytic Phosphorus(V)-Mediated Nucleophilic SubstitutionReactions: Development of a Catalytic Appel Reaction". Journal of Organic Chemistry. 76 (16): 6749–6767...
The Chichibabin reaction (pronounced ' (chē')-chē-bā-bēn) is a method for producing 2-aminopyridine derivatives by the reaction of pyridine with sodium...
a certain level of competition between the elimination reaction and nucleophilic substitution. More precisely, there are competitions between E2 and SN2...
In chemistry, the haloform reaction is a chemical reaction in which a haloform (CHX3, where X is a halogen) is produced by the exhaustive halogenation...
route, substitution can also induced by NaOH or NaBH4. The catalyst attacks a CO ligand, which labilizes another CO ligand toward substitution. The electrophilicity...
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