|
Substitution reaction (also known as single displacement reaction or single replacement reaction) is a chemical reaction during which one functional group in a chemical compound is replaced by another functional group. 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. There are other classifications as well that are mentioned below. Organic substitution reactions are classified in several main organic reaction types depending on whether the reagent that brings about the substitution is considered an electrophile or a nucleophile, whether a reactive intermediate involved in the reaction is a carbocation, a carbanion or a free radical or 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 (Cl-Cl) is irradiated, some of the molecules are split into two chlorine radicals (Cl.) whose free electrons are strongly nucleophilic. One of them breaks a weak C-H covalent bond and grabs the liberated proton to form the electrically neutral H-Cl. The other radical reforms a covalent bond with the CH3. to form CH3Cl (methyl chloride). ==Nucleophilic substitution== In organic (and inorganic) chemistry, nucleophilic substitution is a fundamental class of reactions in which a nucleophile selectively bonds with or attacks the positive or partially positive charge on an atom or a group of atoms. As it does so, it replaces a weaker nucleophile which then becomes a leaving group; The remaining positive or partially positive atom becomes an electrophile. The whole molecular entity of which the electrophile and the leaving group are part is usually called the substrate.()() The most general form for the reaction may be given as where R-LG indicates the substrate. : Nuc: + R-LG → R-Nuc + LG: The electron pair (:) from the nucleophile (Nuc:) attacks the substrate (R-LG) forming a new covalent bond Nuc-R-LG. The prior state of charge is restored when the leaving group (LG) departs with an electron pair. The principal product in this case is R-Nuc. In such reactions, the nucleophile is usually electrically neutral or negatively charged, whereas the substrate is typically neutral or positively charged. An example of nucleophilic substitution is the hydrolysis of an alkyl bromide, R-Br, under basic conditions, where the ''attacking'' nucleophile is the base OH− and the leaving group is Br−. : R-Br + OH− → R-OH + Br− Nucleophilic substitution reactions are commonplace in organic chemistry, and they can be broadly categorized as taking place at a carbon of a saturated aliphatic compound carbon or (less often) at an aromatic or other unsaturated carbon center.() 抄文引用元・出典: フリー百科事典『 ウィキペディア（Wikipedia）』 ■ウィキペディアで「Substitution reaction」の詳細全文を読む スポンサード リンク
|