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A nucleophilic substitution is a class of chemical reactions in which an electron-rich chemical species (known as a nucleophile) replaces a functional group within another electron-deficient molecule (known as the electrophile). The molecule that contains the electrophile and the leaving functional group is called the substrate. The most general form of the reaction may be given as the following: The electron pair (:) from the nucleophile (Nuc) attacks the substrate (R-LG) and bonds with it. Simultaneously, the leaving group (LG) departs with an electron pair. The principal product in this case is R-Nuc. The nucleophile may be 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 OH− and the leaving group is Br−. Nucleophilic substitution reactions are common in organic chemistry (especially introductory organic chemistry). Nucleophiles often attack a saturated aliphatic carbon. Less often, they may attack an aromatic or unsaturated carbon.
References
- S. R. Hartshorn, Aliphatic Nucleophilic Substitution, Cambridge University Press, London, 1973. ISBN:0-521-09801-7
- Introducing Aliphatic Substitution with a Discovery Experiment Using Competing Electrophiles Timothy P. Curran, Amelia J. Mostovoy, Margaret E. Curran, and Clara Berger Journal of Chemical Education 2016 93 (4), 757-761 doi:10.1021/acs.jchemed.5b00394 https://doi.org/10.1021%2Facs.jchemed.5b00394
- 253. Reaction kinetics and the Walden inversion. Part II. Homogeneous hydrolysis, alcoholysis, and ammonolysis of -phenylethyl halides Edward D. Hughes, Christopher K. Ingold and Alan D. Scott, J. Chem. Soc., 1937, 1201 doi:10.1039/JR9370001201 https://doi.org/10.1039%2FJR9370001201
- N.S.Imyanitov. Electrophilic Bimolecular Substitution as an Alternative to Nucleophilic Monomolecular Substitution in Inorganic and Organic Chemistry. J. Gen. Chem. USSR (Engl. Transl.) 1990; 60 (3); 417-419.
- Unimolecular Nucleophilic Substitution does not Exist! / N.S.Imyanitov. SciTecLibrary http://sciteclibrary.ru/eng/catalog/pages/9330.html
