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In chemistry, a nucleophilic substitution is a class of chemical reactions in which an electron-rich chemical species replaces a functional group within another electron-deficient molecule. The molecule that contains the electrophile and the leaving functional group is called the substrate.
An elimination reaction is a type of organic reaction in which two substituents are removed from a molecule in either a one- or two-step mechanism. The one-step mechanism is known as the E2 reaction, and the two-step mechanism is known as the E1 reaction. The numbers refer not to the number of steps in the mechanism, but rather to the kinetics of the reaction: E2 is bimolecular (second-order) while E1 is unimolecular (first-order). In cases where the molecule is able to stabilize an anion but possesses a poor leaving group, a third type of reaction, E1CB, exists. Finally, the pyrolysis of xanthate and acetate esters proceed through an "internal" elimination mechanism, the Ei mechanism.
The SN1 reaction is a substitution reaction in organic chemistry, the name of which refers to the Hughes-Ingold symbol of the mechanism. "SN" stands for "nucleophilic substitution", and the "1" says that the rate-determining step is unimolecular. Thus, the rate equation is often shown as having first-order dependence on the substrate and zero-order dependence on the nucleophile. This relationship holds for situations where the amount of nucleophile is much greater than that of the intermediate. Instead, the rate equation may be more accurately described using steady-state kinetics. The reaction involves a carbocation intermediate and is commonly seen in reactions of secondary or tertiary alkyl halides under strongly basic conditions or, under strongly acidic conditions, with secondary or tertiary alcohols. With primary and secondary alkyl halides, the alternative SN2 reaction occurs. In inorganic chemistry, the SN1 reaction is often known as the dissociative substitution. This dissociation pathway is well-described by the cis effect. A reaction mechanism was first proposed by Christopher Ingold et al. in 1940. This reaction does not depend much on the strength of the nucleophile, unlike the SN2 mechanism. This type of mechanism involves two steps. The first step is the ionization of alkyl halide in the presence of aqueous acetone or ethyl alcohol. This step provides a carbocation as an intermediate.
In chemistry, a leaving group is defined by the IUPAC as an atom or group of atoms that detaches from the main or residual part of a substrate during a reaction or elementary step of a reaction. However, in common usage, the term is often limited to a fragment that departs with a pair of electrons in heterolytic bond cleavage. In this usage, a leaving group is a less formal but more commonly used synonym of the term nucleofuge. In this context, leaving groups are generally anions or neutral species, departing from neutral or cationic substrates, respectively, though in rare cases, cations leaving from a dicationic substrate are also known.
The SN2 reaction is a type of reaction mechanism that is common in organic chemistry. In this mechanism, one bond is broken and one bond is formed in a concerted way, i.e., in one step. The name SN2 refers to the Hughes-Ingold symbol of the mechanism: "SN" indicates that the reaction is a nucleophilic substitution, and "2" that it proceeds via a bi-molecular mechanism, which means both the reacting species are involved in the rate-determining step. The other major type of nucleophilic substitution is the SN1, but many other more specialized mechanisms describe substitution reactions.
In chemistry, a reaction mechanism is the step by step sequence of elementary reactions by which overall chemical reaction occurs.
A substitution 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, 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.
In physical organic chemistry, a kinetic isotope effect (KIE) is the change in the reaction rate of a chemical reaction when one of the atoms in the reactants is replaced by one of its isotopes. Formally, it is the ratio of rate constants for the reactions involving the light (kL) and the heavy (kH) isotopically substituted reactants (isotopologues):
In chemical kinetics, the overall rate of a reaction is often approximately determined by the slowest step, known as the rate-determining step or rate-limiting step. For a given reaction mechanism, the prediction of the corresponding rate equation is often simplified by using this approximation of the rate-determining step.
A limiting factor is a variable of a system that causes a noticeable change in output or another measure of a type of system. The limiting factor is in a pyramid shape of organisms going up from the producers to consumers and so on. A factor not limiting over a certain domain of starting conditions may yet be limiting over another domain of starting conditions, including that of the factor.
In chemistry, molecularity is the number of molecules that come together to react in an elementary (single-step) reaction and is equal to the sum of stoichiometric coefficients of reactants in the elementary reaction with effective collision and correct orientation. Depending on how many molecules come together, a reaction can be unimolecular, bimolecular or even trimolecular.
Enzyme kinetics is the study of the rates of enzyme-catalysed chemical reactions. In enzyme kinetics, the reaction rate is measured and the effects of varying the conditions of the reaction are investigated. Studying an enzyme's kinetics in this way can reveal the catalytic mechanism of this enzyme, its role in metabolism, how its activity is controlled, and how a drug or a modifier might affect the rate.
The E1cB elimination reaction is a type of elimination reaction which occurs under basic conditions, where the hydrogen to be removed is relatively acidic, while the leaving group is a relatively poor one. Usually a moderate to strong base is present. E1cB is a two-step process, the first step of which may or may not be reversible. First, a base abstracts the relatively acidic proton to generate a stabilized anion. The lone pair of electrons on the anion then moves to the neighboring atom, thus expelling the leaving group and forming double or triple bond. The name of the mechanism - E1cB - stands for Elimination Unimolecular conjugate Base. Elimination refers to the fact that the mechanism is an elimination reaction and will lose two substituents. Unimolecular refers to the fact that the rate-determining step of this reaction only involves one molecular entity. Finally, conjugate base refers to the formation of the carbanion intermediate, which is the conjugate base of the starting material.
In chemistry, a stepwise reaction is a chemical reaction with one or more reaction intermediates, which by definition involves at least two consecutive elementary reactions.
Reactions on surfaces are reactions in which at least one of the steps of the reaction mechanism is the adsorption of one or more reactants. The mechanisms for these reactions, and the rate equations are of extreme importance for heterogeneous catalysis. Via scanning tunneling microscopy, it is possible to observe reactions at the solid gas interface in real space, if the time scale of the reaction is in the correct range. Reactions at the solid–gas interface are in some cases related to catalysis.
Hammond's postulate, is a hypothesis in physical organic chemistry which describes the geometric structure of the transition state in an organic chemical reaction. First proposed by George Hammond in 1955, the postulate states that:
If two states, as, for example, a transition state and an unstable intermediate, occur consecutively during a reaction process and have nearly the same energy content, their interconversion will involve only a small reorganization of the molecular structures.
In theoretical chemistry, an energy profile is a theoretical representation of a chemical reaction or process as a single energetic pathway as the reactants are transformed into products. This pathway runs along the reaction coordinate, which is a parametric curve that follows the pathway of the reaction and indicates its progress; thus, energy profiles are also called reaction coordinate diagrams. They are derived from the corresponding potential energy surface (PES), which is used in computational chemistry to model chemical reactions by relating the energy of a molecule(s) to its structure.
In chemical kinetics, the Lindemann mechanism is a schematic reaction mechanism for unimolecular reactions. Frederick Lindemann and J. A. Christiansen proposed the concept almost simultaneously in 1921, and Cyril Hinshelwood developed it to take into account the energy distributed among vibrational degrees of freedom for some reaction steps.
George Simms Hammond was an American scientist and theoretical chemist who developed "Hammond's postulate", and fathered organic photochemistry,–the general theory of the geometric structure of the transition state in an organic chemical reaction. Hammond's research is also known for its influence on the philosophy of science. His research garnered him the Norris Award in 1968, the Priestley Medal in 1976, the National Medal of Science in 1994, and the Othmer Gold Medal in 2003. He served as the executive chairman of the Allied Chemical Corporation from 1979 to 1989.
In organosulfur chemistry, the thiol-ene reaction is an organic reaction between a thiol and an alkene to form a thioether. This reaction was first reported in 1905, but it gained prominence in the late 1990s and early 2000s for its feasibility and wide range of applications. This reaction is accepted as a click chemistry reaction given the reactions' high yield, stereoselectivity, high rate, and thermodynamic driving force.
References
- ↑ Louden, Marc G. Organic Chemistry, Fourth Edition, Oxford University Press, Oxford, New York City, 2002
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