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Acid–base reactions typically occur faster than any other step which may determine the product of a reaction. The conjugate base is more electron-rich than the molecule which can alter the reactivity of the molecule. For example, deprotonation of an alcohol forms the negatively charged alkoxide, which is a much stronger nucleophile.
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. [2] 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 ...
Protonation. In chemistry, protonation (or hydronation) is the adding of a proton (or hydron, or hydrogen cation), usually denoted by H +, to an atom, molecule, or ion, forming a conjugate acid. [1] (. The complementary process, when a proton is removed from a Brønsted–Lowry acid, is deprotonation.) Some examples include. The protonation of ...
Example of the preferential elimination of fluorine in an E1cB-elimination reaction. In an E2-elimination reaction, both the deprotonation of the α-carbon and the loss of the leaving group occur simultaneously in one concerted step. Molecules that undergo E2-elimination mechanisms have more acidic α-carbons than those that undergo E1 ...
The kinetic and thermodynamic deprotonation of 2-methylcyclohexanone. If a much weaker base is used, the deprotonation will be incomplete, and there will be an equilibrium between reactants and products. Thermodynamic control is obtained, however the reaction remains incomplete unless the product enolate is trapped, as in the example below.
The Wolff–Kishner reduction is a reaction used in organic chemistry to convert carbonyl functionalities into methylene groups. [1] [2] In the context of complex molecule synthesis, it is most frequently employed to remove a carbonyl group after it has served its synthetic purpose of activating an intermediate in a preceding step.
Henry reaction. The Henry reaction is a classic carbon–carbon bond formation reaction in organic chemistry. Discovered in 1895 by the Belgian chemist Louis Henry (1834–1913), it is the combination of a nitroalkane and an aldehyde or ketone in the presence of a base to form β-nitro alcohols. [1][2][3] This type of reaction is also referred ...
In organometallic chemistry, organolithium reagents are chemical compounds that contain carbon – lithium (C–Li) bonds. These reagents are important in organic synthesis, and are frequently used to transfer the organic group or the lithium atom to the substrates in synthetic steps, through nucleophilic addition or simple deprotonation. [1]