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In accordance with an E2 elimination the reaction with t-butyl chloride results in a KIE of 2.3. The methyl chloride reaction (only S N 2 possible) on the other hand has a KIE of 0.85 consistent with a S N 2 reaction because in this reaction type the C-H bonds tighten in the transition state. The KIE's for the ethyl (0.99) and isopropyl (1.72 ...
When menthyl chloride is drawn in the chair conformation, it is easy to explain the unusual product distribution. Formation of the Zaytsev product requires elimination at the 2-position, but the isopropyl group – not the proton – is anti-periplanar to the chloride leaving group; this makes elimination at the 2-position impossible. In order ...
The physical manifestation of leaving group ability is the rate at which a reaction takes place. Good leaving groups give fast reactions. By transition state theory, this implies that reactions involving good leaving groups have low activation barriers leading to relatively stable transition states.
Upon removal of the sulfonyl group with desulfonylation or reductive elimination, the net result is the formation of a carbon-carbon bond single or double bond between two unfunctionalized carbons, a ubiquitous motif in synthetic targets.
In organic chemistry, the E i mechanism (Elimination Internal/Intramolecular), also known as a thermal syn elimination or a pericyclic syn elimination, is a special type of elimination reaction in which two vicinal (adjacent) substituents on an alkane framework leave simultaneously via a cyclic transition state to form an alkene in a syn elimination. [1]
In the elimination reaction, all five participating reaction centers are coplanar and, therefore, the reaction stereochemistry is syn. Oxidizing agents used are hydrogen peroxide, ozone or MCPBA. This reaction type is often used with ketones leading to enones. An example is acetylcyclohexanone elimination with benzeneselenylchloride and sodium ...
β-Hydride elimination is a reaction in which a metal-alkyl centre is converted into the corresponding metal-hydride-alkene. [1] β-Hydride elimination can also occur for many alkoxide complexes as well. The main requirements are that the alkyl group possess a C-H bond β to the metal and that the metal be coordinatively unsaturated.
Another key step in the Wacker process is the migration of the hydrogen from oxygen to chloride and formation of the C-O double bond. This step is generally thought to proceed through a so-called β-hydride elimination with a cyclic four-membered transition state: Wacker hydride elimination