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NBS reacts with alkenes in aqueous solvents to give bromohydrins. The preferred conditions are the portionwise addition of NBS to a solution of the alkene in 50% aqueous DMSO, DME, THF, or tert-butanol at 0 °C. [3] Formation of a bromonium ion and immediate attack by water gives strong Markovnikov addition and anti stereochemical selectivities ...
Formally, the reaction is an example of a group transfer reaction. However, an analysis of the orbitals involved reveals that the reaction is 'pseudopericyclic' and not subject to the Woodward–Hoffmann rules for pericyclic reactivity. Hydroboration of a terminal alkene to a trialkylborane, showing idealized image of the cyclic transition state.
The amount of energy released during a hydrogenation reaction, known as the heat of hydrogenation, is inversely related to the stability of the starting alkene: the more stable the alkene, the lower its heat of hydrogenation. Examining the heats of hydrogenation for various alkenes reveals that stability increases with the amount of ...
The same is true when an alkene reacts with water in an additional reaction to form an alcohol that involves carbocation formation. The hydroxyl group (OH) bonds to the carbon that has the greater number of carbon-carbon bonds, while the hydrogen bonds to the carbon on the other end of the double bond, that has more carbon–hydrogen bonds.
N-bromosuccinimide (NBS), the bromine analog of N-chlorosuccinimide. [ 5 ] Other N -chloro compounds that are commercially available include chloramine-T , trichloroisocyanuric acid ((OCNCl) 3 ), 1,3-dichloro-5,5-dimethylhydantoin.
The Woodward cis-hydroxylation (also known as the Woodward reaction) is the chemical reaction of alkenes with iodine and silver acetate in wet acetic acid to form cis-diols. [1] [2] (conversion of olefin into cis-diol) The reaction is named after its discoverer, Robert Burns Woodward. The Woodward cis-hydroxylation
In organic chemistry, regioselectivity is the preference of chemical bonding or breaking in one direction over all other possible directions. [1] [2] It can often apply to which of many possible positions a reagent will affect, such as which proton a strong base will abstract from an organic molecule, or where on a substituted benzene ring a further substituent will be added.
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.