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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 ...
Based on this trend, Zaytsev proposed that the alkene formed in greatest amount is that which corresponded to removal of the hydrogen from the alpha-carbon having the fewest hydrogen substituents. For example, when 2-iodobutane is treated with alcoholic potassium hydroxide (KOH), but-2-ene is the major product and but-1-ene is the minor product ...
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.
Main group elements can also form π-complexes with alkenes and alkynes. The β-diketiminato aluminum(I) complex Al{HC(CMeNAr) 2 } (Ar = 2,6-diisopropylphenyl), which bears an Al-based sp x lone pair, reacts with alkenes and alkynes to give alumina (III) cyclopropanes and alumina (III) cyclopropenes in a process analogous to the formation of π ...
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.
This chemical reaction is useful in the organic synthesis of organic compounds. [1] Hydroboration produces organoborane compounds that react with a variety of reagents to produce useful compounds, such as alcohols, amines, or alkyl halides. The most widely known reaction of the organoboranes is oxidation to produce alcohols from alkenes.
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.
Reaction is slower with alkynes than alkenes. [3]: 750 In the paradigmatic example, hydrogen bromide radicalyzes to monatomic bromine. These bromine atoms add to an alkene at the most accessible site, to give a bromoalkyl radical, with the radical on the more substituted carbon.