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In organic chemistry, the oxymercuration reaction is an electrophilic addition reaction that transforms an alkene (R 2 C=CR 2) into a neutral alcohol. In oxymercuration, the alkene reacts with mercuric acetate (AcO−Hg−OAc) in aqueous solution to yield the addition of an acetoxymercury (−HgOAc) group and a hydroxy (−OH) group across the ...
When alkenes undergo hydrobromination, the alkyl bromides are formed Markovnikov. Alkyne oxymercuration-demercuration: In this reaction, HgSO 4 reacts with an alkyne in a Markovnikov regioselective manner to form an enol that is tautomerized into a ketone. This process utilizes anti addition of an OH group to the more substituted carbon, making ...
Alkenes can be oxidized with ozone to form alcohols, aldehydes or ketones, or carboxylic acids.In a typical procedure, ozone is bubbled through a solution of the alkene in methanol at −78 °C (−108 °F; 195 K) until the solution takes on a characteristic blue color, which is due to unreacted ozone.
Hydroboration–oxidation reaction is a two-step hydration reaction that converts an alkene into an alcohol. [1] The process results in the syn addition of a hydrogen and a hydroxyl group where the double bond had been. Hydroboration–oxidation is an anti-Markovnikov reaction, with the hydroxyl group attaching to the less-substituted carbon.
General overview of addition reactions. Top to bottom: electrophilic addition to alkene, nucleophilic addition of nucleophile to carbonyl and free-radical addition of halide to alkene. Depending on the product structure, it could promptly react further to eject a leaving group to give the addition–elimination reaction sequence.
For small rings (fewer than eight atoms), a trans alkene cannot be achieved without substantial ring and angle strain (the p orbitals are improperly aligned for a π bond). Bredt's rule also applies to carbocations and, to a lesser degree, free radicals , because these intermediates also prefer a planar geometry with 120° angles and sp 2 ...
Mercury sulfate, as well as other mercury(II) compounds, are commonly used as catalysts in oxymercuration-demercuration, a type of electrophilic addition reaction that results in hydration of an unsaturated compound. The hydration of an alkene gives an alcohol. The regioselectivity is that predicted by Markovnikov's rule.
Alkenes react with percarboxylic acids and even hydrogen peroxide to yield epoxides: RCH=CH 2 + RCO 3 H → RCHOCH 2 + RCO 2 H. For ethylene, the epoxidation is conducted on a very large scale industrially using oxygen in the presence of silver-based catalysts: C 2 H 4 + 1/ 2 O 2 → C 2 H 4 O. Alkenes react with ozone, leading to the scission ...