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Videos de Conceptos Relacionados

Formation of Halohydrin from Alkenes02:41

Formation of Halohydrin from Alkenes

An alkene, such as propene, reacts with bromine in the presence of water to yield a halohydrin. Halohydrins contain a halogen and a hydroxyl group attached to adjacent carbons. When the halogen is bromine, it is called a bromohydrin, while a chlorohydrin has chlorine as the halogen.
Regioselectivity of Electrophilic Additions-Peroxide Effect02:35

Regioselectivity of Electrophilic Additions-Peroxide Effect

In the presence of organic peroxides, the addition of hydrogen bromide to an alkene yields the isomer that is not predicted by Markovnikov’s rule. For example, the addition of hydrogen bromide to 2-methylpropene in the presence of peroxides gives 1-bromo-2-methylpropane. This addition reaction proceeds via a free radical mechanism, which reverses the regioselectivity. The free radical reaction mechanism involves three stages: initiation, propagation, and termination.
Radical Anti-Markovnikov Addition to Alkenes: Mechanism01:17

Radical Anti-Markovnikov Addition to Alkenes: Mechanism

The reaction of hydrogen bromide with alkenes in the presence of hydroperoxides or peroxides proceeds via anti-Markovnikov addition. The radical chain reaction comprises initiation, propagation, and termination steps.
The mechanism starts with chain initiation, which involves two steps. In the first chain initiation step, a weak peroxide bond is homolytically cleaved upon mild heating to form two alkoxy radicals. In the second initiation step, a hydrogen atom is abstracted by the alkoxy radical...
Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
Radical Anti-Markovnikov Addition to Alkenes: Overview01:25

Radical Anti-Markovnikov Addition to Alkenes: Overview

The addition of hydrogen bromide to alkenes in the presence of hydroperoxides or peroxides proceeds via an anti-Markovnikov pathway and yields alkyl bromides.
Halogenation of Alkenes02:46

Halogenation of Alkenes

Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.

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Video Experimental Relacionado

Updated: Jul 12, 2026

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)
06:34

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)

Published on: June 20, 2014

Síntesis de halohidrocarburos por la bromoperoxidasa.

R Theiler, J C Cook, L P Hager

    Science (New York, N.Y.)
    |December 8, 1978
    PubMed
    Resumen

    La enzima bromoperoxidasa de las algas rojas marinas incorpora el bromo en sustratos orgánicos. Esta enzima produce hidrocarburos bromados volátiles, lo que sugiere un papel en los procesos naturales de halogenación.

    Área de la Ciencia:

    • Biología marina Biología marina.
    • La bioquímica es la bioquímica.
    • Enzimología Enzimología.

    Sus antecedentes:

    • Los organismos marinos también producen halometabolitos.
    • Las bromoperoxidasas son enzimas involucradas en la halogenación.

    Objetivo del estudio:

    • Para investigar la actividad enzimática de la bromoperoxidasa de Bonnemaisonia hamifera.
    • Para identificar los compuestos bromados producidos por la enzima.

    Principales métodos:

    • Extracción y purificación parcial de bromoperoxidasa de algas rojas marinas.
    • Ensayos enzimáticos utilizando peróxido de hidrógeno, ion bromuro y ácido 3-oxooctanoico.
    • Análisis de hidrocarburos bromados volátiles utilizando cromatografía de gases y espectrometría de masas.

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    Principales resultados:

    • La bromoperoxidasa incorporó el bromo en el ácido 3-oxooctanoico.
    • Se observó la formación de dibromometano, bromoformo y bromuro de 1-pentilo.
    • La actividad enzimática fue óptima en el rango de pH de 5 a 8.

    Conclusiones:

    • La bromoperoxidasa de Bonnemaisonia hamifera cataliza la formación de halohidrocarburos volátiles.
    • La halogenación enzimática por bromoperoxidasas puede contribuir a la producción natural de halometabolitos en entornos marinos.