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Related Concept Videos

Reactions at the Benzylic Position: Oxidation and Reduction00:59

Reactions at the Benzylic Position: Oxidation and Reduction

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The benzylic position describes the position of a carbon atom attached directly to a benzene ring. Benzene by itself does not undergo oxidation. In contrast, the benzylic carbon is quite reactive in the presence of strong oxidizing agents such as KMnO4 or H2CrO4. Therefore, alkylbenzenes are readily oxidized to benzoic acid, irrespective of the type of alkyl groups.
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Radical Autoxidation01:20

Radical Autoxidation

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The oxidation of an organic compound in the presence of air or oxygen is called autoxidation. For example, cumene reacts with oxygen to form hydroperoxide. Autoxidation involves initiation, propagation, and termination steps. Many organic compounds are susceptible to autoxidation—especially ethers in the presence of oxygen, which form hydroperoxides. Even though this reaction is slow, old ether bottles contain small amounts of peroxide, which leads to laboratory explosions during ether...
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Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

12.8K
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.
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Radical Oxidation of Allylic and Benzylic Alcohols01:21

Radical Oxidation of Allylic and Benzylic Alcohols

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Activated manganese(IV) oxide can selectively oxidize allylic and benzylic alcohols via a radical intermediate mechanism. Primary allylic alcohols are oxidized to aldehydes, while secondary allylic alcohols yield ketones. The redox reaction of potassium permanganate with an Mn(II) salt such as manganese sulfate (under either alkaline or acidic conditions), followed by thorough drying, yields the oxidizing agent: activated MnO2. While MnO2 is insoluble in the solvents used for the reaction, the...
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Oxidation of Phenols to Quinones01:17

Oxidation of Phenols to Quinones

5.4K
In the presence of oxidizing agents, phenols are oxidized to quinones. Quinones can be easily reduced back to phenols using mild reducing agents. The electron-donating hydroxyl group enhances the reactivity of the aromatic ring, enabling oxidation of the ring even in the absence of an α hydrogen.
o-hydroxy phenols are oxidized to o-quinones and p-hydroxy phenols to p-quinones. Such redox reactions involve the transfer of two electrons and two protons. The reversible redox...
5.4K
Radical Anti-Markovnikov Addition to Alkenes: Mechanism01:17

Radical Anti-Markovnikov Addition to Alkenes: Mechanism

5.2K
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...
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Are We Truly Accurately Quantifying HO• Using Benzoic Acid Hydroxylation in Engineered HO•-Producing Systems?

Wenxiao Zheng1, Qiaoxin Li1, Hengyi Fu1

  • 1Key Laboratory of Pollution Control and Ecosystem Restoration in Industry Clusters, Ministry of Education, School of Environment and Energy, South China University of Technology, Guangzhou 510006, P. R. China.

Environmental Science & Technology
|April 17, 2026
PubMed
Summary

Benzoic acid hydroxylation signals may misinterpret hydroxyl radical (HO•) presence. This study reveals benzoic acid forms radical cations and interferes with HO• detection systems, compromising quantification reliability.

Keywords:
aromatic hydroxylationbenzoic acidhydroxyl radicalsoxidation productsreaction mechanism

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Area of Science:

  • Environmental Chemistry
  • Chemical Kinetics
  • Radical Chemistry

Background:

  • Hydroxyl radical (HO•) is a highly reactive environmental intermediate.
  • Aromatic hydroxylation probes like benzoic acid (BA) are used for indirect HO• detection.
  • BA-derived signals can be unreliable due to potential misinterpretations.

Purpose of the Study:

  • To evaluate the reliability of BA hydroxylation signals for HO• quantification.
  • To investigate confounding factors in engineered HO•-producing systems.

Main Methods:

  • Systematic testing of three engineered HO•-producing systems: UV/H2O2, homogeneous Fenton, and heterogeneous Fenton.
  • Analysis of BA's reaction pathways and interference mechanisms.

Main Results:

  • BA forms a radical cation (BA•+) via electron transfer, leading to hydroxybenzoic acid.
  • BA and its oxidation products interfere with HO• detection by competing for photons, altering metal ion reactivity, and blocking catalytic sites.
  • These interferences compromise the validity of BA hydroxylation for HO• quantification.

Conclusions:

  • Aromatic hydroxylation using BA is not a universally reliable method for HO• quantification.
  • Probe-induced interferences significantly impact the accuracy of HO• detection.
  • Understanding these interferences is crucial for reliable characterization of HO•-involved environmental processes.