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Related Concept Videos

Conversion of Alcohols to Alkyl Halides02:48

Conversion of Alcohols to Alkyl Halides

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This lesson delves into the conversion of alcohols to corresponding alkyl halides and the mechanism of action for different reagents. Typically, the hydroxyl group is first protonated to convert it to a stable leaving group. Consequently, based on the starting alcohol, the mechanism undergoes either of the nucleophilic substitution routes, SN1 or SN2. Tertiary alkyl halides are made using the two-step SN1 mechanism that occurs via a carbocation intermediate, which is stabilized by...
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Radical Substitution: Halogenation of Alkanes and Alkyl Substituents01:27

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In the presence of heat or light, alkanes react with molecular halogens to form alkyl halides by a substitution reaction called radical halogenation. This reaction has three steps: initiation, propagation, and termination, as seen in the radical chlorination of methane to produce methyl chloride.
In the initiation step of the reaction, the chlorine molecule undergoes homolytic cleavage in the presence of light or heat, forming two highly reactive chlorine radicals. Propagation occurs in two...
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Radical Substitution: Allylic Chlorination01:31

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Typically, when alkenes react with halogens at low temperatures, an addition reaction occurs. However, upon increasing the temperature or under reaction conditions that form radicals, providing a low but steady concentration of halogen radicals, allylic substitution reaction is favored. This is because allylic hydrogens are very reactive as the formed intermediate is resonance stabilized. For example, when propene is treated with chlorine in the gas phase at 400 °C, it undergoes allylic...
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Preparation of Alcohols via Substitution Reactions01:38

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Overview
Alcohols can be synthesized from alkyl halides via nucleophilic substitution reactions. The highly polar carbon-halogen bond in the substrate makes halide a good leaving group.  The hydroxide ion or water can act as a nucleophile to take the place of halide and form an alcohol. The substitution reactions occur via two different reaction pathways, SN1 or SN2,  depending on the nature of carbon attached to the halide.
Primary alcohols are synthesized from primary alkyl halides, and the...
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Oxidation of Alcohols02:37

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In this lesson, the oxidation of alcohols is discussed in depth. The various reagents used for oxidation of primary and secondary alcohols are detailed, and their mechanism of action is provided.
The process of oxidation in a chemical reaction is observed in any of the three forms:
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Acid Halides to Esters: Alcoholysis01:12

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Alcoholysis is a nucleophilic acyl substitution reaction in which an alcohol functions as a nucleophile. Acid halides react with alcohol to produce esters. The mechanism proceeds in three steps:
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Alcohols as reactive species modulators: Rethinking quenching in UV/chlorine process.

Boqiang Li1, Longjie Cheng1, Lei Wang2

  • 1Shenzhen Key Laboratory of Organic Pollution Prevention and Control, State Key Laboratory of Urban Water Resource and Environment, School of Eco-Environment, Harbin Institute of Technology Shenzhen, Shenzhen, 518055, PR China.

Water Research
|November 1, 2025
PubMed
Summary

Alcohols used in UV/chlorine processes can alter chlorine decay unexpectedly. Tert-butanol inhibits it, while others accelerate it, challenging assumptions about radical quenching in advanced oxidation.

Keywords:
AlcoholsQuenching processRadicalsReactive speciesUV/chlorine

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Area of Science:

  • Environmental Chemistry
  • Advanced Oxidation Processes
  • Radical Chemistry

Background:

  • Alcohols are commonly used as quenchers in UV/chlorine processes to study radical reactions.
  • The assumption is that alcohols selectively react with target radicals (HO•, Cl•) without influencing other reactions.
  • This study investigates potential unrecognized alcohol-dependent phenomena in UV/chlorine systems.

Purpose of the Study:

  • To challenge the principle of selective radical quenching by alcohols in UV/chlorine processes.
  • To elucidate the mechanisms by which different alcohols affect chlorine decay.
  • To develop a reliable protocol for radical quantification in advanced oxidation research.

Main Methods:

  • Experimental investigation of chlorine decay kinetics in the presence of various alcohols (tert-butanol, methanol, ethanol, isobutanol).
  • Mechanistic analysis to understand the role of secondary species generated from alcohol quenching.
  • Development of a quantitative structure-activity relationship (QSAR) model correlating alcohol properties with chlorine decay.

Main Results:

  • Tert-butanol inhibited chlorine decay, while methanol, ethanol, and isobutanol accelerated it significantly.
  • Alcohols quench HO• and Cl• but also generate secondary species that alter chlorine consumption.
  • QSAR model identified molecular polarizability and LUMO energy as key descriptors for chlorine decay (R² = 0.949).

Conclusions:

  • Alcohols significantly perturb UV/chlorine processes, affecting radical speciation and reaction pathways.
  • Using methanol as a quencher can lead to misattribution of radical roles, overestimating primary radicals and underestimating secondary species.
  • A two-step strategy using tert-butanol for qualitative assessment and multi-probe kinetics for quantification is proposed for reliable radical assessment.