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Radical Substitution: Halogenation of Alkanes and Alkyl Substituents01:27

Radical Substitution: Halogenation of Alkanes and Alkyl Substituents

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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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Nucleophilic Substitution Reactions02:34

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Historical perspective
In 1896, the German chemist Paul Walden discovered that he could interconvert pure enantiomeric (+) and (-) malic acids through a series of reactions. This conversion suggested the involvement of optical inversion during the substitution reaction. Further, in 1930, Sir Christopher Ingold described for the first time two different forms of nucleophilic substitution reactions, which are known as SN1 (nucleophilic substitution unimolecular) and SN2 (nucleophilic substitution...
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Radical Substitution: Allylic Chlorination01:31

Radical Substitution: Allylic Chlorination

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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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Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene01:15

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Chlorination and bromination are important classes of electrophilic aromatic substitutions, where benzene reacts with chlorine or bromine in the presence of a Lewis acid catalyst to give halogenated substitution products. A Lewis acid such as aluminium chloride or ferric chloride catalyzes the chlorination, and ferric bromide catalyzes the bromination reactions. During the bromination of alkenes, bromine polarizes and becomes electrophilic. However, in the bromination of benzene, the bromine...
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SN2 Reaction: Kinetics02:14

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Kinetic Studies and Significance
In a chemical reaction, a relationship exists between the concentration of reactants and the rate at which the reaction proceeds. The study to measure this relationship is known as the kinetics of a chemical reaction. Kinetic studies are used to deduce the rate law of a chemical reaction, which provides information about the species involved during the transition state of the rate-determining step. Thus, kinetic studies help to derive the mechanism of a...
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Reactions at the Benzylic Position: Halogenation01:11

Reactions at the Benzylic Position: Halogenation

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Benzylic halogenation takes place under conditions that favor radical reactions such as heat, light, or a free radical initiator like peroxide.
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Chloramination of Nitromethane: Incomplete Chlorination and Unexpected Substitution Reaction.

Jiaming Lily Shi1, Euna Kim1, Georgia B Cardosa1

  • 1Astani Department of Civil and Environmental Engineering, University of Southern California, Los Angeles, California 90089, United States.

Environmental Science & Technology
|May 16, 2023
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Summary

Nitromethane transformation by chloramines yields various products, unlike chlorination. This study reveals pH-dependent speciation and a novel nucleophilic pathway, impacting water reuse disinfection strategies.

Keywords:
chloraminationchloropicrindisinfection byproductshalonitromethanesnitratewastewater reuse

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Area of Science:

  • Environmental Chemistry
  • Water Treatment Chemistry

Background:

  • Ozone is a common predisinfectant in water reuse.
  • Nitromethane is an ozone byproduct and precursor to chloropicrin with chlorine.
  • Chloramines are increasingly used as secondary disinfectants, but their reaction with nitromethane is uncharacterized.

Purpose of the Study:

  • To investigate the kinetics, mechanism, and products of nitromethane transformation by chloramines.
  • To compare nitromethane chloramination with its known chlorination pathway.
  • To identify disinfection byproducts in water reuse treatment trains.

Main Methods:

  • Studied the reaction kinetics and mechanism of nitromethane with chloramines.
  • Analyzed transformation products using various analytical techniques.
  • Investigated the influence of pH on reaction pathways and product formation.

Main Results:

  • Chloropicrin yields varied significantly with pH.
  • Monochloronitromethane and dichloronitromethane were detected under basic conditions.
  • A novel nucleophilic pathway forming nitrate was identified, particularly at neutral pH, explaining mass balance discrepancies.

Conclusions:

  • Nitromethane chloramination produces a diverse range of byproducts, unlike chlorination.
  • Product speciation is highly dependent on pH and reaction time.
  • The findings are critical for understanding and managing disinfection byproducts in water reuse.