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Carboxylic Acids to Acid Chlorides01:18

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Carboxylic acids react with SOCl2 or PCl5 to form acid chlorides. Amongst the carboxylic acid derivatives, acid chlorides are the most reactive and synthetically important derivatives. They are useful reagents for Friedel–Crafts acylation of some aromatic compounds.
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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 Addition to Alkynes: Hydrohalogenation02:35

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Electrophilic addition of hydrogen halides, HX (X = Cl, Br or I) to alkenes forms alkyl halides as per Markovnikov's rule, where the hydrogen gets added to the less substituted carbon of the double bond. Hydrohalogenation of alkynes takes place in a similar manner, with the first addition of HX forming a vinyl halide and the second giving a geminal dihalide.
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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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Electrophiles

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This lesson explains the definition, classification, and characteristic features of an electrophile that are key features of nucleophilic substitution reactions. An analysis of their charge and orbital picture helps understand their reactivity for seeking electrons. Electrophiles can be classified into positive and neutral species. Other classes include free radicals and polar functional groups.
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Hydrolysis of acid halides is a nucleophilic acyl substitution reaction in which acid halides react with water to give carboxylic acids. The reaction occurs readily and does not require acid or a base catalyst.
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Combining Solid-state and Solution-based Techniques: Synthesis and Reactivity of ChalcogenidoplumbatesII or IV
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PhICl2 is activated by chloride ions.

Tania1, Tiffany B Poynder1, Aishvaryadeep Kaur1

  • 1Department of Chemistry and Physics, La Trobe University, Melbourne, Victoria, Australia. j.dutton@latrobe.edu.au.

Dalton Transactions (Cambridge, England : 2003)
|August 11, 2021
PubMed
Summary

Soluble chloride ions significantly accelerate electrophilic chlorination reactions using PhICl2. This discovery also reveals chloride

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Area of Science:

  • Organic Chemistry
  • Reaction Mechanisms
  • Catalysis

Background:

  • Electrophilic aromatic substitution is a fundamental organic reaction.
  • Hypervalent iodine reagents like PhICl2 are used for chlorination.
  • The role of additives in modulating reactivity is crucial.

Purpose of the Study:

  • To investigate the potential activating role of pyridine in PhICl2-mediated chlorination.
  • To explore the effect of chloride ions on the reaction rate and reagent decomposition.
  • To understand the mechanistic pathways involved in PhICl2 activation.

Main Methods:

  • Study of electrophilic chlorination of anisole using PhICl2.
  • Investigation of reaction kinetics in the presence of pyridine and chloride sources.
  • Analysis of PhICl2 decomposition products.

Main Results:

  • Soluble chloride ions were found to activate PhICl2 at catalytic loadings.
  • A significant increase in the rate of anisole chlorination was observed.
  • Chloride presence was shown to accelerate the decomposition of PhICl2 into iodobenzene and chlorine gas.

Conclusions:

  • Chloride ions act as potent activators for PhICl2 in electrophilic chlorination.
  • The rate acceleration is linked to enhanced PhICl2 decomposition.
  • The precise mechanism of chloride-induced activation and decomposition requires further elucidation.