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Related Concept Videos

Nucleophilic Aromatic Substitution: Elimination–Addition01:11

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Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is...
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Organomagnesium halides, commonly known as Grignard reagents, convert acid halides to tertiary alcohols. The reaction requires two equivalents of the Grignard reagent and proceeds via a ketone intermediate.
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Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
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Acid Halides to Alcohols: LiAlH4 Reduction01:19

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Acid halides are reduced to alcohols in the presence of a strong reducing agent like lithium aluminum hydride.
The mechanism proceeds in three steps. First, the nucleophilic hydride ion attacks the carbonyl carbon of the acid halide to form a tetrahedral intermediate. Next, the carbonyl group is re-formed, and the halide ion departs as a leaving group, generating an aldehyde. A second nucleophilic attack by the hydride yields an alkoxide ion, which, upon protonation, gives a primary alcohol as...
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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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Conversion of Alcohols to Alkyl Halides02:48

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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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Updated: May 11, 2025

Extraction of Lignin with High &#946;-O-4 Content by Mild Ethanol Extraction and Its Effect on the Depolymerization Yield
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Producing aryl halides from lignin.

Yongqian Liu1,2, Yi Li1,2, Zhiyang He1,2

  • 1State Key Laboratory of Utilization of Woody Oil Resource, Northeast Forestry University, Harbin, China.

Nature Communications
|April 17, 2025
PubMed
Summary
This summary is machine-generated.

Researchers developed a mild method to depolymerize and halogenate lignin, a biomass resource, into valuable aryl halides. This sustainable approach utilizes hydrogen bond activation for efficient C-C bond cleavage in lignin.

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Comprehensive Compositional Analysis of Plant Cell Walls Lignocellulosic biomass Part I: Lignin
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Area of Science:

  • Biomass valorization
  • Organic chemistry
  • Sustainable chemistry

Background:

  • Lignin is the most abundant aromatic biomass resource.
  • Lignin refinery offers a sustainable route to aromatic chemicals.
  • Converting lignin into aryl halides is currently challenging.

Purpose of the Study:

  • To develop a simple and mild method for lignin depolymerization and halogenation.
  • To produce valuable aryl halides from lignin.
  • To enable sustainable access to synthetically useful aryl halides.

Main Methods:

  • Utilizing hydrogen bond activation for halogenation reagents.
  • Achieving efficient cleavage of carbon-carbon bonds in lignin.
  • Selective breaking of C(sp2)-C(sp3) bonds in lignin linkages.

Main Results:

  • A simple and mild method for lignin depolymerization and halogenation was established.
  • The method efficiently produces useful aryl halides from lignin.
  • Hydrogen bond activation significantly enhanced reagent reactivity and C-C bond cleavage.

Conclusions:

  • The developed method provides a sustainable and efficient pathway to aryl halides from lignin.
  • Precise depolymerization and halogenation are achievable from lignin models to native lignin.
  • This work offers valuable aryl halides for academic and industrial applications.