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Related Concept Videos

Base-Promoted α-Halogenation of Aldehydes and Ketones00:51

Base-Promoted α-Halogenation of Aldehydes and Ketones

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α-Halogenation of aldehydes and ketones is a reaction involving the substitution of α hydrogens with halogens in the presence of a base.  The reaction begins with the abstraction of  α hydrogen by the base to produce a nucleophilic enolate ion. This intermediate undergoes a subsequent nucleophilic substitution with the halogen to produce a monohalogenated carbonyl compound. If the starting substrate has more than one α hydrogen, it is difficult to stop the reaction...
4.3K
Acid-Catalyzed α-Halogenation of Aldehydes and Ketones01:21

Acid-Catalyzed α-Halogenation of Aldehydes and Ketones

5.0K
By replacing an α-hydrogen with a halogen, acid-catalyzed α-halogenation of aldehydes or ketones yields a monohalogenated product
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic halogen to form a...
5.0K
Halogenation of Alkenes02:46

Halogenation of Alkenes

20.6K
Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
20.6K
Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

5.3K
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...
5.3K
Acid Halides to Carboxylic Acids: Hydrolysis01:01

Acid Halides to Carboxylic Acids: Hydrolysis

3.7K
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.
As shown below, the mechanism involves a nucleophilic attack by water at the carbonyl carbon to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen π bond along with the departure of a halide ion. A final proton transfer step yields carboxylic...
3.7K
E1 Reaction: Kinetics and Mechanism02:46

E1 Reaction: Kinetics and Mechanism

18.2K
Here, in contrast to the E2 reaction mechanism, we delve into the aspects of the E1 reaction mechanism, which has two steps: rate-limiting loss of the leaving group and abstraction of the beta hydrogen by a weak base. Typically, the experimental proof for the E1 mechanism is via kinetic studies or isotope studies. While the former demonstrates the first-order kinetics—the dependence of the reaction solely on substrate concentration—the latter proves the abstraction of hydrogen only...
18.2K

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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
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Substrate-Mediated C-C and C-H Coupling after Dehalogenation.

Huihui Kong, Sha Yang, Hongying Gao1,2

  • 1Physikalisches Institut, Westfälische Wilhelms-Universität Münster , Wilhelm-Klemm-Strasse 10, 48149 Münster, Germany.

Journal of the American Chemical Society
|February 11, 2017
PubMed
Summary
This summary is machine-generated.

Researchers achieved selective C-H coupling on silver surfaces, enabling the synthesis of novel organic molecules and polymeric chains. This breakthrough advances surface chemistry beyond traditional polymer fabrication.

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Area of Science:

  • Surface Chemistry
  • Organic Synthesis
  • Nanotechnology

Background:

  • Intermolecular carbon-carbon (C-C) coupling via carbon-halogen (C-X) bond cleavage is vital for synthesizing polymeric nanostructures.
  • Uncontrolled C-H coupling at terminal carbons hinders the extension of covalent polymers, limiting their synthesis.
  • Selective C-H coupling after dehalogenation remains an underexplored area in surface chemistry.

Purpose of the Study:

  • To investigate selective C-H coupling on different metal surfaces.
  • To explore the potential for synthesizing novel organic molecules and polymeric chains via controlled coupling reactions.
  • To advance the field of surface-assisted organic synthesis.

Main Methods:

  • Scanning Tunneling Microscopy (STM) for high-resolution surface imaging.
  • X-ray Photoelectron Spectroscopy (XPS) for surface elemental and chemical state analysis.
  • Density Functional Theory (DFT) calculations to understand reaction mechanisms and energetics.

Main Results:

  • Predominant C-C coupling was observed on Gold (Au)(111) surfaces.
  • Selective C-H coupling was achieved on Silver (Ag)(111) surfaces, a novel finding.
  • The selective C-H coupling on Ag(111) enabled the distinct synthesis of polymeric chains or new organic molecules.

Conclusions:

  • Demonstrated a novel method for selective C-H coupling on Ag(111) surfaces.
  • This selective coupling opens new avenues for surface-assisted synthesis of complex organic molecules.
  • The findings expand the scope of surface chemistry beyond in situ polymer fabrication.