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Related Concept Videos

Electrophilic Addition to Alkynes: Halogenation02:38

Electrophilic Addition to Alkynes: Halogenation

8.4K
Introduction
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
8.4K
π Molecular Orbitals of the Allyl Cation and Anion01:18

π Molecular Orbitals of the Allyl Cation and Anion

4.4K
An allyl group is a three-carbon conjugated system where the sp³-hybridized allylic carbon is bonded to a CH=CH2 group via a single bond. Allyl anions can be obtained by treating propene with a strong base that can deprotonate methyl groups. Allyl cations are formed as intermediates during substitution reactions involving allylic halides. In both cases, the hybridization of the allylic carbon changes from sp3 to sp2, giving rise to a carbon chain with three sp2-hybridized carbons, each with...
4.4K
Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

2.8K
Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
Due to the absence of continuous...
2.8K
Acidity of 1-Alkynes02:42

Acidity of 1-Alkynes

9.9K

The acidic strength of hydrocarbons follows the order: Alkynes > Alkenes > Alkanes. The strength of an acid is commonly expressed in units of pKa — the lower the pKa, the stronger the acid. Among the hydrocarbons, terminal alkynes have lower pKa values and are, therefore, more acidic. For example, the pKa values for ethane, ethene, and acetylene are 51, 44, and 25, respectively, as shown here.
9.9K
Electrophilic Aromatic Substitution: Friedel–Crafts Acylation of Benzene01:11

Electrophilic Aromatic Substitution: Friedel–Crafts Acylation of Benzene

7.3K
The Friedel–Crafts acylation reactions involve the addition of an acyl group to an aromatic ring. These reactions proceed via electrophilic aromatic substitution by employing an acyl chloride and a Lewis acid catalyst such as aluminum chloride to form aryl ketone.
7.3K
Acid-Catalyzed α-Halogenation of Aldehydes and Ketones01:21

Acid-Catalyzed α-Halogenation of Aldehydes and Ketones

4.0K
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...
4.0K

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Related Experiment Video

Updated: Aug 2, 2025

Simultaneous Multi-surface Anodizations and Stair-like Reverse Biases Detachment of Anodic Aluminum Oxides in Sulfuric and Oxalic Acid Electrolyte
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Simultaneous Multi-surface Anodizations and Stair-like Reverse Biases Detachment of Anodic Aluminum Oxides in Sulfuric and Oxalic Acid Electrolyte

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An acyclic aluminyl anion.

Ross A Jackson1, Aidan J R Matthews2, Petra Vasko3

  • 1Department of Chemistry, University of Bath, Bath, BA2 7AY, UK. d.j.liptrot@bath.ac.uk.

Chemical Communications (Cambridge, England)
|April 15, 2023
PubMed
Summary
This summary is machine-generated.

Researchers synthesized a novel potassium aluminyl complex, K2[Al{N(Dipp)SiMe3}2]2, the first aluminyl anion with an acyclic ligand. This complex acts as a nucleophilic aluminum source, enabling the formation of a unique magnesium aluminyl compound.

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Facile Preparation of Ultrafine Aluminum Hydroxide Particles with or without Mesoporous MCM-41 in Ambient Environments
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Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
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Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts

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Simultaneous Multi-surface Anodizations and Stair-like Reverse Biases Detachment of Anodic Aluminum Oxides in Sulfuric and Oxalic Acid Electrolyte
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Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
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Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts

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Area of Science:

  • Organometallic Chemistry
  • Main Group Chemistry
  • Inorganic Synthesis

Background:

  • Aluminyl anions are crucial intermediates in organoaluminum chemistry.
  • Previous studies focused on cyclic ligands for stabilizing aluminum species.
  • The development of acyclic ligand frameworks offers new avenues for exploring unique aluminum coordination environments.

Purpose of the Study:

  • To synthesize and characterize a novel potassium aluminyl complex with an acyclic ligand framework.
  • To investigate the reactivity of the synthesized aluminyl complex as a nucleophilic aluminum source.
  • To explore the potential for forming new acyclic organometallic compounds.

Main Methods:

  • Synthesis of potassium aluminyl complex K2[Al{N(Dipp)SiMe3}2]2 via reduction of [AlI{N(Dipp)SiMe3}2].
  • Utilizing bulky aryl (Dipp) and silyl (SiMe3) groups to stabilize the acyclic aluminyl ligand.
  • Reaction of the potassium aluminyl complex with a magnesium(II) iodide precursor.

Main Results:

  • The first synthesis of an aluminyl anion supported by an acyclic ligand framework, K2[Al{N(Dipp)SiMe3}2]2, was achieved.
  • Attempts to use a larger ligand framework resulted in undesired C-H bond cleavage, highlighting the importance of ligand steric bulk.
  • The potassium aluminyl complex successfully reacted as a nucleophilic aluminum source to form a monomeric, acyclic magnesium aluminyl complex.

Conclusions:

  • The study demonstrates the successful synthesis and characterization of a novel acyclic aluminyl complex.
  • The findings establish a new class of aluminum compounds with potential applications in catalysis and materials science.
  • The reactivity profile of the synthesized complex opens doors for further exploration of acyclic main group chemistry.