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Related Concept Videos

Structure and Physical Properties of Alkynes02:37

Structure and Physical Properties of Alkynes

14.2K
Introduction:
In nature, compounds containing both carbon and hydrogen are known as "hydrocarbons". Aliphatic hydrocarbons are compounds whose molecules contain saturated single bonds (i.e., alkanes) or unsaturated double or triple bonds. Alkenes contain carbon–carbon double bonds and have a structural formula CnH2n. Unsaturated hydrocarbons containing carbon–carbon triple bonds are called "alkynes" and are structurally represented by the formula CnH2n-2.
The...
14.2K
Electrophilic Addition to Alkynes: Halogenation02:38

Electrophilic Addition to Alkynes: Halogenation

10.3K
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.
10.3K
Alkyl Halides02:45

Alkyl Halides

20.7K
Structural Properties
Alkyl halides are halogen-substituted alkanes wherein one or more hydrogen atoms of an alkane is replaced by a halogen atom such as fluorine, chlorine, bromine, or iodine. The carbon atom in an alkyl halide is bonded to the halogen atom, which is sp3-hybridized and exhibits a tetrahedral shape.
Unlike alkyl halides, compounds in which a halogen atom is bonded to an sp2 -hybridized carbon atom of a carbon-carbon double bond (C=C) are called vinyl halides. Whereas aryl...
20.7K
Nomenclature of Alkynes02:39

Nomenclature of Alkynes

22.1K
Alkynes are unsaturated hydrocarbons characterized by the presence of carbon-carbon triple bonds and have a general formula CnH2n-2. The nomenclature of alkynes follows a set of rules similar to alkanes and alkenes; however, alkynes bear the suffix "-yne" instead of "-ane" or "-ene." There are two approaches to naming alkynes:
22.1K
Preparation of Alkynes: Alkylation Reaction02:27

Preparation of Alkynes: Alkylation Reaction

12.5K
Introduction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
12.5K
Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

4.1K
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...
4.1K

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Related Experiment Video

Updated: Mar 1, 2026

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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A Structurally Characterized Fluoroalkyne.

Lewis M Hall1, David P Tew2, Natalie E Pridmore1

  • 1Department of Chemistry, The University of York, Heslington, York, YO10 5DD, UK.

Angewandte Chemie (International Ed. in English)
|May 26, 2017
PubMed
Summary
This summary is machine-generated.

Researchers synthesized a stable fluoroalkynyl compound, M-C≡CF, using ruthenium precursors and electrophilic fluorination. This breakthrough allows for detailed study of the CCF motif, unlike previous unstable fluoroalkynes.

Keywords:
alkynesalkynylselectrophilic fluorinationfluorinevinylidenes

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Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes
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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
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Area of Science:

  • Organometallic Chemistry
  • Fluorine Chemistry
  • Synthetic Chemistry

Background:

  • Fluoroalkynes are rare and highly reactive, limiting their study.
  • Previous synthetic methods have not yielded stable, isolable fluoroalkyne compounds.

Purpose of the Study:

  • To report the facile synthesis of a stable and isolable fluoroalkynyl compound.
  • To explore the structure and bonding of the CCF motif in a stable complex.
  • To investigate further fluorination reactions of fluoroalkynyl complexes.

Main Methods:

  • Reaction of a ruthenium-alkynyl precursor with an electrophilic fluorinating agent (N-fluorobenzenesulfonimide, NFSI).
  • Deprotonation of the resulting fluorovinylidene complex using lithium bis(trimethylsilyl)amide.
  • Structural characterization of the synthesized fluoroalkynyl complex.

Main Results:

  • A stable fluoroalkynyl complex, [Ru(C≡CF)(η⁵-C₅Me₅)(dppe)], was successfully synthesized and isolated.
  • The synthesized compound is stable enough for structural characterization, unlike previously reported fluoroalkynes.
  • Further electrophilic fluorination yielded a difluorovinylidene complex.

Conclusions:

  • The development of a stable fluoroalkynyl complex provides new opportunities for studying the CCF motif.
  • This synthetic route offers a viable method for accessing previously inaccessible fluoroalkynyl compounds.
  • The study highlights the potential for further exploration of fluorinated organometallic compounds.