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Related Concept Videos

Nomenclature of Alkynes02:39

Nomenclature of Alkynes

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:
Acidity of 1-Alkynes02:42

Acidity of 1-Alkynes


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.
Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis01:07

Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis

Acetoacetic ester synthesis is a method to obtain ketones from alkyl halides and β-keto esters. The reaction occurs in the presence of an alkoxide base that abstracts the acidic proton of the β-keto esters. The step results in an enolate ion which is doubly stabilized. The enolate then reacts with an alkyl halide via the SN2 process to produce an alkylated ester intermediate with a new C–C bond. The hydrolysis of the intermediate, followed by acidification, results in an alkylated β-keto acid.
Preparation of Alkynes: Alkylation Reaction02:27

Preparation of Alkynes: Alkylation Reaction

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.
Alkylation of β-Diester Enolates: Malonic Ester Synthesis01:14

Alkylation of β-Diester Enolates: Malonic Ester Synthesis

Malonic ester synthesis is a method to obtain α substituted carboxylic acids from ꞵ-diesters such as diethyl malonate and alkyl halides.
Phase II Reactions: Acetylation Reactions01:24

Phase II Reactions: Acetylation Reactions

Acetylation, a phase II biotransformation reaction, introduces an acetyl group to drugs or their metabolites. Acetyltransferase enzymes facilitate this reaction, which resembles α-amino acid conjugation due to the addition of a functional group to the drug molecule.
The substrates for acetylation are typically drugs or their metabolites with an amino, sulfonamide, or hydrazine functional group. Acetylation can occur at several points in the drug molecule, including primary, secondary, and...

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Related Experiment Video

Updated: Jun 1, 2026

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
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Published on: June 21, 2017

Bis(2-thien-yl)acetyl-ene.

Emily M Harcourt, Daniel E Lynch, Darren G Hamilton

    Acta Crystallographica. Section E, Structure Reports Online
    |May 18, 2011
    PubMed
    Summary
    This summary is machine-generated.

    This study details the crystal structure of a symmetrical C(10)H(6)S(2) molecule, revealing rotational disorder in its thiophene rings and precise bond distances. The findings offer insights into molecular arrangement and disorder in organic sulfur compounds.

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    Area of Science:

    • Crystallography
    • Organic Chemistry
    • Materials Science

    Background:

    • Understanding the precise three-dimensional arrangement of atoms in organic molecules is crucial for predicting their properties and designing new materials.
    • Organic sulfur compounds, particularly those containing thiophene rings, exhibit diverse electronic and structural characteristics.
    • Crystallographic studies provide fundamental data on molecular geometry, symmetry, and packing in the solid state.

    Purpose of the Study:

    • To determine the detailed crystal structure of the title compound, C(10)H(6)S(2).
    • To investigate the molecular symmetry and identify any structural disorder within the crystalline lattice.
    • To precisely measure key bond distances, such as the carbon-carbon triple bond, and their implications for molecular planarity.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to collect diffraction data.
    • The crystal structure was solved and refined using standard crystallographic software.
    • Analysis included assessing molecular planarity, symmetry elements, and atomic site occupancies.

    Main Results:

    • The molecule C(10)H(6)S(2) adopts a planar symmetrical structure, with a maximum deviation of 0.0066(4) Å.
    • The molecule lies across a crystallographic inversion center, indicating specific symmetry.
    • Significant rotational disorder was observed in the thiophene rings around the acetylene bond, with sulfur atoms occupying two distinct pseudo-inversion-related sites (0.80:0.20 occupancy).
    • A short C-C bond distance of 1.195(9) Å was measured, characteristic of an acetylene linkage.

    Conclusions:

    • The crystal structure of C(10)H(6)S(2) is characterized by planarity and high symmetry, despite rotational disorder in the thiophene moieties.
    • The observed disorder provides valuable information on the dynamic behavior and conformational flexibility of the molecule in the solid state.
    • The precise structural data contribute to the fundamental understanding of organic sulfur compounds and their packing in crystals.