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Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.
Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism01:18

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Birch reduction uses solvated electrons as reducing agents. The reaction converts benzene to 1,4-cyclohexadiene. The reaction proceeds by the transfer of a single electron to the ring to form a benzene radical anion. This anion is highly basic—it abstracts a proton from the alcohol to form a cyclohexadienyl radical. Another single electron transfer gives the cyclohexadienyl anion. A proton transfer from the alcohol forms 1,4-cyclohexadiene. Since this reduction occurs via radical anion...
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 confirmed through isotopic...
Aromatic Hydrocarbon Cations: Structural Overview01:18

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Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group with both...
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Depending upon the different spatial orientation of the substituents, the disubstituted cycloalkanes exhibit two types of stereoisomers. The cis isomers have the substituents on the same side of the ring, whereas the trans isomers have the substituents on the opposite sides. These stereoisomers exhibit different physical properties and cannot be interconverted without breaking the carbon-carbon bonds.
In cyclohexane, the substituents can occupy different positions generating distinct isomers.

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N-Cyclo-hexyl-3-fluoro-benzamide.

Aamer Saeed, Rasheed Ahmad Khera, Naeem Abbas

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

    This study details the molecular structure of C(13)H(16)FNO, revealing specific amide plane orientation and crystal packing via hydrogen bonds. The fluorine atom exhibits disorder across two positions in the crystal lattice.

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    Area of Science:

    • Crystallography
    • Organic Chemistry
    • Molecular Structure Analysis

    Background:

    • Understanding the three-dimensional arrangement of atoms in organic molecules is crucial for predicting their properties and reactivity.
    • Crystal structure analysis provides precise details on molecular conformation and intermolecular interactions.

    Purpose of the Study:

    • To elucidate the crystal structure of the molecule C(13)H(16)FNO.
    • To determine the spatial orientation of the amide plane relative to the aromatic ring.
    • To identify and characterize intermolecular interactions within the crystal lattice.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
    • Analysis of bond lengths, bond angles, and torsion angles.
    • Identification of hydrogen bonding and other non-covalent interactions.

    Main Results:

    • The amide (N-C=O) plane is oriented at 29.9(2)° with respect to the aromatic ring.
    • The cyclohexane ring adopts a chair conformation.
    • Intermolecular N-H⋯O hydrogen bonds form chains along the [100] direction.
    • A weak C-H⋯F interaction was observed.
    • The fluorine atom is disordered over two positions with occupancies of 0.873(3) and 0.127(3).

    Conclusions:

    • The crystal structure of C(13)H(16)FNO is characterized by specific conformational preferences and intermolecular hydrogen bonding.
    • The observed molecular geometry and packing provide insights into the solid-state behavior of this compound.
    • The fluorine atom disorder suggests potential flexibility or multiple stable packing arrangements.