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Nomenclature of Aromatic Compounds with a Single Substituent01:23

Nomenclature of Aromatic Compounds with a Single Substituent

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Benzene is the simplest aromatic hydrocarbon or arene. The IUPAC names for simple monosubstituted benzene derivatives are derived by adding the substituent's name as a prefix to the parent benzene. For example, halobenzene, where the halogen could be fluoro (F), chloro (Cl), bromo (Br), and iodo (I).
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According to the molecular orbital (MO) model, benzene has a planar structure with a regular hexagon of six sp2 hybridized carbons. As shown in Figure 1, each carbon is bonded to three other atoms with C–C–C and H–C–C bond angles of 120°. The C–H bond length is 109 pm, and the C–C bond length is 139 pm which is midway between the single bond length of sp3 hybridized carbons (154 pm) and sp2 hybridized carbons (133 pm).
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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...
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Nomenclature of Aromatic Compounds with Multiple Substituents01:11

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When more than one substituent is present on the benzene ring, the IUPAC nomenclature depends on the number of substituents present.
For disubstituted benzene derivatives, with two groups attached to the benzene ring, three constitutional isomers are possible. For example, consider dimethyl benzene, often called xylene, where the second methyl group can be substituted at the second, third, or fourth carbon. The relative position of the substituents is represented by prefixes ortho, meta, or...
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10.3K
Simple unsubstituted benzene has six aromatic protons, all chemically equivalent. Therefore, benzene exhibits only a singlet peak at δ 7.3 ppm in the 1H NMR spectrum. The observed shift is far downfield because the aromatic ring current strongly deshields the protons. Any substitution on the benzene ring makes the aromatic protons nonequivalent, and the protons split each other. The peak is, therefore, no longer a singlet and the splitting pattern and their associated coupling...
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Reactions at the Benzylic Position: Halogenation01:11

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Benzylic halogenation takes place under conditions that favor radical reactions such as heat, light, or a free radical initiator like peroxide.
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1,4-Bis(hex-yloxy)benzene.

Hua Cheng1

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Summary
This summary is machine-generated.

This study details the crystal structure of C18H30O2, revealing an extended all-trans alkyl chain conformation. Molecular packing analysis showed no significant intermolecular interactions in the crystal structure.

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Area of Science:

  • Crystallography
  • Organic Chemistry
  • Materials Science

Background:

  • Understanding molecular conformation and crystal packing is crucial for predicting material properties.
  • The specific compound C18H30O2 has potential applications influenced by its solid-state structure.

Purpose of the Study:

  • To elucidate the crystal structure of C18H30O2.
  • To analyze the conformation of the alkyl chain and its orientation relative to the benzene ring.
  • To investigate intermolecular interactions within the crystal lattice.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
  • Analysis of atomic coordinates and bond parameters provided conformational details.
  • Crystal packing was examined to identify any significant intermolecular contacts.

Main Results:

  • The asymmetric unit contains half a molecule located on an inversion center.
  • The C18H30O2 molecule features a fully extended all-trans conformation of its alkyl chain.
  • The alkyl chain's carbon atoms are nearly coplanar and inclined at a slight angle (6.80°) to the central benzene ring.
  • No short intermolecular contacts were observed in the crystal packing.

Conclusions:

  • The determined crystal structure provides fundamental insights into the solid-state behavior of C18H30O2.
  • The observed conformation and packing suggest limited intermolecular forces, potentially influencing bulk properties.
  • This structural data serves as a basis for further studies on related compounds and their applications.