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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.
π Molecular Orbitals of 1,3-Butadiene01:24

π Molecular Orbitals of 1,3-Butadiene

Conjugated dienes have lower heats of hydrogenation than cumulated and isolated dienes, making them more stable. The enhanced stabilization of conjugated systems can be understood from their π molecular orbitals.
The simplest conjugated diene is 1,3-butadiene: a four-carbon system where each carbon is sp2-hybridized and has an unhybridized p orbital that contains an unpaired electron. According to molecular orbital theory, atomic orbitals combine to form molecular orbitals such that the number...
Structure of Conjugated Dienes01:16

Structure of Conjugated Dienes

Introduction
Conjugated dienes are compounds characterized by the presence of alternating double and single bonds. In a conjugated system like 1,3-butadiene, the unhybridized 2p orbital on each carbon overlaps continuously, allowing the π electrons to be delocalized across the entire molecule. In contrast, this type of overlap does not occur in cumulated and isolated dienes, such as 2,3-pentadiene and 1,4-pentadiene, respectively. Instead, the π electrons remain localized between the double...
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...
Disubstituted Cyclohexanes: cis-trans Isomerism02:37

Disubstituted Cyclohexanes: cis-trans Isomerism

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.
Nomenclature of Aromatic Compounds with Multiple Substituents01:11

Nomenclature of Aromatic Compounds with Multiple Substituents

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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Continuous Flow Chemistry: Reaction of Diphenyldiazomethane with p-Nitrobenzoic Acid
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Published on: November 15, 2017

1,3-diphenylisobenzofuran.

René T Boeré1, Peter W Dibble, Kristapher E Fischer

  • 1Department of Chemistry and Biochemistry, University of Lethbridge, Lethbridge, AB, Canada T1K 3M4.

Acta Crystallographica. Section E, Structure Reports Online
|January 5, 2011
PubMed
Summary

The structure of 1,3-diphenyl-2-benzofuran reveals alternating short and long carbon-carbon bonds, suggesting a polyene character. This is the first reported crystal structure of the parent compound, distinct from its Diels-Alder adducts.

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Area of Science:

  • Organic Chemistry
  • Crystallography

Background:

  • 1,3-diphenyl-2-benzofuran is a commercially available furan derivative.
  • Over 60 Diels-Alder adducts of this compound have been structurally characterized.
  • The crystal structure of the parent compound itself has not been previously reported.

Purpose of the Study:

  • To determine and report the crystal structure of 1,3-diphenyl-2-benzofuran.
  • To analyze the bond lengths and electronic character of the benzofuran ring system in the parent compound.

Main Methods:

  • Single-crystal X-ray diffraction analysis was employed to elucidate the molecular structure.
  • Analysis of bond lengths within the benzofuran ring system was performed.

Main Results:

  • The crystal structure of 1,3-diphenyl-2-benzofuran (C(20)H(14)O) was determined.
  • A distinct alternation of short (mean 1.361 Å) and long (mean 1.431 Å) C-C bonds was observed around the benzofuran ring.
  • These bond length variations indicate a predominantly polyene character for the benzofuran system.

Conclusions:

  • The study provides the first crystallographic report on the parent 1,3-diphenyl-2-benzofuran.
  • The observed bond alternation confirms a significant polyene character, influencing its chemical reactivity.