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Related Concept Videos

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

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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.
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Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene01:15

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Chlorination and bromination are important classes of electrophilic aromatic substitutions, where benzene reacts with chlorine or bromine in the presence of a Lewis acid catalyst to give halogenated substitution products. A Lewis acid such as aluminium chloride or ferric chloride catalyzes the chlorination, and ferric bromide catalyzes the bromination reactions. During the bromination of alkenes, bromine polarizes and becomes electrophilic. However, in the bromination of benzene, the bromine...
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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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Alkyl Halides02:45

Alkyl Halides

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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...
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Halogenation of Alkenes

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Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
17.3K
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...
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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
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2-Bromo-5-fluoro-benzaldehyde.

Robert E Tureski1, Joseph M Tanski

  • 1Department of Chemistry, Vassar College, Poughkeepsie, NY 12604, USA.

Acta Crystallographica. Section E, Structure Reports Online
|October 11, 2013
PubMed
Summary
This summary is machine-generated.

This study reveals the crystal structure of a bromofluorobenzaldehyde compound. Key findings include trans orientation of the oxygen and bromine atoms, and significant intermolecular bromine-fluorine and pi-stacking interactions.

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Area of Science:

  • Crystallography
  • Organic Chemistry
  • Supramolecular Chemistry

Background:

  • Understanding the solid-state behavior of halogenated aromatic compounds is crucial for predicting their reactivity and physical properties.
  • Benzaldehyde derivatives with halogen substituents offer a versatile platform for studying intermolecular interactions.

Purpose of the Study:

  • To elucidate the crystal structure of a specific bromofluorobenzaldehyde compound.
  • To investigate the nature and significance of intermolecular interactions, including halogen bonding and pi-stacking, in the solid state.

Main Methods:

  • Single-crystal X-ray diffraction analysis was employed to determine the three-dimensional molecular and crystal structure.
  • Analysis of crystallographic data to identify and quantify short intermolecular contacts, such as Br abbitF and pi-stacking interactions.

Main Results:

  • The crystal structure of C7H4BrFO was determined, revealing a trans configuration between the benzaldehyde oxygen and the 2-bromo substituent.
  • Short bromine-fluorine (Br abbitF) interactions were observed with distances of approximately 3.19–3.37 Å.
  • Offset face-to-face pi-stacking interactions were identified between independent molecules in the asymmetric unit, with centroid-centroid distances around 3.87 Å.

Conclusions:

  • The crystal packing is significantly influenced by Br abbitF interactions and pi-stacking, dictating the solid-state architecture.
  • The observed intermolecular interactions provide insights into the self-assembly behavior of halogenated benzaldehydes.
  • This structural information is valuable for the design of new materials and understanding reaction mechanisms involving similar compounds.