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Related Concept Videos

Halogenation of Alkenes02:46

Halogenation of Alkenes

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.
Formation of Halohydrin from Alkenes02:41

Formation of Halohydrin from Alkenes

An alkene, such as propene, reacts with bromine in the presence of water to yield a halohydrin. Halohydrins contain a halogen and a hydroxyl group attached to adjacent carbons. When the halogen is bromine, it is called a bromohydrin, while a chlorohydrin has chlorine as the halogen.
Radical Substitution: Allylic Bromination01:27

Radical Substitution: Allylic Bromination

In organic synthesis, the formation of products can be altered by changing the reaction conditions. For example, a dibromo addition product is formed when propene is treated with bromine at room temperature. In contrast, propene undergoes allylic substitution in non-polar solvents at high temperatures to give 3-bromopropene. In order to avoid the addition reaction, the bromine concentration must be kept as low as possible throughout the reaction. This can be achieved using N-bromosuccinimide...
Alkyl Halides02:45

Alkyl Halides

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...
Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene01:14

Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene

Electrophilic addition of halogens to alkenes proceeds via a cyclic halonium ion to form a 1,2-dihalide or a vicinal dihalide.
Electrophilic 1,2- and 1,4-Addition of HX to 1,3-Butadiene01:17

Electrophilic 1,2- and 1,4-Addition of HX to 1,3-Butadiene

The electrophilic addition of hydrogen halides such as HBr to alkenes and nonconjugated dienes gives a single product as per Markovnikov’s rule.

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2-Bromo-1-mesitylethanone.

Lei Chen1, Qing-Bing Xu, Guang-Liang Song

  • 1Department of Applied Chemistry, College of Science, Nanjing University of Technology, Nanjing 210009, People's Republic of China.

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

The crystal structure of C(11)H(13)BrO reveals near-planar aromatic rings. Molecules are linked into chains by weak intermolecular interactions, with an additional weak C-H⋯π interaction observed.

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Area of Science:

  • Crystallography
  • Organic Chemistry
  • Molecular Structure

Background:

  • Understanding molecular arrangements in the solid state is crucial for predicting material properties.
  • Intermolecular forces, such as hydrogen bonds and van der Waals interactions, dictate crystal packing.
  • Aromatic compounds with halogen and oxygen substituents offer diverse structural possibilities.

Purpose of the Study:

  • To elucidate the crystal structure of the title compound, C(11)H(13)BrO.
  • To identify and characterize the intermolecular interactions present in the crystal lattice.
  • To analyze the planarity of the molecule and its constituent parts.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the three-dimensional molecular structure.
  • Crystallographic data were analyzed to assess bond lengths, bond angles, and deviations from planarity.
  • Intermolecular interactions were identified using geometric criteria and visualization software.

Main Results:

  • The crystal structure of C(11)H(13)BrO was successfully determined.
  • Adjacent carbon atoms in the molecule exhibit near-coplanarity with the aromatic ring, with a maximum deviation of 0.035(3) Å.
  • Weak intermolecular C-H⋯O interactions were observed, forming chains along the b-axis.
  • A very weak C-H⋯π interaction was also identified within the crystal structure.

Conclusions:

  • The crystal packing of C(11)H(13)BrO is primarily influenced by weak C-H⋯O intermolecular interactions, leading to chain formation.
  • The near-planarity of the aromatic system is maintained in the solid state.
  • The presence of both C-H⋯O and C-H⋯π interactions contributes to the overall stability of the crystal lattice.