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Related Concept Videos

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.
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Simple aryl halides do not react with nucleophiles under normal conditions. However, the reaction can proceed under drastic conditions involving high temperatures and high pressure to give the substituted products. For example, chlorobenzene is converted to phenol using aqueous sodium hydroxide at 350 °C under high pressure by the Dow process. The reaction follows an elimination-addition mechanism involving a benzyne intermediate. Here, the chloride ion is eliminated to generate the benzyne...
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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.
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The concept of prochirality leads to the nomenclature of the individual faces of a molecule and plays a crucial role in the enantioselective reaction. It is a concept where two or more achiral molecules react to produce chiral products. A typical process is the reaction of an achiral ketone to generate a chiral alcohol. Here, the achiral reactant reacts with an achiral reducing agent, sodium borohydride, to generate an equimolar mixture of the chiral enantiomers of the product. For example, an...
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In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.

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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
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3,3'-[(4-Nitro-phen-yl)methyl-ene]bis-(4-hy-droxy-2H-chromen-2-one).

N Ravikumar1, G Gopikrishna, K Anand Solomon

  • 1Sankar Foundation Research Institute, Naiduthota, Vepagunta, Visakhapatnam, Andhra Pradesh 530 047, India.

Acta Crystallographica. Section E, Structure Reports Online
|February 21, 2012
PubMed
Summary
This summary is machine-generated.

This study reveals the molecular structure of C(25)H(15)NO(8), highlighting intramolecular hydrogen bonds and pi-pi stacking interactions. These structural features influence the compound's crystal packing and overall conformation.

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Area of Science:

  • Crystallography
  • Organic Chemistry
  • Supramolecular Chemistry

Background:

  • Understanding molecular conformation is crucial for predicting chemical properties and designing new materials.
  • Intramolecular interactions play a significant role in stabilizing molecular structures.
  • Crystal engineering relies on identifying and controlling intermolecular forces like pi-pi stacking.

Purpose of the Study:

  • To elucidate the detailed molecular conformation of the title compound, C(25)H(15)NO(8).
  • To investigate the role of intramolecular hydrogen bonding in stabilizing the molecular structure.
  • To analyze the intermolecular interactions, specifically pi-pi stacking, present in the crystal lattice.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
  • Analysis of hydrogen bonding networks using geometric parameters.
  • Computational methods may be used to further analyze electronic interactions (though not explicitly stated in abstract).

Main Results:

  • The molecular conformation is stabilized by strong intramolecular O-H⋯O hydrogen bonds, forming S(1)(7) ring motifs.
  • Significant pi-pi stacking interactions were observed between nitrobenzene and pyranone rings with a centroid-centroid distance of 3.513(12) Å.
  • Specific dihedral angles were measured, indicating the relative orientation of the aromatic and heterocyclic ring systems.

Conclusions:

  • The title compound exhibits a conformation dictated by robust intramolecular hydrogen bonds.
  • Intermolecular pi-pi stacking interactions contribute to the crystal packing, influencing the solid-state structure.
  • The findings provide insights into the structure-property relationships of this class of organic molecules.