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Formation of Halohydrin from Alkenes02:41

Formation of Halohydrin from Alkenes

15.0K
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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Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule02:17

Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule

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If a set of reactants can yield multiple constitutional isomers, but one of the isomers is obtained as the major product, the reaction is said to be regioselective. In such reactions, bond formation or breaking is favored at one reaction site over others.
The hydrohalogenation of an unsymmetrical alkene can yield two haloalkane products, depending on which vinylic carbon takes up the halogen. However, one product usually predominates, where hydrogen adds to the vinylic carbon bearing the...
18.2K
Halogenation of Alkenes02:46

Halogenation of Alkenes

20.8K
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.
20.8K
Acid-Catalyzed α-Halogenation of Aldehydes and Ketones01:21

Acid-Catalyzed α-Halogenation of Aldehydes and Ketones

5.1K
By replacing an α-hydrogen with a halogen, acid-catalyzed α-halogenation of aldehydes or ketones yields a monohalogenated product
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic halogen to form a...
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Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

9.7K
A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.
9.7K
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

4.0K
Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
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Related Experiment Video

Updated: Mar 19, 2026

From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
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From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding

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Insights into halogen bond-driven enantioseparations.

Paola Peluso1, Victor Mamane2, Emmanuel Aubert3

  • 1Istituto di Chimica Biomolecolare ICB, CNR, UOS di Sassari, Traversa La Crucca 3, Regione Baldinca, I-07100 Li Punti, Sassari, Italy.

Journal of Chromatography. A
|June 23, 2016
PubMed
Summary

This study reveals halogen bonding (XB) in solution using HPLC, highlighting iodine

Keywords:
AtropisomersBipyridinesChiral recognitionElectrostatic potential surfacesHalogen bondPolysaccharide-based chiral stationary phases

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Area of Science:

  • Analytical Chemistry
  • Physical Chemistry
  • Organic Chemistry

Background:

  • Halogen bonding (XB) is primarily studied in silico and solid states.
  • Its role in solution-based interactions remains underexplored.
  • Understanding solution-phase XB is crucial for various chemical applications.

Purpose of the Study:

  • To systematically investigate halogen bonding in a solvated environment using HPLC.
  • To explore the impact of different halogens (Cl, Br, I) on enantioseparation.
  • To elucidate the role of XB in chiral recognition mechanisms.

Main Methods:

  • Utilized high-performance liquid chromatography (HPLC) with chiral stationary phases (CSPs).
  • Employed atropisomeric polyhalogenated-4,4'-bipyridines (HBipys) as halogen bond donors.
  • Performed electrostatic potential (EP) computations and van't Hoff studies.
  • Incorporated molecular dynamics (MD) simulations to model XB interactions.

Main Results:

  • Demonstrated the effectiveness of halogen bonding in HPLC enantioseparation.
  • Identified iodine as a key element for enantioseparation in non-polar media.
  • Quantified thermodynamic parameters governing halogen-dependent separations.
  • Computational studies supported experimental findings on XB interactions.

Conclusions:

  • Halogen bonding is a versatile interaction applicable in HPLC.
  • XB exhibits chemo-, regio-, site-, and stereoselectivity in solution.
  • This study provides a foundation for utilizing XB in chromatographic separations.