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Related Concept Videos

Halogenation of Alkenes02:46

Halogenation of Alkenes

16.9K
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.
16.9K
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

2.9K
Electrophilic addition of halogens to alkenes proceeds via a cyclic halonium ion to form a 1,2-dihalide or a vicinal dihalide.
2.9K
Acid-Catalyzed α-Halogenation of Aldehydes and Ketones01:21

Acid-Catalyzed α-Halogenation of Aldehydes and Ketones

4.1K
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...
4.1K
Base-Promoted α-Halogenation of Aldehydes and Ketones00:51

Base-Promoted α-Halogenation of Aldehydes and Ketones

3.7K
α-Halogenation of aldehydes and ketones is a reaction involving the substitution of α hydrogens with halogens in the presence of a base.  The reaction begins with the abstraction of  α hydrogen by the base to produce a nucleophilic enolate ion. This intermediate undergoes a subsequent nucleophilic substitution with the halogen to produce a monohalogenated carbonyl compound. If the starting substrate has more than one α hydrogen, it is difficult to stop the reaction...
3.7K
Electrophilic Addition to Alkynes: Hydrohalogenation02:35

Electrophilic Addition to Alkynes: Hydrohalogenation

10.5K
Electrophilic addition of hydrogen halides, HX (X = Cl, Br or I) to alkenes forms alkyl halides as per Markovnikov's rule, where the hydrogen gets added to the less substituted carbon of the double bond. Hydrohalogenation of alkynes takes place in a similar manner, with the first addition of HX forming a vinyl halide and the second giving a geminal dihalide.
10.5K
ortho–para-Directing Deactivators: Halogens01:24

ortho–para-Directing Deactivators: Halogens

6.1K
Halogens are ortho–para directors. They are more electronegative than carbon. Therefore, as ring substituents, they can withdraw electrons through the inductive effect and deactivate the aromatic ring towards electrophilic substitution. Halogens also have an electron-donating resonance effect on the ring, which influences the orientation of the incoming electrophile. If an electrophile attacks at the ortho or the para position, the halogen donates electrons and stabilizes the intermediate...
6.1K

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Related Experiment Video

Updated: Oct 26, 2025

Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex
10:52

Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex

Published on: July 27, 2022

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Dehydrohalogenation reactions in second-sphere coordination complexes.

Javier Martí-Rujas1, Fang Guo

  • 1Department of Chemistry, Materials and Chemical Engineering "Giulio Natta", Politecnico di Milano, Piazza L. da Vinci 32, 20133 Milan, Italy. javier.marti@polimi.it.

Dalton Transactions (Cambridge, England : 2003)
|July 29, 2021
PubMed
Summary
This summary is machine-generated.

Solid-state dehydrohalogenation and halogenation reactions in halometallate salts are reported. These reactions transform second sphere coordination to first sphere coordination, enabling structure-function correlations.

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

  • Solid-state chemistry
  • Coordination chemistry
  • Halogenation reactions

Background:

  • Focus on outer sphere adducts with protonated organic cations and transition metal anions.
  • Investigates dehydrohalogenation/hydrohalogenation as transformations between second and first sphere coordination.

Purpose of the Study:

  • Analyze solid-state dehydrohalogenation/hydrohalogenation reactions.
  • Explore unique reactivity in outer sphere adducts.
  • Establish structure-function correlations.

Main Methods:

  • Mechanochemical and thermal stimuli used to induce reactions.
  • Cleavage of C-H, N-H, and M-X bonds.
  • Formation of M-N and H-X bonds.

Main Results:

  • Observed varying reactivities based on metal lability, functional group position, and cation-anion arrangement.
  • Demonstrated reverse hydrohalogenation via gas-solid chemisorption in non-porous materials.
  • Showcased dynamic material behavior.

Conclusions:

  • Dehydrohalogenation/halogenation reactions offer a unique pathway for solid-state transformations.
  • These reactions enable structure-function correlations in optical, sensing, and magnetic properties.
  • Highlights the dynamic nature of halometallate salts in solid-state reactions.