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Halogenation of Alkenes02:46

Halogenation of Alkenes

15.8K
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.
15.8K
Formation of Halohydrin from Alkenes02:41

Formation of Halohydrin from Alkenes

13.1K
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.
13.1K
Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene01:15

Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene

8.3K
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...
8.3K
Radical Substitution: Allylic Bromination01:27

Radical Substitution: Allylic Bromination

5.2K
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...
5.2K
Reactions at the Benzylic Position: Halogenation01:11

Reactions at the Benzylic Position: Halogenation

2.6K
Benzylic halogenation takes place under conditions that favor radical reactions such as heat, light, or a free radical initiator like peroxide.
2.6K
α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction01:15

α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction

3.1K
The method to achieve α-brominated carboxylic acids using a mixture of phosphorus tribromide and bromine is known as the Hell–Volhard–Zelinski reaction. The reaction is catalyzed by phosphorus tribromide, which can be used directly or produced in situ from red phosphorus and bromine. The mechanism comprises PBr3 catalyzed conversion of acid to acid bromide and hydrogen bromide. The acid bromide enolizes to its enol form in the presence of HBr. The nucleophilic enol attacks the...
3.1K

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Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
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Bromination of

Demet Demirci Gültekin1, Arif Daştan2, Yavuz Taşkesenligil3

  • 1Askale Vocational College, Department of Metallurgical Program, Atatürk University 25500 Erzurum, Turkey.

Beilstein Journal of Organic Chemistry
|June 7, 2023
PubMed
Summary

This study confirms the original structure of a brominated norbornene adduct using X-ray crystallography, refuting a recent computational claim and proposed alternative mechanism. The findings reinforce established stereochemical assignment methods in organic chemistry.

Keywords:
NMRNOE-Diff experimentsbrominationcomputational NMRγ-gauche effect

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Area of Science:

  • Organic Chemistry
  • Stereochemistry
  • Computational Chemistry

Background:

  • Previous work reported bromination of endo-7-bromonorbornene and structural elucidation via NMR spectroscopy.
  • A recent study challenged these findings using machine learning-augmented DFT, proposing a revised structure and mechanism.

Purpose of the Study:

  • To definitively confirm the structure of the brominated norbornene adduct.
  • To refute the revised structure and proposed mechanism from Novitskiy and Kutateladze.
  • To validate the reliability of NMR spectroscopy in stereochemical assignments.

Main Methods:

  • Nuclear Magnetic Resonance (NMR) spectroscopy for initial structural elucidation.
  • X-ray crystallography for ultimate structural confirmation.
  • Mechanistic reasoning to evaluate proposed reaction pathways.

Main Results:

  • The original structure assigned via NMR spectroscopy was confirmed by X-ray crystallography.
  • The revised structure proposed by Novitskiy and Kutateladze was disproven.
  • An alternative reaction mechanism involving skeletal rearrangement was refuted.

Conclusions:

  • The study reaffirms the accuracy of the originally assigned structure through definitive crystallographic evidence.
  • The computational NMR approach and proposed mechanism by Novitskiy and Kutateladze were shown to be erroneous.
  • This work underscores the importance of experimental validation in organic structure determination and mechanistic studies.