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Halogenation of Alkenes

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 Alkenes

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 Bromination

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...

Reactions at the Benzylic Position: Halogenation

Reactions at the Benzylic Position: Halogenation

Benzylic halogenation takes place under conditions that favor radical reactions such as heat, light, or a free radical initiator like peroxide.

Regioselectivity of Electrophilic Additions-Peroxide Effect

Regioselectivity of Electrophilic Additions-Peroxide Effect

In the presence of organic peroxides, the addition of hydrogen bromide to an alkene yields the isomer that is not predicted by Markovnikov’s rule. For example, the addition of hydrogen bromide to 2-methylpropene in the presence of peroxides gives 1-bromo-2-methylpropane. This addition reaction proceeds via a free radical mechanism, which reverses the regioselectivity. The free radical reaction mechanism involves three stages: initiation, propagation, and termination.

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

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.

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2-Bromo-1-phenyl-ethanone.

Richard Betz¹, Cedric McCleland, Harold Marchand

¹Nelson Mandela Metropolitan University, Summerstrand Campus, Department of Chemistry, University Way, Summerstrand, PO Box 77000, Port Elizabeth 6031, South Africa.

Acta Crystallographica. Section E, Structure Reports Online

|July 15, 2011

Summary

This study details the crystal structure of a brominated acetophenone derivative, C(8)H(7)BrO. Molecular symmetry and intermolecular C-H⋯O contacts forming sheet-like structures were observed.

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Area of Science:

Crystallography
Organic Chemistry
Solid-State Chemistry

Background:

Acetophenone derivatives are important in organic synthesis.
Halogenated organic compounds exhibit unique chemical properties.
Understanding molecular structure is key to predicting chemical behavior.

Purpose of the Study:

To elucidate the crystal structure of the title compound, a halogenated acetophenone derivative.
To analyze the molecular symmetry and bonding characteristics.
To investigate intermolecular interactions within the crystal lattice.

Main Methods:

Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
Analysis of bond lengths, bond angles, and intermolecular contacts.
Symmetry analysis of the molecule.

Main Results:

The compound, C(8)H(7)BrO, exhibits noncrystallographic C(s) symmetry.
Intra-cyclic C-C-C angles range from 118.8(2)° to 120.4(3)°.
Intermolecular C-H⋯O contacts link molecules into undulating sheets parallel to the crystallographic c axis.

Conclusions:

The crystal packing is governed by specific intermolecular interactions.
The determined structure provides a basis for understanding the reactivity and properties of this halogenated acetophenone.
This research contributes to the knowledge of halogenated organic compounds in the solid state.