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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...

Alkyl Halides

Alkyl Halides

Structural Properties
Alkyl halides are halogen-substituted alkanes wherein one or more hydrogen atoms of an alkane is replaced by a halogen atom such as fluorine, chlorine, bromine, or iodine. The carbon atom in an alkyl halide is bonded to the halogen atom, which is sp3-hybridized and exhibits a tetrahedral shape.
Unlike alkyl halides, compounds in which a halogen atom is bonded to an sp2 -hybridized carbon atom of a carbon-carbon double bond (C=C) are called vinyl halides. Whereas aryl...

π Molecular Orbitals of the Allyl Cation and Anion

π Molecular Orbitals of the Allyl Cation and Anion

An allyl group is a three-carbon conjugated system where the sp³-hybridized allylic carbon is bonded to a CH=CH2 group via a single bond. Allyl anions can be obtained by treating propene with a strong base that can deprotonate methyl groups. Allyl cations are formed as intermediates during substitution reactions involving allylic halides. In both cases, the hybridization of the allylic carbon changes from sp3 to sp2, giving rise to a carbon chain with three sp2-hybridized carbons, each with an...

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.

π Molecular Orbitals of the Allyl Radical

π Molecular Orbitals of the Allyl Radical

Allyl radicals are three-carbon conjugated systems. They are readily formed as intermediates in halogenation reactions of alkenes involving the addition of halogen to the allylic carbon instead of the double bond. As seen in allyl cations and anions, each of the three sp2-hybridized carbon atoms in allyl radicals has an unhybridized p orbital. These orbitals combine to give three π molecular orbitals.
The allyl systems have identical molecular orbitals but differ in the number of π electrons.

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.

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Updated: May 22, 2026

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions

Published on: July 30, 2017

4-Allyl-morpholin-4-ium bromide.

Meng Ting Han¹

¹Ordered Matter Science Research Center, College of Chemistry and Chemical, Engineering, Southeast University, Nanjing 211189, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online

|May 17, 2012

Summary

This summary is machine-generated.

The reaction of 4-allyl-morpholine with hydrogen bromide yielded a novel salt. This compound forms a unique three-dimensional crystal network through specific hydrogen bonding interactions.

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Area of Science:

Crystallography
Chemical Synthesis
Supramolecular Chemistry

Background:

Hydrogen bonding plays a crucial role in molecular self-assembly and crystal engineering.
Morpholine derivatives are versatile building blocks in organic synthesis and medicinal chemistry.

Purpose of the Study:

To synthesize and characterize a novel salt derived from 4-allyl-morpholine and hydrogen bromide.
To investigate the crystal structure and intermolecular interactions of the synthesized compound.

Main Methods:

Chemical synthesis involving the reaction of 4-allyl-morpholine with hydrogen bromide.
Single-crystal X-ray diffraction analysis to determine the molecular and crystal structure.

Main Results:

Successful synthesis of the title compound, C(7)H(14)NO(+)·Br(-).
The crystal structure reveals the formation of a three-dimensional network.
Intermolecular interactions are dominated by N-H⋯Br and C-H⋯Br hydrogen bonds.

Conclusions:

The study successfully synthesized and structurally characterized a new salt.
The observed hydrogen bonding patterns dictate the formation of an extended 3D network in the solid state.
This work contributes to understanding the supramolecular assembly of morpholine-based salts.