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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...

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.

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.

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.

Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene

Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene

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...

VSEPR Theory and the Effect of Lone Pairs

VSEPR Theory and the Effect of Lone Pairs

Effect of Lone Pairs of Electrons on Molecule Geometry

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Related Experiment Video

Updated: May 21, 2026

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of Phosphorus(I)

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of Phosphorus(I)

Published on: November 22, 2016

4-Cyano-pyridinium bromide.

¹College of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online

|June 22, 2012

Summary

This study reveals how protonated pyridine and bromide anions form crystal structures. Hydrogen bonds link molecules into chains and networks, detailing pyridinium bromide crystal packing.

Area of Science:

Crystal engineering
Supramolecular chemistry
Solid-state chemistry

Background:

Understanding crystal structures is key to designing materials with specific properties.
Hydrogen bonding plays a crucial role in molecular self-assembly and crystal formation.
Pyridinium salts are common motifs in various chemical applications.

Purpose of the Study:

To elucidate the crystal structure of pyridinium bromide.
To investigate the role of hydrogen bonding and intermolecular interactions in its assembly.
To describe the resulting network architecture.

Main Methods:

Single-crystal X-ray diffraction was used to determine the molecular structure and packing.
Analysis of intermolecular interactions, including hydrogen bonds (N-H⋯Br, C-H⋯N) and C-H⋯Br interactions.

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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)

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Last Updated: May 21, 2026

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of Phosphorus(I)

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of Phosphorus(I)

Published on: November 22, 2016

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

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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)

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Identification of the unit cell and crystallographic axes.

Main Results:

The pyridine nitrogen atom is protonated, forming pyridinium cation (C(6)H(5)N(2)+).
Intermolecular N-H⋯Br hydrogen bonds link pyridinium cations into chains along the c axis.
Weak C-H⋯Br interactions further connect these chains into a network parallel to the bc plane.

Conclusions:

The crystal structure of pyridinium bromide is characterized by a hydrogen-bonded chain motif.
These chains are interconnected via weaker interactions, forming a 2D network.
This detailed structural analysis provides insights into the supramolecular assembly of simple organic salts.