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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...

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...

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...

Preparation of Acid Anhydrides

Preparation of Acid Anhydrides

One of the methods for preparing symmetrical or unsymmetrical acid anhydrides involves the treatment of acid chlorides with the sodium salt of carboxylic acids. The reaction proceeds via a nucleophilic acyl substitution.
The carboxylate ion acts as a nucleophile that attacks the carbonyl carbon of the acid chloride to form a tetrahedral intermediate. Subsequently, the re-formation of the carbonyl group with the loss of the chloride ion as a leaving group leads to the formation of an acid...

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Related Experiment Video

Updated: May 20, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Published on: January 19, 2016

4-Chloro-anilinium bromide.

¹College of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, P. R. China.

Acta Crystallographica. Section E, Structure Reports Online

|July 19, 2012

Summary

This summary is machine-generated.

This study details the crystal structure of a protonated amino compound, revealing a planar cation and ribbon-like arrangements formed by hydrogen bonds between ions in the solid state.

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

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Area of Science:

Crystallography
Chemical Physics
Materials Science

Background:

Understanding the solid-state structures of organic salts is crucial for predicting their physical and chemical properties.
Protonation of amino groups significantly alters molecular geometry and intermolecular interactions.

Purpose of the Study:

To elucidate the crystal structure of the title compound, C(6)H(7)ClN(+)·Br(-).
To characterize the intermolecular interactions governing the solid-state arrangement.

Main Methods:

Single-crystal X-ray diffraction analysis was employed to determine the molecular and crystal structure.
Analysis of atomic coordinates and bond lengths/angles provided insights into the cation's geometry.

Main Results:

The amino nitrogen atom in the cation is protonated.
The non-hydrogen atoms of the cation exhibit near-planarity, with a root-mean-square deviation of 0.004(3) Å.
N-H⋯Br hydrogen bonds link the cations and bromide anions into a ribbon-like structure along the [010] direction.

Conclusions:

The crystal structure is dominated by ionic interactions and hydrogen bonding.
The observed planar geometry of the cation and the ribbon-like supramolecular architecture are key features of this compound's solid state.