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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...

Reactions of α-Halocarbonyl Compounds: Nucleophilic Substitution

Reactions of α-Halocarbonyl Compounds: Nucleophilic Substitution

Nucleophilic substitution in α-halocarbonyl compounds can be achieved via an SN2 pathway. The reaction in α-haloketones is generally carried out with less basic nucleophiles. The use of strong basic nucleophiles leads to the generation of α-haloenolate ions, which often participate in other side reactions.

Electrophilic Addition to Alkynes: Halogenation

Electrophilic Addition to Alkynes: Halogenation

Introduction
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.

Multiple Halogenation of Methyl Ketones: Haloform Reaction

Multiple Halogenation of Methyl Ketones: Haloform Reaction

A method involving the transformation of methyl ketones to carboxylic acids using excess base and halogen is called the haloform reaction. It begins with the deprotonation of α hydrogen to form an enolate ion which reacts with the electrophilic halogen to give an α-halo ketone. The step continues until all the α protons are substituted to form a trihalomethyl ketone. The resulting molecule is unstable, and in the presence of a hydroxide base, it readily undergoes nucleophilic...

Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule

Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule

If a set of reactants can yield multiple constitutional isomers, but one of the isomers is obtained as the major product, the reaction is said to be regioselective. In such reactions, bond formation or breaking is favored at one reaction site over others.
The hydrohalogenation of an unsymmetrical alkene can yield two haloalkane products, depending on which vinylic carbon takes up the halogen. However, one product usually predominates, where hydrogen adds to the vinylic carbon bearing the...

Radical Halogenation: Thermodynamics

Radical Halogenation: Thermodynamics

The thermodynamic favorability of a reaction is determined by the change in Gibbs free energy (ΔG). ΔG has two components- enthalpy (ΔH) and entropy (ΔS). The entropy component is negligible for alkane halogenation because the number of reactants and product molecules are equal. In this case, the ΔG is governed only by the enthalpy component. The most crucial factor that determines ΔH is the strength of the bonds. ΔH can be determined by comparing the energy...

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Related Experiment Video

Updated: Apr 25, 2026

From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding

From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding

Published on: March 24, 2018

A new tool to guide halofunctionalization reactions: the halenium affinity (HalA) scale.

Kumar Dilip Ashtekar¹, Nastaran Salehi Marzijarani, Arvind Jaganathan

¹Engineering and Process Sciences, The Dow Chemical Company , Midland, Michigan 48674, United States.

Journal of the American Chemical Society

|August 26, 2014

Summary

This summary is machine-generated.

We introduce HalA, a new scale measuring halenium ion affinity, to predict reaction selectivity. This tool quantifies bond strengths, aiding in the discovery of new chemical reactions.

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Area of Science:

Organic Chemistry
Computational Chemistry

Background:

Predicting chemoselectivity in reactions with multiple nucleophilic sites is challenging.
Existing methods often rely on qualitative chemical intuition, which can be insufficient for complex systems.

Purpose of the Study:

To introduce a novel quantitative descriptor, halenium affinity (HalA), for assessing functional group bond strengths to halenium ions.
To develop a predictive tool for chemoselectivity in halofunctionalization reactions.

Main Methods:

Development of the HalA scale to rank potential halenium ion acceptors.
Classification of various Lewis bases, including alkenes, amines, amides, carbonyls, and ethers, on the HalA scale.
Utilizing HalA computations to intrinsically account for electronic, steric, anchimeric, and stereoelectronic effects.

Main Results:

The HalA scale provides a quantitative measure of halenium ion stabilization by different functional groups.
Alkenes, amines, amides, carbonyls, and ethers have been successfully classified.
HalA computations offer quantitative assessments that go beyond traditional chemical intuition.

Conclusions:

The HalA scale enables rapid and straightforward prediction of chemoselectivity in complex reaction systems.
This theoretical-experimental approach facilitates the prediction and identification of novel chemical reactions.
HalA serves as a valuable tool for understanding and controlling reactivity in halofunctionalization.