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E2 Reaction: Kinetics and Mechanism

E2 Reaction: Kinetics and Mechanism

SN2 substitutions and E2 eliminations of alkyl halides proceed via a concerted pathway. While the nucleophile attacks the alpha carbon in SN2 reactions, it functions as a strong base and abstracts a beta hydrogen in the E2 mechanism. The rate-limiting transition state in E2 elimination reactions is characterized by partially broken carbon–hydrogen and carbon–halogen bonds and a partially formed pi bond between the alpha and beta carbons. The beta hydrogen and halide are eliminated...

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.

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...

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.

E1 Reaction: Kinetics and Mechanism

E1 Reaction: Kinetics and Mechanism

Here, in contrast to the E2 reaction mechanism, we delve into the aspects of the E1 reaction mechanism, which has two steps: rate-limiting loss of the leaving group and abstraction of the beta hydrogen by a weak base. Typically, the experimental proof for the E1 mechanism is via kinetic studies or isotope studies. While the former demonstrates the first-order kinetics—the dependence of the reaction solely on substrate concentration—the latter proves the abstraction of hydrogen only...

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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Related Experiment Video

Updated: Sep 29, 2025

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

An emerging deep eutectic solvent based on halogen-bonds.

Ruifen Shi¹, Dongkun Yu¹, Fengyi Zhou¹

¹Department of Chemistry, Renmin University of China, Beijing 100872, China. tcmu@ruc.edu.cn.

Chemical Communications (Cambridge, England)

|March 21, 2022

Summary

This summary is machine-generated.

Researchers developed novel deep eutectic solvents (DES) utilizing halogen bonding (XB). These new liquid mixtures, formed from quaternary ammonium salts and dihalogens, expand solvent possibilities.

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Area of Science:

Supramolecular Chemistry
Materials Science

Background:

Deep eutectic solvents (DES) are tunable solvents with broad applications.
Halogen bonding (XB) is a non-covalent interaction with potential for novel material design.

Purpose of the Study:

To explore a new class of deep eutectic solvents (DES) driven by halogen bonding (XB).
To investigate the formation mechanism of these novel DES.

Main Methods:

Synthesis of eutectic mixtures from quaternary ammonium salts and dihalogens.
Experimental characterization of the liquid mixtures.
Density Functional Theory (DFT) calculations to elucidate the formation mechanism.

Main Results:

Successful formation of a family of liquid eutectic mixtures.
Demonstration that halogen bonding can drive the formation of DES.
Elucidation of the formation mechanism through combined experimental and computational approaches.

Conclusions:

This work expands the scope of known DES systems.
Halogen bonding complexes represent a new avenue for solvent development.