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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 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.

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.

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 HX to 1,3-Butadiene

Electrophilic 1,2- and 1,4-Addition of HX to 1,3-Butadiene

The electrophilic addition of hydrogen halides such as HBr to alkenes and nonconjugated dienes gives a single product as per Markovnikov’s rule.

Cationic Chain-Growth Polymerization: Mechanism

Cationic Chain-Growth Polymerization: Mechanism

The cationic polymerization mechanism consists of three steps: initiation, propagation, and termination. In the initiation step of the polymerization process, the π bond of a monomer gets protonated by the Lewis acid catalyst, which is formed from boron trifluoride and water. The protonation of the π bond generates a carbocation stabilized by the electron‐donating group. In the propagation step, the π bond of the second monomer acts as a nucleophile and attacks the generated carbocation,...

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Related Experiment Video

Updated: May 13, 2026

Synthesis of Cyclic Polymers and Characterization of Their Diffusive Motion in the Melt State at the Single Molecule Level

Synthesis of Cyclic Polymers and Characterization of Their Diffusive Motion in the Melt State at the Single Molecule Level

Published on: September 26, 2016

A multistep single-crystal-to-single-crystal bromodiacetylene dimerization.

Tobias N Hoheisel¹, Stephen Schrettl, Roman Marty

¹Ecole Polytechnique Fédérale de Lausanne, Institute of Materials, Laboratory of Macromolecular and Organic Materials, EPFL STI IMX LMOM, Building MXG 037, Station 12, CH-1015 Lausanne, Switzerland.

Nature Chemistry

|March 21, 2013

Summary

This study details a novel single-crystal-to-single-crystal reaction where a bromodiacetylene undergoes dimerization via [2 + 1] photocycloaddition. This transformation yields valuable dibromodiethynylethenes, showcasing crystal-engineering potential.

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Published on: February 7, 2017

Area of Science:

Organic Chemistry
Solid-State Chemistry
Crystallography

Background:

Organic molecules exhibit unique properties in crystalline states due to packing constraints.
Single-crystal-to-single-crystal (SCSC) reactions allow for controlled transformations without losing structural integrity.

Purpose of the Study:

To investigate the SCSC dimerization of a bromodiacetylene.
To elucidate the reaction mechanism and explore its synthetic utility.

Main Methods:

Single-crystal X-ray diffraction to monitor the transformation.
Density Functional Theory (DFT) computations to model the reaction pathway.
Preparative scale synthesis.

Main Results:

Observed an SCSC dimerization involving significant atom displacements and bond rearrangements.
Identified a [2 + 1] photocycloaddition mechanism favored by crystal packing.
Achieved high conversion without loss of crystallinity and demonstrated preparative scalability.
Synthesized (E)-1,2-dibromo-1,2-diethynylethenes for the first time.

Conclusions:

The study expands the repertoire of SCSC reactions.
Highlights the potential of SCSC transformations as a synthetic tool for complex molecular architectures.
The synthesized compounds are valuable intermediates for molecular carbon scaffolds.