Jove
Visualize
Contact Us
JoVE
x logofacebook logolinkedin logoyoutube logo
ABOUT JoVE
OverviewLeadershipBlogJoVE Help Center
AUTHORS
Publishing ProcessEditorial BoardScope & PoliciesPeer ReviewFAQSubmit
LIBRARIANS
TestimonialsSubscriptionsAccessResourcesLibrary Advisory BoardFAQ
RESEARCH
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchive
EDUCATION
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualFaculty Resource CenterFaculty Site
Terms & Conditions of Use
Privacy Policy
Policies

Related Concept Videos

Alkyl Halides02:45

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 Alkenes02:46

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 Alkenes02:41

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 Addition to Alkynes: Halogenation02:38

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.
Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene01:14

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.
Acid-Catalyzed α-Halogenation of Aldehydes and Ketones01:21

Acid-Catalyzed α-Halogenation of Aldehydes and Ketones

By replacing an α-hydrogen with a halogen, acid-catalyzed α-halogenation of aldehydes or ketones yields a monohalogenated product
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic halogen to form a...

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by
Same author

Anterior Intercostal Artery Perforator Flap for Delayed Implant Exposure Salvage After Prepectoral Breast Reconstruction.

Aesthetic surgery journal. Open forum·2026
Same author

An open-access dataset of odontocete acoustic signals from the Madeira archipelago.

Scientific data·2026
Same author

Acoustic characterization of sperm whale (Physeter macrocephalus) population structure and social organization in the South China Sea.

The Journal of the Acoustical Society of America·2026
Same author

Preliminary characterization of underwater noise from a salmon farm in northern Patagonia.

Marine pollution bulletin·2026
Same author

Seminal plasma concentrations of long-acting cabotegravir in men receiving HIV pre-exposure prophylaxis.

Antimicrobial agents and chemotherapy·2026
Same author

Identification and classification of repeated whistle types from free-ranging rough-toothed dolphins (Steno bredanensis).

Scientific reports·2026
Same journal

RETRACTED: Atta et al. Effect of Montmorillonite Nanogel Composite Fillers on the Protection Performance of Epoxy Coatings on Steel Pipelines. <i>Molecules</i> 2017, <i>22</i>, 905.

Molecules (Basel, Switzerland)·2026
Same journal

Correction: Chen et al. Chemical Composition of <i>Litsea pungens</i> Essential Oil and Its Potential Antioxidant and Antimicrobial Activities. <i>Molecules</i> 2023, <i>28</i>, 6835.

Molecules (Basel, Switzerland)·2026
Same journal

Correction: Ruan et al. Comparison of Extraction, Isolation, Purification, Structural Characterization and Immunomodulatory Activity of Polysaccharides from Two Species of <i>Cistanche</i>. <i>Molecules</i> 2025, <i>30</i>, 4754.

Molecules (Basel, Switzerland)·2026
Same journal

Correction: Li et al. Gastrodin Ameliorates Cognitive Dysfunction in Vascular Dementia Rats by Suppressing Ferroptosis via the Regulation of the Nrf2/Keap1-GPx4 Signaling Pathway. <i>Molecules</i> 2022, <i>27</i>, 6311.

Molecules (Basel, Switzerland)·2026
Same journal

Correction: Zueva et al. Steady-State Kinetics of Enzyme-Catalyzed Hydrolysis of Echothiophate, a P-S Bonded Organophosphorus as Monitored by Spectrofluorimetry. <i>Molecules</i> 2020, <i>25</i>, 1371.

Molecules (Basel, Switzerland)·2026
Same journal

1,4-Diazatriphenylene and Its Hetero-Fused Analogs: Synthesis and Applications.

Molecules (Basel, Switzerland)·2026
See all related articles

Related Experiment Video

Updated: May 9, 2026

From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
06:44

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

Published on: March 24, 2018

Halogen bonding in (Z)-2-iodocinnamaldehyde.

Pakorn Bovonsombat1, Francesco Caruso, Andrew Jdaydani

  • 1Mahidol University International College, Mahidol University, Salaya Campus, Nakorn Pathom 73170, Thailand. pakorn.bov@mahidol.ac.th

Molecules (Basel, Switzerland)
|July 27, 2013
PubMed
Summary
This summary is machine-generated.

The study reveals that a specific compound exhibits a planar molecular structure, contrary to expectations. This planarity is attributed to the carbonyl double bond and supported by a weak halogen bond interaction.

More Related Videos

Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
06:31

Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators

Published on: November 27, 2015

Synthesis and Purification of Iodoaziridines Involving Quantitative Selection of the Optimal Stationary Phase for Chromatography
10:14

Synthesis and Purification of Iodoaziridines Involving Quantitative Selection of the Optimal Stationary Phase for Chromatography

Published on: May 16, 2014

Related Experiment Videos

Last Updated: May 9, 2026

From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
06:44

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

Published on: March 24, 2018

Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
06:31

Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators

Published on: November 27, 2015

Synthesis and Purification of Iodoaziridines Involving Quantitative Selection of the Optimal Stationary Phase for Chromatography
10:14

Synthesis and Purification of Iodoaziridines Involving Quantitative Selection of the Optimal Stationary Phase for Chromatography

Published on: May 16, 2014

Area of Science:

  • Organic Chemistry
  • Crystallography
  • Computational Chemistry

Background:

  • The bulkiness of iodine atoms typically suggests non-planar molecular conformations.
  • Understanding molecular geometry is crucial for predicting chemical properties and interactions.

Purpose of the Study:

  • To determine the experimental and theoretical molecular structure of the title compound.
  • To investigate the factors contributing to the observed planarity.
  • To explore the presence and nature of halogen bonding.

Main Methods:

  • Single crystal X-ray diffraction for experimental structure determination.
  • Density Functional Theory (DFT) calculations for theoretical confirmation.
  • Analysis of intermolecular distances and angles.

Main Results:

  • The compound adopts a planar conformation, contradicting initial expectations based on iodine atom bulkiness.
  • Planarity is linked to the presence of the carbonyl double bond.
  • Experimental and theoretical data indicate a weak halogen bond interaction (I•••O) between molecules.
  • DFT calculations suggest a stronger halogen bond than observed in crystal packing.

Conclusions:

  • The planarity of the molecule is primarily due to the carbonyl double bond, not crystal packing forces.
  • A significant halogen bond interaction exists, influencing molecular arrangement and properties.
  • The study provides insights into structure-property relationships in organic molecules.