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

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.
Acidity and Basicity of Alcohols and Phenols02:36

Acidity and Basicity of Alcohols and Phenols

Like water, alcohols are weak acids and bases. This is attributed to the polarization of the O–H bond making the hydrogen partially positive. Moreover, the electron pairs on the oxygen atom of alcohol make it both basic and nucleophilic. Protonation of an alcohol converts hydroxide, a poor leaving group, into water—a good one. The two acid–base equilibria corresponding to ethanol are depicted below.
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.
Reactions at the Benzylic Position: Halogenation01:11

Reactions at the Benzylic Position: Halogenation

Benzylic halogenation takes place under conditions that favor radical reactions such as heat, light, or a free radical initiator like peroxide.
Structure and Nomenclature of Alcohols and Phenols02:23

Structure and Nomenclature of Alcohols and Phenols

Overview
Alcohols are one of the most important functional groups in organic chemistry. The name of alcohol comes from the hydrocarbon from which it is derived. Alcohols are organic molecules containing the functional hydroxyl or –OH group directly bonded to carbon. Phenols have an OH group directly attached to a benzene ring. While alcohols are colorless, phenol is a white crystalline compound with a characteristic "hospital smell" odor.
As with other organic compounds, alcohols and phenols...
Hydrolysis of Chlorobenzene to Phenol: Dow Process01:10

Hydrolysis of Chlorobenzene to Phenol: Dow Process

Simple aryl halides do not react with nucleophiles under normal conditions. However, the reaction can proceed under drastic conditions involving high temperatures and high pressure to give the substituted products. For example, chlorobenzene is converted to phenol using aqueous sodium hydroxide at 350 °C under high pressure by the Dow process. The reaction follows an elimination-addition mechanism involving a benzyne intermediate. Here, the chloride ion is eliminated to generate the benzyne...

You might also read

Related Articles

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

Sort by
Same author

Low-Dimensional Silver(I) Coordination Polymers Based on a Flexible Dithione Ligand: Anion-Dependent Structures and Iodine Capture.

Langmuir : the ACS journal of surfaces and colloids·2026
Same author

Tuning Pd Catalyst Performance in Transfer Hydrogenation Reactions: Ligand Electronic Properties, Hydrogen Source and Ionic Liquid-Mediated-Effects.

Inorganic chemistry·2026
Same author

l-Valine ethyl ester hydro-chloride.

IUCrData·2026
Same author

2-(4-Chloro-phen-yl)-1,3-dioxane - localization of hydrogen atoms.

IUCrData·2026
Same author

Synthesis, Crystal Structure, Antitumor, and Antimicrobial Activity of Novel Copper(II) Complexes with a Coumarin Derivative Containing a Histamine Substituent.

Molecules (Basel, Switzerland)·2026
Same author

Reactivity of δ-Functionalized Para-Quinone Methides in Nucleophilic Addition Reactions.

Chemistry (Weinheim an der Bergstrasse, Germany)·2025

Related Experiment Video

Updated: Jun 5, 2026

Elucidating the Metabolism of 2,4-Dibromophenol in Plants
06:54

Elucidating the Metabolism of 2,4-Dibromophenol in Plants

Published on: February 10, 2023

2,3,4,5,6-Penta-bromo-phenol.

Richard Betz1, Peter Klüfers, Peter Mayer

  • 1Department Chemie und Biochemie, Ludwig-Maximilians-Universität, Butenandtstrasse 5-13 (Haus D), 81377 München, Germany.

Acta Crystallographica. Section E, Structure Reports Online
|January 5, 2011
PubMed
Summary

This study details the crystal structure of perbrominated phenol (C(6)HBr(5)O), revealing molecular symmetry and hydrogen bonding. The findings describe the arrangement of molecules in the solid state, highlighting specific intermolecular interactions.

More Related Videos

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
19:58

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions

Published on: July 30, 2017

Scale-up Chemical Synthesis of Thermally-activated Delayed Fluorescence Emitters Based on the Dibenzothiophene-S,S-Dioxide Core
08:51

Scale-up Chemical Synthesis of Thermally-activated Delayed Fluorescence Emitters Based on the Dibenzothiophene-S,S-Dioxide Core

Published on: October 24, 2017

Related Experiment Videos

Last Updated: Jun 5, 2026

Elucidating the Metabolism of 2,4-Dibromophenol in Plants
06:54

Elucidating the Metabolism of 2,4-Dibromophenol in Plants

Published on: February 10, 2023

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
19:58

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions

Published on: July 30, 2017

Scale-up Chemical Synthesis of Thermally-activated Delayed Fluorescence Emitters Based on the Dibenzothiophene-S,S-Dioxide Core
08:51

Scale-up Chemical Synthesis of Thermally-activated Delayed Fluorescence Emitters Based on the Dibenzothiophene-S,S-Dioxide Core

Published on: October 24, 2017

Area of Science:

  • * Organic Chemistry
  • * Crystallography
  • * Solid-State Chemistry

Background:

  • * Phenol derivatives are fundamental in organic chemistry.
  • * Perbromination introduces unique electronic and steric properties.
  • * Understanding crystal packing is crucial for predicting material properties.

Purpose of the Study:

  • * To elucidate the crystal structure of the perbrominated phenol derivative, C(6)HBr(5)O.
  • * To analyze the molecular symmetry and intermolecular interactions within the crystal lattice.
  • * To characterize the bonding and packing arrangements of this highly brominated organic compound.

Main Methods:

  • * Single-crystal X-ray diffraction was employed to determine the three-dimensional structure.
  • * Analysis of bond lengths, bond angles, and intermolecular contacts was performed.
  • * Hydrogen bonding and other non-covalent interactions were identified and characterized.

Main Results:

  • * The molecule C(6)HBr(5)O exhibits non-crystallographic mirror symmetry.
  • * Normal carbon-bromine bond lengths were observed.
  • * Infinite strands of molecules are formed via O-H⋯O hydrogen bonds, with dispersive Br⋯Br contacts also present.

Conclusions:

  • * The crystal structure of perbrominated phenol is characterized by specific hydrogen bonding and Br⋯Br interactions.
  • * The molecular symmetry and packing arrangement provide insights into the solid-state behavior of highly halogenated phenols.
  • * The study contributes to the understanding of structure-property relationships in organic materials.