Search research articles

ABOUT JoVE

Overview Leadership Blog JoVE Help Center

AUTHORS

Publishing Process Editorial Board Scope & Policies Peer Review FAQ Submit

LIBRARIANS

Testimonials Subscriptions Access Resources Library Advisory Board FAQ

RESEARCH

JoVE Journal Methods Collections JoVE Encyclopedia of Experiments Archive

EDUCATION

JoVE Core JoVE Business JoVE Science Education JoVE Lab Manual Faculty Resource Center Faculty Site

Terms & Conditions of Use

Related Concept Videos

Preparation of Diols and Pinacol Rearrangement

Preparation of Diols and Pinacol Rearrangement

Compounds bearing two hydroxyl groups are known as diols. When the hydroxyl groups are located on adjacent carbon atoms, the diols are called vicinal diols or glycols. Under acidic conditions, vicinal diols undergo a specific reaction called pinacol rearrangement.
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.

Nomenclature of Carboxylic Acid Derivatives: Acid Halides, Esters, and Acid Anhydrides

Nomenclature of Carboxylic Acid Derivatives: Acid Halides, Esters, and Acid Anhydrides

Naming Acid Halides
The IUPAC and common names of acid halides are derived from the corresponding carboxylic acids, by changing “ic acid” to “yl halide.” For example, as shown below, the IUPAC name ethanoyl chloride is derived from ethanoic acid, and the common name, acetyl chloride, is obtained from acetic acid.

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.

Alkylation of β-Diester Enolates: Malonic Ester Synthesis

Alkylation of β-Diester Enolates: Malonic Ester Synthesis

Malonic ester synthesis is a method to obtain α substituted carboxylic acids from ꞵ-diesters such as diethyl malonate and alkyl halides.

[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.

Organic Compounds

Organic Compounds

All living things are formed mostly of carbon compounds called organic compounds. The category of organic compounds includes both natural and synthetic compounds that contain carbon. Although a single, precise definition has yet to be identified by the chemistry community, most agree that a defining trait of organic molecules is the presence of carbon as the principal element, bonded to hydrogen and other carbon atoms. However, some carbon-containing compounds such as carbonates, cyanides, and...

You might also read

Related Articles

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

Sort by

Same author

Threefold helical assembly <i>via</i> hy-droxy hydrogen bonds: the 2:1 co-crystal of bi-cyclo-[3.3.0]octane-<i>endo</i>-3,<i>endo</i>-7-diol and bi-cyclo-[3.3.0]octane-<i>endo</i>-3,<i>exo</i>-7-diol.

Acta crystallographica. Section E, Crystallographic communications·2021

Same author

Formation of an unexpected 3,3-diphenyl-3<i>H</i>-indazole through a facile intramolecular [2 + 3] cycloaddition of the diazo intermediate.

Beilstein journal of organic chemistry·2019

Same author

Antiproliferative activities of alkaloid-like compounds.

MedChemComm·2018

Same author

Solvent-guest control of two extremely similar tetrahydrofuran inclusion structures.

Acta crystallographica Section B, Structural science, crystal engineering and materials·2014

Same author

Preparation of α- and β-D-glucoseptanose pentaacetates.

Carbohydrate research·2012

Same author

Regulation of π-stacked anthracene arrangement for fluorescence modulation of organic solid from monomer to excited oligomer emission.

Chemistry (Weinheim an der Bergstrasse, Germany)·2012

Search research articles

Related Experiment Video

Updated: Jun 1, 2026

Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile

Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile

Published on: October 30, 2018

2,8-Dimethyl-tricyclo-[5.3.1.1]dodecane-syn-2,syn-8-diol-propanoic acid (1/1).

Yuji Mizobe¹, Roger Bishop, Donald C Craig

¹School of Chemistry, University of New South Wales, Sydney, New South Wales 2052, Australia.

Acta Crystallographica. Section E, Structure Reports Online

|May 18, 2011

Summary

This study reveals a novel 1:1 cocrystal formed between a diol and propanoic acid. The crystal structure features infinite chains stabilized by hydrogen bonds, creating a layered arrangement with opposite handedness in adjacent layers.

More Related Videos

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols

Published on: April 4, 2014

A Strategy for Sensitive, Large Scale Quantitative Metabolomics

A Strategy for Sensitive, Large Scale Quantitative Metabolomics

Published on: May 27, 2014

Related Experiment Videos

Last Updated: Jun 1, 2026

Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile

Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile

Published on: October 30, 2018

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols

Published on: April 4, 2014

A Strategy for Sensitive, Large Scale Quantitative Metabolomics

A Strategy for Sensitive, Large Scale Quantitative Metabolomics

Published on: May 27, 2014

Area of Science:

Crystallography
Supramolecular Chemistry
Organic Chemistry

Background:

Cocrystals are crystalline solids composed of two or more different molecules in a stoichiometric ratio.
Hydrogen bonding plays a crucial role in the assembly of supramolecular structures.
Understanding crystal packing and intermolecular interactions is essential for materials science.

Purpose of the Study:

To characterize the crystal structure of a novel 1:1 diol/carboxylic acid cocrystal.
To elucidate the hydrogen bonding network and supramolecular architecture.
To investigate the disorder in the crystal lattice.

Main Methods:

Single-crystal X-ray diffraction analysis.
Crystallographic data collection and refinement.
Analysis of hydrogen bonding and crystal packing.

Main Results:

The racemic title compound crystallizes as a 1:1 diol/propanoic acid cocrystal in the monoclinic space group P2(1)/c.
Infinite chains of alcohol-carboxylic acid-alcohol synthons form a layered structure stabilized by hydrogen bonds.
The crystal lattice exhibits disorder in the central carbon atom of the diol and the methyl group of the propanoic acid.

Conclusions:

The study successfully determined the crystal structure and supramolecular assembly of the diol-propanoic acid cocrystal.
The hydrogen bonding pattern leads to a unique layered structure with chiral recognition potential.
The observed disorder provides insights into the flexibility and packing of the molecules within the crystal lattice.