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Related Concept Videos

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...
Preparation of Diols and Pinacol Rearrangement01:57

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.
Carboxylic Acids to Methylesters: Alkylation using Diazomethane01:33

Carboxylic Acids to Methylesters: Alkylation using Diazomethane

Carboxylic acids react with diazomethane in an ether solvent via alkylation at the carboxylate oxygen atom to give methyl esters of the corresponding acid with excellent yields.
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.
meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H01:13

meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H

All meta-directing substituents are deactivating groups. These substituents withdraw electrons from the aromatic ring, making the ring less reactive toward electrophilic substitution. For example, the nitration of nitrobenzene is 100,000 times slower than that of benzene because of the deactivating effect of the nitro group. The first step in an electrophilic aromatic substitution is the addition of an electrophile to form a resonance-stabilized carbocation. The energy diagrams for the...
Reactivity of Enols01:18

Reactivity of Enols

Enols are a class of compounds where a hydroxyl group is attached to a carbon–carbon double bond, which implies that it is a vinyl alcohol. A carbonyl compound with an α hydrogen undergoes keto–enol tautomerism and remains in equilibrium with its tautomer, the enol form. Usually, the keto tautomer is present in a higher concentration than the enol tautomer due to the higher bond energy of C=O compared to C=C. Moreover, the direction of the keto–enol equilibrium is governed by factors like...

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Related Experiment Video

Updated: Jun 5, 2026

Modification and Functionalization of the Guanidine Group by Tailor-made Precursors
09:45

Modification and Functionalization of the Guanidine Group by Tailor-made Precursors

Published on: April 27, 2017

2,2'-(3,5-Dinitro-benzyl-imino)diethanol.

Gul S Khan1, George R Clark, David Barker

  • 1Chemistry Department, The University of Auckland, Private Bag 92019, Auckland, New Zealand.

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

Researchers synthesized a novel compound using (3,5-dinitro-benzyl)methane-sulfonate and diethanolamine. Structural analysis revealed four independent molecules forming hydrogen-bonded sheets, with van der Waals forces between them.

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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
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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

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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
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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

Area of Science:

  • Organic Chemistry
  • Crystallography
  • Supramolecular Chemistry

Background:

  • The synthesis of novel organic compounds is crucial for developing new materials.
  • Understanding molecular interactions and crystal packing is fundamental in solid-state chemistry.

Purpose of the Study:

  • To synthesize and characterize a new compound with the chemical formula C(11)H(15)N(3)O(6).
  • To investigate the crystal structure and intermolecular interactions of the synthesized compound.

Main Methods:

  • Chemical synthesis involving the reaction of (3,5-dinitro-benzyl)methane-sulfonate with diethanolamine.
  • Single-crystal X-ray diffraction to determine the crystal structure and molecular conformation.
  • Analysis of hydrogen bonding and van der Waals interactions within the crystal lattice.

Main Results:

  • Successful synthesis of the title compound, C(11)H(15)N(3)O(6).
  • The asymmetric unit contains four independent molecules with variations in rotational conformation.
  • A hydrogen-bonding network involving hydroxyl groups links molecules into sheets.
  • Van der Waals forces mediate interactions between these molecular sheets.

Conclusions:

  • The study provides a detailed structural characterization of a newly synthesized organic compound.
  • The findings elucidate the role of hydrogen bonding in the supramolecular assembly of the molecules.
  • This work contributes to the understanding of crystal engineering and molecular design.