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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...
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.
Nitrosation of Enols01:19

Nitrosation of Enols

The nitrosation reaction is one of the methods of preparing 1,2-diketones. The enol tautomer of the starting ketone reacts with sodium nitrite in hydrochloric acid, generating the 1,2-diketone after hydrolysis.
Oxidation of Phenols to Quinones01:17

Oxidation of Phenols to Quinones

In the presence of oxidizing agents, phenols are oxidized to quinones. Quinones can be easily reduced back to phenols using mild reducing agents. The electron-donating hydroxyl group enhances the reactivity of the aromatic ring, enabling oxidation of the ring even in the absence of an α hydrogen.
o-hydroxy phenols are oxidized to o-quinones and p-hydroxy phenols to p-quinones. Such redox reactions involve the transfer of two electrons and two protons. The reversible redox property is crucial in...
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism01:37

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism

Nitrous acid is a relatively weak and unstable acid prepared in situ by the reaction of sodium nitrite and cold, dilute hydrochloric acid. In an acidic solution, the nitrous acid undergoes protonation when it loses water to form a nitrosonium ion—an electrophile. Nitrous acid reacts with primary amines to give diazonium salts. The reaction is called diazotization of primary amines.
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...

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Related Experiment Video

Updated: Jun 1, 2026

Continuous Flow Chemistry: Reaction of Diphenyldiazomethane with p-Nitrobenzoic Acid
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Published on: November 15, 2017

2-(2-Nitro-phen-yl)-1,3-dioxan-5-ol.

Jin Chen1, Xukang Ren, Zhaobo Li

  • 1State Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, Zhejiang University of Technology, Hangzhou 310014, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online
|May 18, 2011
PubMed
Summary

The crystal structure of C(10)H(11)NO(5) reveals a stable chair conformation for its 1,3-dioxane ring. Molecules form chains via intermolecular hydrogen bonds, optimizing crystal packing.

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Area of Science:

  • Crystallography
  • Organic Chemistry
  • Molecular Structure

Background:

  • Understanding molecular conformation and intermolecular interactions is crucial in crystal engineering.
  • The 1,3-dioxane ring is a common motif in organic molecules with diverse applications.
  • Steric and electronic factors influence the preferred conformation and packing of organic compounds.

Purpose of the Study:

  • To elucidate the crystal structure and molecular arrangement of the title compound, C(10)H(11)NO(5).
  • To investigate the conformational preferences of the 1,3-dioxane ring within the crystalline state.
  • To identify and characterize the intermolecular interactions governing crystal packing.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the three-dimensional structure.
  • Analysis of bond lengths, bond angles, and torsion angles provided conformational details.
  • Intermolecular interactions, including hydrogen bonding, were identified using crystallographic data.

Main Results:

  • The title compound, C(10)H(11)NO(5), crystallizes with a 1,3-dioxane ring adopting a chair conformation.
  • Both the hydroxyl and 2-nitrophenyl substituents are found in equatorial positions, minimizing steric strain.
  • Molecules are organized into chains along the b-axis through intermolecular O-H⋯O hydrogen bonds.

Conclusions:

  • The observed chair conformation with equatorial substituents is energetically favorable for the title compound.
  • Intermolecular hydrogen bonding plays a significant role in the self-assembly and stability of the crystal lattice.
  • This study provides valuable insights into structure-property relationships for related organic molecules.