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Related Concept Videos

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...
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.
Formation of Halohydrin from Alkenes02:41

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

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Nomenclature of Aromatic Compounds with Multiple Substituents01:11

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When more than one substituent is present on the benzene ring, the IUPAC nomenclature depends on the number of substituents present.
For disubstituted benzene derivatives, with two groups attached to the benzene ring, three constitutional isomers are possible. For example, consider dimethyl benzene, often called xylene, where the second methyl group can be substituted at the second, third, or fourth carbon. The relative position of the substituents is represented by prefixes ortho, meta, or...

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2,3-Dichloro-benzene-1,4-diol.

Paul D Ahn1, Roger Bishop, Donald C Craig

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

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

This study details the crystal structure of an achiral compound, C(6)H(4)Cl(2)O(2). Molecular interactions, including hydrogen bonds and halogen bonds, form layered structures and chains.

Area of Science:

  • Crystallography
  • Solid-state chemistry
  • Supramolecular chemistry

Background:

  • Understanding intermolecular forces is crucial for predicting and controlling material properties.
  • Crystal structure analysis provides fundamental insights into molecular arrangement and interactions.

Purpose of the Study:

  • To elucidate the crystal structure of the achiral compound C(6)H(4)Cl(2)O(2).
  • To identify and characterize the intermolecular interactions governing the compound's solid-state architecture.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
  • Analysis of interatomic distances and angles was performed to identify non-covalent interactions.

Main Results:

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  • The compound C(6)H(4)Cl(2)O(2) crystallizes with a layered structure.
  • O-H⋯O hydrogen bonds link molecules into layers.
  • Chains of Cl⋯Cl⋯Cl interactions (3.274(2) and 3.742(2) Å) exist between layers.
  • Additional C-H⋯Cl (2.97, 3.17 Å) and Cl⋯π (3.40, 3.54 Å) interactions were observed.

Conclusions:

  • The crystal packing of C(6)H(4)Cl(2)O(2) is dictated by a combination of hydrogen bonding, halogen bonding, and other non-covalent interactions.
  • These interactions result in a unique layered and chained supramolecular architecture.
  • The detailed structural analysis provides a foundation for further studies on related compounds and materials.