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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.
Structure and Nomenclature of Ethers02:28

Structure and Nomenclature of Ethers

Structure and Bonding
Ethers are organic compounds with an ether functional group which is characterized by an oxygen atom connected to two — identical or different — alkyl, aryl, or vinyl groups. The C–O–C linkage in dimethyl ether — the simplest ether — has an approximately tetrahedral bond angle of 110.3 degrees. The oxygen atom is sp3- hybridized, with the C–O distance being about 140 pm.
Classification of Ethers
Based on their attached substituent groups, ethers can be classified into two...
[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement01:24

[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement

The Claisen rearrangement is a [3,3] sigmatropic rearrangement of allyl vinyl ethers to unsaturated carbonyl compounds. The rearrangement is a concerted pericyclic reaction proceeding via a chair-like transition state.
Ketones with Nonenolizable Aromatic Aldehydes: Claisen–Schmidt Condensation01:01

Ketones with Nonenolizable Aromatic Aldehydes: Claisen–Schmidt Condensation

Benzaldehyde, like formaldehyde, lacks an α hydrogen and cannot enolize to form an enolate. Hence, the reaction of benzaldehyde with a ketone in the presence of an aqueous base forms a single crossed product. This reaction is referred to as Claisen–Schmidt condensation.
As the self-condensation of ketones is generally not favored in basic conditions, the self-condensed products do not form in the reaction between ketones and benzaldehyde. The general reaction of Claisen–Schmidt condensation is...
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.

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Related Experiment Video

Updated: Jun 1, 2026

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)
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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)

Published on: June 20, 2014

(E)-1-(4-Chloro-phen-yl)ethanone semi-carbazone.

Hoong-Kun Fun, Ching Kheng Quah, Mahesh Padaki

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

    This study details the crystal structure of a novel semicarbazone compound, revealing intricate hydrogen bonding patterns. These interactions form unique molecular trimers and 2D networks, enhancing crystal stability.

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    Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
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    Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
    07:12

    Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions

    Published on: July 17, 2020

    Area of Science:

    • Crystallography
    • Chemical Physics
    • Materials Science

    Background:

    • Semicarbazone derivatives are known for diverse biological activities.
    • Understanding the solid-state structure is crucial for predicting chemical properties and applications.

    Purpose of the Study:

    • To elucidate the crystal structure of the title compound C(9)H(10)ClN(3)O.
    • To investigate the intermolecular interactions and their role in crystal packing.
    • To characterize the hydrogen bonding network and its influence on the solid-state architecture.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
    • Analysis of bond lengths, bond angles, and dihedral angles provided geometric insights.
    • Hydrogen bond analysis (N-H⋯O, N-H⋯N, C-H⋯O) was performed to identify intermolecular interactions.
    • Topological analysis of the hydrogen bond network was conducted to characterize the resulting supramolecular structures.

    Main Results:

    • The semicarbazone group exhibits near planarity (r.m.s. deviation of 0.054 Å).
    • A significant dihedral angle of 30.46° exists between the semicarbazone plane and the benzene ring.
    • Intermolecular N-H⋯O and N-H⋯N hydrogen bonds form R(2)(2)(9) and R(2)(2)(8) ring motifs, leading to a rare molecular trimer.
    • Further stabilization is achieved through R(2)(1)(7) ring motifs formed by N-H⋯O and C-H⋯O hydrogen bonds.
    • These interactions result in the formation of two-dimensional networks parallel to the (100) plane.

    Conclusions:

    • The crystal structure is stabilized by a complex network of hydrogen bonds, including N-H⋯O, N-H⋯N, and C-H⋯O interactions.
    • The formation of a molecular trimer and 2D networks highlights the intricate self-assembly capabilities of this semicarbazone derivative.
    • The findings provide valuable insights into the structure-property relationships of semicarbazone compounds in the solid state.