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Related Concept Videos

IUPAC Nomenclature of Aldehydes01:16

IUPAC Nomenclature of Aldehydes

Aldehydes are named based on the systematic nomenclature rules set by the IUPAC. For acyclic aldehydes, the longest carbon chain containing the aldehydic (–CHO) group is considered the parent chain. The aldehyde is named by replacing the last letter “e” in the hydrocarbon name with “al”. For instance, a simple, seven-carbon-membered acyclic aldehyde is called heptanal, derived from heptane. The carbon chain is numbered starting from the aldehydic carbon, although the aldehydic carbon’s locant...
Nomenclature of Aromatic Compounds with a Single Substituent01:23

Nomenclature of Aromatic Compounds with a Single Substituent

Benzene is the simplest aromatic hydrocarbon or arene. The IUPAC names for simple monosubstituted benzene derivatives are derived by adding the substituent's name as a prefix to the parent benzene. For example, halobenzene, where the halogen could be fluoro (F), chloro (Cl), bromo (Br), and iodo (I).
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...
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...
Common Names of Aldehydes and Ketones01:11

Common Names of Aldehydes and Ketones

Some common aldehydes and ketones are popularly known by their common names used historically and predate the IUPAC nomenclature.
Common names of aldehydes are derived from the names of their corresponding acid. For instance, the two-carbon aldehyde–acetaldehyde derives its name from the corresponding acid–acetic acid. Similarly, formaldehyde derives its name from formic acid and benzaldehyde from benzoic acid.
Aliphatic ketones are named by suffixing the word “ketone” to the alphabetically...
Reactions of Aldehydes and Ketones: Baeyer–Villiger Oxidation01:22

Reactions of Aldehydes and Ketones: Baeyer–Villiger Oxidation

Baeyer–Villiger oxidation converts aldehydes to carboxylic acids and ketones to esters. The reaction uses peroxy acids or peracids and is often catalyzed by acid. The reaction is named after its pioneers, Adolf von Baeyer and Victor Villiger. The reaction is achieved by a wide range of peracids such as m-chloroperoxybenzoic acid (mCPBA), perbenzoic acid (C6H5COOOH), peracetic acid (CH3COOOH), hydrogen peroxide (H2O2), and tert-butyl hydroperoxide (t-BuOOH).
The carbonyl center is activated by...

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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
08:43

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Published on: January 19, 2016

4-(Prop-2-yn-1-yl-oxy)benzaldehyde.

Ikue Doi1, Tsunehisa Okuno

  • 1Department of Material Science and Chemistry, Wakayama University, Sakaedani, Wakayama 640-8510, Japan.

Acta Crystallographica. Section E, Structure Reports Online
|March 12, 2013
PubMed
Summary

This study reveals the coplanar structure of C10H8O2, highlighting effective conjugation. Molecular interactions in the crystal form a unique ladder-like arrangement through hydrogen bonds and pi-pi stacking.

Area of Science:

  • Crystallography
  • Molecular structure analysis
  • Organic chemistry

Background:

  • Understanding molecular planarity is crucial for predicting electronic properties.
  • Intermolecular interactions dictate crystal packing and material properties.

Purpose of the Study:

  • To elucidate the three-dimensional structure and intermolecular interactions of the title molecule, C10H8O2.
  • To investigate the electronic conjugation within the molecule based on its structural features.

Main Methods:

  • X-ray crystallography was employed to determine the crystal structure.
  • Analysis of atomic coordinates to assess molecular planarity (r.m.s. deviation).
  • Identification and analysis of intermolecular interactions, including pi-pi stacking and hydrogen bonds.

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Main Results:

  • The non-hydrogen atoms of C10H8O2 were found to be essentially coplanar (r.m.s. deviation = 0.0192 Å).
  • Effective conjugation was observed between the carbonyl group, benzene ring, and the propyn-yloxy oxygen lone pair.
  • Molecules form inversion dimers through pi-pi stacking (centroid-centroid distance = 3.5585(15) Å).
  • These dimers are further linked by Csp-H⋯O=C hydrogen bonds, resulting in a ladder-like crystal structure.

Conclusions:

  • The coplanar nature of C10H8O2 facilitates significant electronic conjugation.
  • The crystal structure is characterized by a unique ladder-like arrangement driven by pi-pi stacking and hydrogen bonding.
  • These findings provide insights into the structure-property relationships of this organic molecule.