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Related Concept Videos

Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis01:07

Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis

Acetoacetic ester synthesis is a method to obtain ketones from alkyl halides and β-keto esters. The reaction occurs in the presence of an alkoxide base that abstracts the acidic proton of the β-keto esters. The step results in an enolate ion which is doubly stabilized. The enolate then reacts with an alkyl halide via the SN2 process to produce an alkylated ester intermediate with a new C–C bond. The hydrolysis of the intermediate, followed by acidification, results in an alkylated β-keto acid.
Alkylation of β-Diester Enolates: Malonic Ester Synthesis01:14

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Malonic ester synthesis is a method to obtain α substituted carboxylic acids from ꞵ-diesters such as diethyl malonate and alkyl halides.
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...
Nomenclature of Carboxylic Acid Derivatives: Acid Halides, Esters, and Acid Anhydrides01:16

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Naming Acid Halides
The IUPAC and common names of acid halides are derived from the corresponding carboxylic acids, by changing “ic acid” to “yl halide.” For example, as shown below, the IUPAC name ethanoyl chloride is derived from ethanoic acid, and the common name, acetyl chloride, is obtained from acetic acid.
α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview01:19

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The pinacol and McMurry reactions involve the reductive coupling of ketones or aldehydes. Similarly, the bimolecular reductive coupling of two ester molecules in the presence of sodium metal in an aprotic solvent yields an α-hydroxy ketone product. The α-hydroxy ketone is also called acyloin, so the reaction is referred to as ‘acyloin condensation.’
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Structures of Carboxylic Acid Derivatives

Structure of Carboxylic Acid Derivatives
Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
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Related Experiment Video

Updated: May 11, 2026

Facile Preparation of 4-Substituted Quinazoline Derivatives
11:51

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Published on: February 15, 2016

Ethyl 2-(quinolin-8-yl-oxy)acetate monohydrate.

Mohan Kumar1, C Mallikarjunaswamy, M A Sridhar

  • 1Department of Studies in Physics, Manasagangotri, University of Mysore, Mysore 570 006, India.

Acta Crystallographica. Section E, Structure Reports Online
|May 2, 2013
PubMed
Summary

This study details the crystal structure of a novel ethyl ester derivative of quinoline. Molecular interactions, including hydrogen bonds and crystal packing, were analyzed to understand its solid-state properties.

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Area of Science:

  • Crystallography
  • Organic Chemistry
  • Materials Science

Background:

  • Quinoline derivatives are important scaffolds in medicinal chemistry and materials science.
  • Understanding the solid-state structure of organic compounds is crucial for predicting their physical and chemical properties.

Purpose of the Study:

  • To elucidate the crystal structure of a specific ethyl ester quinoline derivative.
  • To investigate the intermolecular interactions and hydrogen bonding in the crystal lattice.
  • To characterize the molecular conformation and packing arrangement.

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.
  • Identification and analysis of hydrogen bonding networks and other intermolecular interactions.

Main Results:

  • The crystal structure of C13H13NO3·H2O was determined.
  • A small dihedral angle (7.94°) was observed between the ethyl ester group and the quinoline ring system.
  • Water molecules participate in O-H⋯O and O-H⋯N hydrogen bonds with the quinoline derivative.
  • C-H⋯O hydrogen bonds link molecules into chains along the [100] direction.

Conclusions:

  • The study provides a detailed crystallographic analysis of the ethyl ester quinoline derivative.
  • The identified hydrogen bonding patterns and molecular arrangement offer insights into the compound's solid-state behavior.
  • This structural information can be valuable for the design and synthesis of related quinoline-based materials.