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Related Concept Videos

Oxidations of Aldehydes and Ketones to Carboxylic Acids01:15

Oxidations of Aldehydes and Ketones to Carboxylic Acids

Oxidation of aldehydes and ketones results in the formation of carboxylic acids. Aldehydes, bearing hydrogen next to the carbonyl group, are easily oxidized compared to ketones. This is because an aldehydic proton can easily be abstracted during oxidation.
Aldehydes readily undergo oxidation in strong oxidizing agents such as potassium permanganate and chromic acid. The oxidation can also be carried out using mild oxidizing agents such as silver oxide. In fact, aldehydes can be easily oxidized...
Aldehydes and Ketones with Alcohols: Hemiacetal Formation01:19

Aldehydes and Ketones with Alcohols: Hemiacetal Formation

Similar to water, alcohols can add to the carbonyl carbon of the aldehydes and ketones. The addition of one molecule of alcohol to the carbonyl compound forms the hemiacetal or half acetal. As depicted below, in a hemiacetal, the carbon is directly linked to an OH and OR group.
Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview01:32

Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview

Cyanohydrins are compounds that contain –CN and –OH groups on the same carbon atom. They are formed by the nucleophilic addition of the cyanide ions to the carbonyl group. Cyanide ions are highly basic and nucleophilic and can be generated from HCN under aqueous conditions. However, since HCN is a weak acid, the number of cyanide ions generated is very small. Hence, a small amount of base or KCN/NaCN is added to HCN to increase the concentration of the cyanide ions in the reaction mixture.
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...
Crossed Aldol Reaction Using Weak Bases01:14

Crossed Aldol Reaction Using Weak Bases

This lesson deals with the crossed aldol reaction using weak bases. The self-condensation of an aldehyde having α hydrogen is prevented by adding it slowly to a mixture of formaldehyde and weak bases like hydroxide and alkoxide. Upon slow addition of the aldehyde, the base deprotonates the α carbon of the aldehyde to form the corresponding enolate. The enolate subsequently attacks the formaldehyde to form a single crossed product. Figure 1 depicts the aforementioned reaction.
Preparation of Aldehydes and Ketones from Alcohols, Alkenes, and Alkynes01:33

Preparation of Aldehydes and Ketones from Alcohols, Alkenes, and Alkynes

Aldehydes and ketones are prepared from alcohols, alkenes, and alkynes via different reaction pathways. Alcohols are the most commonly used substrates for synthesizing aldehydes and ketones. The conversion of alcohol to aldehyde, which involves the oxidation process, depends on the class of the alcohol used and the strength of the oxidizing agent. For instance, primary alcohol will form an aldehyde when treated with a weak oxidizing agent; however, it gets over-oxidized to a carboxylic acid in...

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Related Experiment Video

Updated: Jun 23, 2026

Capturing Actively Produced Microbial Volatile Organic Compounds from Human-Associated Samples with Vacuum-Assisted Sorbent Extraction
09:19

Capturing Actively Produced Microbial Volatile Organic Compounds from Human-Associated Samples with Vacuum-Assisted Sorbent Extraction

Published on: June 1, 2022

Acetaldehyde and hexanaldehyde from cultured white cells.

Hye-Won Shin1, Brandon J Umber, Simone Meinardi

  • 1Department of Biomedical Engineering, University of California, Irvine, Irvine, CA 92697, USA. hyewons@uci.edu

Journal of Translational Medicine
|May 1, 2009
PubMed
Summary
This summary is machine-generated.

Human immune cells, like neutrophils, generate measurable volatile organic compounds. This discovery opens new avenues for noninvasive detection of innate immune function in clinical settings.

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High Content Screening Analysis to Evaluate the Toxicological Effects of Harmful and Potentially Harmful Constituents (HPHC)
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Extraction of Aqueous Metabolites from Cultured Adherent Cells for Metabolomic Analysis by Capillary Electrophoresis-Mass Spectrometry
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Extraction of Aqueous Metabolites from Cultured Adherent Cells for Metabolomic Analysis by Capillary Electrophoresis-Mass Spectrometry

Published on: June 9, 2019

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Last Updated: Jun 23, 2026

Capturing Actively Produced Microbial Volatile Organic Compounds from Human-Associated Samples with Vacuum-Assisted Sorbent Extraction
09:19

Capturing Actively Produced Microbial Volatile Organic Compounds from Human-Associated Samples with Vacuum-Assisted Sorbent Extraction

Published on: June 1, 2022

High Content Screening Analysis to Evaluate the Toxicological Effects of Harmful and Potentially Harmful Constituents (HPHC)
11:38

High Content Screening Analysis to Evaluate the Toxicological Effects of Harmful and Potentially Harmful Constituents (HPHC)

Published on: May 10, 2016

Extraction of Aqueous Metabolites from Cultured Adherent Cells for Metabolomic Analysis by Capillary Electrophoresis-Mass Spectrometry
11:39

Extraction of Aqueous Metabolites from Cultured Adherent Cells for Metabolomic Analysis by Capillary Electrophoresis-Mass Spectrometry

Published on: June 9, 2019

Area of Science:

  • Biomedical Science
  • Analytical Chemistry
  • Immunology

Background:

  • Noninvasive detection of innate immune cell function, particularly neutrophil accumulation, presents a significant clinical challenge.
  • Investigating the potential for granulocytes to produce volatile organic compounds (VOCs) offers a novel diagnostic approach.

Purpose of the Study:

  • To explore the hypothesis that granulocytes generate volatile organic compounds.
  • To develop and validate a system for detecting and quantifying trace gases emitted by immune cells.

Main Methods:

  • A specialized bioreactor coupled with an analytical gas chromatography-mass spectrometry (GC-MS) system was engineered.
  • Human promyelocytic leukemia (HL60) cells, a model for neutrophil function, were cultured in serum-free medium.
  • Trace gas concentrations (parts per billion) in the cell culture headspace were accurately identified and quantified over time.

Main Results:

  • HL60 cells exhibited time-dependent release of acetaldehyde and hexanaldehyde.
  • Acetaldehyde concentrations increased from 157 ppbv at 4 hours to 698 ppbv at 48 hours.
  • Hexanaldehyde levels rose from 1 ppbv at 4 hours to 11 ppbv at 48 hours, with styrene identified as a contaminant.

Conclusions:

  • This study confirms that human immune cells, mimicking innate immune cells like neutrophils, produce measurable volatile gases in vitro.
  • The findings demonstrate the potential for using VOCs as noninvasive biomarkers for innate immune cell activity.