Jove
Visualize
Contact Us
JoVE
x logofacebook logolinkedin logoyoutube logo
ABOUT JoVE
OverviewLeadershipBlogJoVE Help Center
AUTHORS
Publishing ProcessEditorial BoardScope & PoliciesPeer ReviewFAQSubmit
LIBRARIANS
TestimonialsSubscriptionsAccessResourcesLibrary Advisory BoardFAQ
RESEARCH
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchive
EDUCATION
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualFaculty Resource CenterFaculty Site
Terms & Conditions of Use
Privacy Policy
Policies

Related Concept Videos

Structures of Aldehydes and Ketones01:04

Structures of Aldehydes and Ketones

12.5K
Vanillin—a flavoring agent in vanilla, cinnamaldehyde—a molecule responsible for the distinct smell of cinnamon, and acetone—a strong-smelling ingredient in nail polish removers, all belong to a class of carbonyl compounds called aldehydes and ketones (Figure 1). Although both aldehydes and ketones contain the characteristic carbonyl (C=O) bond, their chemical structures vary with respect to the groups directly attached to the carbonyl carbon.
In aldehydes (Figures 1a and 1b), the...
12.5K
NMR Spectroscopy and Mass Spectrometry of Aldehydes and Ketones01:15

NMR Spectroscopy and Mass Spectrometry of Aldehydes and Ketones

5.7K
In aldehydes, the hydrogen atom connected to the carbonyl carbon helps distinguish aldehydes from other carbonyl compounds using ¹H NMR spectroscopy. The closeness of aldehydic hydrogen to the electrophilic carbonyl carbon highly deshields the hydrogen atom causing its signal to appear around 10 ppm in the ¹H NMR spectra. α hydrogens split the aldehydic proton signal, which helps identify the number of α hydrogens in the molecule. For instance, one α hydrogen creates a...
5.7K
Structures of Carboxylic Acid Derivatives01:28

Structures of Carboxylic Acid Derivatives

3.8K
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.
The three sp2 orbitals of the carbonyl carbon form three σ bonds, one each with the carbonyl oxygen, the α carbon, and the heteroatom, whereas the other two sp2 orbitals of the carbonyl oxygen are occupied by the lone pairs. Further, the unhybridized p...
3.8K
Aldehydes and Ketones with Alcohols: Hemiacetal Formation01:19

Aldehydes and Ketones with Alcohols: Hemiacetal Formation

10.1K
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.
10.1K
IUPAC Nomenclature of Ketones01:09

IUPAC Nomenclature of Ketones

7.7K
Like aldehydes, ketones are named using IUPAC rules; in this case, by replacing “e” in the name of the longest hydrocarbon chain with “one.” In acyclic ketones, the ketonic carbon is given the lowest locant value. For instance, as shown below, a simple five-carbon ketone is named pentan-2-one, instead of pentan-4-one. IUPAC rules also allow the placing of the locant value before the parent name to give an alternate name, 2-pentanone.
7.7K
α-Alkylation of Ketones via Enolate Ions01:10

α-Alkylation of Ketones via Enolate Ions

4.0K
Ketones with α protons are deprotonated by strong bases like lithium diisopropylamide (LDA) to form enolate ions. The anion is stabilized by resonance, and its hybrid structure exhibits negative charges on the carbonyl oxygen and the α carbon. This ambident nucleophile can attack an electrophile via two possible sites: the carbonyl oxygen, known as O-attack, or the α carbon, known as C-attack. The nucleophilic attack via the carbanionic site is preferred. This is due to the...
4.0K

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by
Same author

How Do DICER1 Syndrome Mutations Disrupt Catalysis? Unveiling Dicer Metal Binding Architecture and Mechanism of Action Using MD Simulations and QM/MM Calculations.

Journal of computational chemistry·2026
Same author

An Experimental and Computational Investigation into the Allylboration/Defluorinative Semipinacol Rearrangement Cascade Reaction.

The Journal of organic chemistry·2026
Same author

Insights into the Debated Lyase Mechanism of Bifunctional DNA Glycosylases from MD and QM/MM MD Simulations: The Case Study of DNA Oxidative Damage Repair by Human 8-Oxoguanine DNA Glycosylase.

Journal of the American Chemical Society·2026
Same author

Decoding the Catalytic Strategy for DNA Alkylation Repair by AlkA: Insights from MD Simulations and QM/MM Calculations.

The journal of physical chemistry. B·2026
Same author

A tale of two mechanisms: Clarification of the pathway for MBD4 catalyzed glycosidic bond cleavage using MD and QM/MM calculations.

DNA repair·2025
Same author

Decarboxylative Redox Bicyclo[1.1.1]pentylation: Benchmarking the Influence of Backbone Substituents on C-C Bond-Forming Reactions.

Organic letters·2025

Related Experiment Video

Updated: Feb 19, 2026

Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
06:31

Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators

Published on: November 27, 2015

10.0K

Solid-State Structure of Protonated Ketones and Aldehydes.

Daniel Stuart1, Stacey D Wetmore1, Michael Gerken1

  • 1Canadian Centre for Research in Advanced Fluorine, Technologies and Department of Chemistry and Biochemistry, University of Lethbridge, 4401 University Drive, Lethbridge, AB, T1K 3M4, Canada.

Angewandte Chemie (International Ed. in English)
|November 7, 2017
PubMed
Summary

Protonated carbonyl compounds, key intermediates in acid catalysis, were synthesized and characterized. This study reveals their structure and increased electrophilicity, advancing organic reaction mechanism understanding.

Keywords:
X-ray diffractiondensity functional calculationsoxonium cationreactive intermediatessuperacidic systems

More Related Videos

Preparation of SNS CobaltII Pincer Model Complexes of Liver Alcohol Dehydrogenase
06:31

Preparation of SNS CobaltII Pincer Model Complexes of Liver Alcohol Dehydrogenase

Published on: March 19, 2020

7.7K
A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
07:06

A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis

Published on: February 16, 2020

8.6K

Related Experiment Videos

Last Updated: Feb 19, 2026

Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
06:31

Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators

Published on: November 27, 2015

10.0K
Preparation of SNS CobaltII Pincer Model Complexes of Liver Alcohol Dehydrogenase
06:31

Preparation of SNS CobaltII Pincer Model Complexes of Liver Alcohol Dehydrogenase

Published on: March 19, 2020

7.7K
A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
07:06

A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis

Published on: February 16, 2020

8.6K

Area of Science:

  • Organic Chemistry
  • Physical Chemistry

Background:

  • Protonated carbonyl compounds are crucial intermediates in acid-catalyzed organic reactions.
  • Understanding their structure and reactivity is essential for reaction mechanism elucidation.

Purpose of the Study:

  • To synthesize and characterize oxonium salts of representative ketones and aldehydes.
  • To investigate the structural and electronic properties of protonated carbonyl intermediates.
  • To quantify the change in electrophilicity upon protonation.

Main Methods:

  • Synthesis of oxonium salts from ketones/aldehydes and SbF5 in anhydrous HF.
  • Characterization using X-ray crystallography and Raman spectroscopy.
  • Density Functional Theory (DFT) calculations for gas-phase cations.
  • Natural Bond Orbital (NBO) analysis.

Main Results:

  • Mononuclear oxonium cations formed from acetone, cyclopentanone, adamantanone, and acetaldehyde.
  • A hemiprotonated, hydrogen-bridged dimeric cation formed from benzaldehyde.
  • Hemiprotonated acetaldehyde was obtained with a 2:1 aldehyde to SbF5 ratio.
  • Experimental and NBO analyses confirmed increased electrophilicity of oxonium cations.

Conclusions:

  • First solid-state synthesis and characterization of protonated carbonyl oxonium salts.
  • Demonstrated varying cation structures based on carbonyl compound and stoichiometry.
  • Quantified significant enhancement in electrophilicity of protonated carbonyls.