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 by atmospheric oxygen. Though stored in airtight containers to delay slow autoxidation, some aldehyde samples are contaminated with traces of carboxylic acid.

Ketones are more resistant and undergo oxidation in the presence of strong oxidizing agents at higher temperatures. The reaction is not as helpful because a mixture of carboxylic acids is obtained as a product.

In the functional-group tests, aldehydes can be differentiated from ketones and other oxidizable functional groups using Tollens’ reagent. Tollens’ reagent is a mixture of silver nitrate in aqueous ammonia to give a diaminosilver(I) ion. It is a weak oxidizing agent and can selectively oxidize aldehydes to carboxylic acid in the presence of other oxidizable functional groups. Simultaneously, the silver ion is reduced to metallic silver. The silver metal is precipitated onto the surface of the reaction vessel to give a mirror-like effect. Hence, this test is popularly known as the silver mirror test or Tollens’ test.

Figure1

Tags
AldehydeKetoneCarboxylic AcidOxidationTollens ReagentSilver Mirror TestPotassium PermanganateChromic AcidSilver OxideAutoxidation

Dal capitolo 12:

article

Now Playing

12.23 : Oxidations of Aldehydes and Ketones to Carboxylic Acids

Aldehydes and Ketones

3.2K Visualizzazioni

article

12.1 : Strutture di aldeidi e chetoni

Aldehydes and Ketones

7.2K Visualizzazioni

article

12.2 : IUPAC Nomenclatura delle aldeidi

Aldehydes and Ketones

5.0K Visualizzazioni

article

12.3 : IUPAC Nomenclatura dei chetoni

Aldehydes and Ketones

5.2K Visualizzazioni

article

12.4 : Nomi comuni di aldeidi e chetoni

Aldehydes and Ketones

3.2K Visualizzazioni

article

12.5 : Spettroscopia IR e UV-Vis di aldeidi e chetoni

Aldehydes and Ketones

4.9K Visualizzazioni

article

12.6 : Spettroscopia NMR e spettrometria di massa di aldeidi e chetoni

Aldehydes and Ketones

3.4K Visualizzazioni

article

12.7 : Preparazione di Aldeidi e Chetoni da Alcoli, Alcheni e Alchini

Aldehydes and Ketones

3.2K Visualizzazioni

article

12.8 : Preparazione di Aldeidi e Chetoni da Nitrili e Acidi Carbossilici

Aldehydes and Ketones

3.2K Visualizzazioni

article

12.9 : Preparazione di Aldeidi e Chetoni da Derivati dell'Acido Carbossilico

Aldehydes and Ketones

2.4K Visualizzazioni

article

12.10 : Addizione nucleofila al gruppo carbonilico: meccanismo generale

Aldehydes and Ketones

4.1K Visualizzazioni

article

12.11 : Aldeidi e chetoni con acqua: formazione di idrati

Aldehydes and Ketones

2.9K Visualizzazioni

article

12.12 : Aldeidi e Chetoni con Alcoli: Formazione Emiacetale

Aldehydes and Ketones

4.9K Visualizzazioni

article

12.13 : Gruppi di protezione per aldeidi e chetoni: Introduzione

Aldehydes and Ketones

5.6K Visualizzazioni

article

12.14 : Acetali e tioacetali come gruppi protettivi per aldeidi e chetoni

Aldehydes and Ketones

3.7K Visualizzazioni

See More

JoVE Logo

Riservatezza

Condizioni di utilizzo

Politiche

Ricerca

Didattica

CHI SIAMO

Copyright © 2025 MyJoVE Corporation. Tutti i diritti riservati