Accedi

Aldehydes are more reactive than carboxylic acids and hence, can get over-reduced to alcohol in the presence of strong reducing agents. Therefore, carboxylic acids areinefficient in preparing aldehydes using LAH.

Carboxylic acid derivatives like acid chlorides and esters are more easily reducible than the corresponding acids. The derivatives reduce in the presence of mild reducing agents to give aldehydes. Aldehydes can also be prepared by Rosenmund reduction, that is, the reduction of acid chloride via hydrogenation over a poisoned catalyst. Catalytic poisoning inhibits the over-reduction of aldehydes. A Grignard reagent reduces an acid chloride to tertiary alcohol via a ketone intermediate. The reaction can be stopped at the ketone stage using a milder reducing agent like the Gilman reagent (R2CuLi). Aryl ketones can be prepared by Friedel–Crafts acylationin which acid chloride is treated with benzene and AlCl3.

Another carboxylic acid derivative, an ester, can be reduced to an aldehyde using DIBAL-H at dry ice temperature to give an aldehyde. Ketones cannot be prepared directly from esters because ketones are more reactive than esters and tend to over-reduce to tertiary alcohol.

Tags
AldehydesKetonesCarboxylic AcidsAcid ChloridesEstersReducing AgentsLAHRosenmund ReductionCatalytic PoisoningGrignard ReagentTertiary AlcoholGilman ReagentFriedel Crafts AcylationDIBAL HOver reduction

Dal capitolo 12:

article

Now Playing

12.9 : Preparation of Aldehydes and Ketones from Carboxylic Acid Derivatives

Aldehydes and Ketones

2.4K Visualizzazioni

article

12.1 : Strutture di aldeidi e chetoni

Aldehydes and Ketones

7.5K Visualizzazioni

article

12.2 : IUPAC Nomenclatura delle aldeidi

Aldehydes and Ketones

5.1K 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

3.3K Visualizzazioni

article

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

Aldehydes and Ketones

5.0K Visualizzazioni

article

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

Aldehydes and Ketones

3.5K Visualizzazioni

article

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

Aldehydes and Ketones

3.3K Visualizzazioni

article

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

Aldehydes and Ketones

3.2K Visualizzazioni

article

12.10 : Addizione nucleofila al gruppo carbonilico: meccanismo generale

Aldehydes and Ketones

4.5K 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

5.1K Visualizzazioni

article

12.13 : Gruppi di protezione per aldeidi e chetoni: Introduzione

Aldehydes and Ketones

6.0K Visualizzazioni

article

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

Aldehydes and Ketones

3.8K Visualizzazioni

article

12.15 : Aldeidi e chetoni con HCN: panoramica sulla formazione di cianoidrina

Aldehydes and Ketones

2.5K Visualizzazioni

See More

JoVE Logo

Riservatezza

Condizioni di utilizzo

Politiche

Ricerca

Didattica

CHI SIAMO

Copyright © 2025 MyJoVE Corporation. Tutti i diritti riservati