Related Experiment Video
Updated: Jan 2, 2026

The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes
Published on: April 10, 2015
Tritium-Labeled Compounds. XI. Mechanism for the Oxidation of Aldehydes and Aldoses-1-t With Sodium Chlorite
Abstract:
Measurements of kinetic isotope-effects (k*/k) for the oxidation of ten aldoses-1-t with sodium chlorite in acid solution gave values ranging from 0.56 to 0.75, with an average of 0.66. The values show that the C1-H* bond is not ruptured in the rate-determining step. For the reaction, a mechanism is proposed which accounts for this fact and for the dependence of the rate of reaction on the concentration of chlorous acid. The mechanism involves formation of a chlorous acid-aldehyde intermediate; this decomposes, giving the aldonic acid and hypochlorous acid. The latter then reacts with more chlorous acid, affording the chlorine dioxide and hydrogen chloride found experimentally.
More Related Videos
09:54Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes
Published on: September 12, 2018
06:00One-pot Microwave-assisted Conversion of Anomeric Nitrate-esters to Trichloroacetimidates
Published on: January 15, 2018
Related Concept Videos
Oxidation of Alcohols
The process of oxidation in a chemical reaction is observed in any of the three forms:
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
Hydroboration-Oxidation of Alkenes
Oxidations of Aldehydes and Ketones to Carboxylic Acids
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...
Conversion of Alcohols to Alkyl Halides
Acid-Catalyzed α-Halogenation of Aldehydes and Ketones
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic halogen to form a...