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Alcohol oxidation is a collection of oxidation reactions in organic chemistry that convert alcohols to aldehydes, ketones, carboxylic acids, and esters. The reaction mainly applies to primary and secondary alcohols. Secondary alcohols form ketones, while primary alcohols form aldehydes or carboxylic acids. [1] A variety of oxidants can be used.
For oxidations to the aldehydes and ketones, two equivalents of chromic acid oxidize three equivalents of the alcohol: 2 HCrO 4 − + 3 RR'C(OH)H + 8 H + + 4 H 2 O → 2 [Cr(H 2 O) 6] 3+ + 3 RR'CO. For oxidation of primary alcohols to carboxylic acids, 4 equivalents of chromic acid oxidize 3 equivalents of the alcohol. The aldehyde is an ...
Substrates are broadly limited to methyl ketones and secondary alcohols oxidizable to methyl ketones, such as isopropanol.The only primary alcohol and aldehyde to undergo this reaction are ethanol and acetaldehyde, respectively. 1,3-Diketones such as acetylacetone also undergo this reaction. β-ketoacids such as acetoacetic acid will also give the test upon heating.
The reaction rate equals the rate of the propagation ... An example is the oxidation of an alcohol to a ketone by ... at low substrate concentrations ...
Another side reaction is the Tischenko reaction of aldehyde products with no α-hydrogen, but this can be prevented by use of anhydrous solvents. [4] Another general side reaction is the migration of the double bond during the oxidation of allylic alcohol substrates. [14] Oppenauer oxidation of a steroid derivative. [15]
Alcohol dehydrogenase activity varies between men and women, between young and old, and among populations from different areas of the world. For example, young women are unable to process alcohol at the same rate as young men because they do not express the alcohol dehydrogenase as highly, although the inverse is true among the middle-aged. [37]
The Zultanski–Zhao–Stahl oxidative amide coupling is a reaction between a primary alcohol and an amine to form an amide. [31] In the Zultanski–Zhao–Stahl reaction, a primary alcohol is oxidized to an aldehyde which, in the presence of an amine, reversibly forms a hemiaminal which is then irreversibly oxidized to the amide by the catalyst.
In organic chemistry, the Swern oxidation, named after Daniel Swern, is a chemical reaction whereby a primary or secondary alcohol (−OH) is oxidized to an aldehyde (−CH=O) or ketone (>C=O) using oxalyl chloride, dimethyl sulfoxide (DMSO) and an organic base, such as triethylamine.