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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 ...
A remarkable feature of these reactions is the ability to conduct carbonyl allylation from the alcohol oxidation state. Due to a kinetic preference for primary alcohol dehydrogenation, diols containing both primary and secondary alcohols undergo site-selective carbonyl allylation at the primary alcohol without the need for protecting groups. [18]
The term alcohol originally referred to the primary alcohol ethanol (ethyl alcohol), which is used as a drug and is the main alcohol present in alcoholic drinks. The suffix -ol appears in the International Union of Pure and Applied Chemistry (IUPAC) chemical name of all substances where the hydroxyl group is the functional group with the ...
A primary alcohol is an alcohol in which the hydroxy group is bonded to a primary carbon atom. It can also be defined as a molecule containing a “–CH 2 OH” group. [ 1 ] In contrast, a secondary alcohol has a formula “–CHROH” and a tertiary alcohol has a formula “–CR 2 OH”, where “R” indicates a carbon-containing group.
PCC is used as an oxidant.In particular, it has proven to be highly effective in oxidizing primary and secondary alcohols to aldehydes and ketones, respectively.The reagent is more selective than the related Jones' Reagent, so there is little chance of over-oxidation to form carboxylic acids if acidified potassium permanganate is used as long as water is not present in the reaction mixture.
In enzymology, an alcohol oxidase (EC 1.1.3.13) is an enzyme that catalyzes the chemical reaction a primary alcohol + O 2 ⇌ {\displaystyle \rightleftharpoons } an aldehyde + H 2 O 2 Thus, the two substrates of this enzyme are primary alcohol and O 2 , whereas its two products are aldehyde and H 2 O 2 .
The reaction was first described by Emil Fischer and Arthur Speier in 1895. [1] Most carboxylic acids are suitable for the reaction, but the alcohol should generally be primary or secondary. Tertiary alcohols are prone to elimination. Contrary to common misconception found in organic chemistry textbooks, phenols can also be esterified to give ...