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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 example, addition of potassium permanganate to an aqueous solution of sugar and sodium hydroxide produces the chemical chameleon reaction, which involves dramatic color changes associated with the various oxidation states of manganese. A related vigorous reaction is exploited as a fire starter in survival kits.
Potassium permanganate (KMnO 4) is a dark violet colored powder. Its reaction with glycerol (commonly known as glycerin or glycerine) (C 3 H 5 (OH) 3) is highly exothermic, resulting rapidly in a flame, along with the formation of carbon dioxide and water vapour:
The direct oxidation of primary alcohols to carboxylic acids normally proceeds via the corresponding aldehyde, which is transformed via an aldehyde hydrate (R−CH(OH) 2) by reaction with water before it can be further oxidized to the carboxylic acid. Mechanism of oxidation of primary alcohols to carboxylic acids via aldehydes and aldehyde hydrates
A tertiary propargylic alcohol is fragmented upon treatment with Fetizon's reagent. Halohydrins that possess a trans stereochemistry have been demonstrated to form epoxides and transposed products in the presence of Fétizon's reagent. Halohydrins possessing a cis-stereochemistry seem to perform a typical Fétizon's oxidation to a ketone. [17]
Glycol cleavage is a specific type of organic chemistry oxidation. The carbon–carbon bond in a vicinal diol (glycol) is cleaved and instead the two oxygen atoms become double-bonded to their respective carbon atoms. Depending on the substitution pattern in the diol, these carbonyls will be ketones and/or aldehydes. [1]
In an acidic solution, permanganate(VII) is reduced to the pale pink manganese(II) (Mn 2+) with an oxidation state of +2. 8 H + + MnO − 4 + 5 e − → Mn 2+ + 4 H 2 O. In a strongly basic or alkaline solution, permanganate(VII) is reduced to the green manganate ion, MnO 2− 4 with an oxidation state of +6. MnO − 4 + e − → MnO 2− 4
Fermentation of sugar to ethanol and CO 2 can also be done by Zymomonas mobilis, however the path is slightly different since formation of pyruvate does not happen by glycolysis but instead by the Entner–Doudoroff pathway. Other microorganisms can produce ethanol from sugars by fermentation but often only as a side product. Examples are [4]