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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.
The process uses an aluminum compound to oligomerize ethylene and allow the resulting alkyl group to be oxygenated. The usually targeted products are fatty alcohols, which are otherwise derived from natural fats and oils. Fatty alcohols are used in food and chemical processing. They are useful due to their amphipathic nature.
The silyl group is a non-polar and relatively unreactive species and is therefore tolerant of many reagents and reaction conditions that might be incompatible with free alcohols. Consequently, the silyl group also eliminates the need for introduction of hydroxyl protecting groups. In short, by deferring introduction of an alcohol to a late ...
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 ...
The reaction of tertiary alcohols containing an α-acetylenic group does not produce the expected aldehydes, but rather α,β-unsaturated methyl ketones via an enyne intermediate. [ 9 ] [ 10 ] This alternate reaction is called the Rupe reaction , and competes with the Meyer–Schuster rearrangement in the case of tertiary alcohols.
If produced from oleochemical feedstock or the Ziegler process, the hydrocarbon chain of the alcohol will be linear. If derived using the oxo process, a low level of branching will appear usually with a methyl or ethyl group at the C-2 position, containing even and odd amounts of alkyl chains. [3] These alcohols react with chlorosulfuric acid:
Geminally-substituted olefins react in the same order of reaction rates as above: [2] Trisubstituted alkenes experience reactivity at the more substituted end of the double bond. The order of reactivity follows that CH 2 > CH 3 > CH: Due to the rearrangement of the double bond, terminal olefins tend to give primary allylic alcohols: