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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.
It is a mild reagent, suitable for both acid and base sensitive compounds. Its great reactivity with lactols makes the Fétizon oxidation a useful method to obtain lactones from a diol. The reaction is inhibited significantly by polar groups within the reaction system as well as steric hindrance of the α-hydrogen of the alcohol.
The alcohol is protonated, the H 2 O group formed leaves, forming a carbocation, and the nucleophile Cl − (which is present in excess) readily attacks the carbocation, forming the chloroalkane. Tertiary alcohols react immediately with Lucas reagent as evidenced by turbidity owing to the low solubility of the organic chloride in the aqueous ...
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 cogenerates dimethyl sulfide and a urea. Dicyclohexylurea ((CyNH) 2 CO) can be difficult to remove from the product. In terms of mechanism, the reaction is proposed to involve the intermediary of an sulfonium group, formed by a reaction between DMSO and the carbodiimide. This species is highly reactive and is attacked by the alcohol.
The order of addition of the reagents of the Mitsunobu reaction can be important. Typically, one dissolves the alcohol, the carboxylic acid, and triphenylphosphine in tetrahydrofuran or other suitable solvent (e.g. diethyl ether), cool to 0 °C using an ice-bath, slowly add the DEAD dissolved in THF, then stir at room temperature for several hours.
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.