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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.
Primary alcohols (R−CH 2 OH) can be oxidized either to aldehydes (R−CHO) or to carboxylic acids (R−CO 2 H). The oxidation of secondary alcohols (R 1 R 2 CH−OH) normally terminates at the ketone (R 1 R 2 C=O) stage. Tertiary alcohols (R 1 R 2 R 3 C−OH) are resistant to oxidation.
2,2,4,4-Tetramethyl-3-t-butyl-pentane-3-ol or tri-tert-butylcarbinol is an organic compound with formula C 13 H 28 O, ((H 3 C) 3 C) 3 COH, or t Bu 3 COH. [1]It is an alcohol that can be viewed as a structural analog of a tridecane isomer (2,2,4,4-tetramethyl-3-t-butylpentane) where the central hydrogen has been replaced by a hydroxyl group -OH.
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.
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 ...
The oxidation is highly selective for secondary alcohols and does not oxidize other sensitive functional groups such as amines and sulfides. [3] Though primary alcohols can be oxidized under Oppenauer conditions, primary alcohols are seldom oxidized by this method due to the competing aldol condensation of aldehyde products. The Oppenauer ...
The inability of Fétizon's reagent to oxidize tertiary alcohols makes it extremely useful in the monooxidation of a [1,2] diol in which one of the alcohols is tertiary while avoiding cleavage of the carbon-carbon bond. [7] Fetizon's reagent oxidizes secondary alcohols selectively in the presence of tertiary alcohols
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.