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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 ...
The Weinreb–Nahm ketone synthesis. The major advantage of this method over addition of organometallic reagents to more typical acyl compounds is that it avoids the common problem of over-addition. For these latter reactions, two equivalents of the incoming group add to form an alcohol rather than a ketone or aldehyde. This occurs even if the ...
Aldehydes and ketones can be reduced respectively to primary and secondary alcohols. In deoxygenation, the alcohol group can be further reduced and removed altogether by replacement with H. Two broad strategies exist for carbonyl reduction. One method, which is favored in industry, uses hydrogen as the reductant.
This page contains tables of azeotrope data for various binary and ternary mixtures of solvents. The data include the composition of a mixture by weight (in binary azeotropes, when only one fraction is given, it is the fraction of the second component), the boiling point (b.p.) of a component, the boiling point of a mixture, and the specific gravity of the mixture.
Steric effects of the alkyl substituents on the carbonyl reactant have been shown to affect both the rates and yields of Büchner–Curtius–Schlotterbeck reaction. Table 1 shows the percent yield of the ketone and epoxide products as well as the relative rates of reaction for the reactions between several methyl alkyl ketones and diazomethane ...
Another side reaction is the Tischenko reaction of aldehyde products with no α-hydrogen, but this can be prevented by use of anhydrous solvents. [4] Another general side reaction is the migration of the double bond during the oxidation of allylic alcohol substrates. [14] Oppenauer oxidation of a steroid derivative. [15]
The reaction conditions allow oxidation of acid-sensitive compounds, which might decompose under the acidic oxidation conditions such as Jones oxidation. For example, in Thompson & Heathcock's synthesis of the sesquiterpene isovelleral, [ 15 ] the final step uses the Swern protocol, avoiding rearrangement of the acid-sensitive ...