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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.
Tertiary alcohols and ketones are unaffected. Because the oxidation is signaled by a color change from orange to brownish green (indicating chromium being reduced from oxidation state +6 to +3), chromic acid is commonly used as a lab reagent in high school or undergraduate college chemistry as a qualitative analytical test for the presence of ...
The Wharton olefin synthesis or the Wharton reaction is a chemical reaction that involves the reduction of α,β-epoxy ketones using hydrazine to give allylic alcohols. [ 1 ] [ 2 ] [ 3 ] This reaction, introduced in 1961 by P. S. Wharton, is an extension of the Wolff–Kishner reduction .
The reaction stoichiometry implicates the Cr(IV) species "CrO 2 OH −", which comproportionates with the chromic acid to give a Cr(V) oxide, which also functions as an oxidant for the alcohol. [ 6 ] The oxidation of the aldehydes is proposed to proceed via the formation of hemiacetal -like intermediates, which arise from the addition of the O ...
Deprotonation of the Seyferth–Gilbert reagent A gives an anion B, which reacts with the ketone to form the oxaphosphetane D. Elimination of dimethylphosphate E gives the vinyl diazo-intermediate Fa and Fb. The generation of nitrogen gas gives a vinyl carbene G, which via a 1,2-migration forms the desired alkyne H.
Since, aldehydes reduce more easily than ketones, they require milder reagents and milder conditions. At the other extreme, carboxylic acids, amides, and esters are poorly electrophilic and require strong reducing agents. [17] The idealized equation for the reduction of a ketone by sodium borohydride is: 4 RCOR' + NaBH 4 → NaB(OCHRR') 4
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Substrates are broadly limited to methyl ketones and secondary alcohols oxidizable to methyl ketones, such as isopropanol.The only primary alcohol and aldehyde to undergo this reaction are ethanol and acetaldehyde, respectively. 1,3-Diketones such as acetylacetone also undergo this reaction. β-ketoacids such as acetoacetic acid will also give the test upon heating.