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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 direct oxidation of primary alcohols to carboxylic acids normally proceeds via the corresponding aldehyde, which is transformed via an aldehyde hydrate (R−CH(OH) 2) by reaction with water before it can be further oxidized to the carboxylic acid. Mechanism of oxidation of primary alcohols to carboxylic acids via aldehydes and aldehyde hydrates
Under acid-catalyzed conditions, carboxylic acids will react with alcohols to form esters via the Fischer esterification reaction, which is also an equilibrium process. Alternatively, diazomethane can be used to convert an acid to an ester. While esterification reactions with diazomethane often give quantitative yields, diazomethane is only ...
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 ...
Under ideal conditions the reaction produces 50% of both the alcohol and the carboxylic acid (it takes two aldehydes to produce one acid and one alcohol). [5] This can be economically viable if the products can be separated and both have a value; the commercial conversion of furfural into furfuryl alcohol and 2-furoic acid is an example of this ...
Like most alcohols, it reacts with carboxylic acids to form esters. In organic synthesis, benzyl esters are popular protecting groups because they can be removed by mild hydrogenolysis. [6] Benzyl alcohol reacts with acrylonitrile to give N-benzylacrylamide. This is an example of a Ritter reaction: [7] C 6 H 5 CH 2 OH + NCCHCH 2 → C 6 H 5 CH ...
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.
It is also possible to realize the kinetic resolution of racemic alcohols by modifying the compositions of the reactants, i.e., by forming MA through reactions between achiral carboxylic acid and the appropriate carboxylic acid anhydride; then, by activating the racemic alcohols using the MA, optically active alcohols and optically active ...