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Reaction mechanism for the amine formation from a carboxylic acid via Schmidt reaction. In the reaction mechanism for the Schmidt reaction of ketones, the carbonyl group is activated by protonation for nucleophilic addition by the azide, forming azidohydrin 3, which loses water in an elimination reaction to diazoiminium 5.
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 Kolbe–Schmitt reaction or Kolbe process (named after Hermann Kolbe and Rudolf Schmitt) is a carboxylation chemical reaction that proceeds by treating phenol with sodium hydroxide to form sodium phenoxide, [1] then heating sodium phenoxide with carbon dioxide under pressure (100 atm, 125 °C), then treating the product with sulfuric acid.
In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group (−C(=O)−OH) [1] attached to an R-group. The general formula of a carboxylic acid is often written as R−COOH or R−CO 2 H, sometimes as R−C(O)OH with R referring to an organyl group (e.g., alkyl, alkenyl, aryl), or hydrogen, or other groups ...
Those reactions proceed comparably to steps of the Schmidt reaction, by which carboxylic acids can be transformed into amines through the addition of hydrazoic acid under acidic aqueous conditions. [26] The Stieglitz rearrangement of azides generally profits from a protonic [16] or thermal [4] activation, which can also be combined. [10]
The formation of the urethane is particularly valuable since it works with carboxylic acids which fail to undergo the Schmidt reaction, and is believed to involve transfer of the azido group to the carboxylic acid. It is now suggested that this reaction proceeds through the intermediate mixed anhydride, resulting from attack by the nucleophilic ...
The first step in the mechanism showing conversion of a carboxylic acid into an amine is incorrect. Protonation of a carboxylic acid occurs at the carbonyl oxygen not the hydroxy oxygen. —Preceding unsigned comment added by 137.48.19.23 20:57, 17 February 2010 (UTC) March supports formation of intermediate 1.
General homologation reaction, Arndt-Eistert has R 2 = H, RXH=H 2 O. In the most basic form, where R 2 = H, RXH=H 2 O, the reaction lengthens the alkyl chain of a carboxylic acid by a methylene. However, there is great synthetic utility in the variety of reactions one can carry out, by varying the diazoalkyl and weak acid.