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In organic chemistry, the Schmidt reaction is an organic reaction in which an azide reacts with a carbonyl derivative, usually an aldehyde, ketone, or carboxylic acid, under acidic conditions to give an amine or amide, with expulsion of nitrogen.
The intermediate collapses and expels the leaving group (X) to give the substitution product 3. While nucleophilic acyl substitution reactions can be base-catalyzed, the reaction will not occur if the leaving group is a stronger base than the nucleophile (i.e. the leaving group must have a higher pK a than the nucleophile). Unlike acid ...
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 equivalents of nucleophile are closely controlled. Overaddition of nucleophiles. The Weinreb–Nahm amide has since been adopted into regular use by organic chemists as a dependable method for the ...
The Buchner–Curtius–Schlotterbeck reaction is the reaction of aldehydes or ketones with aliphatic diazoalkanes to form homologated ketones. [1] It was first described by Eduard Buchner and Theodor Curtius in 1885 [ 2 ] and later by Fritz Schlotterbeck in 1907. [ 3 ]
The Darzens reaction (also known as the Darzens condensation or glycidic ester condensation) is the chemical reaction of a ketone or aldehyde with an α-haloester in the presence of a base to form an α,β-epoxy ester, also called a "glycidic ester". [1] [2] [3] This reaction was discovered by the organic chemist Auguste Georges Darzens in 1904 ...
Kowalski ester homologation, an alternative to the Arndt-Eistert synthesis. Has been used to convert β-amino esters from α-amino esters through an ynolate intermediate. [2] Seyferth–Gilbert homologation in which an aldehyde is converted to a terminal alkyne and then hydrolyzed back to an aldehyde. Some reactions increase the chain length by ...
Esters can also undergo condensations with ketone and aldehyde enolates to give β-dicarbonyl compounds. [28] A specific example of this is the Baker–Venkataraman rearrangement , in which an aromatic ortho -acyloxy ketone undergoes an intramolecular nucleophilic acyl substitution and subsequent rearrangement to form an aromatic β-diketone ...
The use of aldehyde in the name comes from its history: aldehydes are more reactive than ketones, so that the reaction was discovered first with them. [2] [3] [4] The aldol reaction is paradigmatic in organic chemistry and one of the most common means of forming carbon–carbon bonds in organic chemistry.