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Because primary and secondary amines react with aldehydes and ketones, the most common variety of these aminocarbonyl compounds feature tertiary amines. Such compounds are produced by amination of α-haloketones and α-haloaldehydes. [1] Examples include cathinones, methadone, molindone, pimeclone, ferruginine, and tropinone.
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 ...
These possibilities have been used to account for the fact that, for certain substrates like α-tetralone, the group that migrates can sometimes change, depending on the conditions used, to deliver either of the two possible amides. [8] Two proposed reaction mechanisms for the amide formation from a ketone via Schmidt reaction
The two major resonance forms of an amide. Another factor that plays a role in determining the reactivity of acyl compounds is resonance. Amides exhibit two main resonance forms. Both are major contributors to the overall structure, so much so that the amide bond between the carbonyl carbon and the amide nitrogen has significant double bond ...
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
The Gewald reaction (or the Gewald aminothiophene synthesis) is an organic reaction involving the condensation of a ketone (or aldehyde when R 2 = H) with a α-cyanoester in the presence of elemental sulfur and base to give a poly-substituted 2-amino-thiophene. [1] [2] The Gewald reaction. The reaction is named after the German chemist Karl ...
The Leuckart reaction is the chemical reaction that converts aldehydes or ketones to amines. The reaction is an example of reductive amination. [1] The reaction, named after Rudolf Leuckart, uses either ammonium formate or formamide as the nitrogen donor and reducing agent. It requires high temperatures, usually between 120 and 130 °C; for the ...
The Baeyer–Villiger oxidation is an organic reaction that forms an ester from a ketone or a lactone from a cyclic ketone, using peroxyacids or peroxides as the oxidant. [1] The reaction is named after Adolf von Baeyer and Victor Villiger who first reported the reaction in 1899. [1] Baeyer-Villiger oxidation