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Some amides can be reduced to aldehydes in the Sonn-Müller method, but most routes to aldehydes involve a well-chosen organometallic reductant. Lithium aluminum hydride reduces an excess of N,N-disubstituted amides to an aldehyde: [citation needed] R(CO)NRR' + LiAlH 4 → RCHO + HNRR' With further reduction the alcohol is obtained.
An amidate/imidate anion is formed upon deprotonation of an amide or imidic acid.Since amides and imidic acids are tautomers, they form the same anion upon deprotonation.The two names are thus synonyms describing the same anion, although arguably, imidate refers to the resonance contributor on the left, while amidate refers to the resonance contributor on the right.
The core −C(=O)−(N) of amides is called the amide group (specifically, carboxamide group). In the usual nomenclature, one adds the term "amide" to the stem of the parent acid's name. For instance, the amide derived from acetic acid is named acetamide (CH 3 CONH 2). IUPAC recommends ethanamide, but this and related formal names are rarely ...
Weerman degradation, also named Weerman reaction, is a name reaction in organic chemistry.It is named after Rudolf Adrian Weerman, who discovered it in 1910. [1] In general, it is an organic reaction in carbohydrate chemistry in which amides are degraded by sodium hypochlorite, forming an aldehyde with one less carbon. [2]
The chemical reactions of dimethylacetamide are typical of N,N-disubstituted amides. Hydrolysis of the acyl-N bond occurs in the presence of acids: CH 3 CON(CH 3) 2 + H 2 O + HCl → CH 3 COOH + (CH 3) 2 NH 2 + Cl −. However, it is resistant to bases. For this reason DMA is a useful solvent for reactions involving strong bases such as sodium ...
Lithium amides are usually prepared in the laboratory through the addition of a titrated solution of n-butyllithium in hexanes to a solution of the amine in ether. Dry glassware and inert atmosphere are required for these reactions. Alternatively, lithium amides may be prepared by the direct action of lithium on the corresponding amine.
O-substituted oximes form a closely related family of compounds. Amidoximes are oximes of amides (R 1 C(=O)NR 2 R 3) with general structure R 1 C(=NOH)NR 2 R 3. Oximes are usually generated by the reaction of hydroxylamine with aldehydes (R−CH=O) or ketones (RR’C=O). The term oxime dates back to the 19th century, a combination of the words ...
The alcohol reaction can also be used to form glycosidic bonds. [7] Similarly, an acid can be used in the place of an alcohol to form the anhydride, although dicyclohexylcarbodiimide is a more typical reagent. The equilibrium can be shifted in the favor of the anhydride by utilizing an acid in a 2:1 ratio that forms an insoluble salt with the ...