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Reagents: bromine and sodium hydroxide: Amide reduction: Amines, aldehydes Reagent: lithium aluminium hydride followed by hydrolysis Vilsmeier–Haack reaction: Aldehyde (via imine) POCl 3, aromatic substrate, formamide Bischler–Napieralski reaction: Cyclic aryl imine: POCl 3, SOCl 2, etc. Tautomeric chlorination: Imidoyl chloride
Acid–base-catalysed hydrolyses are very common; one example is the hydrolysis of amides or esters. Their hydrolysis occurs when the nucleophile (a nucleus-seeking agent, e.g., water or hydroxyl ion) attacks the carbon of the carbonyl group of the ester or amide. In an aqueous base, hydroxyl ions are better nucleophiles than polar molecules ...
The reaction of bromine with sodium hydroxide forms sodium hypobromite in situ, which transforms the primary amide into an intermediate isocyanate. The formation of an intermediate nitrene is not possible because it implies also the formation of a hydroxamic acid as a byproduct, which has never been observed.
Sodium amide is a common reagent with a long history of laboratory use. [9] It can decompose violently on contact with water, producing ammonia and sodium hydroxide: NaNH 2 + H 2 O → NH 3 + NaOH. When burned in oxygen, it will give oxides of sodium (which react with the produced water, giving sodium hydroxide) along with nitrogen oxides:
Typically aqueous sodium hydroxide solutions are used. [1] [2] It is an important type of alkaline hydrolysis. When the carboxylate is long chain, its salt is called a soap. The saponification of ethyl acetate gives sodium acetate and ethanol: C 2 H 5 O 2 CCH 3 + NaOH → C 2 H 5 OH + NaO 2 CCH 3
Sodium hydroxide can be used for the base-driven hydrolysis of esters (also called saponification), amides and alkyl halides. [16] However, the limited solubility of sodium hydroxide in organic solvents means that the more soluble potassium hydroxide (KOH) is often preferred.
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 ...
These reactions proceed via the intermediacy of amides. The intramolecular reaction of a carboxylic acid with an amide is far faster than the intermolecular reaction, which is rarely observed. They may also be produced via the oxidation of amides, particularly when starting from lactams. [6] R(CO)NHCH 2 R' + 2 [O] → R(CO)N(CO)R' + H 2 O