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The Knorr pyrrole synthesis is a widely used chemical reaction that synthesizes substituted pyrroles (3). [1] [2] [3] The method involves the reaction of an α-amino-ketone (1) and a compound containing an electron-withdrawing group (e.g. an ester as shown) α to a carbonyl group (2). [4] The Knorr pyrrole synthesis
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.
Alkaline hydrolysis of esters is also known as saponification. A base such as sodium hydroxide is required in stochiometric amounts. Unlike acid-catalyzed ester hydrolysis, it is not an equilibrium reaction and proceeds to completion. Hydroxide ion attacks the carbonyl carbon to give a tetrahedral intermediate, which then expels an alkoxide ion.
This reaction is related to several classic named reactions: The acylated reaction product can be converted into the alkylated product via a Clemmensen or a Wolff-Kishner reduction. [17] The Gattermann–Koch reaction can be used to synthesize benzaldehyde from benzene. [18] The Gatterman reaction describes arene reactions with hydrocyanic acid ...
The Dakin oxidation (or Dakin reaction) is an organic redox reaction in which an ortho- or para-hydroxylated phenyl aldehyde (2-hydroxybenzaldehyde or 4-hydroxybenzaldehyde) or ketone reacts with hydrogen peroxide (H 2 O 2) in base to form a benzenediol and a carboxylate. Overall, the carbonyl group is oxidised, whereas the H 2 O 2 is reduced.
In addition to the ordinary thermal phenyl ester reaction a photochemical variant is possible. The photo-Fries rearrangement can likewise give [1,3] and [1,5] products, [7] [8] which involves a radical reaction mechanism. This reaction is also possible with deactivating substituents on the aromatic group. Because the yields are low this ...
The classic example of a dehydration reaction is the Fischer esterification, which involves treating a carboxylic acid with an alcohol to give an ester RCO 2 H + R′OH ⇌ RCO 2 R′ + H 2 O. Often such reactions require the presence of a dehydrating agent, i.e. a substance that reacts with water.
Acyloin condensation is a reductive coupling of two carboxylic esters using impure metallic sodium to yield an α-hydroxyketone, also known as an acyloin. [1] [2] [3] The acyloin condensation. The reaction is most successful when R is aliphatic and saturated, and typically performed with a silyl chloride reactant to trap the product as a ...