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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.
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.
Ortho esters are readily hydrolyzed in mild aqueous acid to form esters: . RC(OR ′) 3 + H 2 O → RCO 2 R ′ + 2 R ′ OH. For example, trimethyl orthoformate CH(OCH 3) 3 may be hydrolyzed (under acidic conditions) to methyl formate and methanol; [5] and may be further hydrolyzed (under alkaline conditions) to salts of formic acid and methanol.
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 primary advantages of Fischer esterification compared to other esterification processes are based on its relative simplicity. Straightforward acidic conditions can be used if acid-sensitive functional groups are not an issue; sulfuric acid can be used; weaker acids can be used with a tradeoff of longer reaction times.
With highly activated phenols such as resorcinol, the reaction can be performed under much milder conditions. This provides a useful route to umbelliferone derivatives: The Pechmann condensation as applied to 7-hydroxy-4-methylcoumarin. For coumarins unsubstituted at the 4-position, the method requires the use of formylacetic acid or ester.
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 ...