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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.
Scheme 2. Hydrolysis of benzoic acid esters. Reaction constants are known for many other reactions and equilibria. Here is a selection of those provided by Hammett himself (with their values in parentheses): the hydrolysis of substituted cinnamic acid ester in ethanol/water (+1.267) the ionization of substituted phenols in water (+2.008)
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.
The carboxylic acid Schmidt reaction starts with acylium ion 1 obtained from protonation and loss of water. Reaction with hydrazoic acid forms the protonated azido ketone 2 , which goes through a rearrangement reaction with the alkyl group R, migrating over the C-N bond with expulsion of nitrogen.
The synthetic procedure [16] is typical for this type of reaction. In the process, in addition to water, an equivalent of ethanol and carbon dioxide are lost in decarboxylation. Ethyl glyoxylate 2 and glutaconate (diethyl-2-methylpent-2-enedioate) 1 react to isoprenetricarboxylic acid 3 (isoprene (2-methylbuta-1,3-diene) skeleton) with sodium ...
Schotten–Baumann reaction also refers to the conversion of acid chloride to esters. The reaction was first described in 1883 by German chemists Carl Schotten and Eugen Baumann. [1] [2] The name "Schotten–Baumann reaction conditions" often indicate the use of a two-phase solvent system, consisting of water and an organic solvent.
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 ...
Download as PDF; Printable version; ... benzene-1,4-dicarboxylate [1] ... It is the product of the glycolysis reaction of PET with Ethylene glycol. References