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Saponification is a process of cleaving esters into carboxylate salts and alcohols by the action of aqueous alkali. 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 ...
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.
In this reaction, sodium hydroxide acts as an agent to make the solution alkaline, which aluminium can dissolve in. 2 Al + 2 NaOH + 2 H 2 O → 2 NaAlO 2 + 3 H 2. Sodium aluminate is an inorganic chemical that is used as an effective source of aluminium hydroxide for many industrial and technical applications.
The conversion of methyl acetate back into its components, by an acid, is a first-order reaction with respect to the ester. The reaction of methyl acetate and a base, for example sodium hydroxide, is a second-order reaction with respect to both reactants. Methyl acetate is a Lewis base that forms 1:1 adducts with a variety of Lewis acids.
In the Tishchenko reaction, the base used is an alkoxide rather than hydroxide, and the product is an ester rather than the separate alcohol and carboxylate groups. After the nucleophilic base attacks an aldehyde, the resulting new oxygen anion attacks another aldehyde to give a hemiacetal linkage between two of the formerly aldehyde-containing ...
For example, sodium acetate dissociates in water into sodium and acetate ions. Sodium ions react very little with the hydroxide ions whereas the acetate ions combine with hydronium ions to produce acetic acid. In this case the net result is a relative excess of hydroxide ions, yielding a basic solution. Strong acids also undergo hydrolysis.
The use of a conventional base may give base hydrolysis products – for example, sodium hydroxide would simply produce sodium malonate and the alcohol, while other alkoxide salts will cause scrambling by transesterification. Only the "same" alkoxide anion as the one that one used to alkylate the deprotonated active methylenic site will prevent ...
Usage of alkoxide anions such as sodium methoxide, instead of sodium hydroxide, yields the ring-contracted ester product. When enolate formation is impossible, the Favorskii rearrangement takes place by an alternate mechanism, in which addition to hydroxide to the ketone takes place, followed by concerted collapse of the tetrahedral ...