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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
Ethyl acetate (systematically ethyl ethanoate, commonly abbreviated EtOAc, ETAC or EA) is the organic compound with the formula CH 3 CO 2 CH 2 CH 3, simplified to C 4 H 8 O 2.This flammable, colorless liquid has a characteristic sweet smell (similar to pear drops) and is used in glues, nail polish removers, and the decaffeination process of tea and coffee.
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 equilibrium constant for such reactions is about 5 for typical esters, e.g., ethyl acetate. [15] The reaction is slow in the absence of a catalyst. Sulfuric acid is a typical catalyst for this reaction. Many other acids are also used such as polymeric sulfonic acids.
Acetoacetic ester synthesis is a chemical reaction where ethyl acetoacetate is alkylated at the α-carbon to both carbonyl groups and then converted into a ketone, or more specifically an α-substituted acetone. This is very similar to malonic ester synthesis. Acetoacetic ester synthesis equation
It is sometimes produced in a laboratory experiment by the reaction of acetic acid, commonly in the 5–18% solution known as vinegar, with sodium carbonate ("washing soda"), sodium bicarbonate ("baking soda"), or sodium hydroxide ("lye", or "caustic soda"). Any of these reactions produce sodium acetate and water.
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When iodine and sodium hydroxide are used as the reagents a positive reaction gives iodoform, which is a solid at room temperature and tends to precipitate out of solution causing a distinctive cloudiness. In organic chemistry, this reaction may be used to convert a terminal methyl ketone into the analogous carboxylic acid.