33) synthesis of mono carboxylic acid from Acetoacetic ester?
Answers
Answer:
Ethyl acetoacetate is alkylated at the α- carbon to both carbonyl groups and they are converted into ketone or more specifically an α-substituted acetone.
Explanation:
Other name of acetoacetic ester is Ethyl acetoacetate and the molecular formula is C9H16N2O4 , Molecular weight 216.23
Acetic acid (also acetoacetate and diacetic acid) is an organic compound with the formula CH3COCH2COOH. It is the simplest beta-keto acid and, like other members of this class, is unstable. Methyl esters and ethyl esters, which are relatively stable, are produced on a large scale industrially as dye precursors. Acetic acid is a weak acid.
How would you prepare acetoacetic ester from ethyl acetate?
Ethyl acetoacetate can be prepared from ethyl acetate by the action of sodium
- sodium ethoxide
- sodamide
- calcium
When the condensation, using sodium ethoxide, is carried out in such a manner as to remove the alcohol formed, the yield is reported to be 80 per cent of the theoretical amount.
A strong base deprotonates the dicarbonyl α-carbon. This carbon is preferred over the methyl carbon because the formed enolate is conjugated and thus resonance stabilized. The carbon then undergoes nucleophilic substitution. When heated with aqueous acid, the newly alkylated ester is hydrolyzed to a β-keto acid, which is decarboxylated to form a methyl ketone.
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