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Self condensation of two moles of ethyl acetate in presence of sodium ethoxide yieldsacetoacetic estermethyl acetoacetateethyl propionateethyl butyrate

Question

Self condensation of two moles of ethyl acetate in presence of sodium ethoxide yields

  • acetoacetic ester
  • methyl acetoacetate
  • ethyl propionate
  • ethyl butyrate
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Solution

The self-condensation of two moles of ethyl acetate in the presence of sodium ethoxide yields acetoacetic ester. Here's the step-by-step process:

  1. Sodium ethoxide acts as a base and deprotonates the alpha hydrogen of one of the ethyl acetate molecules. This forms a carbanion.

  2. This carbanion then attacks the carbonyl carbon of the second ethyl acetate molecule. This forms a tetrahedral intermediate.

  3. The tetrahedral intermediate then collapses, kicking out the ethoxide ion and forming a new carbon-carbon bond.

  4. The ethoxide ion then deprotonates the alpha hydrogen of the newly formed molecule, forming a carbanion.

  5. This carbanion then attacks the carbonyl carbon of the same molecule, forming a five-membered ring. This is the acetoacetic ester.

So, the correct answer is acetoacetic ester.

This problem has been solved

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