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Self condensation of two moles of ethyl acetatein presence of sodium ethoxide yields [2006]
  • a)
    acetoacetic ester
  • b)
    methyl acetoacetate
  • c)
    ethyl propionate
  • d)
    ethyl butyrate
Correct answer is option 'A'. Can you explain this answer?
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Self condensation of two moles of ethyl acetatein presence of sodium e...
It is an example of Claisen condensation. The
product is acetoacetic ester.
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Self condensation of two moles of ethyl acetatein presence of sodium e...
Self-Condensation of Ethyl Acetate

The self-condensation of ethyl acetate takes place in the presence of sodium ethoxide to yield acetoacetic ester.

Reaction:

The reaction can be represented as:

2CH3COOCH2CH3 + NaOCH2CH3 → CH3COCH2COOCH2CH3 + NaOCH2CH3 + CH3CH2OH

Mechanism:

The mechanism of the self-condensation of ethyl acetate involves the following steps:

1. Deprotonation: Sodium ethoxide acts as a base and deprotonates one molecule of ethyl acetate.

CH3COOCH2CH3 + NaOCH2CH3 → CH3COO-CH2CH3 + Na+ + CH3CH2OH

2. Nucleophilic attack: The deprotonated ethyl acetate molecule acts as a nucleophile and attacks the carbonyl carbon of another molecule of ethyl acetate.

CH3COO-CH2CH3 + CH3COOCH2CH3 → CH3COCH2COOCH2CH3 + CH3CH2OH

3. Protonation: The intermediate formed in step 2 is protonated by the acidic proton of the alcohol formed in step 1.

CH3COCH2COOCH2CH3 + CH3CH2OH → CH3COCH2COOCH2CH3 + CH3CH2OH

4. Formation of sodium ethoxide: The acidic proton of the alcohol formed in step 1 reacts with sodium ethoxide to form sodium ethoxide and water.

CH3CH2OH + NaOCH2CH3 → Na+ + CH3CH2O-CH2CH3 + H2O

Overall reaction:

2CH3COOCH2CH3 → CH3COCH2COOCH2CH3 + CH3CH2OH

Conclusion:

Thus, the self-condensation of ethyl acetate in the presence of sodium ethoxide yields acetoacetic ester.
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Self condensation of two moles of ethyl acetatein presence of sodium ethoxide yields [2006]a)acetoacetic esterb)methyl acetoacetatec)ethyl propionated)ethyl butyrateCorrect answer is option 'A'. Can you explain this answer?
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