Would the base sodium phenoxide be a good choice for deprotonation of ethyl acetoacetate (pKa = 11)? Explain your answer fully. b) Why is ethyl acetoacetate so acidic compared to the average ketone or ester, which have pKa values in the lower 20s?

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10.) Would the base sodium phenoxide be a good choice for deprotonation of ethyl acetoacetate (pKa = 11)? Explain your answer fully. b) Why is ethyl acetoacetate so acidic compared to the average ketone or ester, which have pKa values in the lower 20s?
This image shows a chemical equilibrium reaction between sodium phenoxide and ethyl acetoacetate.

**Reactants:**
1. **Sodium Phenoxide (C₆H₅ONa)**  
   - Structure: A benzene ring with an oxygen anion (\(O^-\)) bonded to it, paired with a sodium cation (\(Na^+\)).

2. **Ethyl Acetoacetate (C₆H₁₀O₃)**  
   - Structure: Contains a ketone group, an ester group (\(OEt\)), and a methylene (\(CH_2\)) group.

**Products:**
1. **Phenol (C₆H₅OH)**  
   - Structure: A benzene ring with a hydroxyl group (\(OH\)) attached.

2. **Sodium Enolate of Ethyl Acetoacetate**  
   - Structure: The enolate form of ethyl acetoacetate, featuring a negatively charged oxygen (\(O^-\)) with sodium cation (\(Na^+\)).

The reaction is represented as an equilibrium process, indicating it can proceed in both forward and reverse directions.
Transcribed Image Text:This image shows a chemical equilibrium reaction between sodium phenoxide and ethyl acetoacetate. **Reactants:** 1. **Sodium Phenoxide (C₆H₅ONa)** - Structure: A benzene ring with an oxygen anion (\(O^-\)) bonded to it, paired with a sodium cation (\(Na^+\)). 2. **Ethyl Acetoacetate (C₆H₁₀O₃)** - Structure: Contains a ketone group, an ester group (\(OEt\)), and a methylene (\(CH_2\)) group. **Products:** 1. **Phenol (C₆H₅OH)** - Structure: A benzene ring with a hydroxyl group (\(OH\)) attached. 2. **Sodium Enolate of Ethyl Acetoacetate** - Structure: The enolate form of ethyl acetoacetate, featuring a negatively charged oxygen (\(O^-\)) with sodium cation (\(Na^+\)). The reaction is represented as an equilibrium process, indicating it can proceed in both forward and reverse directions.
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