Chemistry
10th Edition
ISBN: 9781305957404
Author: Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher: Cengage Learning
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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?
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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