Which will undergo deprotonation most readily in basic medium?

Question

Canvas Classes · Accepted Answer

Step 1: Acidity of Active Methylene Protons
Deprotonation occurs most readily where the conjugate base is most stable. 
- Structure A: 2,4-pentanedione. The active methylene hydrogens are flanked by two methyl ketones. The  and  effects of two keto groups stabilize the anion.
- Structure B: Dimethyl malonate. Esters are less electron-withdrawing than ketones due to the  effect of the alkoxy group.
- Structure C: Ethyl acetoacetate. One ketone and one ester.

Step 2: Conclusion
Structure A has tw

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