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AP Chemistry/Unit 8: Acids and Bases
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Resonance Stabilization Of A Conjugate Base

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Which statement best explains why the protons on the central methylene (CH₂) group of 2,4-pentanedione (CH₃COCH₂COCH₃) are unexpectedly acidic?

A

The methylene group forms a stronger acid-base adduct

B

The conjugate base is stabilized by extensive delocalization

C

Hydrogen bonding with solvent increases proton dissociation

D

The central carbon is sp hybridized, increasing bond polarity

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