Destroyer Orgo Questions

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GenieG

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Problem 23, says that a hydroxyl oxygen on a benzylic ring is more acidic than an alpha hydrogen that can be stabilized through conjugation to the same benzylic ring. Is this correct? resonance structures would suggest otherwise.

Problem 26 (and this one I feel really stupid for not getting) has a 13C spectrum with four different C's. The solution says that 2-pentanone gives rise to 5 signals. What am I missing?:scared:
 
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