u/Bulky-Peanut4808

Acidity ranking help

Acidity ranking help

https://preview.redd.it/qfadv4381jth1.png?width=640&format=png&auto=webp&s=6983b5ae62cf4b957f38b652aaf174ed49ca2720

Hi everyone, I'm having a lot of trouble with this conceptually. I thought it would be Most acidic: I > III > II Least acidic, but I'm not sure why that's wrong, since II is adjacent to some pi bonds doesn't that stabilize the structure? And I is the most acidic because its conjugate base is stabilized by resonance with the carbonyl, while III is also somewhat stabilized by resonance, so I'm confused about why II would be considered more acidic than III.

This is from my second year uni organic chemistry practice questions, any explanation is appreciated

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u/Bulky-Peanut4808 — 11 days ago