clarinethero214

Hi there. I'm having SO much trouble trying to figure out the reasoning to this answer. I'm given this molecule (with some hydrogens I labeled A, B, C, D, and E): I need to rank the hydrogens in order of increasing acidity. I know the answer is DACEB, but I'm a little confused as to why. My textbook tells me that the most important contributing factor is what atom the hydrogen is bonded to (with the most acidic lying to the right of a period and down a group). This would, undoubtedly, make hydrogen E the most acidic since it's bonded to oxygen while the others are bonded to carbon, but this isn't the case. It must be due to the resonance stabilization that the double bonded oxygens supply to hydrogen B, but this seems to go straight against my textbook in which order of significance I look at things at! I understand that B and C are affected by resonance stabilization, but my main concern is why B is the MOST acidic if I'm supposed to look at what atom the hydrogen is bonded to first and foremost (even this website says so: http://masterorganic...luence-acidity/ Please, any help will be MUCH appreciated.