[treadlightly]

I have a question about acidic hydrogen, but it's mostly about sulfur-containing compounds.

I attached a picture of the compound that I am focusing on. From what I can tell, there are two hydrogens that I would consider to be the most acidic. 1) the hydrogens alpha between both carbonyls and 2) the hydrogens alpha between the middle carbonyl and the sulfonyls.

My guess is that the latter is the most acidic, because the carbanion formed there after deprotonation is triply stabilized by the two sulfonyls and the carbonyl left of it. Also, the methoxy group attached to the sulfur is electron-withdrawing, making the latter hydrogens even more acidic.

Could anyone confirm my answer? Also, did I miss anything to mention in my explanation?

[spirochete]

My guess is that the latter is the most acidic, because the carbanion formed there after deprotonation is triply stabilized by the two sulfonyls and the carbonyl left of it. Also, the methoxy group attached to the sulfur is electron-withdrawing, making the latter hydrogens even more acidic.

Could anyone confirm my answer? Also, did I miss anything to mention in my explanation?

All good sound logic except a methoxy group is electron donating by resonance and withdrawing by induction. You cannot say unequivocally that it is withdrawing unless you know more than you are letting on here.

Normally we would expect resonance donation to be the dominant effect with a methoxy group, but resonance between sulfur and oxygen is relatively weak due to poor orbital overlap so who knows.

The rest of your argument is good, just try to not throw in partially untrue tidbits when overall you're making a good point!

[treadlightly]

Ahh I see what you're talking about in regards to the methoxy group.

thanks for confirming my argument
I have one more question, though, if you're willing to help me out some more: does the fact that there is a sulfur present have any significant effects on the carbon next to it? Or can I think of it as something similar to another carbon? My professor did not really go into great details about sulfur analogs in his powerpoint lecture.

[spirochete]

I am not 100% sure but I would imagine that an electron deficient sulfur would be very electron withdrawing via polarized induction, as well as through resonance with the lone pair on the conjugate base.

[Sophia7X]

for sulfur-oxygen compounds, in this case, we have a sulfone— the double bond character in an S-O bond is actually quite weak due to the nature of sulfur. The structure is better represented with a single bond, with resultant formal charges. But you normally see S=O since old habits die hard.

This is reinforces the fact that sulfur would be carrying a partial positive charge.

[spirochete]

for sulfur-oxygen compounds, in this case, we have a sulfone— the double bond character in an S-O bond is actually quite weak due to the nature of sulfur. The structure is better represented with a single bond, with resultant formal charges. But you normally see S=O since old habits die hard.

This is reinforces the fact that sulfur would be carrying a partial positive charge.

All true. But then doesn't this increase the electron withdrawing ability of the sulfur via polarizable induction?