Hydrogen acidity.

[Astra]

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Is the alpha hydrogen of a Aldehyde less or more acidic than the hydrogen of a carbon bound to flourine?

i.e.

Does resonance stabilization outweigh the increased withdrawing capacity?

 

[theonlytycrane]

this is a judgement call that I don't think we would have to make because it's apples to oranges. What I mean is that we might compare acidity of a proton of a carbon bound to fluorine vs. chlorine or acidity of a proton at the alpha of only one carbonyl vs. two carbonyls

 

[Astra]

this is a judgement call that I don't think we would have to make because it's apples to oranges. What I mean is that we might compare acidity of a proton of a carbon bound to fluorine vs. chlorine or acidity of a proton at the alpha of only one carbonyl vs. two carbonyls

I hope so lol.

I am really going in depth this last month of reviewing and find myself asking weird questions I guess :O

 

[yeasureyoubetcha]

this is a judgement call that I don't think we would have to make because it's apples to oranges. What I mean is that we might compare acidity of a proton of a carbon bound to fluorine vs. chlorine or acidity of a proton at the alpha of only one carbonyl vs. two carbonyls

This is what they will do on the mcat.

 

[aldol16]

The answer to this question depends on the compound. Since there are no hard and fast rules, the MCAT would give you enough information to solve this without knowing the specific pKas.

 

[NextStepTutor_2]

Is the alpha hydrogen of a Aldehyde less or more acidic than the hydrogen of a carbon bound to flourine?

i.e.

Does resonance stabilization outweigh the increased withdrawing capacity?

This is beyond the level of reasoning expected by the AAMC. Both inductance AND resonance play a role in determining acidity.

Inductance can further be broken down into:

quantity (how many ewg you have)
quality (how electronegative they are)
proximity (how close to the H are they).

Quantifying the exact relative contributions of the two properties is nit-picky and something your chem professor may ask, but not the MCAT.

hope this helps, good luck!