orgo/acidity question

[SmilezAllDay]

I'm having trouble figuring out which is more acidic.

4-fluoro butanoic acid or 2-fluoro butanoic acid?

I would think 2-fluoro butanoic acid!!

I know that halogens (e-withdrawing groups) make a compound more acidic by the inductive effect, so does the fluorine being closer to the COOH make it more acidic? ...Better stabilized the anion?

 

[orgoman22]

I'm having trouble figuring out which is more acidic.

4-fluoro butanoic acid or 2-fluoro butanoic acid?

I would think 2-fluoro butanoic acid!!

I know that halogens (e-withdrawing groups) make a compound more acidic by the inductive effect, so does the fluorine being closer to the COOH make it more acidic? ...Better stabilized the anion?

Indeed so......I will give you a great example.....CH3COOH has a pKa of about 5........CF3COOH has a pKa of about NEGATIVE.......yes...you read that right...... -.25

The Fluorine atoms help to stabilize the anion by a significant INDUCTIVE EFFECT.

Hope this helps

Dr. Romano

 

[dentalstudent2021]

I would say the same. since the F is going to stabilize the anion made when deprotonation happens as you said!