orgo/acidity question

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SmilezAllDay

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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?
 
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
 
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