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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?
 

orgoman22

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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?

    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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    dentalstudent2021

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