orgo/acidity question

SmilezAllDay

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Mar 30, 2016
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  1. Pre-Dental
    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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    1. Non-Student
      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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