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Rank Acidity of Alcohols

Discussion in 'DAT Discussions' started by ephesus32, Jan 3, 2009.

  1. ephesus32

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    Can somebody please rank the acidity of a phenol, methanol, primary alcohol, secondary alcohol, and tertiary alcohol? Thanks.
     
  2. doc3232

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    Sure...
    hmmm so
    methanol vs primary alcohol: the alkyl group donates electrons so it is less acidic.
    Same concept with everything else.
    FROM MOST ACIDIC TO LEAST
    Phenol, methanol, primary , secondary, tertiary alcohol.

    Phenol had resonance so it doesn't apply. Resonance trumps substituents.
     
  3. OP
    OP
    ephesus32

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    cool... thanks.. that was what i was thinking
     
  4. yankees27th

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    Are you sure? I thought tertiary would be more acidic than secondary which would be more acidic than primary. But I could be wrong...
     
  5. joonkimdds

    joonkimdds Senior Member
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    I also thought the order is alkyne>alkene>alkane, but it's been 1 week since I studied so I forgot.
     
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  6. doc3232

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    The alkyl groups donate electrons, so the Oxygen has more negative charge, hence more basic and less acidic.

    We are talking number of R groups, not bonds. You would be right if bonds though.
     
  7. joonkimdds

    joonkimdds Senior Member
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    Oh yeah! that's right! OMG...I forgot everything about organic chemistry already :(
     
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  8. Danny289

    Danny289 Member
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    always try to think about conjugate base, stronger acid has week cojugate base, and visa versa, I like doc resoning.
     

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