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Another OCHEM practice question

Discussion in 'MCAT: Medical College Admissions Test' started by babinski bob, Apr 13, 2004.

  1. babinski bob

    babinski bob Senior Member
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    Here's a question to brush up on your organic chemistry acidity trend knowledge.

    Rank the following compounds in order of decreasing acidity


    4-methoxybenzoic acid
    4-chlorobenzoic acid
    Benzoic acid
    4-nitrobenzoic acid
    3-nitrobenzoic acid
    3-methoxybenzoic acid
    4-N,N-dimethylaminobenzoic acid

    HINT.... the "acid" is at position 1 since it's not explicitly stated.
     
  2. babinski bob

    babinski bob Senior Member
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    i'll bump this up for all the ochem-o-philes...
     
  3. sdnstud

    sdnstud 1K Member
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    most acidic to least acidic:

    4-nitrobenzoic acid > 3-nitrobenzoic acid > 4-chlorobenzoic acid > Benzoic acid > 3-methoxybenzoic acid > 4-methoxybenzoic acid


    this is probably a trick question, but this is how i would think it through. i used benzoic acid as a reference. nitro and chloro are e withdrawing group so they are more acidic. nitro is a stronger e withdrawing gruop than chloro. nitro is a meta director, thus 4-nitrobenzoic acid is stronger than 3-nitrobenzoic acid.

    methoxy is e donating and make the acid less acidic. methoxy is ortho para directing, thus 3-methoxybenzoic acid > 4-methoxybenzoic acid
     

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