1. Not finding help here? Sign up for a free 30min tutor trial with Chegg Tutors
    Dismiss Notice
Dismiss Notice
Join Physics Forums Today!
The friendliest, high quality science and math community on the planet! Everyone who loves science is here!

Jones Oxidation

  1. Jul 20, 2007 #1
    1. The problem statement, all variables and given/known data

    I am trying to figure out the complete reaction equation for the oxidation of a secondary alcohol, 2-butanol, with CrO3 (and H2SO4).



    2. Relevant equations

    See below.

    3. The attempt at a solution

    In this oxidation, the alcohol is turned into a ketone, not a carboxylic acid, correct?

    Therefore, the simple synthesis setup would be:

    CH3CH2CH(OH)CH3 + CrO3 + H2SO4 -> CH3CH2C(=O)CH3

    Now for the redox reaction with the chromium ions:

    (Please note that I am slightly rusty on balancing redox reactions, and I really don’t know if this is remotely valid.)

    CrO3 -> Cr(+3)
    CH3CH2CH(OH)CH3 -> CH3CH2C(=O)CH3 ??

    3 e- + CrO3 + 6 H(+) -> Cr(+3) + 3H2O
    CH3CH2CH(OH)CH3 -> CH3CH2C(=O)CH3 + H(+) + 1 e-

    3 e- + CrO3 + 6 H(+) -> Cr(+3) + 3H2O
    3*(CH3CH2CH(OH)CH3 -> CH3CH2C(=O)CH3 + H(+) + 1 e-)


    3 e- + CrO3 + 6 H(+) -> Cr(+3) + 3H2O
    3 CH3CH2CH(OH)CH3 -> 3 CH3CH2C(=O)CH3 + 3H(+) + 3 e-
    CrO3 + 6 H(+) + 3 CH3CH2CH(OH)CH3 -> Cr(+3) + 3H2O + 3 CH3CH2C(=O)CH3 + 3H(+)

    CrO3 + 3 H(+) + 3 CH3CH2CH(OH)CH3 -> Cr(+3) + 3H2O + 3 CH3CH2C(=O)CH3 ?

    Thank you.
     
  2. jcsd
  3. Jul 22, 2007 #2
    Yeah. Looks right.
     
  4. Jul 22, 2007 #3
    I just came across this equation for the oxidation in a book.

    2CrO3 + 6 H(+) + 3 CH3CH2CH(OH)CH3 -> 2Cr(+3) + 6H2O + 3 CH3CH2C(=O)CH3

    Why is it that the bold coefficients are two times more than those in my equation?

    Did I do something wrong?

    Thanks again.
     
    Last edited: Jul 22, 2007
  5. Jul 24, 2007 #4

    chemisttree

    User Avatar
    Science Advisor
    Homework Helper
    Gold Member


    Rethink this... pay attention to the hydrogens I have bolded.
     
Know someone interested in this topic? Share this thread via Reddit, Google+, Twitter, or Facebook

Have something to add?



Similar Discussions: Jones Oxidation
  1. Oxidation of pyrite (Replies: 1)

  2. Jones reduction (Replies: 0)

Loading...