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Conversion of Ethanol to Acetone

  1. Jan 22, 2008 #1
    1. The problem statement, all variables and given/known data
    Q] How would you convert Ethanol to Acetone?

    2. Relevant equations
    none..

    3. The attempt at a solution
    What I need is a C=O group at the second carbon in a 3-carbon chain. What I need first is a 3rd carbon. To do this, I first could:

    i] React Ethanol with Ethanoic Acid [itex]\textrm{CH}_3\textrm{COOH}[/itex] to get Ethyl Ethanoate [itex]\textrm{C}_2\textrm{H}_5\textrm{COOCH}_3[/itex].

    The problem here is that I have an extra [O]. Can a peroxide remove this? I'm not sure how to get rid of this.

    ii] I could do HCN addition to gain an extra carbon in the chain. But how could I convert the CN to a ketonic group. Also, the problem is that it is on the terminal carbon, but i want it on the 2nd.

    EDIT:

    With Ethyl Ethanoate, if i could replace the [itex]-\textrm{OCH}_3[/itex] group with a [itex]-\textrm{CH}_3[/itex] (methyl) group.. I could get acetone. How do i go about doing it? Would Methyl Chloride help??
     
    Last edited: Jan 22, 2008
  2. jcsd
  3. Jan 22, 2008 #2

    chemisttree

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    Hard to do with an alcohol. Not so hard to do with an aldehyde.
     
  4. Jan 22, 2008 #3
    k then.. i could reduce it to an aldehyde using PCC. I will get [itex]\textrm{CH}_3\textrm{CHO}[/itex]. How can i get propanone from this?
     
  5. Jan 22, 2008 #4

    chemisttree

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    You need to add one carbon to it.
     
  6. Jan 22, 2008 #5

    Bystander

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    Think about the way acetone was produced in "the old" days.
     
  7. Jan 22, 2008 #6
    how exactly did they do it in old days?? I have no idea whatsoever...
     
  8. Jan 22, 2008 #7

    chemisttree

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    Consult either Dr. Grignard or Dr. Wittig.
     
  9. Jan 22, 2008 #8
    is this sarcasm or a hint telling me to consider using Grignard Reagents?
     
  10. Jan 23, 2008 #9
    you can dehydrogenate the alcohol. pass the vapours of the alcohol over copper as catalyst at about 400 degrees. you will get the corresponding ketone and hydrogen.
     
  11. Jan 23, 2008 #10

    chemisttree

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    It's not sarcasm. You have two paths from the aldehyde...
     
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