How Can Ethanol Be Converted to Acetone?

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    Acetone Ethanol
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Discussion Overview

The discussion revolves around the conversion of ethanol to acetone, exploring various chemical pathways and reactions. Participants are examining theoretical approaches, potential reactions, and the challenges involved in achieving the desired transformation.

Discussion Character

  • Homework-related
  • Exploratory
  • Technical explanation
  • Debate/contested

Main Points Raised

  • One participant suggests starting with the reaction of ethanol and ethanoic acid to form ethyl ethanoate, but expresses concern about the presence of an extra oxygen atom.
  • Another participant mentions the difficulty of converting an alcohol to acetone and suggests that it may be easier with an aldehyde.
  • A later reply proposes reducing the product to an aldehyde using PCC to obtain CH3CHO and questions how to convert this to propanone.
  • Another participant notes that an additional carbon needs to be added to the aldehyde to achieve acetone.
  • There are references to historical methods of acetone production, prompting questions about those methods.
  • One participant suggests consulting historical chemists, Dr. Grignard or Dr. Wittig, which raises questions about the use of Grignard reagents.
  • Another participant proposes dehydrogenating the alcohol over copper at high temperatures to yield the corresponding ketone and hydrogen.
  • Clarification is provided that the mention of historical chemists is not sarcasm and indicates two possible pathways from the aldehyde.

Areas of Agreement / Disagreement

Participants express differing views on the feasibility of various methods for converting ethanol to acetone, with no consensus reached on the best approach. Multiple competing ideas and pathways remain under consideration.

Contextual Notes

Participants highlight challenges such as the need for additional carbon atoms and the complexities involved in converting functional groups. There are unresolved questions regarding the specific reactions and conditions required for successful conversion.

Who May Find This Useful

Individuals interested in organic chemistry, particularly those studying reaction mechanisms and synthesis pathways, may find this discussion relevant.

rohanprabhu
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Homework Statement


Q] How would you convert Ethanol to Acetone?

Homework Equations


none..

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 \textrm{CH}_3\textrm{COOH} to get Ethyl Ethanoate \textrm{C}_2\textrm{H}_5\textrm{COOCH}_3.

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 -\textrm{OCH}_3 group with a -\textrm{CH}_3 (methyl) group.. I could get acetone. How do i go about doing it? Would Methyl Chloride help??
 
Last edited:
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Hard to do with an alcohol. Not so hard to do with an aldehyde.
 
chemisttree said:
Hard to do with an alcohol. Not so hard to do with an aldehyde.

k then.. i could reduce it to an aldehyde using PCC. I will get \textrm{CH}_3\textrm{CHO}. How can i get propanone from this?
 
You need to add one carbon to it.
 
Think about the way acetone was produced in "the old" days.
 
Bystander said:
Think about the way acetone was produced in "the old" days.

how exactly did they do it in old days?? I have no idea whatsoever...
 
Consult either Dr. Grignard or Dr. Wittig.
 
chemisttree said:
Consult either Dr. Grignard or Dr. Wittig.

is this sarcasm or a hint telling me to consider using Grignard Reagents?
 
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.
 
  • #10
rohanprabhu said:
is this sarcasm or a hint telling me to consider using Grignard Reagents?

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

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