How Can Ethanol Be Converted to Acetone?

[rohanprabhu]

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??

 

[chemisttree]

Hard to do with an alcohol. Not so hard to do with an aldehyde.

 

[rohanprabhu]

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?

 

[chemisttree]

You need to add one carbon to it.

 

[Bystander]

Think about the way acetone was produced in "the old" days.

 

[rohanprabhu]

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...

 

[chemisttree]

Consult either Dr. Grignard or Dr. Wittig.

 

[rohanprabhu]

Consult either Dr. Grignard or Dr. Wittig.

is this sarcasm or a hint telling me to consider using Grignard Reagents?

 

[Kushal]

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.

 

[chemisttree]

is this sarcasm or a hint telling me to consider using Grignard Reagents?

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