Desperately needed help for organic 1

[Gunner1412]

Homework Statement

Design and describe a step-by-step total synthesis, using appropriate reagents, and drawing the reactants and the products resulting from each step-by step reaction to obtain B from A. Total # of carbons must stay the same.
A is cyclopentanol, B is cyclopentane with a double bonded Oxygen where the OH used to be

Homework Equations

I don't think there's any equations really, but I can use basic Alkene and Alkyne Rxns.

The Attempt at a Solution

I was told to work backwards to find a solution, and it was under acidic conditions. I tried to to use oxidation with (i)KMnO4(ii)H20/OH- but that just breaks a double bond and adds two hydroxyl groups. Apparently there's a way to go straight from A to B but its an Organic 2 reaction that I can't use. I went through all my notes and the textbook I really can't figure it out.

I'm really stressed out, I need as much help as possible :(
Thanks in advance

 

[sjb-2812]

Homework Statement

Design and describe a step-by-step total synthesis, using appropriate reagents, and drawing the reactants and the products resulting from each step-by step reaction to obtain B from A. Total # of carbons must stay the same.
A is cyclopentanol, B is cyclopentane with a double bonded Oxygen where the OH used to be

Homework Equations

I don't think there's any equations really, but I can use basic Alkene and Alkyne Rxns.

The Attempt at a Solution

I was told to work backwards to find a solution, and it was under acidic conditions. I tried to to use oxidation with (i)KMnO4(ii)H20/OH- but that just breaks a double bond and adds two hydroxyl groups. Apparently there's a way to go straight from A to B but its an Organic 2 reaction that I can't use. I went through all my notes and the textbook I really can't figure it out.

I'm really stressed out, I need as much help as possible :(
Thanks in advance

I'm not sure what Organic 1 & 2 are, but it seems strange that you're not allowed a more straightforward pathway just because it's in the wrong course. Anyway, what will happen first to your alcohol under acidic conditions?

 

[chemisttree]

Why are you bothering thinking about alkenes? You have an alcohol and you want to transform it into a ketone. Can you think of any reactions that might do that conversion?

 

[sjb-2812]

Why are you bothering thinking about alkenes? You have an alcohol and you want to transform it into a ketone. Can you think of any reactions that might do that conversion?

Yeah, this was what I was alluding to when I said "...it seems strange that you're not allowed a more straightforward pathway just because it's in the wrong course..." Could it be that this reaction is in the scope of the mystery Organic 2?

 

[chemisttree]

No, I don't think so. I think the OP just got a little confused when OP saw the phrase "...cyclopentane with a double bonded oxygen..." and immediately thought of cyclopentene... which is carbon double bonded to carbon, of course. It's a minor point of confusion but confounded OP's further analysis of the problem. Sometimes it helps to step back and take another look and try not to stress out!

Easily said, I know.