A Reaction Mechanism

[Sportfreunde]

Can someone propose a reaction mechanism for this or explain how it would happen?

[kingchemist]

Not an expert but the reaction is probably a dehydration where OH is eliminated (as H₂O) to leave a carbocation which eventually results in a double bond. However, here it appears that ring is made to accomodate the shortage of hydrogen.
The mechanism for the dehydration of alkanols to alkenes is shown in the attachment. Somewhere after the loss of the proton, a ring is formed.

[kyle1990]

I decided to take a stab at this myself, so this is the mechanism I came up with. I'm no expert either, but it makes sense if you ask me. Note that I redrew the molecule in a more appropriate configuration relative to the product (since rotation around single bonds is possible).

[chrisf]

I came up with something very similar to Kyle's but slightly different in a couple of aspects. Actually... no it's not. It's exactly the same. Nevermind.

[kyle1990]

lol

[chrisf]

lol

Good job, by the way. Looks like you're very knowledgeable.

[kyle1990]

I must say, I was a bit impressed as well. I wish there were more questions like this....it's great practice that's for sure

[chrisf]

I must say, I was a bit impressed as well. I wish there were more questions like this....it's great practice that's for sure

http://www.mychemistrytutor.com/forums/organic-chemistry/out-of-curiousity-what-would-you-give-me-as-an-answer/

[kyle1990]

It's too funny you posted that link. Only a few months ago, I found those questions difficult. But now I look at it and it's no problem. Lol I tried to incorporate stereochemistry on the double bond in the ring! 

[chrisf]

It's too funny you posted that link. Only a few months ago, I found those questions difficult. But now I look at it and it's no problem. Lol I tried to incorporate stereochemistry on the double bond in the ring! 

I though you'd appreciate that.

[kyle1990]

I though you'd appreciate that.

Yes, very much so