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Sportfreunde
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« on: June 03, 2009, 10:14:53 AM » |
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Can someone propose a reaction mechanism for this or explain how it would happen?  |
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kingchemist
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« Reply #1 on: June 03, 2009, 10:41:25 AM » |
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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.
hey
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'Chemistry is not just the study of matter; Chemistry is the study which matters!' - Kingchemist
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kyle1990
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« Reply #2 on: June 04, 2009, 12:55:29 PM » |
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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).  hey |
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"Theories are nets cast to catch what we call 'the world': to rationalize, to explain, and to master it. We endeavor to make the mesh ever finer and finer."
-Karl Popper
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chrisf
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« Reply #3 on: June 05, 2009, 05:57:30 PM » |
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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. ::)
hey
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kyle1990
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« Reply #4 on: June 05, 2009, 11:14:36 PM » |
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lol
hey
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"Theories are nets cast to catch what we call 'the world': to rationalize, to explain, and to master it. We endeavor to make the mesh ever finer and finer."
-Karl Popper
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chrisf
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« Reply #5 on: June 08, 2009, 05:35:44 PM » |
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lol
Good job, by the way. Looks like you're very knowledgeable. hey |
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kyle1990
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« Reply #6 on: June 08, 2009, 09:50:59 PM » |
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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
hey
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"Theories are nets cast to catch what we call 'the world': to rationalize, to explain, and to master it. We endeavor to make the mesh ever finer and finer."
-Karl Popper
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kyle1990
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« Reply #8 on: June 08, 2009, 10:09:12 PM » |
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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! :P
hey
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"Theories are nets cast to catch what we call 'the world': to rationalize, to explain, and to master it. We endeavor to make the mesh ever finer and finer."
-Karl Popper
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chrisf
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« Reply #9 on: June 09, 2009, 11:03:36 AM » |
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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! :P
I though you'd appreciate that. :) hey |
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kyle1990
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« Reply #10 on: June 09, 2009, 11:44:32 AM » |
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I though you'd appreciate that. :)
Yes, very much so hey |
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"Theories are nets cast to catch what we call 'the world': to rationalize, to explain, and to master it. We endeavor to make the mesh ever finer and finer."
-Karl Popper
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