Chemical Forums
Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: Fischer on December 12, 2013, 09:33:14 AM
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Hey guys.
So my professor was doing some problems on the board,
He did the following;
Cyclohexane + Na :rarrow: cyclohexane (secondary carbocation) + NaH
I am very confused about this... He formed a secondary carbocation from adding Na to cyclohexane. I did not ask him in class as I just realized what he did when reading through my notes. Is this even possible.
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Any ideas guys?
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I would think that this reaction would not proceed. I rinse my sodium before using it with hexanes all the time and there is no reaction. I just do not think the protons are acidic enough. I would email and ask him. I do not think that is good theory to teach. I could be wrong due to some interaction I am not taking into account when it is in the chair conformation. But like I said, do not believe there will be a reaction. He could just be doing as theory, not practical.
Ask him..Id like to know what he says.
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Yeah I'm going to ask him... Unless as you stated, we are not taking something into account but I highly doubt that.
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May be your teacher thought about cyclohexanol?
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No, it's nonsense; CyH + Na :rarrow: Cy+ + NaH is not even balanced.
The reaction with cyclohexanol is CyOH + Na :rarrow: CyONa + 1/2 H2
He's made a mistake, you should ask him to clarify.
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Often we can guess what might have been meant, even when there is an error. In this case, I can't even do that. Sodium metal is an electron donor and the net result shows sodium has donated its electron, but the recipient ends up with a positive charge. This is clearly an error (assuming the notes are correct). A simple test, the net charges on each side of the arrow must balance. In this case, they do not.