[Fischer]

Hey guys.

So my professor was doing some problems on the board,

He did the following;

Cyclohexane + Na  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.

[Fischer]

Any ideas guys?

[AlphaScent]

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.

[Fischer]

Yeah I'm going to ask him... Unless as you stated, we are not taking something into account but I highly  doubt that.

[AWK]

May be your teacher thought about cyclohexanol?

[Dan]

No, it's nonsense; CyH + Na Cy⁺ + NaH is not even balanced.

The reaction with cyclohexanol is CyOH + Na CyONa + ¹/₂ H₂

He's made a mistake, you should ask him to clarify.

[orgopete]

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.