[zerodeniro]

My question.  Does the reaction occure between cyclohexanol and NaOH that yields Cyclohexane-O-Na  + H20.  Explain.  I believe the question wants me to think about the acidity of the alcohol and how the reaction might occur.  I am lost.  can someone help?

[HP]

This is reverse reaction:
R-OH + NaOH to R-O:-Na+ and water formed...
But water + RONa if R aliphatic compound turn the equilibrium left to starting compounds. Of course if you work with solid powdered NaOH in organic solvent like dioxane at temp about 100C then you may manage the equilibrium right to desired alcoxide. Dioxane associate the formed water ...
But if you seriously want to obtain your RONa then using elemental Na or better NaH will work best. Good heterogenic source of Na or K these are the intercalating compounds of graphite with alkali methals: for example LiC6, KC8,KC24 and so on  

[yummyyang]

Very good explaination. Normally I use NaH as a base to obtain RO-, doing a williamson etherification.