Alcohol Reaction Questions

1.) Suggest a chemical test that would allow you to distinguish between tert-butyl alcohol and 1 butanol, both of which give a positive ceric nitrate test?

2.) Why are axial and equatorial hydroxyl isomers for 4 tert butylcyclohexanone, but not for cyclohexanol itself? ( I was thinking steric factors?)

3.)I have to balance this:

O OH
= -
C-C-C-C-C-C + NaBH4 ---> C-C-C-C-C-C

so basically its a 6 carbon chain, and on the 4th carbon there is a double bond on the "oxygen" plus NaBH4 yields another 6 carbon chain with a OH on the fourth carbon.

4.) 2-Pentanol, the product, has a asymmetric carbon as a result of the reduction. A solution of the product shows no optical rotation. Explain this observation in full showing the mechanism of the reaction