Experiment 7: Oxidation of 4-tert-Butylcyclohexanol

Chemical Safety Information:

Experimental Spectra:

Stock GC-MS 4-tert-butylcyclohexanone

Stock IR 4-tert-butylcyclohexanone

Sample NMR 4-tert-butylcyclohexanol and 4-tert-butylcyclohexanone (not available for submission for credit)

Stock NMR 4-tert-butylcyclohexanone (available for submission for credit, see laboratory manual for details)

Frequently Asked Questions:

Q1) Why are we not obtaining an ¹H-NMR spectrum of our oxidized product?

A1) It turns out that a simple ¹H-NMR spectrum is not particularly useful; it cannot be used to assign protons in a straightforward manner.  The spectrum below was obtained from a student sample and demonstrates the difficulty of assigning spectra for this compound.  Only the 9 H-atoms in the tert-butyl group are readily discernible.  For this molecule, IR and GC-MS are more useful methods of simple analysis.

Q2) What is a drying agent?  Why do we need them?  What do they do?

A2) See this explanation from the S_N1/S_N2 experiment page.