Experiment 7: Oxidation of 4-tert-Butylcyclohexanol

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oxidation

Due Dates:

27 Feb / 28 Feb A/B

Chemical Safety Information:

Reagents and Solvents
4-tert-butylcyclohexanol acetic acid acetone
sodium hypochlorite dichloromethane sodium bisulfite
sodium bicarbonate diethyl ether magnesium sulfate
4-tert-butylcyclohexanone    

 

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.

1H-NMR of the Oxidation Product

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

A2) See this explanation from the SN1/SN2 experiment page.