[redpiccato]

Hi, guys. I am working on a lab experiment on reduction of camphor for my OChem class. Can you help me with these problems?

- How do you know whether or not your reduction was successful?
- What are some of the important side reactions that can occur during this lab experiment?
- Explain why the isoborneol NMR spectrum shows 3 separate methyl peaks but in borneol NMR spectrum the 3 different methyl groups are not resolved.

Thanks.

[OrgXemProf]

So, let's take 'em one at a time:

1. Which functional group in camphor is likely to be most susceptible to reaction with a common reducing agent under ambient conditions? Which reducing agent(s) is/are suitable to perform this reduction in a student laboratory?

2. After you have answered question #1, above, can you now suggest possible side reaction product(s)?

3. The proton NMR spectrum of L-(-)-borneol (CAS #464-45-9) obtained at 400 MHz (solvent not specified) displays three distinct methyl group singlet absorptions at delta
0.845, 0.855 and 0.866

(Online reference: http://www.chemicalbook.com/SpectrumEN_464-45-9_1HNMR.htm).

If your reference spectrum of borneol was obtained by using a spectrometer with field strength <400 MHz, this might explain why the spectral dispersion was insufficient to permit clear eyeball-resolution of the three chemically and magnetically nonequivalent methyl groups in borneol.

4. And now, a question for YOU: Suppose that you opened a cabinet and found two unlabeled bottles that contain colorless oils. Lying next to the bottles, in no particular order, you found two labels; one label is clearly marked "borneol" and the other is marked "isoborneol". Describe an NMR experiment that you could perform that potentially would permit you to distinguish between these two isomeric compounds, thereby permitting you to affix the labels correctly onto the two bottles.