1) Interpret the major absorption bands in the IR spectra of camphor, borneol, and isoborneol.

2) Explain why the gem-dimethyl groups appear as separate peaks in the proton NMR spectrum of isoborneol, although they almost overlap in borneol.

3) A sample of borneol prepared by reduction of camphor was analyzed by IR and showed a band at 1750 cm^-1. This result was unexpected. Why?

% Transmittance 60 50 40 30- 4000 3500 3000 CH3 CH3 CH3 2500 O 2000 1500 Wavenumbers Infrared spectrum of camphor (KBr pellet). mp 1000