How could IR spectroscopy be used to distinguish between cyclohexanol and cyclohexene?

Answer 1

Both compounds will give C_sp3 stretching vibrations between 2900 and 3000 cm^-1. Cyclohexene will also display C_sp2 stretching vibrations between 2700 and 2900 cm^-1; however, what will give irrefutable evidence of the presence of cyclohexanol in comparison with cyclohexene, is the broad stretching vibration between 2500 and 3500 cm^-1 of an hydroxyl group, due to H-bonding.