The IR spectra of nonane (C,H20) and 1-hexanol (C,H13OH) are shown below. Assign each spectrum to the correct compound and identify the frequencies and the functional groups used to support your assignment. λ (μη) 6 7 8 9 10 11 12 1314 15 2.5 100 3 5 20 4 90 80 70 60 50 40 30 20 10 4000 3600 3200 2800 2400 2000 1800 1600 1400 1200 1000 800 600 400 Frequency (cm¬') A (µm) 2.5 100 8 9 10 11 12 13 14 15 3 4 5 7 20 90 80 70 60 50 40 30 20 10 4000 3600 3200 2800 2400 2000 1800 1600 1400 1200 1000 800 600 400 Frequency (cm¬!) (%) Transmission (%) Transmission

4. Is the C=O stretching frequency the same for acetone and deuterated acetone? Explain your answer. Identify C O overtone in acetone spectrum which corresponds to the transitionn from ground level n= 0, to the second excited lev

Molecular Formula: C₁1H15O₂N ¹H spectrum 160 2H, d J = 7.5 Hz 13C spectrum 140 2H, d J = 7.5 Hz 120 100 5 PPM 80 PPM 60 1H, quintet J = 7 Hz 3 1 6H. triplet J = 7 Hz 4H, quintet J = 7 Hz 40 20

Instructions: Calculate the degrees of unsaturation for the molecule with Formula: C3H6O2, draw the possible structures and identify in each of the spectra the information that confirms its structure No need to calculate the degrees of unsaturation or possible structures, only identify the spectra