Question

Fill in the blank s=singlet d= doublet q= quartet and so on also which molecule match the HNMR and CNMR spectra

Observed 1H NMR and 13C NMR spectra: NMR Data Table for Predicting Expected Signals ЗН # of 'H Alcohol Ester Esterification Product with Acetic Acid # of 13C Ester NMR signals NMR signals 1H Ester NMR Integration & splitting (from left to right) HO Ethanol 4 3 3H(s), 2H(q), 3H(t) Ethyl acetate НО 1-Butanol Butyl acetate 2H 3H 4H 2H i но 1-Pentanol Pentyl acetate HO 1 8 1 3 11 10 9 7 6 5 4 2 1 0 HSP-03-935 ppm Cyclopentanel Cyclopentyl acetate Two signals here 28.23 and 28.48 ppm il 3-Methyl-1-butanol Isoamyl acetate 200 180 160 140 120 100 80 60 40 20 0 COS-03-271 ppm

Answer 1

Alcohol Esterification product with acetic acid 0 # of 13C Ester NMR Signals # of 1H Ester NMR Signals 1H Ester NMR Integration and splitting (from left to right) HO 6 1-butanol 5 3H(s), 2H(t), 2H(pentet), 2H(sextet), 3H (t) butyl acetate HO 1-pentanol 7 6 (5 if overlapped) pentyl acetate 3H(S), 2H(t), 2H(pentet), 2H(pentet), 2H(sextet), 3H (t) (note that the red marked H can appear as a multiplet together) НО. O 5 4 3H(s), 1H(pentet), 4H(m), 4H(m) cyclopentanol cyclopentyl acetate nh HO 6 4 3H (S), 2H (t), 2H(), 1H (n), 6H (d) 3-methyl-1-butanol isoamyl acetate In the spectrum given in the question there are o ppm 4.1 (t, 2H), 2.0 (s, 3H), 1.8 (p, 2H which is overlapped), 1.4 (m, 4H), 0.9 (t, 3H). 13C NMR peaks ô ppm 171, 64, 28.48, 28.23, 22, 21, 14., total 7 signals. For 7 different carbons. The spectrum contains total 5 signals in which one multiplet for 4H is an overlap. Total the spectrum has 14H. This resembles pentyl acetate as described above. pentyl acetate