Shown below are five NMR spectra for five different C₆H₁₀O₂ compounds. For each spectrum, draw the structure of the compound, and assign the spectrum by labeling H's in your structure (or in a second drawing of the structure) with the chemical shifts of the corresponding signals (which can be estimated to nearest 0.1 ppm). IR information is also provided. As a reminder, a peak near 1700 cm^-1 is consistent with the presence of a carbonyl (C=O), and a peak near 3300 cm^-1 is consistent with the presence of an OH.

(f) The spectra in (a) and (e) both have triplets near 1 ppm, and the J values are about the same (about 7 Hz). Why does the pattern in (a) look so much wider?

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(a) A strong band was observed in the IR at 1716 cm-1 t, 6H 9,4H 90 MHz 10 9 8 7 6 5 4 3 2 1 (b) A strong band was observed in the IR at 1718 cm 1 s, 6H S, 4H 90 MHz 10 9 T 0 8 7 6 5 4 3 2 1 (c) A strong band was observed in the IR at 1717 cm 1 S, 3H s, 3H d, 3H q, 1H 400 MHz T T T T T 9 1 7 | 5 1 4 1 3 T 0 -N 8 6 2 1 (d) Note that bs= broad singlet. This peak, 4.16 ppm, was not observed in a second spectrum after a drop of D.O was added to the sample. A strong band was observed in the IR at 3320 cm-1 d, 6H q, 2H bs, 2H mu 90 MHz T 10 9 00 7 6 5 4 3 2 1 0 le) A strong band was observed in the IR at 1717 cm 1 s, 3H t, 3H t, 2H h, 2H 300 MHz T 1 9 1 8 I 7 1 1 6 5 4 3 2 0 (f) The spectra in (a) and (e) both have triplets near 1 ppm, and the values are about the same (about 7 Hz). Why does the pattern in (a) look so much wider