Question

The following spectroscopic data below corresponds to an unknown carbonyl compound with the molecular formula C8H12O. Deduce and draw the structure of the compound that corresponds to the data. The letter \"m\" refers to an uninterpretable multiplet in the spectra. 1H NMR: δ 0.94 (t, 3H), 1.48 (sextet, 2H), 2.21 (q, 2H), 5.8-7.1 (m, 4H), and 9.56 (d, 1H) ppm. 13C NMR: δ 13.6, 21.9, 35.2, 129.0, 135.2, 146.7, 152.5, 193.2 ppm.

Answer 1

Based on the NMR data of 1H NMR (proton spectrum) or H spectrum and 13C NMR,

Ar C C-C CEC C-C C-X 220 200 180 160 140 120 100 8060 40 20 0 ppm

based on the above information, our compound have 3, C-C bonds, 3 C=C bonds and one C=O, since the C8H12O with three double bond can only be a linear compound with one carbonyl attached to it. same goes for 1H NMR data.

so the possible structure is

$InChI=1/C8H12O/c1-2-3-4-5-6-7-8-9/h4-8H,2-3H2,1H3/b5-4+,7-6+$ ANswer