The following spectroscopic data are for two carbonyl compounds with the formula C 8 H 12 O.

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The following spectroscopic data are for two carbonyl compounds with the formula C8H12O. Suggest a structure for each compound. The letter “m” stands for the appearance of this particular part of the spectrum as an uninterpretable multiplet. 

(a) 1H NMR: δ = 1.60 (m, 4 H), 2.15 (s, 3 H), 2.19 (m, 4 H), and 6.78 (t, 1 H) ppm. 13C NMR: δ = 21.8, 22.2, 23.2, 25.0, 26.2, 139.8, 140.7, and 198.6 ppm. 

(b) 1H NMR: δ =0.94 (t, 3 H), 1.48 (sex, 2 H), 2.21 (q, 2 H), 5.8 – 7.1 (m, 4 H), and 9.56 (d, 1 H) ppm. 13C NMR: d 5 13.6, 21.9, 35.2, 129.0, 135.2, 146.7, 152.5, and 193.2 ppm.

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Organic Chemistry structure and function

ISBN: 978-1429204941

6th edition

Authors: K. Peter C. Vollhardt, Neil E. Schore

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