Question

A variety of spectra for an organic compound with molecular formula C₁₀H₁₆O are presented below. The experimental accurate mass using (+) APCI source is 153.1280 u. The 1H, 13C, COSY, HSQC and HMBC NMR spectra are given in the following slides. Propose a structure for this unknown and answer or address the following questions or requirements:

a. Using the most abundant isotopes of C, H and O, what are the errors in ppm and milli-Daltons for the experimental accurate mass?

MASS SPECTRUM 100 ← 81 80 60 d 40 20- 91 109 152 123 ill.. ala. 0 160 120 80 m/z 40 0.0 7 2. H-NMF 6.1 ppm 6.2 6.3 6.4 6.6 6.5 6.7 6.9 6.8 7.1 7.0 ppm 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 15 1.0 0.5 ppm 2. C-NMR T71 6 9 10 4 200 190 180 170 60 0 140 130120 110 100 080 0 60 50 40 30 20 ppm 2. COSY ppm 2 8 9 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 ppm 2. HSQC ppm 20 40 60 80 100 120 140 160 180 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 ppm 2. HMBC 10 40 6 60 80 100 120 140 4 160 2 180 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 45 4.0 3.5 3.0 2.5 2.0 1.5 1.0 ppm

Answer 1

1.S5 の68 ppm го, н. 1S2 621 13 NM 309 117 3S1 141 0 2 128. 1301 M/2こ152.