Question

The elemental analysis of an Unknown reveals that compound X contains only the three elements C, H, & O and that the molecular weight is m/z = 148. Also, consider the (i) IR and (ii) proton NMR spectra of the unknown compound "X" provided. Briefly, yet completely interpret the two parts (1) IR & (ii) proton NMR and then in (iii) the elemental analysis, including unsaturation calculation of the unknown. Finally, determine by a circle which of the structures listed below is consistent with the structure for compound "X". i) Interpretation: i) 3000 2000 700 1500 1200 1000 900 800 Frequency, cm) ii) Interpretation: 2H 13 8.0 7.0 6.0 5 0.0 4.0 3.0 2.0 1.0 6. ppm iii) Interpretation: Determine by a circle which of the structures listed is consistent with the structure for compound "X" H-CH -CH-CHCH, -o-CH-CH=CHCH, CC-CH,CHỊCH, -CH2CH2-O-CH.CH None of the above.

Please answer all parts.

Answer 1

m/z 148 means Compound may be in the form - C₁₀H₁₂O

First , I interprete the IR data .

IR shows 1 peak near 1700 cm^-1 that refers carbonyl group.

Peaks near 3000 cm^-1 refers sp² and sp³ C-H bonds.

Peaks near 1600 cm^-1 refers C=C double bonds.

Peaks near 1200 cm^-1 refers C-C single bonds.

Now,¹H NMR data .

From 7.0 to 8.0 , total 5 protons are there referring to the aromatic protons . Thus , a benzene is there .

Then 3 proton triplet and 2 proton quartet suggests a presence of -CH₂-CH₃ functionality.

So, finally , the solve is ,

HACCH2

TH Estimation 7.53 7.97 0.90 7.53 797 296 1.59 PPM