Identify the structure of the compound having the following molecular formula, IR, and 1H NMR spectra (integrals and multiplicity shown in the boxes: s-singlet, d-doublet, t-triplet, q-quartet, etc.). Label the spectra with the information (functional groups, number of protons, formula, Compound formula. C4H8O Questions to help you decide the structure.  What is the

Fundamentals Of Analytical Chemistry
9th Edition
ISBN:9781285640686
Author:Skoog
Publisher:Skoog
Chapter29: Mass Spectrometry
Section: Chapter Questions
Problem 29.5QAP
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Identify the structure of the compound having the following molecular formula, IR, and 1H NMR spectra (integrals and multiplicity shown in the boxes: s-singlet, d-doublet, t-triplet, q-quartet, etc.). Label the spectra with the information (functional groups, number of protons, formula,

Compound formula. C4H8O

Questions to help you decide the structure. 

  1. What is the element of unsaturation of the molecular formula? Show the math you use:
  2. What are the functional groups present in this molecule? Show all of them below:
  3. Draw at least two possible structures that have the required element of unsaturation as well as the observed functional
  4. Based on the 1H NMR above, what molecular fragmentations do you see
  5. Draw your final decision of the structure below:
Compound formula. C4H3O
90
IR
80
70
60
50
40
30
20
10
-0-
4000
3500
3000
2500
2000
1500
1000
500
Wavenumbers (cm-1)
% Transmittance
2965.21
2879.49
2821.37
2721.47
1727.43
1461.21
1388.31
1268.95
1216.48 S
1119.85
1048.12
995.89
962.68
781.48
520.13
Transcribed Image Text:Compound formula. C4H3O 90 IR 80 70 60 50 40 30 20 10 -0- 4000 3500 3000 2500 2000 1500 1000 500 Wavenumbers (cm-1) % Transmittance 2965.21 2879.49 2821.37 2721.47 1727.43 1461.21 1388.31 1268.95 1216.48 S 1119.85 1048.12 995.89 962.68 781.48 520.13
3H, t
1Η ΝMR
TMS
2H, t 2H, m (6)
1H, t
10
8.
7
4
LO
-CO
Transcribed Image Text:3H, t 1Η ΝMR TMS 2H, t 2H, m (6) 1H, t 10 8. 7 4 LO -CO
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