Compound 15 is a high-boiling liquid with the chemical formula: C,H₁0O. The disappears when D₂O is added to the sample. Using this information, as well determine its structure. peak at 4.15 ppm in its ¹H NMR data provided below, as the spectral

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter13: Structure Determination: Nuclear Magnetic Resonance Spectroscopy
Section13.SE: Something Extra
Problem 59GP: The mass spectrum and 13C NMR spectrum of a hydrocarbon are shown. Propose a structure for this...
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Compound 15 is a high-boiling liquid with the chemical formula: C,H₁0O. The peak at 4.15 ppm in its 'H NMR
disappears when D₂O is added to the sample. Using this information, as well as the spectral data provided below,
determine its structure.
3000
911
100 110 120 130 140 150 160 170
2000
1500
1000
500
li
ppm, 4.
13C Spectral Data (8, ppm): 140.2, 128.4, 127.9, 125.7, 68.5, 44.6
Transcribed Image Text:Intensity 4000 Compound 15 is a high-boiling liquid with the chemical formula: C,H₁0O. The peak at 4.15 ppm in its 'H NMR disappears when D₂O is added to the sample. Using this information, as well as the spectral data provided below, determine its structure. 3000 911 100 110 120 130 140 150 160 170 2000 1500 1000 500 li ppm, 4. 13C Spectral Data (8, ppm): 140.2, 128.4, 127.9, 125.7, 68.5, 44.6
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