10.The following spectra were acquired from a compound made by dehydration of a secondary alcoholand sulfuric acid, with heat. In the 'H-NMR, the signals at 5.4, 2.0, 1.6 and 1.4 are multiplets, the signal at 0.9 isa triplet. Propose a structure which is consistent with the spectra, and using that structure assign the 'H-nmr andthe infrared spectra.LODassign the characteristicvibrations.1673137830252863145696529314000300020001500100050HAVENUMBERI -l2H2H3Hintegrations:3H2HAssign the proton NMRproton nmr (left)carbon – nmr(below)35132125221418111ppm 010864220018016014012010080604020 ppm o10055Likely parent ion?Base peak?8060Your answer:40846920-102030405060708090100m/zRelative Intensity

From the given data; The given compound is a disubstituted alkene and it is confirmed by the…

10. The following spectra were acquired from a compound made by dehydration of a secondary alcohol and sulfuric acid, with heat. In the 'H-NMR, the signals at 5.4, 2.0, 1.6 and 1.4 are multiplets, the signal at 0.9 is a triplet. Propose a structure which is consistent with the spectra, and using that structure assign the 'H-nmr and the infrared spectra. L00 assign the characteristic vibrations. 1673 1378 3025 2863 1456 965 2931 4000 3000 2000 1000 KAVENUMBERIl 2H 2H 3H Assign the proton NMR proton nmr (left) integrations: 3H 2H carbon – nmr(below) 132 125 22 14 18 10 8 6 5 3. 2 1ppm o 11 4 200 180 160 140 120 100 80 60 40 20 ppm o 100 - 55 Likely parent ion? Base peak? 80 - Your answer: 40 84 69 20 - 10 20 30 40 50 60 70 80 90 100 m/z Relative Intensity

10. The following spectra were acquired from a compound made by dehydration of a secondary alcohol and sulfuric acid, with heat. In the 'H-NMR, the signals at 5.4, 2.0, 1.6 and 1.4 are multiplets, the signal at 0.9 is a triplet. Propose a structure which is consistent with the spectra, and using that structure assign the 'H-nmr and the infrared spectra. L00 assign the characteristic vibrations. 1673 1378 3025 2863 1456 965 2931 4000 3000 2000 1000 KAVENUMBERIl 2H 2H 3H Assign the proton NMR proton nmr (left) integrations: 3H 2H carbon – nmr(below) 132 125 22 14 18 10 8 6 5 3. 2 1ppm o 11 4 200 180 160 140 120 100 80 60 40 20 ppm o 100 - 55 Likely parent ion? Base peak? 80 - Your answer: 40 84 69 20 - 10 20 30 40 50 60 70 80 90 100 m/z Relative Intensity

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter12: Structure Determination: Mass Spectrometry And Infrared Spectroscopy

Section12.SE: Something Extra

Problem 48AP: The infrared spectrum of the compound with the mass spectrum shown below lacks any significant...

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