An unknown compound has the following spectroscopic properties: Mass Spectrometry: m/z 102 (very small), 87 & 43 are the largest ions ¹Hnmr: 8 1.4 & 3.9 ppm (both singlets, intensity ratio 3:2) 13 Cnmr: 8 108, 64 & 25 ppm, Infrared Spectroscopy: several strong absorptions in the 1000 to 1300 cm¹ regiom Which of the following is the most likely formula of this compound? OA B Xo с D

An unknown compound has the following spectroscopic properties: Mass Spectrometry: m/z 102 (very small), 87 & 43 are the largest ions ¹Hnmr: 8 1.4 & 3.9 ppm (both singlets, intensity ratio 3:2) 13 Cnmr: 8 108, 64 & 25 ppm, Infrared Spectroscopy: several strong absorptions in the 1000 to 1300 cm¹ regiom Which of the following is the most likely formula of this compound? OA B Xo с D

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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The mass spectrum and 13C NMR spectrum of a hydrocarbon are shown. Propose a structure for this hydrocarbon, and explain the spectral data.
Following is the mass spectrum of an unknown compound. The two highest peaks are at m/z 120 and 122. Suggest a structure for this compound. (Data from http://webbook.nist.gov/chemistry/.)
Oxidation of citronellol, a constituent of rose and geranium oils, with PCC in the presence of added NaOCOCH3 forms compound A. A has amolecular ion in its mass spectrum at 154 and a strong peak in its IRspectrum at 1730 cm−1, in addition to C—H stretching absorptions.Without added NaOCOCH3, oxidation of citronellol with PCC yieldsisopulegone, which is then converted to B with aqueous base. B has amolecular ion at 152 and a peak in its IR spectrum at 1680 cm−1, inaddition to C—H stretching absorptions. a.) Identify the structures of A and B.b.) Draw a mechanism for the conversion of citronellol to isopulegone.c.) Draw a mechanism for the conversion of isopulegone to B.
The NMR spectra for compound 1 were acquired in a 7.5 mg / 0.6 mL solution ofCDCl3 .. The 1H and 13C peaks are also listedbelow. Provide a full analysis of the NMR spectra for compound 1.1H NMR (400 MHz, CDCl3) δ 7.73 (d, J = 9.5 Hz, 1H), 7.56 (ddd, J = 8.5, 7.5, 1.6 Hz, 1H),7.51 (dd, J = 7.5, 1.6 Hz, 1H), 7.36 (d, J = 8.5 Hz, 1H), 7.30 (dd, J = 8.5, 7.5 Hz, 1H), 6.45(d, J = 9.5 Hz, 1H).13C NMR (101 MHz, CDCl3) δ 160.79, 154.09, 143.43, 131.85, 127.87, 124.44, 118.86,116.94, 116.74. Include: correct assignment of NMR spectra of 1H spectra. correct rationalisation of 1H spectrum
The NMR spectra for compound 1 were acquired in a 7.5 mg / 0.6 mL solution ofCDCl3 The 1H and 13C peaks are also listedbelow. Provide a full analysis of the NMR spectra for compound 1.1H NMR (400 MHz, CDCl3) δ 7.73 (d, J = 9.5 Hz, 1H), 7.56 (ddd, J = 8.5, 7.5, 1.6 Hz, 1H),7.51 (dd, J = 7.5, 1.6 Hz, 1H), 7.36 (d, J = 8.5 Hz, 1H), 7.30 (dd, J = 8.5, 7.5 Hz, 1H), 6.45(d, J = 9.5 Hz, 1H).13C NMR (101 MHz, CDCl3) δ 160.79, 154.09, 143.43, 131.85, 127.87, 124.44, 118.86,116.94, 116.74.
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The mass spectrum of 2,3-dimethylpentane [(CH3)2CHCH(CH3)CH2CH3]shows fragments at m/z = 85 and 71. Propose possible structures for theions that give rise to these peaks.
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a) Predict the proton spectrum chemical shift, coupling and integration of the following molecule? vanillin C8H8O3 b) Also predict its cross-peaks in COSY and 1H-13C HETCOR?
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