The following spectroscopic data were obtained for compound X (molecular formula C10H140), a naturalproduct.UV spectrumA broad and intense peak at 276 nm is observedIR spectrumThymolMaewwy8060ai40-tae20-350030002500200015001000WavenumbersMS spectrum (EIMS)MASS SPECTRUM100806040200.0+0.04080120160m/zRel. Intensity NMR spectrum'H NMR spectrum6 H3H1H3H1HlilppmAnswer the following questions in relation to compound X (not general theory)Calculate the double bond equivalenceWhat structural information may be deduced from the UV data?3. What structural information may be deduced from the IR spectrum?1.2.4. What structural information may be deduced from the mass spectrum?5. Tabulate the NMR data as follows:Chemical shift MultiplicityIntegrationStructural information(8)1.32.33.24.76.556.77.16. Propose a structure for compound X. Explain your reasoning clearly.

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The following spectroscopic data were obtained for compound X (molecular formula C10H140), a natural product. UV spectrum A broad and intense peak at 276 nm is observed IR spectrum Thymol Mae wwy 80 60 a in m i 40- t a e 20- 3500 3000 2500 2000 1500 1000 Wavenumbers MS spectrum (EIMS) MASS SPECTRUM 100 80 60 40 20 0.0+ 0.0 40 80 120 160 m/z Rel. Intensity

The following spectroscopic data were obtained for compound X (molecular formula C10H140), a natural product. UV spectrum A broad and intense peak at 276 nm is observed IR spectrum Thymol Mae wwy 80 60 a in m i 40- t a e 20- 3500 3000 2500 2000 1500 1000 Wavenumbers MS spectrum (EIMS) MASS SPECTRUM 100 80 60 40 20 0.0+ 0.0 40 80 120 160 m/z Rel. Intensity

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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