Compounds C and D are isomers with a molecular formula of CsH100 that give a negative Tollens' test. Compound C has two (2) peaks in the 'H NMR spectrum, while compound D has four (4) peaks. i) Propose the structures of compounds C and D. ii) Sketch a predicted 'H NMR spectrum of compound D with the estimated chemical shifts and multiplicity. ii) State the number of peaks for compound C in the 19C NMR spectrum. iv) Suggest a suitable chemical test to differentiate between compounds C and D. Explain the observation.

Compounds C and D are isomers with a molecular formula of CsH100 that give a negative Tollens' test. Compound C has two (2) peaks in the 'H NMR spectrum, while compound D has four (4) peaks. i) Propose the structures of compounds C and D. ii) Sketch a predicted 'H NMR spectrum of compound D with the estimated chemical shifts and multiplicity. ii) State the number of peaks for compound C in the 19C NMR spectrum. iv) Suggest a suitable chemical test to differentiate between compounds C and D. Explain the observation.

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter13: Nuclear Magnetic Resonance Spectroscopy

Section: Chapter Questions

Problem 13.17P: Following are 1H-NMR spectra for compounds G, H, and I, each with the molecular formula C5H12O. Each...

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