5. Consider the molecular formula of C,H,O a) Draw three constitutional isomers with this formula. b) Predict the chemical shift for each proton in each of the compounds you drew in part a). c) NMR and IR spectra were measured for a compound with the formula C,H,O, and the following was observed: 'H NMR & 5.21 (s); IR (diagnostic region) 1770 cm-', 3068 cm-' and 3096 cm-'. Which of the structures you drew in part a) would be most consistent with this data, briefly explain your reasoning?

5. Consider the molecular formula of C,H,O a) Draw three constitutional isomers with this formula. b) Predict the chemical shift for each proton in each of the compounds you drew in part a). c) NMR and IR spectra were measured for a compound with the formula C,H,O, and the following was observed: 'H NMR & 5.21 (s); IR (diagnostic region) 1770 cm-', 3068 cm-' and 3096 cm-'. Which of the structures you drew in part a) would be most consistent with this data, briefly explain your reasoning?

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

Chapter21: Benzene And The Concept Of Aromaticity

Section: Chapter Questions

Problem 21.30P

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