8. a) A compound has IR absorptions at 3400-3500 cm-1, and the following nmr spectrum: 8 2.07 (6H, singlet) 8 2.16 (3H, singlet) 8 3.19 (broad) 8 6.63 (2H, singlet) Which of the following structures represents the compound? Briefly explain your answer. i) N,N-Dimethyl-4-methylaminobenzene ii) 2,4,6-Trimethylaminobenzene iii) 2,4-Dimethylbenzylamine iv) 3,5-Dimethyl-N-methylaniline b) Draw the structures of all isomeric amines with molecular formula C6H15N that are not expected to produce any signal above 3000 cm³¹ in their IR spectra.

8. a) A compound has IR absorptions at 3400-3500 cm-1, and the following nmr spectrum: 8 2.07 (6H, singlet) 8 2.16 (3H, singlet) 8 3.19 (broad) 8 6.63 (2H, singlet) Which of the following structures represents the compound? Briefly explain your answer. i) N,N-Dimethyl-4-methylaminobenzene ii) 2,4,6-Trimethylaminobenzene iii) 2,4-Dimethylbenzylamine iv) 3,5-Dimethyl-N-methylaniline b) Draw the structures of all isomeric amines with molecular formula C6H15N that are not expected to produce any signal above 3000 cm³¹ in their IR spectra.

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 13.26P: Ascaridole is a natural product that has been used to treat intestinal worms. Explain why the two...

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