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...

See similar textbooks

Similar questions

Ascaridole is a natural product that has been used to treat intestinal worms. Explain why the two methyls on the isopropyl group in ascaridole appear in its 1H-NMR spectrum as four lines of equal intensity, with two sets of two each separated by 7 Hz.
A compound with molecular mass 114 and in IR spectrum, absorption bands are formed at 1770 cm¹ (s), 1650 cm-¹ (m) and 1200 cm¹ (w). In ¹H NMR six signals are observed, 8 1.0 (t, 3H), 1.7 (m 2H), 2.4 (t, 2H), 4.6 (d, 1H), 4.9 (d, 1H), 7.4 (d, 1H). Predict the molecular structure of the unknown compound and justify your answer.
Draw the structure of a compound, CaH8O3 that exhibits IR absorptions at 1710 and 2500-3000 cm³¹ and the following ¹H NMR signals: 11.1 (1H, singlet), 4.14 (2H, singlet), 3.63 (2H, quartet), 1.26 (3H, triplet) ppm.
Draw the structure of a compound, C4H8O3 that exhibits IR absorptions at 1710 and 2500-3000 cm-1 and thefollowing 1H NMR signals: 11.1 (1H, singlet), 4.14 (2H, singlet), 3.63 (2H, quartet), 1.26 (3H, triplet) ppm.
Reaction of butanenitrile (CH3CH2CH2CN) with methylmagnesium bromide (CH3MgBr), followed by treatment with aqueous acid, forms compound G. G has a molecular ion in its mass spectrum at m/z = 86 and a base peak at m/z = 43. G exhibits a strong absorption in its IR spectrum at 1721 cm−1 and has the 1H NMR spectrum given below. What is the structure of G?
(asap plz
Treatment of 2-methylpropanenitrile [(CH3)2CHCN] withCH3CH2CH2MgBr, followed by aqueous acid, affords compound V, whichhas molecular formula C7H14O. V has a strong absorption in its IRspectrum at 1713 cm−1, and gives the following 1H NMR data: 0.91(triplet, 3 H), 1.09 (doublet, 6 H), 1.6 (multiplet, 2 H), 2.43 (triplet, 2 H), and2.60 (septet, 1 H) ppm. What is the structure of V?
Draw the structure of the compound identified by the simulated 'H NMR and C NMR spectra. The molecular formula of the compound is C,0H,O. 12 (Blue numbers next to the lines in the 'H NMR spectra indicate the integration values.) H NMR 1H 2H 2H 2H 2H|| 3H 10 8. 4 (dd) g 13C NMR 220 200 180 160 140 120 100 80 60 40 20 8 (ppm) Deduce the structure from the spectra. Select Draw Rings More Erase
What is the structure of a compound of molecular formula C10H14O2 that shows a strong IR absorption at 3150–2850 cm-1 and gives the following 1H NMR absorptions: 1.4 (triplet, 6 H), 4.0 (quartet, 4 H), and 6.8 (singlet, 4 H) ppm?
what is is the structure of a compound of molecular formula c 10 h 14 o 2 that shows a strong ir absorption at 3150-2850 cm − 1 and give the following 1 h nmr absorptions: 1.4 (triplet, 6 h), 4.0 (quarter, 4h), and 6.8 (singlet, 4h) ppm?
Find the structures of the compounds with closed formulas on each 1H-NMR spectrum given below by evaluating them on the spectra.
Please give the correct answer to the following NMR spectroscopy question and provide detailed solutions of the answer.