Concept explainers
Reaction of p-cresol with two equivalents of
Want to see the full answer?
Check out a sample textbook solutionChapter 18 Solutions
Organic Chemistry
- Compound H (C8H6O3) gives a precipitate when treated with hydroxylamine in aqueous ethanol and a silver mirror when treated with Tollens solution. Following is its 1H-NMR spectrum. Deduce the structure of compound H.arrow_forwardFollowing are 1H-NMR spectra for compounds G, H, and I, each with the molecular formula C5H12O. Each is a liquid at room temperature, is slightly soluble in water, and reacts with sodium metal with the evolution of a gas. (a) Propose structural formulas of compounds G, H, and I. (b) Explain why there are four lines between 0.86 and 0.90 for compound G. (c) Explain why the 2H multiplets at 1.5 and 3.5 for compound H are so complex.arrow_forwardPropose a structural formula for each compound consistent with its 1H-NMR and 13C-NMR spectra. (a) C5H10O2 (b) C7H14O2 (c) C6 H12O2 (d) C7H12O4 (e) C4H7ClO2 (f) C4H6O2arrow_forward
- Reaction of aldehyde D with amino alcohol E in the presence of NaH forms F (molecular formula C11H15NO2). F absorbs at 1730 cm−1 in its IR spectrum. F also shows eight lines in its 13C NMR spectrum, and gives the following 1H NMR spectrum: 2.32 (singlet, 6 H), 3.05 (triplet, 2 H), 4.20 (triplet, 2 H), 6.97 (doublet, 2 H), 7.82 (doublet, 2 H), and 9.97 (singlet, 1 H) ppm. Propose a structure for F. We will learn about this reaction in Chapter 18.arrow_forwardWhat is the structure of a compound of molecular formula C1H1402 that shows a strong IR absorption at 3150-2850 cm1 and gives the following 'H NMR absorptions: 1.4 (triplet, 6 H), 4.0 (quartet, 4 H), and 6.8 (singlet, 4 H) ppm?arrow_forwardWhen heated with chromic acid, compound A forms benzoic acid. Identify compound A from its 1H NMR spectrum.arrow_forward
- Using the following NMR data, and the molecular formula C9H120, select the best compound. NMR Data triplet 1.15 ppm (3H) quartet 2.75 ppm (2H) singlet 3.75 ppm (3H) split quartet 7.5 ppm (4H) Multiple choice options A: 1-ethyl-4-methoxybenzene B: 1-ethoxy-4-methylbenzene C: 1-bromo-4-methylbenzene D: 1-bromo-4-ethylbenzenearrow_forwardPropose a structural formula for each compound consistent with its 1H-NMR and 13C-NMR spectra.arrow_forwardDeduce the structure of an unknown compound using the data. C,H,O: 10 NMR: 8 9.8 (1 H, s), 8 1.1 (9 H, s)arrow_forward
- Identify products A and B from the given 1H NMR data.a. Treatment of CH2 = CHCOCH3 with one equivalent of HCl forms compound A. A exhibits the following absorptions in its 1H NMR spectrum: 2.2 (singlet, 3 H), 3.05 (triplet, 2 H), and 3.6 (triplet, 2 H) ppm. What is the structure of A?b. Treatment of acetone [(CH3)2C = O] with dilute aqueous base forms B. Compound B exhibits four singlets in its 1H NMR spectrum at 1.3 (6 H), 2.2 (3 H), 2.5 (2 H), and 3.8 (1 H) ppm. What is the structure of B?arrow_forwardIdentify products A and B from the given 1H NMR data. a.Treatment of CH2=CHCOCH3 with one equivalent of HCl forms compound A. A exhibits the following absorptions in its 1H NMR spectrum: 2.2 (singlet, 3 H), 3.05 (triplet, 2 H), and 3.6 (triplet, 2 H) ppm. What is the structure of A? b.Treatment of acetone [(CH3)2C=O] with dilute aqueous base forms B. Compound B exhibits four singlets in its 1H NMR spectrum at 1.3 (6 H), 2.2 (3 H), 2.5 (2 H), and 3.8 (1 H) ppm. What is the structure of B?arrow_forwardThe compound with the closed formula C4H9Br gives the following 1H NMR data. Write the clear formula of the compound with reasons. 1.0 ppm (triplet, 3 H); 1.7 ppm (dublet, 3H); 1.8 ppm (multiplet, 2H); 4.2 ppm (multiplet, 1H)arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning