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Reaction of p-cresol with two equivalents of
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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
- Compound X (molecular formula C10H120) was treated with NH2NH2, ¯OH to yield compound Y (molecular formula C10H14). Match the 1H NMR spectra of X and Y to the corresponding structures of X and Y. Compound NH2NH2 Compound 'H NMR of X 6 H OH Y 1 H 5H 8. 6. 4 ppm or H NMR of Y 6 H 2H 5H 1 H multiplet multiplet 8. 6. 4. 3. 1 nnm 2. 2. 3, O: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_forwardUsing 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_forward
- Compound X (molecular formula C10H12O) was treated with NH2NH2, −OH to yield compound Y (molecular formula C10H14). Based on the 1HNMR spectra of X and Y given below, what are the structures of X and Y?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_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
- 8) CH3 CH3 O 36 Hu H CH3 CH3 Fo H H Answer the following questions, which refer to the two acetonide diastereomers shown above. a) Would you expect any difference in the number of peaks in the ¹H NMR spectra of each acetonide? (Y or N). b) Would you expect any difference in the number of peaks in the 13C NMR spectra of each acetonide? (Y or N) c) Would you expect any difference in the integral values for the peaks in the ¹H NMR spectra of each acetonide? (Y or N) d) Would you expect any difference in the multiplicities for the peaks in the ¹H NMR spectra of each acetonide? (Y or N). e) Would you expect any difference in the chemical shifts for the peaks in the ¹H NMR spectra of each acetonide? (Y or N)arrow_forwardCompound A has molecular formula C7H7X. Its ¹H-NMR spectrum shows a singlet at 2.26 ppm and two doublets, one at 6.95 ppm and one at 7.28 ppm. The singlet has an integral of three and the doublets each have an integral of two. Its 13C- NMR shows five signals. The mass spectrum of A shows a peak at m/z 170 and another peak at m/z = 172; the relative height of the two peaks is 1:1 respectively. - Identify what atom X is, explaining your reasoning - Identify Compound A, explaining your reasoning Compound A is treated with a mixture of nitric and sulfuric acids to generate Compound B. The ¹H-NMR spectrum of B shows two singlets, one at 2.52 pm and one at 8.13 ppm. The 13C-NMR spectrum of B shows five signals. The mass spectrum of B shows a peak at m/z = 260 and another peak at m/z = 262; the relative height of the two peaks is 1:1 respectively. - Identify compound B, explaining your reasoning Compound B is treated with sodium ethoxide to generate compound C. The ¹H-NMR spectrum of C shows…arrow_forwardWhat is the 1H NMR data (chemical shift, integration, multiplicty) of hte compound shown below?arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning