Concept explainers
Which of the diethylbenzene isomers (ortho, meta, or para) corresponds to each set of 13C NMR spectral data?
[A]
[B]
[C]
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Chapter 17 Solutions
ORGANIC CHEMISTRY (LOOSELEAF) >CUSTOM<
- Following 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_forwardThe 1H NMR spectrum of bullvalene at 100 C consists only of a single peak at 4.22 . Explain.arrow_forwardCompound B has molecular formula C9H12. It shows five signals in the 1H-NMR spectrum - a doublet of integral 6 at 1.22 ppm, a septet of integral 1 at 2.86 ppm, a singlet of integral 1 at 5.34 ppm, a doublet of integral 2 at 6.70 ppm, and a doublet of integral 2 at 7.03 ppm. The 13C-NMR spectrum of B shows six unique signals (23.9, 34.0, 115.7, 128.7, 148.9, and 157.4). Identify B and explain your reasoning.arrow_forward
- 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?arrow_forwardA compound of molecular formula C4H8O2 shows no IR peaks at 3600–3200 or 1700 cm-1. It exhibits one singlet in its 1H NMR spectrum at 3.69 ppm, and one line in its 13C NMR spectrum at 67 ppm. What is the structure of this unknown?arrow_forwardIdentify A and B, isomers of molecular formula C3H4Cl2, from the given 1H NMR data: Compound AJ = 6.9 Hz) and 5.89 (quartet, 1 H, J = 6.9 Hz) ppm. Compound B exhibits signals at 4.16 (singlet, 2 H), 5.42 (doublet, 1 H, J = 1.9 Hz), and 5.59 (doublet, 1 H, J = 1.9 Hz) ppm.arrow_forward
- What is the structure of the compound with the formula C4H10O, if it shows 1H-NMR spectrum: 1.20 ppm (6H doublet) 3.30 ppm (3H singlet) 3.55 (1H septet)arrow_forwardCompound A exhibits two signals in its 1H NMR spectrum at 2.64 and 3.69 ppm and the ratio of the absorbing signals is 2:3. Compound B exhibits two signals in its 1 H NMR spectrum at 2.09 and 4.27 ppm and the ratio of the absorbing signals is 3:2. Which compound corresponds to dimethyl succinate and which compound corresponds to ethylene diacetate?arrow_forwardIdentify below compound from its spectral data. Molecular formula: C4H7N IR:2250 cm−1 1H NMR data:1.08 (triplet, 3 H), 1.70 (multiplet, 2 H), and 2.34 (triplet,2 H) ppmarrow_forward
- Propose a structure consistent with each set of data.a. Compound A:Molecular formula: C8H10OIR absorption at 3150–2850 cm–11H NMR data: 1.4 (triplet, 3 H), 3.95 (quartet, 2 H), and 6.8–7.3 (multiplet, 5 H) ppm b. Compound B:Molecular formula: C9H10O2IR absorption at 1669 cm–11H NMR data: 2.5 (singlet, 3 H), 3.8 (singlet, 3 H), 6.9 (doublet, 2 H), and 7.9 (doublet, 2 H) ppmarrow_forwardCompound A exhibits two signals in its 1H NMR spectrum at 2.64 and 3.69 ppm, and the ratio of the absorbing signals is 2:3. Compound B exhibits two signals in its 1H NMR spectrum at 2.09 and 4.27 ppm, and the ratio of the absorbing signals is 3:2. Which compound corresponds to dimethyl succinate, and which compound corresponds to ethylene diacetate?arrow_forwardWhat 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?arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning