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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 15 Solutions
EBK ORGANIC CHEMISTRY
- 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.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_forwardThe compound whose 1H NMR spectrum is shown has the molecular formula C3H6Br2. Propose a structure.arrow_forward
- The 'H NMR spectrum of compound A (C3H100) has four signals: a multiplet at 8 = 7.25-7.32 ppm (5 H), a singlet at d = 5.17 ppm (1 H), a quartet at d = 4.98 ppm (1 H), and a doublet at ô = 1.49 ppm (3 H). There are 6 signals in its 13C NMR spectrum. The IR spectrum has a broad absorption in the -3200 cm-1 region. Compound A reacts with KMNO4 in a basic solution followed by acidification to give compound B with the molecular formula C7H6O2. Draw structures for compounds A and B.arrow_forwardPredict the structure of the molecule with molecular formula C8 H10 O using given information about its 1H NMR, 13C NMR, and IR.arrow_forwardCompound A, with molecular formula C4H9Cl, shows two signals in its 13C NMR spectrum. Compound B, an isomer of compound A, shows four signals, and in the proton-coupled mode, the signal farthest downfield is a doublet. Identify compounds A and Barrow_forward
- How many NMR signals? -methyl propanoate -C2H5Narrow_forwardA compound with a molecular formula C12H24 exhibits an H+ NMR spectrum with only one signal and a 13 C NMR spectrum with two signals. Draw the structure of the compound.arrow_forwardHow can 1H NMR distinguish between the compounds in each of the following pairs?arrow_forward
- How many signals would be in the 1°C NMR spectrum of structure A below? 4 8. 9. 12 IMGarrow_forwardWhat is the structure of the compound with the formula C8H10O, that shows six signals in its 13C-NMR spectrum, The 1H-NMR spectrum is: 1.98 ppm (1H singlet) 2.82 ppm (2H triplet) 3.80 ppm (2H triplet) 7.22 ppm (5H broad multiplet)arrow_forwardCompound A, with molecular formula C4H9Cl, shows two signals in its 13C NMR spectrum. Compound B, an isomer of compound A, shows foursignals, and in the proton-coupled mode, the signal farthest downfield is a doublet. Identify compounds A and B.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
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