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 15 Solutions
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
- Identify the carbon atoms that give rise to the signals in the 13C NMR spectrum of each compound. a.CH3CH2CH2CH2OH; 13C NMR: 14, 19, 35, and 62 ppm b.(CH3)2CHCHO; 13C NMR: 16, 41, and 205 ppm c.CH2=CHCH(OH)CH3; 13C NMR: 23, 69, 113, and 143 ppmarrow_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_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
- A 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_forwardidentify the compound with molecular formula C2H6O that gives this 1H NMR spectrum.arrow_forwardCompound P has molecular formula C5H9ClO2. Deduce the structure of Pfrom its 1H and 13C NMR spectra.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning