Concept explainers
Deduce the structure of each of the following compounds on the basis of their
Spectra and molecular formulas:
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Organic Chemistry - Standalone book
- Propose 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_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_forwardMolecular formula of an unknown compound is, C10H14O. Proton NMR: 1.3 (6H, doublet), 3.2 (1H septet), 4.6 (1H singlet), 2.25 (3H, singlet) 6.7 (1H, singlet), 6.9 (1H, doublet), 7.2 (1H, doublet). What is the name of an unknown compound? 2-isopropyl-5-methylphenol 2-(p-tolyl)propan-2-ol 1-isopropyl-4-methoxybenzene 4-isopropylphenyl)methanolarrow_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_forwardThe 1H-NMR spectrum of Compound C shows five signals – δ 2.38 (1H, dt), 2.72 (1H, dt), 5.34 (1H, t), 5.49 (2H, ddd), 6.27 (2H, dd) ppm. Its 13C-NMR spectrum has four signals – δ 26, 58, 127, 129 ppm. In the compound’s mass spectrum, the M+1 peak appears at m/z = 115. An M+2 peak, whose intensity is roughly one-third that of the M+1 peak, also appears. Suggest a structure for this compound.arrow_forwardFollowing are the 'H and 13C NMR spectra for each of three isomeric ketones with formula C7H14O. Determine a structure to each pair of spectra and assign each H and C. Carbon spectrum B Carbon spectrum C,H140 А C,H140 CDCI3 CDCI3 200 150 100 50 200 150 100 50 Proton spectrum C,H140 В Proton spectrum A C,H140 2.9 2.8 2.7 1.96 2.00 2.91 1.04 6.18 3.0 2.5 2.0 1.5 1.0 0.5 0.0 3.0 2.5 2.0 1.5 0.5 0.0 211.04 -44.79 –17.39 – 13.78 -218.40 -38.85 –18.55arrow_forward
- An unknown compound has the molecular formula C7H14O, and its 1H NMR and 13C NMR spectra are shown below. Determine the structure of the unknown compound and draw it below. Note that there are no peaks above 3 ppm in the 1H NMR, and the numbers present on the 1H NMR are the integration values for each set of peaks.arrow_forwardFollowing are the 'H and 13C NMR spectra for each of three isomeric ketones with formula C7H14O. Determine a structure to each pair of spectra and assign each H and C. Carbon spectrum А C,H140 Carbon spectrum В C;H140 CDCI3 200 150 100 50 Proton spectrum CDC13 A C,H140 200 150 100 50 1.96 2.00 2.91 3.0 2.5 2.0 1.5 1.0 0.5 0.0 211.04 -44.79 –17.39 – 13.78 -218.40 - 38.85 –18.55arrow_forwardIdentify A and B, isomers of molecular formula C3H4Cl2, from the given 1H NMR data: Compound A exhibits peaks at 1.75 (doublet, 3 H, J = 6.9 Hz) and 5.89 (quartet, 1 H, J = 6.9 Hz) ppm. Compound B exhibits peaks 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
- 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_forward1Compound 1 has molecular formula C7H16. It shows three signals in the 1H-NMR spectrum, one at 0.85 ppm, one at 1.02 ppm, and one at 1.62 ppm. The relative integrals of these three signals are 6, 1, and 1, respectively. Compound 2 has molecular formula C7H14. It shows three signals in the 1H-NMR spectrum, one at 0.98 ppm, one at 1.36 ppm, and one at 1.55 ppm. The relative integrals of these three signals are 3, 2, and 2, respectively. Propose structures for compounds 1 and 2, explaining how you reach your conclusion.arrow_forwardHow many peaks will the following molecule show in its ¹H NMR spectrum? 1 2 IN 3 6 H3C CH3 methyl acetatearrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning