Concept explainers
Treatment of anisole
(several peaks),
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ORGANIC CHEMISTRY
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- The 1H-NMR spectrum of compound B,C7H14O , consists of the following signals: δ 0.9 (t, 6H), 1.6 (sextet, 4H), and 2.4 (t, 4H). Draw the structural formula of compound B.arrow_forwardDraw the structure for C5H10O with 1H NMR signals: δ 1.2 (s, 6H), 2.1 (bs, 1H), 5.0 (dd, 1H), 5.2 (dd, 1H), and 5.9 (dd, 1H).arrow_forwardTreatment of 2-methylpropanenitrile [(CH3)2CHCN] with CH3CH2CH2MgBr, followed by aqueous acid, affords compound V, which has molecular formula C7H14O. V has a strong absorption in its IR spectrum at 1713 cm−1, and gives the following 1H NMR data: 0.91 (triplet, 3 H), 1.09 (doublet, 6 H), 1.6 (multiplet, 2 H), 2.43 (triplet, 2 H), and 2.60 (septet, 1 H) ppm. What is the structure of V? We will learn about this reaction in Chapter 20.arrow_forward
- Addition of m-xylene to the strongly acidic solvent HF/SbF5 at 45C gives a new species, which shows 1H-NMR resonances at 2.88 (3H), 3.00 (3H), 4.67 (2H), 7.93 (1H), 7.83 (1H), and 8.68 (1H). Assign a structure to the species giving this spectrum.arrow_forwardDo (8) (b) asap pleasearrow_forwardTreatment of compound D with LiAlH4 followed by H2O forms compound E. D shows a molecular ion in its mass spectrum at m/z = 71 and IR absorptions at 3600–3200 and 2263 cm−1. E shows a molecular ion in its mass spectrum at m/z = 75 and IR absorptions at 3636 and 3600–3200 cm−1. Propose structures for D and E from these data and the given 1H NMR spectra.arrow_forward
- an unknown has the formula C₆H₁₂O. The IR spectrum of this substance has a strong vibration near 1700 cm⁻¹ . Which structure below is consistent with these data?arrow_forwardName the following compounds A and B. How could you distinguish these two molecules by using 1H NMR and IR techniques? Propose an analytical technique to determine the iron content of these compounds. Calculate the mass percentages of C and H of compound B (C: 12.01 g/mol; H: 1.008 g/mol; Fe: 55.845 g/mol).arrow_forwardA chemist is summoned to an abandoned waste-disposal site to determine the contents of a leaking, corroded barrel. Thebarrel reeks of an overpowering fishy odor. The chemist dons a respirator to approach the barrel and collect a sample,which she takes to her laboratory for analysis.The mass spectrum shows a molecular ion at m>z 101, and the most abundant fragment is at m>z 86. The IR spectrum shows no absorptions above 3000 cm-1, many absorptions between 2800 and 3000 cm-1, no absorptions between1500 and 2800 cm-1, and a strong absorption at 1200 cm-1. The proton NMR spectrum shows a triplet (J = 7 Hz) at d1.0and a quartet (J = 7 Hz) at d2.4, with integrals of 17 spaces and 11 spaces, respectively.(a) Show what structural information is implied by each spectrum, and propose a structure for the unknown toxic waste.(b) Current EPA regulations restrict the disposal of liquid wastes because they tend to leak out of their containers.Propose an inexpensive method for converting this…arrow_forward
- Compound B of molecular formula C9H19N shows a noteworthy infrared absorption at 3300 cm-1. Its 1H-NMR spectrum shows three singlets – δ 1.0 (6H), 1.1 (12H), 1.4 (1H) ppm. Its 13C-NMR spectrum has four signals – δ 25, 28, 41, 64 ppm. Suggest a structure for this compound. Please show work.arrow_forwardThe infrared spectrum of a compound has a strong absorption at 1669 cm. The mass spectrum of the compound is provided below. What is the structure of the compound? 100 - 80 - 60 40 20 0- 50 75 100 125 m/z OH NH2 Relative Intensityarrow_forwardShown below is th carbon NMR spectrum of a compound of the formula C7H14. The compound decolorizes a solution of bromine in dichloromethane. Assign a structure to this hydrocarbon. Correlation of spectrum with number of hydrogen atoms attached to each carbon=arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning