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Treatment of anisole
(several peaks),
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- 7barrow_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_forwardAs reaction of (CH3)2CO with LIC≡CH followed by H2O affords compound D, which has a molecular ion in its mass spectrum at 84 and prominent absorptions in its IR spectrum at 3600−3200, 3303, 2938, and 2120 cm−1. D shows the following 1H NMR spectral data: 1.53 (singlet, 6 H), 2.37 (singlet, 1 H), and 2.43 (singlet, 1 H) ppm. What is the structure of D?arrow_forward
- Treatment 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_forwardan 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_forward7aarrow_forward
- An unknown compound C3H2NCl shows moderately strong IR absorptions around 1650 cm-1 and 2200 cm-1. Its NMR spectrum consists of two doublets (J = 14 Hz) at δ 5.9 and δ 7.1. Propose a structure consistent with this 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_forwardAn organic compound B with formula C6H14O has the following: IR Spectroscopy 2974 cm-1, 1080 cm-1 Mass Spectrometry 102 (M+), 87, 73 1H NMR Spectroscopy Eight signals at δ 1.10 (d, 3H), 1.13 (dd, 3H), 1.14 (dd, 3H), 1.59 (ddq, 1H), 1.60 (ddq, 1H), 3.19 (ddq, 1H), 3.51 (dq, 1H), 3.50 (dq, 1H). Compound B is obtained by the reaction of compound A with NaH followed by CH3CH2Br. The stereochemistry of A is "S" Using this information, deduce a plausible structure for Compound A with correct stereochemistry.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning