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Practice Problem 13.7
Two compounds, A and B, have the same molecular formula,
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- Deduce the structure of compound C.arrow_forward14. Compound 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_forwardA compound (L) with the molecular formula C9H10 reacts with bromine and gives an IR absorption spectrum that includes the following absorption peaks: 3035 cm ¹(m), 3020 cm ¹(m), 2925 cm ¹(m), 2853 cm ¹(w), 1640 cm ¹1(m), 990 cm ¹(s), 915 cm ¹(s), 740 cm ¹(s), 695 cm ¹(s). The ¹H NMR spectrum of L consists of: Doublet 3.1 ppm (2H) Multiplet 5.1 ppm Multiplet 7.1 (5H) ppm Multiplet 4.8 ppm Multiplet 5.8 ppm The UV spectrum shows a maximum at 255 nm. Propose a structure for compound L. Edit Drawing harrow_forward
- Treatment of 2-methylpropanenitrile [(CH3)2CHCN] withCH3CH2CH2MgBr, followed by aqueous acid, affords compound V, whichhas molecular formula C7H14O. V has a strong absorption in its IRspectrum 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), and2.60 (septet, 1 H) ppm. What is the structure of V?arrow_forwardCompound A has molecular formula C8H18. It shows one singlet in the ¹H-NMR spectrum. Identify A and explain your reasoning. For the toolbar, press ALT+F10 (PC) or ALT+FN+F10 (Mac). BIUS Paragraph V Arial = = = = +8HE {} X² X₂ PR хо 23 V 10pt >¶ ¶< - ABC :3 v V ✓ Ev AV ¶T "Ω Θ I 用く x B Q ► 8. Earrow_forwardDraw the structural formulas of the following compounds and indicate the number of NMR signals that would be expected for each compound. (a) methyl iodide (b) 2,4-dimethylpentane (c) cyclopentane (d) propylene (propene)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_forwardProvide the structure of three compounds with the molecular formula C4H,O that give an absorption peak at 1600-1640 cm¹ in the infrared spectrum, but no significant peaks at 3000-3600 cm²¹ or at 1650-1750 cm-¹.arrow_forwardThe 1H-NMR spectrum of ethanol shows a triplet at 1.23 ppm, a singlet at 2.61 pm, and a quartet at 3.69 ppm. Assign each signal to the protons it corresponds to in the molecule. Explain the splitting pattern observed for each signal.arrow_forward
- The NMR spectra for compound 1 were acquired in a 7.5 mg / 0.6 mL solution ofCDCl3 and are found in the accompanying file. The 1H are also listedbelow. Identify the name of compound 1 and Provide a full analysis of the NMR spectra for compound 1 with table showing peak name and assignment 1H NMR (400 MHz, CDCl3) δ 7.73 (d, J = 9.5 Hz, 1H), 7.56 (ddd, J = 8.5, 7.5, 1.6 Hz, 1H),7.51 (dd, J = 7.5, 1.6 Hz, 1H), 7.36 (d, J = 8.5 Hz, 1H), 7.30 (dd, J = 8.5, 7.5 Hz, 1H), 6.45(d, J = 9.5 Hz, 1H).arrow_forwardThe 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_forwardAccount for the following observations: (a) The 1H NMR spectrum of cyclohexane shows a single peak at room temperature, but when the temperate is lowered significantly the peak starts to broaden and then separates into two. (b) At room temperature, the 19F NMR spectrum of PF5 shows two lines, and even at the lowest experimentally accessible temperatures the spectrum is substantially unchanged. (c) In the 1H NMR spectrum of a casually prepared sample of ethanol a triplet and a quartet are seen. These multiplets show additional splittings if the sample is prepared with the careful exclusion of water.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning