Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 13, Problem 7PP
Practice Problem 13.7
Two compounds, A and B, have the same molecular formula,
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Following is the 1H-NMR spectrum of compound O, molecular formula C7H12. Compound O reacts with bromine in carbon tetrachloride to give a compound with the molecular formula C7H12Br2. The 13C-NMR spectrum of compound O shows signals at d 150.12, 106.43, 35.44, 28.36, and 26.36. Deduce the structural formula of compound O.
Compound 1 has molecular formula C7H15Cl. It shows two signals in the 1H-NMR spectrum, one at 1.08 ppm and one at 1.59 ppm. The relative integrals of these two signals are 3 and 2, respectively.
Propose structures for compound 1, explaining how you reach your conclusion.
14. 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.
Chapter 13 Solutions
Organic Chemistry
Ch. 13 - Prob. 1PPCh. 13 - Prob. 2PPCh. 13 - Prob. 3PPCh. 13 - Practice Problem 13.4 From each set of resonance...Ch. 13 - Practice Problem 13.5 The following enol (an...Ch. 13 - Prob. 6PPCh. 13 - Practice Problem 13.7
Two compounds, A and B, have...Ch. 13 - Prob. 8PPCh. 13 - Prob. 9PPCh. 13 - Prob. 10PP
Ch. 13 - Prob. 11PPCh. 13 - Prob. 12PPCh. 13 - Prob. 13PPCh. 13 - Prob. 14PPCh. 13 - Prob. 15PPCh. 13 - Practice Problem 13.16
Diels–Alder reactions also...Ch. 13 - Prob. 17PPCh. 13 - Prob. 18PCh. 13 - What product would you expect from the following...Ch. 13 - Prob. 20PCh. 13 - Prob. 21PCh. 13 - Provide the reagents necessary for each of the...Ch. 13 - Prob. 23PCh. 13 - Prob. 24PCh. 13 - Prob. 25PCh. 13 - When 1-pentene reacts with N-bromosuccinimide...Ch. 13 - Prob. 27PCh. 13 - Prob. 28PCh. 13 - Prob. 29PCh. 13 - Prob. 30PCh. 13 - 13.31 Provide a mechanism that explains formation...Ch. 13 - 13.32 Provide a mechanism that explains formation...Ch. 13 - Treating either 1-chloro-3-methyl-2-butene or...Ch. 13 - Prob. 34PCh. 13 - Prob. 35PCh. 13 - Although both 1-bromobutane and 4-bromo-1-butene...Ch. 13 - Prob. 37PCh. 13 - Prob. 38PCh. 13 - Prob. 39PCh. 13 - Prob. 40PCh. 13 - Prob. 41PCh. 13 - Prob. 42PCh. 13 - Prob. 43PCh. 13 - 13.44 When furan and maleimide undergo a...Ch. 13 - Two controversial hard insecticides are aldrin and...Ch. 13 - Prob. 46PCh. 13 - Prob. 47PCh. 13 - Prob. 48PCh. 13 - Prob. 49PCh. 13 - Prob. 50PCh. 13 - Explain the product distribution below based on...Ch. 13 - Mixing furan (Problem 13.44) with maleic anhydride...Ch. 13 - Prob. 53PCh. 13 - Prob. 54PCh. 13 - Prob. 1LGPCh. 13 - Prob. 2LGP
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- 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_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_forwardThe '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_forward
- Provide 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_forwardO2N 1 3 7H 6 4 HO 6 8 A Predict the number of signals in the 13C NMR spectrum. Provide a rough sketch of the 13C NMR spectrum of compound A.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_forwardPlease give the correct answer to the following NMR spectroscopy question and provide detailed solutions of the answer.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_forward
- The 1H and 13C NMR for a compound with the formula C5H12O are shown. Determine the structure of this compound. Assign the peaks: assign “a” to the most shielded hydrogen(s) in your structure, “b” to next-most shielded, etc; use capital letters for carbons).arrow_forwardIdentify A and B, isomers of molecular formula C3H4Cl2, from the given 1H NMR data: Compound AJ = 6.9 Hz) and 5.89 (quartet, 1 H, J = 6.9 Hz) ppm. Compound B exhibits signals 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_forwardwhat is the structure of these compounds and assign their data whilst talking about their couplingsarrow_forward
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