Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Textbook Question
Chapter 14, Problem 33P
Give a structure for compound F that is consistent with the
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Compound K, molecular formula C6H14O, readily undergoes acid-catalyzed dehydration when warmed with phosphoric acid to give compound L, molecular formula C6H12, as the major organic product. The 1H-NMR spectrum of compound K shows signals at d 0.90 (t, 6H), 1.12 (s, 3H), 1.38 (s, 1H), and 1.48 (q, 4H). The 13C-NMR spectrum of compound K shows signals at d 72.98, 33.72, 25.85, and 8.16. Deduce the structural formulas of compounds K and L.
draw the structure of the solid organic compound by the the help of c13 NMR spectra, label each equivalent set of Carbons as A, B,C etc and explain the whole process of determining the identity of the compound.
Give the structure that corresponds to the following molecular formula and H1 NMR spectrum::
C7H16O4: δ 1.93 (triplet); δ 3.35 (s); δ 4.49 (triplet); relative integral 1:6:1.
Chapter 14 Solutions
Organic Chemistry
Ch. 14 - PRACTICE PROBLEM 14.1 Provide a name for each of...Ch. 14 - Prob. 2PPCh. 14 - Prob. 3PPCh. 14 - Practice Problem 14.4 Apply the polygon-and-circle...Ch. 14 - Practice Problem 14.5 Apply the polygon-and-circle...Ch. 14 - Practice Problem 14.6 1,3,5-Cycloheptatriene is...Ch. 14 - Prob. 7PPCh. 14 - Prob. 8PPCh. 14 - Practice Problem 14.9 In 1967 R. Breslow (of...Ch. 14 - Prob. 10PP
Ch. 14 - Practice Problem 14.11 In addition to a signal...Ch. 14 - PRACTICE PROBLEM 14.12
Azulene has an appreciable...Ch. 14 - Practice Problem 14.13 (a) The -Sh group is...Ch. 14 - Practice Problem 14.14
Explain how NMR...Ch. 14 - PRACTICE PROBLEM 14.15 Four benzenoid compounds,...Ch. 14 - Prob. 16PCh. 14 - Write structural formulas and give acceptable...Ch. 14 - Prob. 18PCh. 14 - Prob. 19PCh. 14 - Prob. 20PCh. 14 - Which of the hydrogen atoms shown below is more...Ch. 14 - 14.22 The rings below are joined by a double bond...Ch. 14 - Prob. 23PCh. 14 - 14.24 (a) In 1960 T. Katz (Columbia University)...Ch. 14 - Prob. 25PCh. 14 - Prob. 26PCh. 14 - 14.27 5-Chloro-1,3-cyclopentadiene (below)...Ch. 14 - Prob. 28PCh. 14 - Furan possesses less aromatic character than...Ch. 14 - 14.30 For each of the pairs below, predict...Ch. 14 - Assign structures to each of the compounds A, B,...Ch. 14 - Prob. 32PCh. 14 - Give a structure for compound F that is consistent...Ch. 14 - Prob. 34PCh. 14 - Prob. 35PCh. 14 - The IR and 1H NMR spectra for compound X(C8H10)...Ch. 14 - Prob. 37PCh. 14 - Prob. 38PCh. 14 - 14.39 Given the following information, predict the...Ch. 14 - Consider these reactions: The intermediate A is a...Ch. 14 - Prob. 41PCh. 14 - Compound E has the spectral features given below....Ch. 14 - Draw all of the molecular orbitals for...Ch. 14 - Prob. 1LGPCh. 14 - Prob. 2LGPCh. 14 - 3. The NMR signals for the aromatic hydrogens of...Ch. 14 - Prob. 4LGPCh. 14 - Prob. 5LGP
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- How could 1H NMR spectroscopy be used to distinguish among isomers A, B, and C?arrow_forwardFollowing 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.arrow_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
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