Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 14, Problem 11PP
Practice Problem 14.11
In addition to a signal downfield, the
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(b) One isomer of dimethoxybenzoic acid has 1H NMR spectrum dµ (ppm) 3.85 (6H, s), 6.63 (1H, t, J 2 Hz),
and 7.17 (2H, d, J 2Hz), One isomer of coumalic acid has 'H NMR spectrum dн (ppm) 6.41 (1H, d, J 10
Hz), 7.82 (1H, dd, J 2 Hz, 10 Hz) and 8.51 (1H, d, J 2Hz). In each case, which isomer is represented
here? The bonds sticking into the centre of the ring can be to any carbon atom.
Note: COOH proton is not indicated in the spectra
MeO
HO₂C
CO2H
MeO
dimethoxybenzoic acid
coumalic acid
Draw the structure of a compound, CaH8O3 that exhibits IR absorptions at 1710 and 2500-3000 cm³¹ and the
following ¹H NMR signals: 11.1 (1H, singlet), 4.14 (2H, singlet), 3.63 (2H, quartet), 1.26 (3H, triplet) ppm.
For each compound shown below,(1) sketch the 13C NMR spectrum (totally decoupled, with a singlet for each type of carbon), showing approximatechemical shifts.(2) show the multiplicity expected for each signal in the off-resonance-decoupled spectrum.(3) sketch the spectra expected using the DEPT-90 and DEPT-135 techniques.(a)OCH3 C O CH2 CH3ethyl acetate
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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- Draw the structure of the compound identified by the simulated 'H NMR and C NMR spectra. The molecular formula of the compound is C,0H,O. 12 (Blue numbers next to the lines in the 'H NMR spectra indicate the integration values.) H NMR 1H 2H 2H 2H 2H|| 3H 10 8. 4 (dd) g 13C NMR 220 200 180 160 140 120 100 80 60 40 20 8 (ppm) Deduce the structure from the spectra. Select Draw Rings More Erasearrow_forwardcould you help me out with these question and explain to me step by step thanksarrow_forwardThe data for four 13C NMR spectra are given below. Match each spectrum with one of the following structures. Briefly justify your reasoning by labeling each struture. ÓH -NH2 А C Spectrum 1: 26, 29, 32, 39, 112, 127, 128, 144 ppm • Spectrum 2: 28, 68 ppm • Spectrum 3: 12, 23, 33, 70 ppm • Spectrum 4: 16, 17, 38, 52 ppmarrow_forward
- In the presence of a small amount of acid, a solution of acetaldehyde (CH3CHO) in methanol (CH3OH) was allowed to stand and a new compound L was formed. L has a molecular ion in its mass spectrum at 90 and IR absorptions at 2992 and 2941 cm−1. L shows three signals in its 13C NMR at 19, 52, and 101 ppm. The 1H NMR spectrum of L is given below. What is the structure of L?arrow_forwardPredict the H-NMR spectra of Diphenylacetylene including number of signals, chemical shift of each signal, multiplicity (splitting) of each signal and integration of each signal.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_forward
- 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.arrow_forwardWhy does the 13C-NMR spectrum of the product only show six signals for the 1,4-di-tert.-butyl-2,5-dimethoxybenzene? Structure and 13C are attachedarrow_forwardThis CANNOT be hand-drawn. Please digitally draw/illustrate and type any explanations.arrow_forward
- Look at the structure of the starting material (9-anthraldehyde) and the product of the Wittigreaction. Describe the main differences you would expect between the 1H NMR of thisstarting material and the product. (Include comments about integration and shift values.)arrow_forwardwhat is is the structure of a compound of molecular formula c 10 h 14 o 2 that shows a strong ir absorption at 3150-2850 cm − 1 and give the following 1 h nmr absorptions: 1.4 (triplet, 6 h), 4.0 (quarter, 4h), and 6.8 (singlet, 4h) ppm?arrow_forwardplease help with this question. thank you. Deduce the identity of the following compound from the 1H NMR data given and briefly explain.arrow_forward
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