Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
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Textbook Question
Chapter 14, Problem 41P
Consider these reactions:
The intermediate A is a covalently bonded compound that has typical
What are the structures of A and B?
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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 - A compound (N) with the molecular formula C9H10O...Ch. 14 - The IR and 1H NMR spectra for compound X(C8H10)...Ch. 14 - Prob. 38PCh. 14 - Prob. 39PCh. 14 - 14.39 Given the following information, predict the...Ch. 14 - Consider these reactions: The intermediate A is a...Ch. 14 - Prob. 42PCh. 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. 5LGPCh. 14 - Prob. 1QCh. 14 - Which is the correct name of the compound shown?...Ch. 14 - Prob. 3QCh. 14 - Prob. 4QCh. 14 - Give the structure of a compound with the formula...Ch. 14 - Prob. 6Q
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- Compound A with molecular formula C6H10 has two peaks in its 1H NMR spectrum, both of which are singlets (with ratio 9 : 1). Compound A reacts with an acidic aqueous solution containing mercuric sulfate to form compound B, which gives a positive iodoform test and has an 1H NMR spectrum that shows two singlets (with ratio 3 : 1). Identify A and B.arrow_forwardCompounds A and B are isomers having the molecular formula C4H8O3. Identify A and B on the basis of their 1H NMR spectra.Compound A: δ 1.3 (3H, triplet); 3.6 (2H, quartet); 4.1 (2H, singlet); 11.1 (1H, broad singlet)Compound B: δ 2.6 (2H, triplet); 3.4 (3H, singlet); 3.7 (2H triplet); 11.3 (1H, broad singlet)arrow_forwardTreatment of compound E (molecular formula C4H8O2) with excess CH3CH2MgBr yields compound F (molecular formula C6H14O) after protonation with H2O. E shows a strong absorption in its IR spectrum at 1743 cm-1. F shows a strong IR absorption at 3600–3200 cm-1. The 1H NMR spectral data of E and F are given. What are the structures of E and F?Compound E signals at 1.2 (triplet, 3 H), 2.0 (singlet, 3 H), and 4.1 (quartet, 2 H) ppmCompound F signals at 0.9 (triplet, 6 H), 1.1 (singlet, 3 H), 1.5 (quartet, 4 H), and 1.55 (singlet, 1 H) ppmarrow_forward
- Compound A, C8H10O, has the IR and 1H NMR spectra shown. Propose a structure consistent with the observed spectra, and label each peak in the NMR spectrum. Note that the absorption at 5.5 î disappears when D2O is added.arrow_forwardCompound I (C11H14O2) is insoluble in water, aqueous acid, and aqueous NaHCO3, but dissolves readily in 10% Na2CO3 and 10% NaOH. When these alkaline solutions are acidified with 10% HCl, compound I is recovered unchanged. Given this information and its 1H-NMR spectrum, deduce the structure of compound I.arrow_forward1, 6-Methanonaphthalene has an interesting 1H NMR spectrum in which the eight hydrogens around the perimeter absorb at 6.9 to 7.3 δ, while the two CH2 protons absorb at -0.5 δ. Tell whether it is aromatic, and explain its NMR spectrum.arrow_forward
- Propose a structure for each of the following two isomers with formula C6H14 given their 1H-NMR spectra. Isomer A: δ = 0.84 (d, 12 H), 1.39 (septet, 2H) ppm Isomer B: δ = 0.84 (t, 3 H), 0.86 (t, 9H), 1.22 (q, 2H) ppmarrow_forwardThe IR spectrum of compound A with a molecular formula of C5H12O is shown below. Compound A is oxidized to give compound B, a ketone with a molecular formula of C5H10O. When compound A is heated with H2SO4, compounds C and D are obtained. Considerably more D is obtained than C.Reaction of compound C with O3, followed by treatment with dimethyl sulfide, gives two products: formaldehyde and compound E, with a molecular formula of C4H8O. Reaction of compound D with O3, followed by treatment with dimethyl sulfide, gives two products: compound F, with a molecular formula of C3H6O, and compound G, with a molecular formula of C2H4O. What are the structures of compounds A through G?arrow_forwardPropose a structure consistent with each set of data.a. Compound A:Molecular formula: C8H10OIR absorption at 3150–2850 cm–11H NMR data: 1.4 (triplet, 3 H), 3.95 (quartet, 2 H), and 6.8–7.3 (multiplet, 5 H) ppm b. Compound B:Molecular formula: C9H10O2IR absorption at 1669 cm–11H NMR data: 2.5 (singlet, 3 H), 3.8 (singlet, 3 H), 6.9 (doublet, 2 H), and 7.9 (doublet, 2 H) ppmarrow_forward
- Reaction of (CH3)3CCHO with (C6H5)3P=C(CH3)OCH3, followed by treatment with aqueous acid, affords R (C7H14O). R has a strong absorption in its IR spectrum at 1717 cm−1 and three singlets in its 1H NMR spectrum at 1.02 (9 H), 2.13 (3 H), and 2.33 (2 H) ppm. What is the structure of R? We will learn about this reaction in Chapter 18.arrow_forward(a) The 'H-NMR spectrum of cyclobutanone shows two signals - signal A at 3.00 ppm and signal B at 1.95 ppm. Give the multiplicity of each signal. cyclobutanone (b) When cyclobutanone is treated with D20 and NaOD, the only signal observable in the 1H-NMR is a singlet at 2.00 ppm. Explain why this is the case. [Note: Deuterium atoms do not display signals in the TH-NMR spectrum]arrow_forwardCompound A has molecular formula C5H8Br4 but shows only one singlet in the 1H-NMR spectrum. Suggest a structure for A and explain your reasoning.arrow_forward
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