Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
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Chapter 9, Problem 38P
Propose a structure that is consistent with each set of
(a)
(b)
(c)
(d)
(e)
(f)
(g)
(h)
(i)
(j)
(k)
(l)
(m)
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Deduce the identity of the following compound from the 1H NMR data given and briefly explain.
Propose a structure for an unknown compound whole molecular formula is C(5)H(10)O(2) and is consistent with the 1H NMR data listed.
doublet, at 1.23 ppm (6H)
singlet, at 2.10 ppm (3H)
septet, at 4.98 ppm (1H)
Compound A has a molecular formula C5H11NO and a HNMR spectrum as such: 8.05 (s, 1H), 3.04 (s, 3H), 2.67 (t, 2H), 1.55 (m, 2H), 0.91 (t, 3H). The CNMR shows one peak above 160ppm. When hydrolyzed with H3O+, two compounds are formed B and C after aqueous workup. Draw the structures of A, B, and C.
Chapter 9 Solutions
Organic Chemistry
Ch. 9 - Prob. 1PPCh. 9 - PRACTICE PROBLEM
9.2 What compound with molecular...Ch. 9 - Prob. 3PPCh. 9 - PRACTICE PROBLEM 9.4 How many signals would each...Ch. 9 - Prob. 5PPCh. 9 - Prob. 6PPCh. 9 - Prob. 7PPCh. 9 - PRACTICE PROBLEM 9.7
The relative chemical shifts...Ch. 9 - Prob. 9PPCh. 9 - PRACTICE PROBLEM 9.9 Propose a structure for...
Ch. 9 - PRACTICE PROBLEM 9.10
What is the dihedral angle...Ch. 9 - PRACTICE PROBLEM 9.11 Draw the most stable chair...Ch. 9 - Prob. 13PPCh. 9 - Prob. 14PPCh. 9 - PRACTICE PROBLEM 9.13 How many signals would you...Ch. 9 - Prob. 16PPCh. 9 - Prob. 17PPCh. 9 - Prob. 18PPCh. 9 - Prob. 19PPCh. 9 - PRACTICE PROBLEM 9.18
What are the expected ratios...Ch. 9 - Given the mass spectrum in Figure 9.44 and the...Ch. 9 - Prob. 22PCh. 9 - 9.23 How many 13C NMR signals would you predict...Ch. 9 - Prob. 24PCh. 9 - 9.25 Propose structures for the compounds G and H...Ch. 9 - Prob. 26PCh. 9 - Prob. 27PCh. 9 - Compound Q has the molecular formula C7H8. The...Ch. 9 - 9.26 Explain in detail how you would distinguish...Ch. 9 - Prob. 30PCh. 9 - A compound with molecular formula C4H8O has a...Ch. 9 - In the mass spectrum of 2, 6-dimethyl-4-heptanol...Ch. 9 - Prob. 33PCh. 9 - What are the masses and structures of the ions...Ch. 9 - Prob. 35PCh. 9 - Ethyl bromide and methoxybenzene (shown below)...Ch. 9 - 9.34 The homologous series of primary amines, ,...Ch. 9 - Propose a structure that is consistent with each...Ch. 9 - 9.39 Propose structures for compounds E and F....Ch. 9 - Regarding compound J, C2HxCly, use the 1H NMR and...Ch. 9 - 9.38 When dissolved in , a compound (K) with the...Ch. 9 - Compound T (C5H8O) has a strong IR absorption band...Ch. 9 - Deduce the structure of the compound that gives...Ch. 9 - 9.45 Deduce the structure of the compound that...Ch. 9 - The 1H NMR spectrum of a solution of 1,...Ch. 9 - Acetic acid has a mass spectrum showing a...Ch. 9 - The 1H NMR peak for the hydroxyl proton of...Ch. 9 - The 1H NMR study of DMF (N, N-dimethylformamide)...Ch. 9 - 9.48 The mass spectra of many benzene derivatives...Ch. 9 - Prob. 52PCh. 9 - 1. Given the following information, elucidate the...Ch. 9 - Two compounds with the molecular formula C5H10O...Ch. 9 - Propose a structure that is consistent with each...Ch. 9 - 9.2 How many 1H NMR signals would the following...Ch. 9 - 9.3. How many 1H NMR signals would...Ch. 9 - 9.4 Which of these C6H14 isomers has the greatest...Ch. 9 - 9.5 How many 13C NMR signals would be given by the...Ch. 9 - Prob. 6QCh. 9 - 9.7 What is the structure of a compound C5H12...
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- Propose a structure consistent with each set of spectral data: a. C4H8Br2: IR peak at 3000–2850 cm−1; NMR (ppm): 1.87 (singlet, 6 H) 3.86 (singlet, 2 H) b.C3H6Br2: IR peak at 3000–2850 cm−1; NMR (ppm): 2.4 (quintet) 3.5 (triplet) c. C5H10O2: IR peak at 1740 cm−1; NMR (ppm): 1.15 (triplet, 3 H) 2.30 (quartet, 2 H) 1.25 (triplet, 3 H) 4.72 (quartet, 2 H) d.C3H6O: IR peak at 1730 cm−1; NMR (ppm): 1.11 (triplet) 2.46 (multiplet) 9.79 (triplet)arrow_forwardA graduate student was making some 4-hydroxybutanoic acid and she obtained an excellent yield of a different compound whose 13C NMR is shown here. Propose a structure for this copound.arrow_forwardA different unknown has an FTIR with a very intense peak at 1735 cm. Its 13C NMR spectrum exhibits a peak at 169.3 ppm, and the 'H NMR spectrum shows a quartet at 4.07 ppm. Which of the following compounds is the unknown most likely to be? (a) (b) (c) (d) (e) O compound (a) O compound (d) compound (e) compound (c) compound (b) (0)arrow_forward
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