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 9, Problem 9PP
PRACTICE PROBLEM 9.9
Propose a structure for compounds A and B whose spectra are shown in Fig. 9.13, and account for the splitting pattern of each signal.
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(a) Compound A has molecular formula C9H18O but shows only one singlet in the 1H-NMR spectrum. Suggest a structure for A and explain your reasoning.
(b) Compound B has molecular formula C10H14. The IR, mass, 1H-NMR, and 13C-NMR speca are shown below, they are also downloadable for closer inspection by clicking the link under the spectral data. Suggest a structure for B and explain your reasoning.
(a) Compound A has molecular formula C5H10O. It shows three signals in the 1H-NMR spectrum - a doublet of integral 6 at 1.1 ppm, a singlet of integral 3 at 2.14 ppm, and a quintet of integral 1 at 2.58 ppm. Suggest a structure for A and explain your reasoning.
(b) Compound B has molecular formula C8H6O2. The IR, 1H-NMR, and 13C-NMR spectra are shown below, they are also downloadable for closer inspection by clicking the link under the spectral data. Suggest a structure for B and explain your reasoning.
(c) Compound C has molecular formula C5H8O. The IR, mass, 1H-NMR, and 13C-NMR spectra are shown below, they are also downloadable for closer inspection by clicking the link under the spectral data. Suggest a structure for C and explain your reasoning.
(a) Compound A has molecular formula C5H10O. It shows three signals in the 1H-NMR spectrum - a doublet of integral 6 at 1.1 ppm, a singlet of integral 3 at 2.14 ppm, and a quintet of integral 1 at 2.58 ppm. Suggest a structure for A and explain your reasoning.
(b) Compound B has molecular formula C8H6O2. The IR, 1H-NMR, and 13C-NMR spectra are shown below, they are also downloadable for closer inspection by clicking the link under the spectral data. Suggest a structure for B and explain your reasoning.
(c) Compound C has molecular formula C5H8O. The IR, mass, 1H-NMR, and 13C-NMR spectra are shown below, they are also downloadable for closer inspection by clicking the link under the spectral data. Suggest a structure for C and explain your reasoning.
Chapter 9 Solutions
Organic Chemistry
Ch. 9 - Prob. 1PPCh. 9 - PRACTICE PROBLEM 9.2 What compound with molecular...Ch. 9 - PRACTICE PROBLEM 9.3
Using the method of Section...Ch. 9 - PRACTICE PROBLEM 9.4 How many signals would each...Ch. 9 - Prob. 5PPCh. 9 - Prob. 6PPCh. 9 - PRACTICE PROBLEM 9.7
The relative chemical shifts...Ch. 9 - Prob. 8PPCh. 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. 12PPCh. 9 - PRACTICE PROBLEM 9.13 How many signals would you...Ch. 9 - Prob. 14PPCh. 9 - Prob. 15PPCh. 9 - Prob. 16PPCh. 9 - Prob. 17PPCh. 9 - PRACTICE PROBLEM 9.18
What are the expected ratios...Ch. 9 - Prob. 19PPCh. 9 - How many 1H NMR signals (not peaks) would you...Ch. 9 - How many 13C NMR signals would you predict for...Ch. 9 - Prob. 22PCh. 9 - Prob. 23PCh. 9 - Prob. 24PCh. 9 - Compound Q has the molecular formula C7H8. The...Ch. 9 - 9.26 Explain in detail how you would distinguish...Ch. 9 - Compound S (C8H16) reacts with one mole of bromine...Ch. 9 - A compound with molecular formula C4H8O has a...Ch. 9 - In the mass spectrum of 2, 6-dimethyl-4-heptanol...Ch. 9 - Prob. 30PCh. 9 - What are the masses and structures of the ions...Ch. 9 - Prob. 32PCh. 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 - 9.36 Propose structures for compounds E and F....Ch. 9 - 9.37 Use the NMR and IR data below to propose a...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 - Prob. 40PCh. 9 - Deduce the structure of the compound that gives...Ch. 9 - Deduce the structure of the compound that gives...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. 49PCh. 9 - 1. Given the following information, elucidate the...Ch. 9 - Two compounds with the molecular formula C5H10O...
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