Organic Chemistry
6th Edition
ISBN: 9781936221349
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
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Chapter 13, Problem 13.53AP
Interpretation Introduction
Interpretation:
The structure of compound A with molecular formula
Concept introduction:
Many nuclei and electrons have spin, due to this spin magnetic moment arises. The energy of this magnetic moment depends on the orientation of the applied magnetic field. In NMR spectroscopy, every nucleus has a spin. There is an
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Compounds 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)
A compound, C7H12O2, exhibits the following 13C NMR shifts and substitution, determined by DEPT.
13C NMR: δ25.5 (2o), 25.9 (2o), 29.0 (2o), 43.1 (3o), 183.0 (4o)
Draw the structure
(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
Chapter 13 Solutions
Organic Chemistry
Ch. 13 - Prob. 13.1PCh. 13 - Prob. 13.2PCh. 13 - Prob. 13.3PCh. 13 - Prob. 13.4PCh. 13 - Prob. 13.5PCh. 13 - Prob. 13.6PCh. 13 - Prob. 13.7PCh. 13 - Prob. 13.8PCh. 13 - Prob. 13.9PCh. 13 - Prob. 13.10P
Ch. 13 - Prob. 13.11PCh. 13 - Prob. 13.12PCh. 13 - Prob. 13.13PCh. 13 - Prob. 13.14PCh. 13 - Prob. 13.15PCh. 13 - Prob. 13.16PCh. 13 - Prob. 13.17PCh. 13 - Prob. 13.18PCh. 13 - Prob. 13.19PCh. 13 - Prob. 13.20PCh. 13 - Prob. 13.21PCh. 13 - Prob. 13.22PCh. 13 - Prob. 13.23PCh. 13 - Prob. 13.24PCh. 13 - Prob. 13.25PCh. 13 - Prob. 13.26PCh. 13 - Prob. 13.27PCh. 13 - Prob. 13.28PCh. 13 - Prob. 13.29PCh. 13 - Prob. 13.30PCh. 13 - Prob. 13.31PCh. 13 - Prob. 13.32PCh. 13 - Prob. 13.33PCh. 13 - Prob. 13.34PCh. 13 - Prob. 13.35PCh. 13 - Prob. 13.36APCh. 13 - Prob. 13.37APCh. 13 - Prob. 13.38APCh. 13 - Prob. 13.39APCh. 13 - Prob. 13.40APCh. 13 - Prob. 13.41APCh. 13 - Prob. 13.42APCh. 13 - Prob. 13.43APCh. 13 - Prob. 13.44APCh. 13 - Prob. 13.45APCh. 13 - Prob. 13.46APCh. 13 - Prob. 13.47APCh. 13 - Prob. 13.48APCh. 13 - Prob. 13.49APCh. 13 - Prob. 13.50APCh. 13 - Prob. 13.51APCh. 13 - Prob. 13.52APCh. 13 - Prob. 13.53APCh. 13 - Prob. 13.54APCh. 13 - Prob. 13.55APCh. 13 - Prob. 13.56APCh. 13 - Prob. 13.57APCh. 13 - Prob. 13.58APCh. 13 - Prob. 13.59APCh. 13 - Prob. 13.60APCh. 13 - Prob. 13.61APCh. 13 - Prob. 13.62APCh. 13 - Prob. 13.63APCh. 13 - Prob. 13.64APCh. 13 - Prob. 13.65APCh. 13 - Prob. 13.67AP
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