Organic Chemistry
6th Edition
ISBN: 9781936221349
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
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Chapter 17, Problem 17.53AP
Interpretation Introduction
Interpretation:
The compounds,
Concept introduction:
Diels Alder reaction is the
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Compounds B and C are isomers with molecular formula C5H9BrO2. The 1H NMR spectrum of compounds B and C are shown below. The IR spectrum corresponding to compound B showed strong absorption bands at 1739, 1225, and 1158 cm-1, while the spectrum corresponding to compound C have strong bands at 1735, 1237, and 1182 cm-1.
1.Based on the information provided, determine the structure of compounds B and C.
2.Assign all peaks in 1H NMR spectrum of compounds B and C.
Two compounds with the molecular formula C5H10O have the following 1H and 13C NMR data. Both compounds have a strong IR absorption band in the 1710–1740-cm_1 region. Elucidate the structure of these two compounds and interpret the spectra. (10)
(a) 1H NMR: d 2.55 (septet, 1H), 2.10 (singlet, 3H), 1.05 (doublet, 6H);
13C NMR: d 212.6, 41.5, 27.2, 17.8
(b) 1H NMR: d 2.38 (triplet, 2H), 2.10 (singlet, 3H), 1.57 (sextet, 2H), 0.88 (triplet, 3H);
13C NMR: d 209.0, 45.5, 29.5, 17.0, 13.2
A compound of formula C6H10O2 shows only two absorptions in the proton NMR: a singlet at 2.67 ppm and a singlet at2.15 ppm. These absorptions have areas in the ratio 2:3. The IR spectrum shows a strong absorption at 1708 cm-1. Proposea structure for this compound.
Chapter 17 Solutions
Organic Chemistry
Ch. 17 - Prob. 17.1PCh. 17 - Prob. 17.2PCh. 17 - Prob. 17.3PCh. 17 - Prob. 17.4PCh. 17 - Prob. 17.5PCh. 17 - Prob. 17.6PCh. 17 - Prob. 17.7PCh. 17 - Prob. 17.8PCh. 17 - Prob. 17.9PCh. 17 - Prob. 17.10P
Ch. 17 - Prob. 17.11PCh. 17 - Prob. 17.12PCh. 17 - Prob. 17.13PCh. 17 - Prob. 17.14PCh. 17 - Prob. 17.15PCh. 17 - Prob. 17.16PCh. 17 - Prob. 17.17PCh. 17 - Prob. 17.18PCh. 17 - Prob. 17.19PCh. 17 - Prob. 17.20PCh. 17 - Prob. 17.21PCh. 17 - Prob. 17.22APCh. 17 - Prob. 17.23APCh. 17 - Prob. 17.24APCh. 17 - Prob. 17.25APCh. 17 - Prob. 17.26APCh. 17 - Prob. 17.27APCh. 17 - Prob. 17.28APCh. 17 - Prob. 17.29APCh. 17 - Prob. 17.30APCh. 17 - Prob. 17.31APCh. 17 - Prob. 17.32APCh. 17 - Prob. 17.33APCh. 17 - Prob. 17.35APCh. 17 - Prob. 17.36APCh. 17 - Prob. 17.37APCh. 17 - Prob. 17.38APCh. 17 - Prob. 17.39APCh. 17 - Prob. 17.40APCh. 17 - Prob. 17.41APCh. 17 - Prob. 17.42APCh. 17 - Prob. 17.43APCh. 17 - Prob. 17.44APCh. 17 - Prob. 17.45APCh. 17 - Prob. 17.46APCh. 17 - Prob. 17.47APCh. 17 - Prob. 17.48APCh. 17 - Prob. 17.49APCh. 17 - Prob. 17.50APCh. 17 - Prob. 17.51APCh. 17 - Prob. 17.52APCh. 17 - Prob. 17.53APCh. 17 - Prob. 17.54APCh. 17 - Prob. 17.55APCh. 17 - Prob. 17.56APCh. 17 - Prob. 17.57APCh. 17 - Prob. 17.58APCh. 17 - Prob. 17.59AP
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- Compound B of molecular formula C9H19N shows a noteworthy infrared absorption at 3300 cm-1. Its 1H-NMR spectrum shows three singlets – δ 1.0 (6H), 1.1 (12H), 1.4 (1H) ppm. Its 13C-NMR spectrum has four signals – δ 25, 28, 41, 64 ppm. Suggest a structure for this compound. Please show work.arrow_forwardDeduce the structures of compounds A and B, two of the major components of jasmine oil, from the given data. Compound A: C9H10O2; IR absorptions at 3091–2895 and 1743 cm-1; 1H NMR signals at 2.06 (singlet, 3 H), 5.08 (singlet, 2 H), and 7.33 (broad singlet, 5 H) ppm. Compound B: C14H12O2; IR absorptions at 3091–2953 and 1718 cm-1; 1H NMR signals at 5.35 (singlet, 2 H) and 7.26–8.15 (multiplets, 10 H) ppm.arrow_forwardFollowing are 1H-NMR spectra for compounds B (C6H12O2) and C (C6H10O). Upon warming in dilute acid, compound B is converted to compound C. Deduce the structural formulas for compounds B and C.arrow_forward
- Compound X, C7H14 undergo hydration to form Y which is optically active. X reacts with cold alkane potassium permanganate (VII) solution to form Z. Ozonolysis of X forms methanal and 3,3-dimethylbutanal. Deduce the structure of X,Y and Zarrow_forwardCompound 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_forwardAddition of m-xylene to the strongly acidic solvent HF/SbF5 at 45C gives a new species, which shows 1H-NMR resonances at 2.88 (3H), 3.00 (3H), 4.67 (2H), 7.93 (1H), 7.83 (1H), and 8.68 (1H). Assign a structure to the species giving this spectrum.arrow_forward
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