Concept explainers
Propose possible structures consistent with each set of data. Assume each compound has an
a. A compound having a molecular ion at
b. A compound having a molecular ion at
c. A compound having a molecular ion of
Want to see the full answer?
Check out a sample textbook solutionChapter 13 Solutions
ORGANIC CHEMISTRY W/ ACCESS >IC<
Additional Science Textbook Solutions
Living by Chemistry
Essential Organic Chemistry (3rd Edition)
General, Organic, and Biological Chemistry (3rd Edition)
General, Organic, & Biological Chemistry
Organic Chemistry (8th Edition)
Chemistry: A Molecular Approach (4th Edition)
- 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, 13.2arrow_forwardPropose 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_forwardAssume a compound with the formula C4H8O. a) How many double bonds and/or rings does your compound contain? b) If your compound shows an infrared absorption peak at 1715 cm-1, what functional group does it have? c) If your compound shows a single 1H NMR absorption peak at 2.1 δ, what is its structure?arrow_forward
- 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.arrow_forwardPropose a structure consistent with each set of data. C8H10 : IR absorptions at 3108–2875, 1606, and 1496 cm−1arrow_forwardA hydrocarbon, compound B, has molecular formula C6H6, and gave an NMR spectrum with two signals: delta 6.55 pm and delta 3.84 pm with peak ratio of 2:1. When warmed in pyridine for three hr, compound B quantitatively converts to benzene. Mild hydrogenation of B yielded another compound C with mass spectrum of m/z 82. Infrared spectrum showed no double bonds; NMR spectrum showed one broad peak at delta 2.34 ppm. With this information, address the following questions. a) How many rings are in compound C? b) How many rings are probably in B? How many double bonds are in B? c) Can you suggest a structure for compounds B and C? d) In the NMR spectrum of B, the up-field signal was a quintet, and the down field signal was a triplet. How must you account for these splitting patterns?arrow_forward
- For each compound shown below,(1) sketch the 13C NMR spectrum (totally decoupled, with a singlet for each type of carbon), showing approximatechemical shifts.(2) show the multiplicity expected for each signal in the off-resonance-decoupled spectrum.(3) sketch the spectra expected using the DEPT-90 and DEPT-135 techniques. 3-chloropropenearrow_forwardPropose a structure consistent with following set of spectral data: C3H6O: IR peak at 1730 cm−1; NMR (ppm): 1.11 (triplet) 2.46 (multiplet) 9.79 (triplet)arrow_forwardTreatment of compound E (molecular formula C4H8O2) with excessCH3CH2MgBr yields compound F (molecular formula C6H14O) afterprotonation with H2O. E shows a strong absorption in its IR spectrum at1743 cm−1. F shows a strong IR absorption at 3600−3200 cm−1. The 1HNMR spectral data of E and F are given. What are the structures of E andF?Compound E signals at 1.2 (triplet, 3 H), 2.0 (singlet, 3 H), and 4.1 (quartet, 2 H) ppm Compound F signals at 0.9 (triplet, 6 H), 1.1 (singlet, 3 H), 1.5 (quartet, 4H), and 1.55 (singlet, 1 H) ppmarrow_forward
- Identify below compound from its spectral data. Molecular formula:C3H5ClO2 IR:3500–2500 cm−1, 1714 cm−1 1H NMR data:2.87 (triplet, 2 H), 3.76 (triplet, 2 H), and 11.8 (singlet, 1H) ppmarrow_forwardDraw a structure consistent with the following set of data: a hydrocarbon with a molecular ion at m/z = 68 and IR absorptions at 3310, 3000−2850, and 2120cm−1.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning